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101 Holiday homes in Weymouth

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  • Abbotsbury (7)
  • Chickerell (4)
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  • Greenhill (5)
  • Nottington (3)
  • Osmington (2)
  • Osmington Mills (1)
  • Portesham (1)
  • Portland (22)
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  • Upwey (11)
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Filters applied: Pets allowed (101)

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101 Results  |  
15 Photos

Barn | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £100 /night

£700 - £1622 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
There are superb views across open countryside to the ocean beyond. Abbotsbury winds along a spectacular part of the World Heritage Jurassic Coast, with two pubs, an excellent butcher, art galleries and tearooms, a swannery, children's farm and sub tropical gardens. Nearby Weymouth and Lyme Regis provide gentle bathing waters and traditional seaside entertainment.  …see more

12 Photos

Barn | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £71 /night

£491 - £1230 / week

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Key info:

  • Nearest beach 3 km
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Extremely peaceful location surrounded by breathtaking countryside but within easy reach of all that the Jurassic Coast has to offer for walking and for families. The Cow Byre is a cosy barn ideal for exploring this fabulous region.  …see more

16 Photos

House | 5 Bedrooms | sleeps 12

Very Good 4.5/5 

Short stays welcome

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from £228 /night

£1590 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
A beautiful home with stunning sea views (Olympic finishing line waters) situated on the Jurassic Coast Ideally situated for all amenities with harbour and Nothe gardens 8min, town centre 10 min & sandy main beach 20 min. Sleeps 11 +1 single bed OR large baby cot.  …see more

Featured properties

20 Photos

Log cabin | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £57 /night

£399 - £1125 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Pine Lodge is the largest on the resort, with massive 120sq feet of external decking situated at the end of a private cul de sac in a quite secluded location , within Warmwell Leisure Resort, offering contemporary living in a peaceful setting close to Dorset's coast. Pine Lodge is truely a one off, one of the best in the resort. Ideal for both in door and outdoor living.  …see more

17 Photos

Cottage | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

3 Nights min stay

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from £79 /night

£550 - £1590 / 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
Jasmine Cottage, is Listed Grade II, has a thatched roof and has under gone extensive renovations in 2010 is now sporting 4 bedrooms, 3 bathrooms, new kitchen dining room with French doors opening into a classic English country cottage garden. Fully Restored in 2010, with thatched roof, local quarried stone walls, set in a tranquil village  …see more

14 Photos

Cottage | 4 Bedrooms | sleeps 10

7 Nights min stay

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from £99 /night

£689 - £1617 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Delightful traditional detached house situated in Weymouth on the Jurrasic Coast  …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

21 Photos

Bungalow | 3 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £50 /night

£350 - £1200 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Spacious 3-bedroom Dorset holiday home with great sea and hill views, just 300 metres from the beach and good family pub. Full Kitchen, large lounge with snooker table, good sized private garden with parking, and access onto coast path. Ideal for families and walkers. Located in the Jurassic Coast World Heritage Site with views of Weymouth Bay  …see more

20 Photos

Cottage | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

2 Nights min stay

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from £46 /night

£320 - £695 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
A beautiful two bedroom cottage in Upwey, Weymouth. Ideal for family or quiet holidays. Beach and country walks near by. With 40ft garden, parking for two cars and stunning rural views down the valley. Shop 50 yards, pub ¼ mile. No smokers please. Pets welcome. The area is one of the sunniest places in Britain.  …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

18 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4.5/5 

3 Nights min stay

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from £83 /night

£578 - £1645 / 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
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

8 Photos

House | 3 Bedrooms | sleeps 6

Short stays welcome

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from £58 /night

£402 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Country views/Four poster bed Situated in a semi-rural location beside a country road with extensive views across the downs towards Hardys Monument is this cosy cottage, the middle one of three  …see more

9 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £70 /night

£485 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.08 km
  • Suitable 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

16 Photos

House | 3 Bedrooms | sleeps 6

Good 3.5/5 

Short stays welcome

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from £46 /night

£320 - £800 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for over 5s only
  • 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

10 Photos

House | 3 Bedrooms | sleeps 6

Short stays welcome

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from £80 /night

£560 - £675 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
Close to the seafront at Chiswell near the southern end of the famous Chesil Beach, this charming refurbished, 200 year old holiday cottage retains period features, offering stylish and comfortable accommodation  …see more

8 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

Short stays welcome

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from £64 /night

£447 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
Sea views from rear of cottage Set at the southern point of Portland with great coastline views  …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

