Complete Portland Holiday Cottage List

Just click on the Holiday Cottage name to be taken directly to its listing. If you are looking for a cottage that will accommodate a certain amount of people then just click on the links below:

Sleeps up to 2 | Sleeps up to 4 | Sleeps up to 5 | Sleeps up to 6 | Sleeps up to 7 | Sleeps up to 8 | Sleeps up to 10+

Sleeps up to 2
Church Ope Studio Church Ope Studio - Church Ope

Church Ope Studio is a tranquil retreat right on the coast path at Church Ope Cove Portland. Sea View in Winter and glimpsed through trees in leaf in summer. The studio is both cosy and warm and light and airy. It is tucked away from the busy world and close to amenities.
Details
Bedrooms: 1
Sleeps: 2
Star Rating: 4
Pets Welcome: Yes
Change Over: Friday
Portland Hideaway Portland Hideaway - Southwell

Portland Hideaway is a romantic getaway in 4 star luxury for 2 people (and a pet if it won't cramp your style!). No matter what your interest is in coming to Portland, Portland Hideaway makes a wonderful centre for an active coastal holiday, sightseeing or a time for unwinding and recharging your batteries.
Details
Bedrooms: 1
Sleeps: 2
Star Rating: 4
Pets Welcome: Yes
Change Over: Friday
Portland Views Portland Views - Wakeham

Portland Views is a second floor, 1 bedroom apartment sleeping 2. It is a passive House Eco-Home with triple glazing, furnished to a high standard throughout. Portland Views, as the name suggests, has far reaching views of Portland Bill and out to sea. There is off-street parking for 1 car.
Details
Bedrooms: 1
Sleeps: 2
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Castle View Castle View - Wakeham

Castle view is a newly built apartment located in the heart of Portland, boasting fantastic views of Pennsylvania Castle and views out to the sea. Castle View is a Passive House Eco-home and is energy efficient, operates low carbon usage and features triple glazed windows.
Details
Bedrooms: 1
Sleeps: 2
Star Rating: 5
Pets Welcome: No
Change Over: Saturday
Gull Cottage Gull Cottage - Southwell

Gull Cottage is a detached property sleeping two in the popular village of Southwell. The property is "upside down" and features a balcony with extensive views of the sea. Gull Cottage is only 2 minutes walk from the coast path and Portland Bill is a picturesque 20 minute walk away.
Details
Bedrooms: 1
Sleeps: 2
Star Rating: 3
Pets Welcome: No
Change Over: Saturday
Chapel Cottage Chapel Cottage - Southwell

Chapel Cottage has been tastefully converted from the Methodist Church that has stood since 1849 and features high panelled ceilings and stained glass windows. With large skylights the chapel is very bright and airy whilst still retaining that snug feeling.
Details
Bedrooms: 1
Sleeps: 2
Star Rating: 3
Pets Welcome: No
Change Over: Saturday
158 Atlantic House 158 Atlantic House - Castletown

158 Atlantic House is a luxury apartment in the Ocean Views complex with contemporary kitchens benefitting from granite works surfaces and integrated appliances and boutique style bathrooms.
Details
Bedrooms: 1
Sleeps: 2
Star Rating: 3
Pets Welcome: No
Change Over: Friday
184 Atlantic House 184 Atlantic House - Castletown

184 Atlantic House is a luxury apartment in the Ocean Views complex with contemporary kitchens benefitting from granite works surfaces and integrated appliances and boutique style bathrooms.
Details
Bedrooms: 1
Sleeps: 2
Star Rating: 3
Pets Welcome: No
Change Over: Friday
Sleeps up to 4
Pollys Cottage Pollys Cottage - Wakeham

Polly’s Cottage is a traditionally built Grade 2 listed cottage dating from around 1700 with many original features. Situated in the heart of Wakeham on Portland it is just a few minutes walk from the coastal path, Church Ope Cove and an excellent selection of local shops, pubs and restaurants.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 3
Pets Welcome: No
Change Over: Saturday
Breeze Cottage Breeze Cottage - Chiswell

