50 Best Dorset Self catering on Holiday Lettings - Cottages

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Dorset

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1,395 Vacation rentals

Travelers going to Dorset are booking June dates now. Secure your vacation rental today and have the perfect trip.

(4) Excellent 

8

Greenhill Vacation apartment rental

Weymouth / Greenhill

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Car not necessary
Located over looking Weymouth's stunning beach, the holiday apartment offers spectacular sea views and sleeps 5 people.It is within easy reach of all the local amenities, restaurants and bars. The spacious apartment offers stunning sea views and all the be  …see more

from $157 / night

$1032 / week

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from $157 / night

(33) Excellent 

33

Swanage Bay Vacation townhouse rental

Swanage / Swanage Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
A light and airy victorian town house with contemporary decor literally only 1-2 mins walk from a clean sandy beach and next to the south west coast path. Ideal for 2 families/large families ,4 couples or groups.With a large enclosed south facing terrace,great kitchen d  …see more

from $163 / night

$863 - $2063 / week

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from $163 / night

28

Bournemouth Vacation apartment rental

Bournemouth / Sandbanks

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
This unique three bedroom three bathroom garden apartment is situated on the prestigious Sandbanks peninsula, a couple of minutes' walk from award-winning sandy beaches and Dorset's beautiful Poole Harbour - the second biggest natural harbour in the world afte  …see more

from $207 / night

$1119 - $2250 / week

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from $207 / night

(32) Excellent 

20

Vacation barn in Melplash

Bridport / Melplash

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 6 mi
  • Child friendly
  • Pet friendly
Roe Barn is a stunning detached barn conversion providing first class holiday accommodation with a large secure garden in a beautiful location. Set in 6 acres of outstanding Dorset countryside there is lots of space for couples, families and dogs to explore and the dra  …see more

from $117 / night

$518 - $1412 / week

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from $117 / night

(53) Very Good 

27

Corfe Castle Vacation cottage rental

Corfe Castle / Kingston, Dorset

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Tucked away in the heart of Enid Blyton country is a charming two-bedroom cottage with lots of living space, a rolling garden and uninterrupted views over the majestic ruins of Corfe Castle and the Purbeck Hills. Furnished with a quirky eye and an emphasis on comfort,  …see more

from $163 / night

$1038 - $1238 / week

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from $163 / night

(4) Very Good 

17

Vacation cottage in West Bay

Bridport / West Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Suitable for children age 5+
Sunset is a spacious 3 Star well equipped south west facing bungalow , situated mid way between Bridport, West Bay Harbour . Just a 10 min flat walk to the the world famous Jurassic Coastline with the Dorset Coastal Path, Chesil Beach and 2 beaches Ideal for all age g  …see more

from $47 / night

$325 - $755 / week

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from $47 / night

(8) Excellent 

33

Vacation home in Bournemouth

Bournemouth / Sandbanks

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 0 mi
  • Child friendly
  • Pet friendly
32 Brownsea Road is a stunning 'New England style' self catering holiday home in the heart of Sandbanks, Poole. The property was completed to a high specification in 2015. Enjoy your holiday in complete luxury with wifi, underfloor heating throughout the gro  …see more

from $272 / night

$1250 - $3625 / week

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from $272 / night

(29) Excellent 

25

Swanage Bay Vacation cottage rental

Swanage / Swanage Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Tucked away in a quiet position in the heart of Swanage, on the beautiful Isle of Purbeck, Taunton Cottage is perfectly situated only a two minute walk away from the safe, award-winning sandy beach, shops, cafés, pubs and restaurants. Built of Purbeck stone, the  …see more

from $125 / night

$750 - $1375 / week

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from $125 / night

(23) Excellent 

28

Vacation apartment in Weymouth

Dorset / Weymouth

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.02 mi
  • Child friendly
Fully self-contained first floor Georgian apartment consisting of one double bedroom, a twin bedroom, and a fully equipped kitchen/lounge boasting three large period sash windows giving superb views of the entire bay. Perfect for families or couples looking for a short  …see more

from $59 / night

$382 - $950 / week

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from $59 / night

(14) Excellent 

31

Vacation cottage in Shaftesbury

Dorset / Shaftesbury

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 45 mi
  • Child friendly
  • Car not necessary
Summer Lodge is a beautiful refurbished cottage, it is cosy, comfortable, light and airy and furnished to a high standard, with thick new carpet throughout, comfortable quality beds and tasteful decor. New TV's lounge and both bedrooms, downstairs cloakroom, patio  …see more

