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81 Results  |  
9 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4/5 

4 Nights min stay

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from £69 /night

£477 - £636 / 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

24 Photos

House | 6 Bedrooms | sleeps 12

Excellent 5/5 

2 Nights min stay

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from £122 /night

£848 - £1696 / 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
  • Private garden
Sleeps up to 12 6 Bedrooms (4 with ensuite showers) Additional bathroom and shower room Family friendly Very close to the beach less than a 2 minute walk! Free WIFI / broadband access Off road car space 2 on street parking permits Stay 2 nights and get a 50% discount on your 3rd night  …see more

21 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £53 /night

£370 - £741 / 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

Featured properties

15 Photos

House | 8 Bedrooms | sleeps 25

Very Good 4.5/5 

1 night min stay

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from £243 /night

£1696 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
For as little as £64.00 for 1 person a week (based on 25 sharing) This property is ideal for a multiple family holiday, Divers, sailing events,Rock climbers, Fishing, Cycling, Jurassic Coastal walkers, Sand/sea and entertainment with the beach only a 2 minute walk away. 1 night stay welcome on weekdays. 2 night minimum on weekends (Fri & Sat)  …see more

20 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

2 Nights min stay

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from £91 /night

£636 - £1272 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Weymouth - self-catering - Victorian terraced Villa - 4 bedrooms – 2 minutes seafront, 5 minutes town, pubs, restaurants, railway station. On road parking permits for two cars. Dogs accepted if confined to kitchen area and walled garden. Please ask.  …see more

24 Photos

House | 3 Bedrooms | sleeps 8

 

2 Nights min stay

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from £144 /night

£1007 / 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
The ideal location for the complete family holiday also great for long weekends. As the house is not double glazed, and in the centre of a very busy little town, it can get noisy  …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

House | 4 Bedrooms | sleeps 10

 

3 Nights min stay

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from £91 /night

£636 - £1483 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • No pets allowed
  • Private garden
A large 4 bedroom period property overlooking Weymouth's famous 'Old Harbour' A short walk to to Weymouth's sandy beach, shopping and Condor Ferries.  …see more

10 Photos

House | 3 Bedrooms | sleeps 7

7 Nights min stay

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from £66 /night

£458 - £1127 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Lynwood Lodge is in an Area of Outstanding Natural Beauty and 2 miles from the coast which is part of the Jurassic World Heritage Site. The nearest beaches are at Ringstead Bay, Osmington and Weymouth. The town of Weymouth (4 miles) is popular for its miles of promen...  …see more

16 Photos

House | 4 Bedrooms | sleeps 6

3 Nights min stay

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from £70 /night

£485 - £1475 / week

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Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
A newly refurbished country house set in a beautiful rural position. A 4 bedroom house sleeping 6. Set in a rural position with 1/3 acre garden. Newly refurbished to a high standard. Short distance to coastal walks along sea cliff edge. Off-street parking for 2 cars.  …see more

9 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £45 /night

£311 - £848 / week

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Key info:

  • Not suitable for children
  • No pets allowed
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. These well-equipped holiday cottages (refs 15897 and 15898) offer a comfortable base for exploring the ...  …see more

17 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
Chesil View House offers stylish accommodation that was originally a fisherman's cottage in the beautiful village of Fortuneswell, nestled amongst the hills of Portland.  …see more

36 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4/5 

Short stays welcome

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from £46 /night

£320 - £800 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • Car advised
  • Pets welcome
  • Private garden
Sleeping up to six people in three bedrooms, this detached holiday home is just over a mile from the sea front, on the edge of Weymouth.  …see more

36 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £48 /night

£332 - £680 / week

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Key info:

  • Suitable for children over
  • Pets welcome
  • Private garden
This is a wonderful Grade II listed, 18th century, thatched cottage, nestling opposite the village church in the picturesque Dorset village of Upwey, just four miles from Weymouth and can sleep four people in two bedrooms.  …see more

20 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £91 /night

£632 - £1633 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated in the heart of Portland, this terraced house is an excellent holiday location to enjoy the best of west Dorset, from Swanage in the east, all the way to Lyme Regis, and taking in some breathtaking coastal views over the famous Jurassic Coast and Chesil Beac...  …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

