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38 Holiday homes in Portland

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Filters applied: Walking holidays (38)

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38 Results  |  
14 Photos

Cottage | 2 Bedrooms | sleeps 5

Very Good 4.5/5 

3 Nights min stay

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from £49 /night

£340 - £689 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Situated in a quiet location at the southern end of the island with stunning sea views just a stone's throw away from beautiful coastal walks and scenery - near Portland Bill lighthouse and the Lobster Pot restaurant.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

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from £37 /night

£254 - £392 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
Very spacious self catering “studio style” apartment close to Portland Bill & Jurassic coastal scenery. Sleeps 2+ cot. Flexible living area. Large enclosed sun-trap patio with safe parking. Very well equipped with 32” Flat screen Sat. TV & WiFi Broadband. Pets welcome. Ideal for young/mature couples. Seating for four plus. Car unnecessary, close to walks/sailing/sports  …see more

9 Photos

House | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £69 /night

£477 - £689 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Pebbles view cottages is the perfect holiday destination whether you just want to get away from it all exploring the Isle of Portland or beaches of Weymouth or a more active holiday with fantastic sailing,diving rock climbing cycling and walking, portland has it all.  …see more

Featured properties

20 Photos

Studio | sleeps 2

Very Good 4.5/5 

3 Nights min stay

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from £34 /night

£233 - £383 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
WEYMOUTH, PORTLAND, DORSET, JURASSIC COAST, CAR ADVISED, SEA VIEW, BEACH, SPA, CLIFF WALKS, SAILING, WATER SPORTS, FISHING,GOLF, ROCK CLIMBING, HORSE RIDING, BIRD WATCHING, ON-SITE CRECHE THIS APARTMENT IS SITUATED IN A STUNNING SETTING OVERLOOKING THE OCEAN AT PORTLAND BILL.  …see more

21 Photos

Cottage | 2 Bedrooms | sleeps 5

Very Good 4/5 

3 Nights min stay

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from £67 /night

£467 - £785 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • No pets allowed
  • Private garden
Seagull Cottage is a lovely holiday house ideal for sailing, beach, and outdoor activity holidays in Portland. It is located a mile from the WPNSA National Sailing Academy, the 2012 Olympic Sailing venue, and just a few minutes walk from the world famous Chesil Beach. The well-equpped cottage offers comfortable, superior two bedroom accommodation in a convenient location.  …see more

14 Photos

Cottage | 3 Bedrooms | sleeps 4

Very Good 4.5/5 

Short stays welcome

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from £31 /night

£212 - £689 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children over
  • Car advised
  • Pets welcome
Cottage newly decorated in good order dog friendly with sea views also from south facing patio looking over Chesil beach In quiet street close to all amenities buses pubs restaurant. Lovely walks along sea front and beach ideal fishing water sports dogs and swimming. Portland was the choice for the Olympic sailing venue chosen from all the places in the UK.  …see more

21 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £53 /night

£370 - £953 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
Very spacious self catering detached house close to Portland Bill and Jurassic coastal scenery. Sleeps up to 8 + cot in 4 bedrooms. Large enclosed family-friendly garden with safe parking. Very well equipped with 42” Flat screen Sat. TV and WiFi Broadband. Pets welcome. Ideal for families/large groups. Large, safe, grass garden. Car unnecessary, close to walks/sailing/sports.  …see more

4 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £61 /night

£423 - £599 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
A beautiful 1 bed luxury apartment with sea views and free parking - close to Weymouth beach and Portland Castle.  …see more

23 Photos

House | 3 Bedrooms | sleeps 7

3 Nights min stay

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from £66 /night

£459 - £1499 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Seagull House in Portland Chesil Beach  …see more

20 Photos

Cottage | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

3 Nights min stay

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from £50 /night

£350 - £895 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Fishermans Cottage is a charming detached 18th century cottage on the edge of Southwell, with excellent sea views. Ideal for Sailing academy, bird watching or just a quiet getaway. The ideal location for the 2012 Olympic Sailing whether supporting, taking part or just for the atmosphere.  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £61 /night