Breeze Cottage is a delightful old fisherman's cottage that has been renovated and decorated to a high standard throughout with the owners own family use in mind. It is located in the Chiswell area of Portland and is ideally placed to access both Chesil Beach and the Weymouth and Portland National Sailing Academy.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Friday
Chesil View Apartment Chesil View Apartment - Fortuneswell

Chesil View Apartment has recently been renovated to a high standard throughout and has spectacular panoramic sea views across Chesil Beach and Lyme Bay that on a clear day will allow you to see from Portland to Lyme Regis.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 3
Pets Welcome: No
Change Over: Saturday
Chesil Cottage Chesil Cottage - Chiswell

Chesil Cottage sleeps up to four and two pets and is just 100 yards from Chesil Beach. It is an ideal location for anyone coming down for sailing events at the Weymouth and Portland National Sailing Academy or looking for the pubs, restaurants and magnificent cove by Chiswell, not forgetting Chesil Beach itself.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
167 Ocean Views 167 Ocean Views - Castletown

167 Ocean Views is a spacious, 4th floor apartment sleeping up to 4. Furnished to a high standard throughout this apartment also benefits from an on-site fitness centre with indoor swimming pool.The apartment is close to Portland Castle, Chesil Beach and Portland Marina.
Details
Bedrooms: 1
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Penn Cottage Penn Cottage - Wakeham

Penn Cottage is wonderfully situated just yards from the coastal path so you can take advantage of the many walks around Portland. Once a part of a grand residence, Penn Cottage dates all the way back to 1860. The interior, however, is clean and modern whilst still retaining some period features.
Details
Bedrooms: 3
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Sea Dog Cottage Sea Dog Cottage - Chiswell

Built in te 1800's Sea Dog promises a truly first rate holiday. Following recent total refurbishment which blends the very best of old with stylish modern fittings and fixtures, this Portland stone cottage sleeps 4 in two bedrooms one king size and 1 twin.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
162 Ocean Views 162 Ocean Views - Castletown

162 Ocean Views is a stylish one bedroom apartment that can accommodate four guests. Externally, the furnished balcony overlooking the beautiful garden is perfect for al fresco dining and relaxing after a busy day.
Details
Bedrooms: 1
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Kivel Cottage Kivel Cottage - Fortuneswell

Kivel Cottage is a traditional looking pretty Portland stone cottage, however, as it is newly built, it benefits from a modern airy interior and good specification including an en-suite shower room to the master bedroom.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 3
Pets Welcome: Yes
Change Over: Friday
Stones Throw Stones Throw - Chiswell

Voted Supreme Winner of the Housing Design Awards, Stones Throw is part of a development of innovative eco-friendly houses that were part of the Olympics used to house sailors from all over the world during the games of 2012. Stones Throw offers both family and pet friendly holidays and comes equipped with a cot, highchair and stairgate.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: A
Pets Welcome: Yes
Change Over: Friday
Silklake Apartment Silklake Apartment - Easton

Silklake is a modern two bedroom, reverse level apartment on the ground floor, boasting access to the on-site indoor heated swimming pool. Internally, the property benefits from an open plan living, kitchen and dining area and is well equipped throughout including the use of wireless internet.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 5
Pets Welcome: No
Change Over: Saturday
Sunset Cottage Sunset Cottage - Chiswell

Sunset Cottage is the perfect place to experience Portlands rugged beauty. Just 200 yards from Chesil Beach. Short distance from sailing academy, Windsurfing, Kite surfing Centres and diving schools. The 200 year old fisherman’s cottage had to be totally refurbished to a high standard.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Cove Cottage Cove Cottage - Chiswell