from $72 / night

$494 - $932 / week

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from $72 / night

(11) Excellent 

10

Vacation cottage in Weymouth

Dorset / Weymouth

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Welcome to Hector is our family friendly luxury self catering self catering holiday cottage. Hector is located in a private gated mews behind Brewers Quay very near to the Weymouth harbour side and only a few minutes from the beach, making it ideal for walking to a loc  …see more

from $68 / night

$475 - $1045 / week

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from $68 / night

(18) Excellent 

18

Bournemouth Vacation apartment rental

Bournemouth / Southbourne

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
A modern top (3rd) floor 2 bedroom apartment to rent. Property will sleep 6 (plus a travel cot if required). The apartment is situated in Southbourne, with stunning sea views, a convenient 2 minute stroll to the beach, a lift to the property and private parking. It offe  …see more

from $125 / night

$782 - $1375 / week

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from $125 / night

(28) Excellent 

25

Vacation cottage in Swanage Bay

Swanage / Swanage Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Steam Railway Cottage is a two storey detached cottage which is adjacent to The Swanage Steam Railway in the heart of the town. It is ideally situated just 500 yards from the town centre and beach. It can accommodate up to 4 adults and 2 children plus a baby and compris  …see more

from $88 / night

$375 - $1219 / week

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from $88 / night

30

Vacation home in Ringstead

Dorset / Ringstead

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Pet friendly
Shore Cottage is a unique detached house bordering the seashore with three double bedrooms, each with truly magnificent views over the sea and rolling countryside. The cottage is the last house on an unmade track in Ringstead Bay, Dorset; the large grassy garden runs  …see more

from $195 / night

$957 - $1875 / week

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from $195 / night

(12) Excellent 

13

Swanage Vacation apartment rental

Isle of Purbeck / Swanage

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Newly listed for 2016! A two bedroom spacious and comfortable flat in a small quiet block of apartments. The flat offers two double bedrooms. One with king size bed and the other with two single beds. In addition in the large living room there is a sofa bed that can ac  …see more

from $107 / night

$719 - $969 / week

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from $107 / night

(10) Very Good 

19

Vacation home in Sherborne

Dorset / Sherborne

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Private garden
Gardeners Cottage is a newly renovated detached property with garden and ample parking. It comprises one downstairs bedroom with luxurious wrought iron kingsize bed with Egyptian cotton bedlinen, wardrobe, dressing table, hairdryer and chairs and an ensuite with large  …see more

from $57 / night

$375 - $607 / week

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from $57 / night

(3) Very Good 

9

Vacation caravan/mobile home with shared pool in Weymouth

Dorset / Weymouth

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
We are delighted to offer the rental of our well-presented and modern holiday home which is situated in the prestigious resort of Weymouth Bay in Dorset. The caravan itself is situated merely 3 minutes walk from the resort facilites complex giving great freedom for comi  …see more

from $63 / night

$350 / week

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from $63 / night

(32) Excellent 

31

Melplash Vacation cottage rental

Bridport / Melplash

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Child friendly
Bluebell Cottage is a pretty stone cottage in a fantastic location fully equipped with modern comfortable furnishings and a large fully enclosed sunny garden. Set in 6 acres of stunning Dorset countryside there is lots of space for couples, families and dogs to explore  …see more

from $93 / night

$415 - $1069 / week

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from $93 / night

6

Vacation apartment in Christchurch

Dorset / Christchurch

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Car not necessary
  • Private garden
Our Flat is situated in superb position on the Christchurch bank of the River Stour. It self contained and south facing in a quiet location about 12 minutes walk from Christchurch town centre and 6 miles from the centre of Bournemouth. The Flat is NON SMOKING.  …see more

from $69 / night

$482 - $799 / week

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from $69 / night

(8) Very Good 

24

Vacation home in Greenhill

Weymouth / Greenhill

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Georgian townhouse sleeps 12 close to beachSeaside House is a holiday home, situated in the heart of Weymouth and within a stone's throw of Weymouth's fabulous beach and esplanade.This elegant Grade II listed Georgian townhouse extends over 4 floors and provid  …see more

