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31 Holiday homes in Portland

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31 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
  • Suitable 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

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
  • Suitable 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

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
  • Suitable 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

Featured properties

14 Photos

Cottage | 3 Bedrooms | sleeps 5

Very Good 4.5/5 

Short stays welcome

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from £41 /night

£281 - £689 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for over 5s only
  • 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
  • Suitable 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

24 Photos

Cottage | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £54 /night

£378 - £780 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
A traditional Portland stone property  …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 0.5 km
  • Suitable 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

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
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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 £40 /night

£280 - £1190 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Suitable 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 | 2 Bedrooms | sleeps 6

Excellent 5/5 

1 night 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
  • Suitable 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

18 Photos

Studio | sleeps 2

Very Good 4.5/5 

3 Nights min stay

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from £43 /night

£295 - £395 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.5 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

24 Photos

Cottage | 3 Bedrooms | sleeps 5

Very Good 4.5/5 

2 Nights min stay

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from £42 /night

£290 - £690 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable 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

18 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £122 /night

£850 - £1350 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for over 5s only
  • Car not necessary
  • May take pets – please enquire
  • 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
  • Suitable for children of all ages
  • May take pets – please enquire
  • 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

24 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4/5 

3 Nights min stay

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from £70 /night

£485 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable 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

17 Photos

House | 1 Bedroom | sleeps 4

Good 3/5 

3 Nights min stay

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from £43 /night

£298 - £723 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable 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

House | 4 Bedrooms | sleeps 7

3 Nights min stay

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from £77 /night

£536 - £1521 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.45 km
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
A 4 bedroom house set over 3 floors, sleeps 7. Newly refurbished to a high standard throughout. Fully furnished, enclosed patio areas at the front and back. Situated just yards from the famous Chesil Beach and within a short walk of the National Sailing Academy.  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 4

rentals_reviews_rating_1 

3 Nights min stay

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from £65 /night

£454 - £961 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Suitable 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

20 Photos

House | 2 Bedrooms | sleeps 4

Very Good 4/5 

3 Nights min stay

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from £62 /night

£433 - £1096 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable 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

18 Photos

Cottage | 3 Bedrooms | sleeps 6

Good 3/5 

3 Nights min stay

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from £65 /night

£454 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable 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

20 Photos

House | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £56 /night

£391 - £1044 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable 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

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
  • Suitable 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

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 0.3 km
  • Suitable 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 | 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 5

Short stays welcome

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from £46 /night

£320 - £720 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • No pets allowed
  • Private garden
The cottage offers a cosy living area with farmhouse style kitchen leading to the courtyard garden to the rear. Two further floos accommodate two double bedrooms and a single bedroom which is to be found on the top floor Character seaside cottage close to Chesil Beach and the National Sailing Academy.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 4

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 over 5s only
  • 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. Relaxing, walking, sailing - some of the options in easy reach of this holiday cottage.  …see more

14 Photos

Cottage | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £43 /night

£295 - £595 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • Car not necessary
  • May take pets – please enquire
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

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
  • Suitable 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

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
  • Suitable 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

11 Photos

House | 4 Bedrooms | sleeps 7

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
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Sea Dragon is a charming four-bedroom property on Portland very close to Chesil Beach. The house is very well equipped and a short walk from the local amenities, including pubs and restaurants. The National Sailing Academy can be reached in a few minutes by car. Weymouth & Portland is an excellent base for exploring South Dorset’s coast and countryside.  …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 0.5 km
  • Suitable 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