This Grade II listed fishermans cottage, built in the 1800's, has been refurbished to a very high standard kepping original features. Cove Cottage is the perfect place to experience Portland's rugged beauty just a stone's throw from Chesil Beach and watch the breathtaking sunsets at the local Cove pub.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Sailing Views Sailing Views - Castletown

Sailing Views is an apartment in the popular Ocean Views development of luxury properties. With contemporary interiors, black granite worktops in the kitchen and integrated Neff appliances and larhe balconies to relax on after a hard day exploring the area.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 3
Pets Welcome: No
Change Over: Saturday
Hillside Hillside - Fortuneswell

Hillside is a stunning two bedroomed Victorian house with views from a southwest facing garden overlooking Portland Harbour and Weymouth and Portland National sailing academy. Hillside is a perfect base for year round holidays on the Dorset Coast.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: N
Pets Welcome: Yes
Change Over: Saturday
159 Atlantic House 159 Atlantic House - Castletown

159 Atlantic House is a luxurious apartment sleeping 4 with partial sea views, fitted out to the highest specification. There is an on site spa and fitness suite including a heated indoor pool, sauna, Jacuzzi and gym.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 3
Pets Welcome: No
Change Over: Friday
82 Ocean Views 82 Ocean Views - Castletown

82 Ocean Views is a 4 star gold-rated apartment with 2 bedrooms, sleeping 4 with a high quality finish throughout. It is in close proximity to the 2012 Olympic sailing venue and coastline and has an on-site fitness centre with indoor swimming pool. Close to Portland Castle, Chesil Beach and Portland Marina.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
101 Ocean Views 101 Ocean Views - Castletown

Ocean Views is a new luxury seafront development of apartments on the Isle of Portland in Dorset, situated on the Jurassic coast beside Chesil Beach, a location guaranteed to inspire. 101 Ocean Views is a stylishly furnished apartment located on the fifth floor of the development with garden views.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
135 Ocean Views 135 Ocean Views - Castletown

135 Ocean Views is a stylish duplex apartment offering garden views. The apartments have been finished to the highest standard with high quality flooring, wooden decked balconies and polished granite worktops exemplifying the kind of craftsmanship and quality materials that define Ocean Views.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
134 Atlantic House 134 Atlantic House - Castletown

134 Atlantic House is a first floor apartment with a contemporary kitchen benefitting from granite works surfaces and integrated appliances and boutique style bathrooms. Balconies overlook the gardens and have partial sea views over the acclaimed waters in Weymouth and Portland.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 3
Pets Welcome: No
Change Over: Friday
83 Ocean Views 83 Ocean Views - Castletown

83 Ocean Views is a fourth floor apartment with 2 bedrooms, sleeping 4 with a high quality finish throughout. It is in close proximity to the 2012 Olympic sailing venue and coastline and has an on-site fitness centre with indoor swimming pool. Close to Portland Castle, Chesil Beach and Portland Marina.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
67 Ocean Views 67 Ocean Views - Castletown

67 Ocean Views is a second floor apartment with 2 bedrooms, sleeping 4 with a high quality finish throughout. Ocean Views is in close proximity to the 2012 Olympic sailing venue and coastline and has an on-site fitness centre with indoor swimming pool. Close to Portland Castle, Chesil Beach and Portland Marina.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Stopes Cottage Stopes Cottage - Portland Bill

Have you ever wanted to stay at a lighthouse? Now you can, right her on Portland. Stopes Cottage is a self-catering cottage attached to the 18th Century lighthouse via a corridor. Stopes Cottage is set in quiet, unspoiled, rural countryside and accessed by a private road. Originally it was a lighthouse keeper’s cottage and is all on the ground floor.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
119 Ocean Views 119 Ocean Views - Castletown

119 Ocean Views has an open plan living area with spectacular sea views and sliding glass doors leading out onto the balcony. Situated close by is the Weymouth and Portland National Sailing Academy and Portland Marina making it an ideal luxury base if you want to explore the extensive watersports available on Portland.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
106 Ocean Views 106 Ocean Views - Castletown

