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283 Results  |  
24 Photos

Cottage | 2 Bedrooms | sleeps 3

Good 3/5 

3 Nights min stay

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from £59 /night

£410 - £835 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Thatched Cob Cottage Adjoining Another Next to Fields. Coast 4 miles, Dorchester 4 miles. Dogs Not Permitted.  …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

24 Photos

Cottage | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £78 /night

£545 - £1085 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
End of terrace, stone cottage with views to fields and hills. Weymouth 3 miles. Dorchester 3 miles. Dogs not permitted. .  …see more

Featured properties

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

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
  • Suitable 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

24 Photos

Cottage | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £67 /night

£465 - £930 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Mid Terrace Victorian House With Sea Views. Chesil Beach 400 yards, Weymouth 5 miles. Dogs not permitted. No Smoking. Short Breaks - All Year.  …see more

14 Photos

Cottage | 2 Bedrooms | sleeps 4

Short stays welcome

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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

24 Photos

Cottage | 1 Bedroom | sleeps 2

3 Nights min stay

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from £53 /night

£365 - £620 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
18th Century Semi-Detached Thatched Cottage, Coast 0.5 miles, Weymouth 3 miles, Dogs not permitted, No Smoking, Short Breaks All Year.  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £61 /night

£425 - £850 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
18th Century Mid Terrace Cottage In Pretty Village With a Rural Outlook. Ringstead Beach 5 miles, Weymouth 3 miles. Dog Not Permitted.  …see more

8 Photos

Cottage | 3 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
  • 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

24 Photos

Cottage | 4 Bedrooms | sleeps 8

3 Nights min stay

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from £119 /night

£830 - £1740 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Detached House with Sea & Inland Views, Beach 300 Yards, Weymouth town centre 2 miles, No Smoking, Short Breaks all Year.  …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

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

24 Photos

Cottage | 4 Bedrooms | sleeps 7

3 Nights min stay

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from £82 /night

£570 - £1150 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Semi Detached House in Quiet Close. Weymouth Beach 400 yards,Town Centre 250 yards Dogs not permitted.  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 3

7 Nights min stay

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from £65 /night

£450 - £850 / week

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Key info:

  • Nearest beach 1 km
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
A two bedroom holiday apartment, close to Portland Harbour, Portland Castle and the National Sailing Academy.  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 3

Excellent 5/5 

3 Nights min stay

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from £58 /night

£400 - £800 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Rural Barn Conversion On a Country Lane with Rolling Countryside Views. Lulworth Cove 5 miles, Dorchester 8 miles. Dogs Not Permitted.  …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
  • Suitable 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

17 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

Short stays welcome

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from £46 /night

£320 - £460 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
The accommodation is a completely self-contained first floor apartment, with a separate access from the garden of Rosehill, a large Victorian detached house. It is within 5 minutes walk of the harbour and close to the town centre and beach. Private off road parking.  …see more

7 Photos

House | 3 Bedrooms | sleeps 6

Min stay varies

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from £34 /night

£237 - £889 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Just a few hundred yards from a cliff top path, this well presented terraced holiday cottage makes a great base for exploring both Portland and Weymouth and the surrounding area  …see more

9 Photos

House | 3 Bedrooms | sleeps 7

Min stay varies

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from £65 /night

£452 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
This detached, 1820's, stone holiday house is tucked away in a quiet spot and has sea views from all rooms  …see more

5 Photos

House | 1 Bedroom | sleeps 2

Min stay varies

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from £38 /night

£260 - £472 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Part of a 16th-century farm barn complex, Stable Cottage lies on the owners' farm, in the village of Nottington, near to the spa house frequented by George III - who made Weymouth so popular  …see more

8 Photos

House | 3 Bedrooms | sleeps 7

Min stay varies

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from £54 /night

£376 - £816 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Open-plan living/dining room with wood-burning stove, sofa-bed (for +2), small dining table (for 2-4 persons) and well-equipped fitted kitchen with breakfast bar (for 4 persons)  …see more

10 Photos

House | 3 Bedrooms | sleeps 6

Min stay varies

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from £39 /night

£270 - £301 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Sea views This terraced holiday cottage retains much of its original charm and has views to the sea and Chesil beach, part of the World Heritage Coast  …see more

5 Photos

House | 2 Bedrooms | sleeps 4

Min stay varies

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from £42 /night

£293 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
This attractive cottage is comfortably furnished and equipped to provide a cosy base for year-round family holidays  …see more

6 Photos

House | 2 Bedrooms | sleeps 5

Min stay varies

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from £44 /night

£303 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Open-plan living/dining room with wood-burning stove, sofa-bed (for alternative sleeping only) and well-equipped fitted kitchen  …see more

7 Photos

House | 2 Bedrooms | sleeps 4

Min stay varies

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from £45 /night

£309 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Set within 30 acres of grounds on the owners working stud farm and surrounded by peaceful, rolling Dorset countryside with the Jurassic Coastline a few miles away  …see more

7 Photos

House | 3 Bedrooms | sleeps 6

Min stay varies

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from £40 /night

£274 - £724 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This holiday apartment is conveniently situated within walking distance of the local amenities and 1/2 mile from Weymouth town centre and the seafront  …see more

13 Photos

House | 4 Bedrooms | sleeps 8

Min stay varies

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from £186 /night

£1297 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Set in an idyllic lane just a stroll away from Abbotsbury Swannery and just 1½ miles from Chesil beach, this spacious, semi-detached, stone holiday cottage has been lovingly restored with open fire and beams in many rooms  …see more

8 Photos

House | 3 Bedrooms | sleeps 5

Min stay varies

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from £32 /night

£221 - £614 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
This traditional, terrace holiday house is set in a residential area just 500 yards from the seafront, sandy beach and harbourside, and is conveniently located behind the train station (some noise may be heard)  …see more

8 Photos

House | 2 Bedrooms | sleeps 4

Very Good 4/5 

Min stay varies

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from £70 /night

£486 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
This comfortable cottage with a wealth of character is just 100 yards walk to the stunning Chesil beach  …see more

7 Photos

House | 3 Bedrooms | sleeps 6

Min stay varies

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from £160 /night

£1119 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
Shared indoor heated swimming pool and many other on-site facilities This lovely, detached holiday cabin is set in a quiet spot on the popular Warmwell Leisure Resort  …see more

8 Photos

House | 2 Bedrooms | sleeps 4

Min stay varies

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from £70 /night

£490 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Nestling down a little lane, this charming holiday cottage dates back to 1830 and has been carefully refurbished to provide very comfortable accommodation  …see more

9 Photos

House | 2 Bedrooms | sleeps 5

Min stay varies

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from £61 /night

£423 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
This cosy, terraced holiday cottage is set in a quiet street, just a few hundred yards from the southern end of Chesil Beach  …see more