£425 - £800 / week

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Key info:

  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Within sound of the breaking surf, take breakfast on the balcony and enjoy stunning views of Chesil Beach. Situated in a quiet area of Fortuneswell yet only a short walk from Shops, Restaurants, Pubs and Beach and 5 minutes from the Olympic Sailing Venue.  …see more

18 Photos

Studio | sleeps 2

Very Good 4.5/5 

3 Nights min stay

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from £43 /night

£295 - £425 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Not suitable for children
  • Car not necessary
  • Pets welcome
Open all year. Tranquil, warm retreat above Church Ope Cove. Self catering Studio for 2 set on the cliff path a 7 minute walk from the nearest village and major amenities. 5 minute drive from Olympic Sailing Academy. Wet room, Wifi, Woodburner, Ipod dock. Pet welcome. Suits romance and retreat, sail, walk, climb, work or study with Wifi, Pets and walkers Welcome Awards.  …see more

17 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £43 /night

£300 - £600 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Hillside is a stunning fully refurbished Victorian house with views from a southwest facing garden overlooking Portland Harbour and WPNSA.Only five minutes walk from Chesil beach, Hillside was refurbished to be our home which we have chosen to allow others to enjoy. What other property on Portland has chandeliers ,roll top bath and feature wallpaper?  …see more

17 Photos

House | 4 Bedrooms | sleeps 10

Very Good 4.5/5 

2 Nights min stay

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from £40 /night

£280 - £1365 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
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 Jurassic Coast. Ideally situated in the centre of the County of Dorset.  …see more

16 Photos

House | 3 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £36 /night

£250 - £1190 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Contemporary Cottages are ideally situated for anyone visiting Weymouth and Portland and Dorset. Short breaks & weekly bookings are accepted throughout the year. You can book from any day of the week and flexible arrival and departure times can be arranged by request. Situated very near to Weymouth & Portland National Sailing Academy & in centre of Dorset's Jurassic Coast  …see more

23 Photos

Cottage | 3 Bedrooms | sleeps 4

Very Good 4.5/5 

2 Nights min stay

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from £45 /night

£310 - £720 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
A character terraced cottage, on a quiet street in the village of Fortuneswell on the Isle of Portland, only a few minutes walk from the famous Chesil Beach, 5 minutes drive from the National Sailing Academy and easy walk ing distance to the Olympic Sailing Village. Excellent restaurants and pubs within walking distance of the cottage. Free Wi-Fi.  …see more

20 Photos

Cottage | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

3 Nights min stay

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from £47 /night

£325 - £795 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Pebble Reef is a traditional Quarryman's Cottage, full of character but lovingly renovated to include all the modern comforts you need. Now has WiFi.  …see more

20 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £69 /night

£480 - £1150 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The Gift House is a beautiful fully renovated and refurbished 4 bedroom house situated 2 minutes walk from the beach, with stunning panoramic sea views from all reception rooms and bedrooms stretching across Chesil Beach to the Olympic Sailing Village. The property is suited to outdoors enthusiasts and families. A perfect retreat with modern luxuries.  …see more

18 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £100 /night

£700 - £1350 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable for children over
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Beautifully renovated family house situated down a quiet lane, minutes from a picturesque cove and lovely cliff top walks.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £69 /night

£477 - £912 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
The perfect base for a beach side holiday. We are close to the National Sailing Academy and a short walk to the Castletown diving centre. The Cove House Inn is a 300 yard walk along the beach and has a lovely atmosphere and good food.  …see more

22 Photos

House | 2 Bedrooms | sleeps 5

Excellent 5/5 

2 Nights min stay

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from £62 /night

£430 - £620 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Stunning location with probably the best sea views on Portland. Attractive 2 bedroom house with gardens and easy parking, next to open hillside with uninterupted views of Weymouth Bay, the ocean and coastline. Close to great beaches, sailing, shops, pubs and restaurants Breath-taking panoramic views. Ideal situation for exploring Portland's natural heritage.  …see more