from $275 / night

$1125 - $2182 / week

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from $275 / night

(40) Excellent 

16

Vacation barn in Frampton

Dorchester / Frampton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 20 mi
  • Ask about children
Beautiful detached self-contained barn conversion with its own patio and wood burner. The barn was converted many years ago and is newly refurbished for the 2015 season to a very high standard with modern appliances. It has an open plan sitting room with drop down kitch  …see more

from $75 / night

$407 - $563 / week

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from $75 / night

(29) Excellent 

20

Warmwell Vacation lodge rental

Weymouth / Warmwell

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Kingfisher Retreat is a luxury lodge on the popular Warmwell Holiday Park, set in a private cul-de-sac accessed via a barrier. It sleeps up to 4 guests in 2 bedrooms plus there is a sofabed in the lounge should this be required. It boasts an open plan fully fitted ki  …see more

from $100 / night

$612 - $1624 / week

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from $100 / night

(7) Excellent 

12

Vacation home with shared pool in Bournemouth

Bournemouth / Southbourne

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Beach View (one of "12 great houses by the sea" The Times April 16th 2016) is a beautifully presented spacious, light and airy detached house occupying a stunning position directly on the sea front and is just two hours drive from London. It has breathtaking  …see more

from $413 / night

$1904 - $4750 / week

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from $413 / night

(40) Excellent 

27

Vacation cottage in Uplyme

Lyme Regis / Uplyme

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Ask about children
A newly-refurbished, one bed self-catering cottage - ideal for two - lovely rural retreat only one mile from Lyme Regis town and the Jurassic coast. Walk to local pub 10 mins, 5 miin drive to Lyme Regis town or leave the car behind and follow lovely riverside walk to t  …see more

from $107 / night

$625 - $750 / week

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from $107 / night

(8) Excellent 

36

Vacation home in Lyme Regis

Dorset / Lyme Regis

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 0.1 mi
  • Suitable for children age 5+
  • Private garden
The mesmerising views and glorious light serve toenhance a lovely house which is as special and iconic as itssetting. Listed Grade II as being of Significant ArchitecturalImportance and Historic Interest, there is a wealth of charmingperi  …see more

from $188 / night

$1744 - $3744 / week

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from $188 / night

(13) Excellent 

25

Vacation lodge in Mudeford

Christchurch / Mudeford

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Whether your ideal holiday is energetic or restful Harbour Lodge (brand new, June 2012) is perfectly situated for either. Located quietly overlooking the harbour, the Lodge's comfortable interior and west facing deck might be all you need to relax and unwind. The  …see more

from $138 / night

$963 - $2013 / week

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from $138 / night

(20) Excellent 

14

Vacation apartment in Swanage Bay

Swanage / Swanage Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Car not necessary
New to the holiday rental market in September 2015, Sea Court 3 is the raised ground floor apartment of this pretty seaside Victorian building, converted in 2008, with stunning sea views. Sitting in the heart of Swanage about 100m uphill from the beaches, restaurants an  …see more

from $90 / night

$525 - $945 / week

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from $90 / night

(17) Very Good 

27

Home rental in Bournemouth

Bournemouth / Boscombe

10 26 2 nights min

  • 10 bedrooms
  • Sleeps 26
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
This huge, modern 3-storey house, centrally located in Bournemouth, has 10 separate bedrooms and a total sleeping capacity of 26.The house is only 250 metres away from the only artificial surf reef in the northern hemisphere, the multimillion pound, award winnin  …see more

from $625 / night

$3125 / week

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from $625 / night

(28) Excellent 

41

Vacation cottage rental

Poole / Poole Quay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Short breaks welcome! The cottage is a beautifully appointed, spacious early Victorian terraced property located within only a few minutes walk of Historic Poole Quay, Old Town, The Heritage Trail, Poole Park and Town Centre with the Dolphin indoor shopping com  …see more

from $232 / night

$1250 - $1563 / week

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from $232 / night

(13) Excellent 

24

Apartment rental in Bournemouth with golf nearby

Bournemouth / West Cliff

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.7 mi
  • Car not necessary
The Coach House is in Bournemouth, Dorset.( Number 1 on trip Advisor in our category with 30 plus reviews - reviews not linked to Holiday Lettings yet) Weekly rates offered, with at least 1 free night discount. Jayne always wanted to live by the sea and now offers 4 h  …see more