Ocean Views is a luxury seafront development of apartments finished to the highest standard. 106 Ocean Views is situated on the fifth floor with a spacious balcony offering spectacular sea views over Portland Harbour, Chesil Beach and Weymouth Bay. The apartment has two double bedrooms.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
105 Ocean Views 105 Ocean Views - Castletown

Ocean Views is a luxury seafront development of apartments finished to the highest standard with a state-of-the-art health and fitness centre complete with an indoor swimming pool. 105 Ocean Views is on the fifth floor with spectacular panoramic views over the 2012 Olympic sailing venue, Chesil Beach and Weymouth Bay.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
65 Ocean Views 65 Ocean Views - Castletown

65 Ocean Views is sleeps up to four people and is finished to the highest standard with high quality flooring, wooden decked balconies and polished granite worktops. The development also boasts a state-of-the-art health and fitness centre complete with an indoor swimming pool, and is set in thoughtfully landscaped grounds.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
108 Ocean Views 108 Ocean Views - Castletown

108 Ocean Views is a modern sixth floor apartment situated at the rear of the development and has been finished to the highest standard with high quality flooring, wooden decked balconies and polished granite worktops exemplifying the kind of craftsmanship and quality materials that define Ocean Views.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Branscombe Cottage Branscombe Cottage - Portland Bill

Branscombe Lodge is a cottage in the grounds of the lighthouse. It is set in quiet unspoiled rural countryside and accessed by a private road. Originally the paraffin store for the lighthouse it has been converted into an “upside down” house. The sitting room is upstairs with magnificent views of sea and coast on all four sides.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Olympus Penthouse Olympus Penthouse - Castletown

The Olympus Penthouse is a two bedroom, fifth floor apartment boasting unrivalled balcony views over Portland Harbour and Dorset coastline. Internally, this apartment benefits from breathtaking sea views from each room. Externally, the large furnished balcony provides a delightful environment for enjoying the panoramic views.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
197 Ocean Views 197 Ocean Views - Castletown

197 Ocean Views is a seventh floor triplex penthouse apartment with 2 bedrooms, sleeping 4. The glass-encased sky loft living room is the undoubted highlight of the property offering spectacular 360 degree views over Portland and out to sea over the 2012 Olympic sailing venue, Chesil Beach, Lyme Bay and Weymouth Bay.
Details
Bedrooms: 2
Sleeps: 4
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Sleeps up to 5
The Chalet The Chalet - Fortuneswell

Portland Sailing Accommodation run by sailors for sailors and their families but not just for sailors! This accommodation will suit anyone looking for self-catering accommodation on Portland throughout the year.
Details
Bedrooms: 1
Sleeps: 5
Star Rating: N
Pets Welcome: Yes
Change Over: Saturday
Sea Far Sea Far - Fortuneswell

Sea Far is a three bedroom maisonette boasting spectacular views. Internally, the property features an inglenook fireplace and benefits from far reaching views of Chesil Beach, Lyme bay and Verne Hill. Externally, the furnished garden and patio areas are perfect for al fresco dining or simply relaxing after a busy day.
Details
Bedrooms: 3
Sleeps: 5
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Kearney Cottage Kearney Cottage - Fortuneswell

Kearney Cottage is a 3 storey Fisherman’s Cottage built in 1850 which sleeps 5 in 3 bedrooms arranged as two doubles and a single. The cottage has been totally refurbished and boasts superb sea views from all levels.
Details
Bedrooms: 3
Sleeps: 5
Star Rating: 3
Pets Welcome: No
Change Over: Saturday
Larkrise Larkrise - Southwell

Larkrise is a Portland Holiday Cottage sleeping up to 5 people. Larkrise will accept up to 2 pets and is ideally placed for walks.
Details
Bedrooms: 3
Sleeps: 5
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Canute Cottage Canute Cottage - Fortuneswell