18 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £53 /night

£371 - £1095 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
Sea Pinks Cottage was built around 1860 and is a fine example of a traditional fisherman's cottage built with Portland stone.  …see more

18 Photos

Cottage | 3 Bedrooms | sleeps 6

Very Good 4/5 

3 Nights min stay

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from £65 /night

£454 - £930 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Great for children of all ages
  • Car advised
  • Pets welcome
Sea Shell Cottage offers spacious accommodation in the heart of the highly desirable Brewers Quay area of Weymouth.  …see more

17 Photos

House | 1 Bedroom | sleeps 4

Good 3/5 

3 Nights min stay

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from £42 /night

£288 - £723 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
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, in a location guaranteed to inspire.  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £53 /night

£371 - £1095 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
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 locate  …see more

20 Photos

House | 2 Bedrooms | sleeps 4

Very Good 4/5 

3 Nights min stay

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from £58 /night

£402 - £1149 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
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, in a location guaranteed to inspire.  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 4

rentals_reviews_rating_1 

3 Nights min stay

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from £62 /night

£433 - £1008 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
A modern apartment with fantastic on-site health facilities, near the 2012 Olympic Sailing venue.  …see more

24 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4/5 

3 Nights min stay

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from £67 /night

£464 - £1312 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
A stylish apartment with fantastic on-site health facilities, situated on the Jurassic coast beside Chesil Beach  …see more

8 Photos

Cottage | 4 Bedrooms | sleeps 8

Very Good 4/5 

7 Nights min stay

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from £65 /night

£450 - £850 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Mallams Cottage is a beautifully finished period cottage, well located for Chesil Beach, Portland Harbour and the National Sailing Academy. Close to the best sailing waters in Europe.  …see more

11 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

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from £72 /night

£500 - £895 / week

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Key info:

  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
This well presented holiday house has a large and sociable open plan living area with kitchen, seating and dining areas, allowing for a relaxed and inclusive holiday atmosphere.  …see more

9 Photos

Cottage | 3 Bedrooms | sleeps 5

Short stays welcome

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from £58 /night

£400 - £550 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
Fabulous sea views from this cottage just a few minutes from Chesil Beach.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £58 /night

£400 - £720 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
4 Sea View offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset. Offering a fabulous kitchen and comfortable accommodation.  …see more

5 Photos

Cottage | 2 Bedrooms | sleeps 4

1 night min stay

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from £65 /night

£450 - £550 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
If you were much closer you would be in the sea!!  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £65 /night

£450 - £850 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Frigate Apartment is a stunning holiday apartment with sea views situated in the eye-catching Ocean Views development, close to Portland Harbour and the National Sailing Academy. The development boasts a state-of-the-art health and fitness centre complete with an indoor swimming pool.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 4

Very Good 4/5 

Short stays welcome

Add to shortlist

from £58 /night

£400 - £720 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
A charming cottage in this pretty road, a short walk down to Chesil Beach and Cove and easy going of the National Sailing Academy at Portland Harbour.  …see more

8 Photos

Cottage | 2 Bedrooms | sleeps 4

Short stays welcome

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from £58 /night

£400 - £720 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Pets welcome
Pet Friendly!! Fabulous views, parking, dog friendly, close to Chesil Beach and a short walk from Weymouth & Portland National Sailing Academy. Ideal for walking, sailing, fishing or just relaxing.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £58 /night

£400 - £720 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Character cottage over three floors, sleeps seven comfortably. A short walk from Chesil Beach and the local amenities, the National Sailing Academy and Portland Harbour. The harbour is found within a short drive or leisurely walk from the property. At the centre of the Jurassic Coast, Portland is an ideal base for water sports, walking & exploring Dorset.  …see more

8 Photos

House | 4 Bedrooms | sleeps 10

Short stays welcome

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from £72 /night

£500 - £895 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Whether you are looking for that relaxing break, or here to sail or just time with the family this charming cottage would suit your needs. Nestled off Wakeham, you will agree this cottage is a real find. This deceptive very comfortable house offers home from home facilities with everything to entertain a family  …see more