from $50 / night

$313 - $563 / week

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from $50 / night

(4) Excellent 

10

Vacation chalet rental

Dorset / Winfrith Newburgh

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Glamping style studio chalet located in country cottage garden in a pretty village in conservation area of the Purbecks.Custom made bed, dining table and chairs. Small kitchenette containing microwave, fridge with ice box and sink. Three piece bathroom with shower, toil  …see more

from $58 / night

$403 / week

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from $58 / night

(19) Excellent 

23

Over Compton Vacation barn rental

Sherborne / Over Compton

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 37 mi
  • Child friendly
Completed in 2007 one of three barns, Meadow View Barn has been converted to give a modern relaxing environment retaining the character of the original structure. Accommodation includes a modern open plan living space with large oak windows and French doors that open  …see more

from $123 / night

$563 - $1000 / week

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from $123 / night

(9) Very Good 

18

Vacation apartment in Swanage Bay

Swanage / Swanage Bay

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
The flat is on the ground floor in a small block of nine situated on the waterfront of Swanage. The lounge/diner and two of the bedrooms feature panoramic views of the whole bay of Swanage. Even in bad weather the views can be spectacular, particularly when the sea is r  …see more

from $100 / night

$500 - $2125 / week

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from $100 / night

20

South Perrott Vacation home rental

Dorset / South Perrott

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
A charming stone and tiled holiday country cottage which used to be the village school. Keeping original features like the school bell, vaulted kitchen/dining room, Gothic arched doors and mullion windows, this luxury self catering cottage has recently been sympathetica  …see more

from $239 / night

$1670 - $2907 / week

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from $239 / night

(13) Excellent 

21

Apartment rental in Poole

Dorset / Poole

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
** A beautiful modern two bedroom apartment with views of Poole harbour and Brownsea Island. Situated just five minutes walk from Poole Quay! **High standard spacious accommodation. Ideal for families and couples and all year round breaks**The apartment is situated on  …see more

from $150 / night

$850 - $1213 / week

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from $150 / night

(17) Very Good 

21

Vacation home rental

Dorset / Weymouth

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Summer Lodge is located a short car ride from Weymouths safe, sandy, lifguarded, beach complete with many restaurants and family attractions. Portland, Chesil Beach, West Bay, Lulworth cove,Corfe Castle, and Swanage are a few places in the surounding area.Summe  …see more

from $478 / night

$2049 - $4125 / week

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from $478 / night

(3) Excellent 

25

Vacation home in Poole

Dorset / Poole

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Fantastic Central Holiday Location. This comfortable two bed home is located on a popular development adjacent to Poole Harbour. Whether walking, cycling or by car you are well placed for so much fun. The ground floor is open plan style with lounge, kitchen and dining  …see more

from $100 / night

$438 - $844 / week

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from $100 / night

(2) Excellent 

19

Vacation barn rental

Dorset / Lyme Regis

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Child friendly
Tucked away in an exceptionally tranquil part of the East Devon Area of Outstanding Natural Beauty, surrounded by wooded hills, country lanes and abundant wildlife, yet only a short drive to the Dorset and East Devon World Heritage Coast.  The popular seaside town  …see more

from $75 / night

$525 - $875 / week

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from $75 / night

(3) Excellent 

15

Cottage rental in Broadwindsor

Dorset / Broadwindsor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 6 mi
  • Child friendly
  • Pet friendly
Barn cottage is a 4 star conversion in local Ham stone set in an area of outstanding natural beauty.There are breathtaking views in all directions.We offer excellent walks or very quiet restful seclusion,with an abundance of wildlife nearby.The Heritage coast is only 6  …see more

from $88 / night

$475 - $819 / week

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from $88 / night

(12) Excellent 

24

Vacation cottage in Leigh, Dorset

Sherborne / Leigh, Dorset

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 32 mi
  • Private garden
On the outskirts of the small village of Leigh amid rural surroundings, this delightful, Grade II listed, part-thatched stone cottage has been beautifully restored by its owners with exceptional attention to detail. Guests arriving at Pound Farm Cottage will immediate  …see more

from $135 / night

$579 - $947 / week

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from $135 / night

1