Canute Cottage is a terraced holiday cottage set in a quiet street, just a few hundred yards from the southern end of Chesil Beach. Portland harbour and castle, Portland Bill, Weymouth, with its Blue Flag beach and harbour, 2 RSPB reserves, a sealife park and marine sanctuary are all nearby.
Details
Bedrooms: 2
Sleeps: 5
Star Rating: A
Pets Welcome: Yes
Change Over: Friday
Anchor Cottage Anchor Cottage - Weston

Anchor Cottage is a charming cottage in a good central location that dates back to the early 1800s when it used to be a pub, The Rifleman. Unlike many Portland properties, Anchor Cottage has two dedicated parking spaces to the front of the property.
Details
Bedrooms: 3
Sleeps: 5
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Fishys Cottage Fishys Cottage - Fortuneswell

Fishy's Cottage is a traditional fisherman's cottage built around 1825. Situated just a five minute walk from Chesil Cove at the eastern end of Chesil Beach, the stone cottage have been extensively refurbished with modern facilities but maintain many original features.
Details
Bedrooms: 3
Sleeps: 5
Star Rating: 3
Pets Welcome: Yes
Change Over: Saturday
Beaufort Cottage Beaufort Cottage - Fortuneswell

Beaufort Cottage is a terraced traditional Portland stone cottage that feels modern whilst retaining lovely character features. The cottage sleeps up to 5 people and will accept one pet.
Details
Bedrooms: 3
Sleeps: 5
Star Rating: 3
Pets Welcome: Yes
Change Over: Saturday
Pebbles Pebbles - Chiswell

Pebbles Cottage is close to the seafront at Chiswell and is a charming 200 year old holiday cottage with many period features. Pebble cottage sleeps 5 but can accommodate 6 as there is an additional z bed that would be suitable for a child. Great views to Chesil Beach and Lyme Bay.
Details
Bedrooms: 3
Sleeps: 5
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Stonelea Stonelea - Easton

Stonelea is a detached dormer bungalow with the added benefit of parking situated centrally on Portland in the village of Easton. Stonelea sleeps up to 5 and makes an ideal base to discover all that Portland has to offer.
Details
Bedrooms: 3
Sleeps: 5
Star Rating: 3
Pets Welcome: No
Change Over: Saturday
Neptune Cottage Neptune Cottage - Chiswell

Dating back some 200 years, Neptune Cottage is just yards from the famous Chesil Beach. Once a terraced fisherman's cottage, Neptune Cottage has been sympathetically refurbished keeping its old world charm whilst being modern and up to date in the areas that matter.
Details
Bedrooms: 3
Sleeps: 5
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Bayview Cottage Bayview Cottage - Fortuneswell

Bayview is situated on Portland's Verne Common overlooking Weymouth Bay, Portland Harbour and the Dorset coast to the north east and Chesil Beach and Lyme Bay to the south west. It has perhaps the most spectacular sea views in the area.
Details
Bedrooms: 2
Sleeps: 5
Star Rating: A
Pets Welcome: No
Change Over: Saturday
Sleeps up to 6
Kendalls Rest Kendalls Rest - Fortuneswell

Kendalls Rest is a contemporary three bedroom duplex apartment which is in a perfect location for both the delights of Portland and exploring Dorset’s Jurassic coastline. Internally, the property benefits from a high standard of furnishing and stylish decor throughout.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Chesil Reach Chesil Reach - Chiswell

Chesil reach is a character holiday cottage on Portland, Dorset, with far reaching sea views over Lyme Bay and Chesil Beach. Chesil Reach sleeps 6.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 3
Pets Welcome: No
Change Over: Saturday
Casita Del Mar Casita Del Mar - Fortuneswell

Casita Del Mar is indeed a cottage by the sea, dating form the 1850s and sleeping up to 6 in recently refurbished splendour
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Alpen Rose Cottage Alpen Rose Cottage - Easton

