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21 Results  |  
14 Photos

Cottage | 2 Bedrooms | sleeps 5

Very Good 4.5/5 

3 Nights min stay

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from £55 /night

£385 - £759 / 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

20 Photos

Studio | sleeps 2

Very Good 4.5/5 

3 Nights min stay

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from £42 /night

£290 - £406 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Not suitable for children
  • 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 4.5/5 

3 Nights min stay

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from £63 /night

£440 - £822 / 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

Featured properties

14 Photos

Cottage | 3 Bedrooms | sleeps 4

Very Good 4.5/5 

Short stays welcome

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from £40 /night

£275 - £748 / 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

45 Photos

Cottage | 3 Bedrooms | sleeps 5

Excellent 5/5 

4 Nights min stay

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from £52 /night

£358 - £875 / week

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Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Portland is a unique place to visit. It sits 40 feet above sea level at the highest point and made up of limestone rock. Portland is part of the Jurassic Coastline. There is so much to explore and see during your stay. Leisure facilities include Sailing, fishing, diving, windsurfing, swimming, bird watching, walking etc  …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

31 Photos

Cottage | 3 Bedrooms | sleeps 5

Short stays welcome

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from £45 /night

£314 - £785 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • No pets allowed
  • Private garden
This charming detached cottage sits in a quiet cul-de-sac in Easton on the Isle of Portland, sleeping five people in three bedrooms.  …see more

19 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £71 /night

£492 - £1150 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
This semi detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.  …see more

21 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £73 /night

£508 - £1165 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
This detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms.  …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

17 Photos

House | 4 Bedrooms | sleeps 10

Very Good 4.5/5 

2 Nights min stay

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from £43 /night

£300 - £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

24 Photos

Studio | sleeps 2

Very Good 4.5/5 

3 Nights min stay

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from £47 /night

£325 - £395 / 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. Comfy four poster bed (new pics coming soon) 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 - £660 / 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

22 Photos

House | 2 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

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from £89 /night

£620 / 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
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 Only 5 minutes from the National Sailing Academy. Ideal situation for exploring Portland's natural heritage.  …see more

10 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

6 Photos

Cottage | 2 Bedrooms | sleeps 4

1 night min stay

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from £43 /night

£295 - £495 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car advised
  • No pets allowed
Cosy two bedroom cottage in the heart of Fortuneswell, Portland.  …see more

14 Photos

Cottage | 2 Bedrooms | sleeps 4

Short stays welcome

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from £43 /night

£295 - £495 / 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
Pet friendly!! Character Stone Cottage with roof terrace, wood burner and sea views - your dog is welcome! Dog friendly two bedroom character cottage on the Isle of Portland  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £65 /night

£450 - £625 / 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

28 Photos

House | 3 Bedrooms | sleeps 7

Very Good 4.5/5 

3 Nights min stay

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from £69 /night

£477 - £1556 / 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

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

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from £69 /night

£480 - £900 / 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

8 Photos

Cottage | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £71 /night

£495 - £946 / 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