14 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £70 /night

£485 - £1312 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
A large Victorian house boasting original, period features and close proximity to Chesil Beach. A 4 bedroom house set over three floors, sleeps 8. Furnished to a high standard throughout with period features. Close to Chesil Beach and the 2012 Olympic Sailing venue.  …see more

12 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £47 /night

£324 - £862 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This terraced holiday home sits in a quiet area between Weymouth and Portland overlooking Portland harbour with sea views. The South West Coastal Path is 220 yards away and offers views across the harbour and along famous Chesil Beach. A 30 minute walk takes you into...  …see more

18 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

3 Nights min stay

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from £74 /night

£516 - £1726 / 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
A newly built four bedroom house, just minutes from the attractions of Weymouth and Portland. A newly built 4 bedroom house, sleeps 8. Fully furnished patio and garden area with access to the Rodwell Trail coastal path.  …see more

10 Photos

House | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £55 /night

£383 - £1189 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located in a charming and secluded environment on the Jurassic and Heritage coastline, Coastline Cottages have been converted to a high specification and are well-equipped with lovely wood-burning stoves. Situated 100 yards off the main road, the cottages are set in ...  …see more

24 Photos

House | 3 Bedrooms | sleeps 5

Excellent 5/5 

7 Nights min stay

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from £65 /night

£450 - £1060 / 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
  • Private garden
Our house is in the perfect location, a few minutes walking distance to Weymouth's famous sandy beach, town and historic harbour. Fantastic sea views across the bay of the much sought after Jurassic Coastline and easy access to Portland to watch the sailing! Set in ideal surroundings this property offers stunning sea views across the bay, Nothe Fort and Gardens.  …see more

24 Photos

House | 3 Bedrooms | sleeps 5

Excellent 5/5 

2 Nights min stay

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from £88 /night

£610 - £1080 / 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
  • Private garden
Tides is a well appointed modern semi-detached house situated at the end of a quite cul-de-sac 100m from the sea. View the cove from kitchen & 2 bedrooms, and of The Green to rear. Visit Britain 4 Star accommodation. Short walk to fantastic old harbour and sandy beach. Overlooking the bay that hosted the 2012 Olympic/Paralympics - Tides is a perfect holiday location!  …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 £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

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

16 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £79 /night

£550 - £1190 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • No pets allowed
  • Private garden
Weymouth and the surrounding area of South Dorset offers a unique blend of attractions and places of interest for visitors of all ages together with the benefits offered by a vibrant town centre with well-known High Street shops and stores. The property is located in a quiet residential area but very close to all local amenities.  …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

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

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

19 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

3 Nights min stay

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from £72 /night

£500 - £650 / 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
  • Private garden
Upstairs there are 3 bedrooms; remodeled bathroom and toilet. Downstairs there is a large modern kitchen, dining room, lounge with access to a large 10 x 10 wooden deck; with a barbecue, table and chairs. Below the deck is a secluded flower and vegetable garden . From the rear of the house there are magnificent views of Weymouth Bay, Portland and the Jurassic coast  …see more

18 Photos

House | 5 Bedrooms | sleeps 12

Very Good 4.5/5 

1 night min stay

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from £115 /night

£800 - £1950 / 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
  • Private garden
A large garden ideal for family holidays. The house is 5 mins walk from the beach and Lodmoor park. Weymouth centre is 1/2 mile away where there are many shops, restaurants and bars. There are several pubs and shops near the house, a log fire, SKY TV, and good parking.  …see more

28 Photos

House | 3 Bedrooms | sleeps 7

Very Good 4.5/5 

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

9 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £67 /night

£464 - £1312 / 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
A modern 3 bedroom split level house, sleeps 6. Passive House Eco-Home with triple glazing. Furnished to a high standard throughout. Private furnished patio ideal for al fresco dining. Off-street parking for 2 cars.  …see more

11 Photos

House | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £40 /night

£274 - £801 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This cosy, terraced holiday cottage is 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 beach and harbour, 2 RSPB reserves, a sealife park and marine sanctuary are al...  …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

11 Photos

House | 2 Bedrooms | sleeps 4

 

3 Nights min stay

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from £50 /night

£350 - £1008 / 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
A contemporary mews style house in the heart of Weymouth, only minutes from the beach. A brand new semi-detached house, sleeps 4. Located in the heart of Weymouth town centre. Close proximity the 2012 Olympic sailing venue. Situated in a mews style development.  …see more