Alpen Rose Cottage in Portland is an original terraced fisherman's cottage which has been delightfully restored. Step inside and you will find a large spacious cottage which has been furnished with care and attention.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Fishermans Cottage Fishermans Cottage - Southwell

Fishermans cottage in Southwell village is a charming, detached 18th century cottage with excellent views across the sea. It has recently been renovated with full central heating throughout making it a great choice for winter breaks as well.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: N
Pets Welcome: No
Change Over: Saturday
Pebble Reef Cottage Pebble Reef Cottage - Wakeham

Pebble Reef cottage is a traditional Quarryman's cottage full of character and lovingly renovated to bring it into the 21st century. The cottage can sleep up to six people in 3 comfortable bedrooms.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: N
Pets Welcome: No
Change Over: Saturday
Spinnaker House Spinnaker House - Fortuneswell

Spinnaker House is a delightful, 4 star rated, 3-bedroomed Victorian cottage, situated only 5 minutes’ walk from Chesil Beach and less than a 1 mile walk to Weymouth and Portland National Sailing Academy (WPNSA). The facilities and location make it an ideal base for year round holidays on the beautiful Dorset Coast.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Brokers Brokers - Wakeham

Brokers is a character cottage in Wakeham, Portland that sleeps up to 6 and will accept up to 2 pets. Close to Curch Ope Cove, the Portland Museum, Pennsylvannia Castle and both coastal and inland walks, Brokers has a lot to offer.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Limestone Cottage Limestone Cottage - Southwell

Limestone cottage in Southwell village is a charming, traditional Portland quarryman's terraced cottage with great south facing coastal views across the English channel. It has recently been refurbished and modernised but retains it’s original character and charm which features wood panelling and Portland stone fireplace.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Sea Stones Sea Stones - Weston

Sea Stones is a grade II listed cottage that is ideally centrally located to explore all that Portland has to offer. Easy access to the coastal paths should make Sea Stones a hit with the walkers.
Details
Bedrooms: 4
Sleeps: 6
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Easton Sunrise Cottage Easton Sunrise Cottage - Easton

Easton Sunrise is a delightful stone cottage built in 1892. It is on the outskirts of the popular small town of Easton and yet is a short walk to Ope Cove (bathing), local eateries, take-aways, the island’s only supermarket and Easton Square with its’ gardens and children’s play park.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Lime House Lime House - Weston

Lime House was built in the 1850s and has now had a total renovation. With a luxurious bathroom featuring a double ended bath, stylish galley kitchen and touches such as local quarried stone fireplaces, the owners of Lime House have spent considerable time ensuring the property is a contemporary home from home.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Chesil Cove Cottage Chesil Cove Cottage - Chiswell

Chesil Cove Cottage is a converted fisherman's cottage in Portland, Dorset that now sleeps 6 and is ideally placed for Chesil Beach and the WPNSA sailing events
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 3
Pets Welcome: No
Change Over: Saturday
Chesil View House Chesil View House - Fortuneswell

Chesil View House sits in the quiet but steep St Martins Road of Foruneswell. The property dates back to 1890 and has been recently renovated to a very high professional standard awarding the property a four star rating by Visit Britain on its first attempt.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Sea Pinks Cottage Sea Pinks Cottage - Fortuneswell

Sea Pinks Cottage nestles at the bottom of a steep hill that is historic Mallams, in Fortuneswell. Built around 1860, this fine Portland Stone fisherman's cottage has been completely refurbished and decorated to exceptional standards to provide a truly inviting retreat for six people.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Shearwater Shearwater - Wakeham

Shearwater is a newly built three bedroom house set over three floors, located on the East coast of Portland, offering views of Pennsylvania Castle and out to the sea. Shearwater sleeps six in three bedrooms, one double and two twins.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 5
Pets Welcome: Yes
Change Over: Saturday
The View The View - Wakeham