9 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £57 /night

£394 - £756 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Ground floor: Living/dining room  …see more

13 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
  • Nearest beach 0.75 km
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
A 3 bedroom house, sleeping 6. Pionerring Passivhaus Eco-Home with triple glazing. Pennsylvania Heights includes a dedicated nature reserve offering large open space free to enjoy for all. Far reaching sea views of Pennsylvania Castle and Portland Bill.  …see more

16 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £48 /night

£332 - £728 / week

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Key info:

  • Suitable for over 5s only
  • 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

5 Photos

House | 1 Bedroom | sleeps 2

Short stays welcome

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from £41 /night

£284 - £316 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
This 17th century cottage, originally the village bake-house, adjoins the owners home 1/2 mile from the village and within a stone's throw of the famous Abbotsbury Swannery  …see more

16 Photos

House | 3 Bedrooms | sleeps 5

3 Nights min stay

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from £62 /night

£433 - £1149 / week

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Key info:

  • Nearest beach 2 km
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
A newly renovated 3 bedroom house, comfortably sleeping 5. Decked terrace, patio area and lawn garden. A 15 minute stroll to Sandsfoot beach. Ideal base to explore Dorset and the Jurassic coastline. Off-street parking for 2 cars.  …see more

13 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £65 /night

£454 - £1251 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
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

9 Photos

House | 3 Bedrooms | sleeps 7

Short stays welcome

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from £74 /night

£512 - £1038 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Situated in a secluded valley on the edge of the 'picture postcard' village of Osmington, this comfortable and sympathetically converted holiday cottage lies just a mile from the Heritage coastline of Dorset  …see more

8 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £59 /night

£411 - £900 / week

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Key info:

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

7 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £50 /night

£344 - £482 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
A delightful holiday cottage with a garden overlooking open fields, nestling peacefully in the village of Portesham  …see more

17 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £50 /night

£350 - £899 / week

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Key info:

  • Nearest beach 5 km
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Stylish open plan 2 bedroom house, sleeping 4. Enclosed, furnished garden with seating for 4 and barbeque. Offers low energy, low carbon living in a sustainably built home. Just a short walk away from Chesil Beach and the National Sailing Academy.  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £70 /night

£485 - £1251 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • Pets welcome
A brand new 3 bedroom house, sleeps 6. Passive House Eco-Home with triple glazing. Furnished to a high standard throughout. Offers views of Pennsylvania Castle and out to sea. Off street parking for 1 car.  …see more

10 Photos

House | 3 Bedrooms | sleeps 5

Short stays welcome

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from £56 /night

£386 - £535 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
With a cosy open fire this cottage was once home to the famous Stone Carver Skylark Durston, his work can be seen throughout  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

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from £50 /night

£350 - £899 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
A modern apartment located in the heart of Weymouth. A spacious 2 bedroom first floor apartment, sleeps 4. Furnished to a high standard throughout, complete with air conditioning. Located in the heart of Weymouth town centre, within 5 minutes walk of the beach.  …see more

8 Photos

House | 3 Bedrooms | sleeps 5

Short stays welcome

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from £61 /night

£423 - £800 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Set in a residential road and within a short walk you can be on coastal footpaths which form part of the Jurassic coast  …see more

12 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 over 5s only
  • 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

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

16 Photos

House | 4 Bedrooms | sleeps 8

Very Good 4/5 

1 night min stay

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from £50 /night

£350 - £995 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
JUNE RENTALS REDUCED - RIGHT IN THE CENTRE OF WEYMOUTH: SLEEPS 8.FOUR STOREY TOWNHOUSE GREAT FOR FAMILIIES OR A GROUP OF FRIENDS. GET IN TOUCH TO DISCUSS RATES. EASY WALKING DISTANCE FOR SEA,HARBOUR,PUBS CINEMA. Bed linen, heat & light and car parking permit included. "We haven't used the car" is a common quote, Nearsea is well placed for all things to do in Weymouth town.  …see more

8 Photos

Cottage | 3 Bedrooms | sleeps 8

3 Nights min stay

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from £69 /night

£477 - £901 / 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

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

24 Photos

Cottage | 3 Bedrooms | sleeps 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
  • Pets welcome
  • Private garden
Very Pretty Mid Row Corner Thatched Cottage. Coast 5 miles,Dorchester 5 miles. Dog Permitted.  …see more

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

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

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 | 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

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

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 | 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

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

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 | 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 | 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

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

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