5 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £37 /night

£253 - £463 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Set in the small village of Southwell, close to Portland Bill and the coastal footpath around the Isle of Portland, these charming stone cottages provide a good base for walkers, birdwatchers and fishermen. Gull Cottage, an 'upside down' property, features a small ba...  …see more

7 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £37 /night

£259 - £480 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Set in the small village of Southwell, close to Portland Bill and the coastal footpath around the Isle of Portland, these charming stone cottages provide a good base for walkers, birdwatchers and fishermen. Gull Cottage, an 'upside down' property, features a small ba...  …see more

7 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £47 /night

£327 - £898 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Anchor Cottage is in a quiet cul-de-sac overlooking Portland and Chesil Beach with stunning panoramic sea views. It is a great base for exploring the delights of the Jurassic Coast scenery and surrounding nature. Famous Chesil Beach lies near the property with breath...  …see more

11 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £40 /night

£277 - £740 / week

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Key info:

  • Not suitable for children
  • No pets allowed
With views overlooking Portland, Weymouth harbour and the start of the Chesil Beach, this end terrace holiday home is next to the main road to Portland and near the South West Coastal Path. This is an excellent location to enjoy Weymouth's beach, harbour, shops and m...  …see more

16 Photos

House | 3 Bedrooms | sleeps 6

Very Good 4/5 

3 Nights min stay

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from £45 /night

£309 - £943 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
Stylish property perfectly located for the 2012 Olympics Sailing venue. A stylish 3 bedroom duplex apartment, sleeps 6. Outdoor patio area with seating for 6. A short walk to Chesil Beach and the 2012 Olympic sailing venue.  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £62 /night

£433 - £1312 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Wessex Ho is a three bedroom property, sleeping up to six people.  It is situated a short drive or a 20 minute walk away from the town centre and beach.  …see more

17 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £90 /night

£630 - £2149 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Nothe View is spacious four bedroom townhouse set over three storeys. Situated within the Admirals Quarter development, Nothe View perfectly combines contemporary comfort and design with environmental sensitivity.  …see more

16 Photos

House | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £96 /night

£671 - £1303 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • No pets allowed
A stylish 3 storey house situated in the popular Brewers Quay area of Weymouth  …see more

10 Photos

House | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £40 /night

£280 - £840 / week

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Key info:

  • Not suitable for children
  • No pets allowed
With a cosy open fire this cottage was once home to the famous Stone Carver Skylark Durston, his work can be seen throughout. From the garden wonderful coastal and sea views can be enjoyed. Portland Bill lighthouse is just a mile walk, which then leads on to wonderfu...  …see more

11 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £35 /night

£241 - £669 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated on the southern edge of Portland and with wonderful views over Freshwater Bay, this semi-detached, single-storey holiday home lies ½ mile form Portland Bill Lighthouse. It is in a great location to explore Portland with its museums, Henry VIII's castle, Nati...  …see more

8 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £36 /night

£251 - £669 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This holiday apartment sits on the first floor adjoining the owners' property and commands wonderful countryside views from the living room picture window. It makes a very comfortable relaxing all year round base for exploring the area, with Weymouth's Georgian seafr...  …see more

17 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4/5 

3 Nights min stay

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from £79 /night

£547 - £1726 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • No pets allowed
Cormorant View is a spacious house situated in a gated cul-de-sac within walking distance of the shops, restaurants, attractions and sandy beaches of Weymouth.Internally this spacious accommodation is furnished to a high standard and offers fan  …see more

32 Photos

House | 2 Bedrooms | sleeps 6

Short stays welcome

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from £40 /night

£275 - £606 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • Pets welcome
  • Private garden
This terraced cottage is situated on the Isle of Portland in Dorset and sleeps six people in two bedrooms.  …see more

13 Photos

House | 3 Bedrooms | sleeps 5

Excellent 5/5 

3 Nights min stay

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from £50 /night

£350 - £1095 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Great for children of all ages
  • Car advised
  • No pets allowed
Situated in an elevated position, Sea Far is a three bedroom maisonette boasting spectacular views of the Jurassic Coast. A 3 bedroom maisonette sleeping 5. Far-reaching views of Chesil Beach and the Jurassic Coastline. Terrace garden featuring a raised sundeck.  …see more