The View, as its name suggests, has great views over Pennsylvania Castle and to the sea beyond. Part of the prestigious Pennyslvania Heights development designed by an award- winning team this three bedroom ‘Passivhaus’ is a highly energy efficient eco- home that operates on a low carbon footprint.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: A
Pets Welcome: Yes
Change Over: Flexible
Dream View Dream View - Wakeham

Dream View is a pioneering Passivhaus Eco-Home with triple glazing with a contemporary layout and well equipped with everything you need for a self-catering holiday. Situated in the prestigious Pennyslvania Heights, a newly built development that was designed by an award winning team, Dream View has views over Pennsylvania Castle and the sea beyond.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: A
Pets Welcome: Yes
Change Over: Friday
Chesil Beach Cottage Chesil Beach Cottage - Chiswell

Chesil Beach Cottage is a Portland holiday cottage sleeping 6 situated opposite the famous Chesil Beach and Lyme Bay. The house is one of a pair of old houses built of Portland stone; inside are some 17th—18th century features and ship’s beams. It is on three floors and can accommodate up to six (4 adults 2 kids).
Details
Bedrooms: 3
Sleeps: 6
Star Rating: A
Pets Welcome: Yes
Change Over: Saturday
66 Ocean Views 66 Ocean Views - Castletown

66 Ocean Views is a modern second floor apartment finished to the highest standard with high quality flooring, wooden decked balconies and polished granite worktops exemplifying the kind of craftsmanship and quality materials that define Ocean Views.
Details
Bedrooms: 2
Sleeps: 6
Star Rating: A
Pets Welcome: No
Change Over: Saturday
65 Fortuneswell 65 Fortuneswell - Fortuneswell

Ideal for small groups, couples and families with extensive sea views, 65 Fortuneswell sleeps up to 6 people comfortably in either single/twin or king-size beds. Situated in a central position on the lower part of the island, it is ideal for guests visiting the Weymouth and Portland National Sailing Academy.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 3
Pets Welcome: No
Change Over: Flexible
204 Ocean Views 204 Ocean Views - Castletown

204 Ocean Views is a stylish duplex apartment sleeping 6 with fantastic facilities, near the 2012 sailing venue with garden views from the large balcony. The Ocean Views development also boasts a state-of-the-art health and fitness centre complete with an indoor swimming pool, and is set in thoughtfully landscaped grounds.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
99 Ocean Views 99 Ocean Views - Castletown

99 Ocean Views is a triplex penthouse apartment sleeping six that has fantastic 360 degree views from the glass-encased mezzanine living area over Portland and out to sea over the 2012 sailing venue. Ocean Views also boasts a state-of-the-art health and fitness centre complete with an indoor swimming pool.
Details
Bedrooms: 3
Sleeps: 6
Star Rating: 4
Pets Welcome: No
Change Over: Saturday
Sleeps up to 7
Wills Retreat Wills Retreat - Fortuneswell

Will's Retreat is a traditional quarryman's cottage built aound 1825. Situated just a five minute walk from Chesil Cove at the eastern end of Chesil Beach, the stone cottage have been extensively refurbished with modern facilities but maintain many original features.
Details
Bedrooms: 3
Sleeps: 7
Star Rating: 3
Pets Welcome: Yes
Change Over: Saturday
Portland Retreat Portland Retreat - Southwell

The Portland Retreat is one of the largest self catering properties on Portland and has been awarded 4 stars (excellent standard throughout) by Visit Britain. As you travel through Southwell you will notice many small, traditional stone cottages so many are surprised by the scale of the Portland Retreat upon arrival.
Details
Bedrooms: 4
Sleeps: 7
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Beachcombers Cottage Beachcombers Cottage - Chiswell

With the garden backing onto Chesil Beach part of the World Heritage Coastline, this comfortable three bedroom cottage is ideally placed for the National Sailing Academy, or for walking the costal path. The cycling is superb, you can take the Rodwell trail right into Weymouth.
Details
Bedrooms: 3
Sleeps: 7
Star Rating: N
Pets Welcome: Yes
Change Over: Saturday
Captains Retreat Captains Retreat - Fortuneswell

Captain's Retreat is a delightful and imposing detached house with a spacious garden that comfortably sleeps 7 people and is pet friendly. The property is tucked well away from any traffic, situated in Manor Place, which is car free. The house is reached by an alleyway that leads down from Fortuneswell High Street.
Details
Bedrooms: 4
Sleeps: 7
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Elizabethan House Elizabethan House - Chiswell

Elizabethan House is located in Portland, situated just 500 yards from Chesil Beach and within a short walk from the National Sailing Academy. Internally, the property has been refurbished throughout and has an Elizabethan character style. Externally, the enclosed front and rear gardens provide the perfect place to relax.
Details
Bedrooms: 4
Sleeps: 7
Star Rating: A
Pets Welcome: Yes
Change Over: Saturday
Quarries Reach Quarries Reach - Southwell

Quarries Reach is a new spacious detached house with a safe, secluded and walled garden. Situated in a prime position on top of the island with spectacular rural and sea views looking towards Dorset’s eastern Jurassic Coast.
Details
Bedrooms: 4
Sleeps: 7
Star Rating: 3
Pets Welcome: No
Change Over: Flexible
Sleeps up to 8
Mums Place Mums Place - Fortuneswell

Mum's Place is a traditional mason's cottage built aound 1825. Situated just a five minute walk from Chesil Cove at the eastern end of Chesil Beach, the stone cottage have been extensively refurbished with modern facilities but maintain many original features.
Details
Bedrooms: 4
Sleeps: 8
Star Rating: 3
Pets Welcome: Yes
Change Over: Saturday
The Tides The Tides - Fortuneswell

The Tides is a four bedroom Victorian house in a perfect location for both the WPNSA and exploring Dorset’s Jurassic coastline. Internally, the property boasts an open plan living and dining area with many period features present including Victorian fireplaces in the bedrooms and exposed floorboards.
Details
Bedrooms: 4
Sleeps: 8
Star Rating: 4
Pets Welcome: Yes
Change Over: Saturday
Pebble Pickers Cottage Pebble Pickers Cottage - Chiswell

With the garden backing onto Chesil Beach part of the World Heritage Coastline, this comfortable three bedroom cottage is ideally placed for the National Sailing Academy, or for walking the costal path. The cycling is superb, you can take the Rodwell trail right into Weymouth.
Details
Bedrooms: 3
Sleeps: 8
Star Rating: N
Pets Welcome: Yes
Change Over: Saturday
Vindelis House Vindelis House - Chiswell

Vindelis House is part of the Olympic legacy, home to the athletes during 2012. Internally, the spacious living areas are completed to a high standard with oak flooring, porcelain tiles and quality modern furnishings throughout. The master bedroom and living room offer beautiful views over Chesil Beach, the English Channel and Weymouth Bay.
Details
Bedrooms: 4
Sleeps: 8
Star Rating: A
Pets Welcome: No
Change Over: Flexible
The Old Portland Courthouse The Old Portland Courthouse - Fortuneswell

The Old Portland Courthouse is a grade II listed building dating back to c1904. It is in a wonderful position with panoramic sea views across Chesil Beach and Lyme Bay. The building has been sympathetically converted to a very high standard and many original features remain giving it a unique character.
Details
Bedrooms: 4
Sleeps: 8
Star Rating: 5
Pets Welcome: No
Change Over: Saturday
Sleeps up to 18
Pennsylvania Castle Pennsylvania Castle - Wakeham

The ethos of The Penn is to provide hospitality totally tailored to each groups needs and staff are happy to recommend and arrange like minded suppliers & services if required, to ensure guests are well looked after during their stay. Alternatively fully self-catered stays are also available.
Details
Bedrooms: 9
Sleeps: 18
Star Rating: N
Pets Welcome: No
Change Over: Flexible