50 Best Dorset Self catering on Holiday Lettings - Cottages

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Apartments Bournemouth
341 properties
Apartments Poole
183 properties
Apartments Weymouth
164 properties
Cottages Bridport
122 properties
Isle of Purbeck
112 properties
Christchurch
80 properties
Condos Lyme Regis
57 properties
Isle of Portland
57 properties
Apartments Dorchester
44 properties
Blandford Forum
42 properties
Estates Shaftesbury
35 properties
Cottages Sherborne
30 properties
Gillingham
19 properties
Wimborne
18 properties
Wareham
17 properties
Whitchurch Canonicorum
17 properties
Beaminster
11 properties
Sturminster Newton
10 properties
Stratton
10 properties
Alderholt
8 properties

Dorset

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1,640 Vacation rentals

(23) Excellent 

25

Vacation apartment in Bournemouth

Dorset / Bournemouth

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
A stunning, contemporary, ground floor apartment located within the East Cliff conservation area in the beautiful seaside town of Bournemouth. The apartment has been completely refurbished to a high standard. Features include a stunning 50" flat screen television, WiF …see more

from $102 / night

$636 - $1,265 / week

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avg. 1 hour 10 minutes

from $102 / night

(4) Excellent 

10

Vacation apartment in Bournemouth

Dorset / Bournemouth

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Car not necessary
Lovely apartment with 4 bedrooms, 1 bathrooms, kitchen and a lounge. The apartment is located in a beautiful old building and situated right in the town centre with lovely views overlooking Bournemouth gardens. There are plenty of shops, pubs, bars and restaurant only m …see more

from $382 / night

$3,815 / week

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from $382 / night

(20) 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
  • Child friendly
  • Car not necessary
The mesmerising views and glorious light serve to enhance a lovely house which is as special and iconic as its setting. Listed Grade II as being of Significant Architectural Importance and Historic Interest, there is a wealth of charming period detail, from the wind …see more

from $191 / night

$1,774 - $4,444 / week

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avg. 3 hours 47 minutes

from $191 / night

(31) 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 $236 / night

$1,462 - $1,653 / week

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avg. 2 hours 56 minutes

from $236 / night

(54) Excellent 

49

Home rental in Bournemouth

Dorset / Bournemouth

8 26 2 nights min

  • 8 bedrooms
  • sleeps 26
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Prices start from £300 per night midweek and £1000 per night weekend. Minumum nights stays apply. For a quote for your stay please contact owner. -- Located on a quiet tree lined road in Bournemouth, minutes from a Blue Flag sandy beach. DETACHED, 1930’s, spacious 8 …see more

from $382 / night

$2,543 / week

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from $382 / night

(80) Excellent 

33

Vacation home in Lyme Regis

Dorset / Lyme Regis

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
The White House is a delightful 18th Century Georgian House with Seven (7) bedrooms situated in the heart of Lyme Regis, just one minute walk from the town's pubs, shops and restaurants and about five minutes from the beach. The newly refurbished White House upgrades t …see more

from $700 / night

$2,925 - $5,722 / week

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avg. 2 hours 24 minutes

from $700 / night

(33) Excellent 

16

Vacation home in Weymouth

Dorset / Weymouth

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Henley House is a large, four bedroomed detached property with sunny private garden and patio areas. It offers comfortable accommodation for up to 8 people ideal for 1 or 2 week holidays, weekend breaks and family occasions throughout the year.The property is particul …see more

from $166 / night

$971 - $1,878 / week

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avg. 1 hour 47 minutes

from $166 / night

(17) Excellent 

31

Weymouth Vacation home rental

Dorset / Weymouth

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Car not necessary

from $160 / night

$893 - $2,169 / week

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from $160 / night

(13) Excellent 

21

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 panoramic …see more

from $162 / night

$1,590 - $5,022 / week

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avg. 2 hours 25 minutes

from $162 / night

(14) Excellent 

31

Vacation lodge in Warmwell

Weymouth / Warmwell

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
The Lodge has a special luxury feel from the moment you arrive. It is a classically designed Gite style and has high specification features. A welcome pack will be provided, for you to enjoy, on arrival including, bread, milk and basic commodities. Kingfisher Breaks is …see more

from $318 / night

$1,653 - $2,035 / week

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avg. 3 hours 56 minutes

from $318 / night

(47) 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 $67 / night

$428 - $1,114 / week

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avg. 1 hour 33 minutes

from $67 / night

(40) 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 $102 / night

$503 - $1,621 / week

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avg. 1 hour 55 minutes

from $102 / night

(32) Excellent 

25

Vacation chalet in Mudeford

Christchurch / Mudeford

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.05 mi
  • Swimming pool
The Shed is named somewhat tongue in cheek by the owners' family as it is about as far from a shed as you can get. Whether sitting out on the decking with its clear view glass balustrade or in the comfort of the lounge you have stunning views across Avon Beach and the …see more

from $125 / night

$822 - $2,551 / week

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avg. 3 hours 56 minutes

from $125 / night

(11) Excellent 

25

Ferndown Vacation cottage rental

Dorset / Ferndown

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Child friendly
Birchcroft nestles in over 1 acre of woodlands but is only 5 miles from the golden sandy beaches of Bournemouth with cinemas, nightclubs and great shopping. Picturesque Christchurch, the New Forest, National Trust properties of Brownsea Island, Kingston Lacey, Corfe Cas …see more

from $222 / night

$1,107 - $2,769 / week

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from $222 / night

(7) Excellent 

22

Warmwell Vacation lodge rental

Weymouth / Warmwell

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
The Keepers Lodge is pure luxury - brand new for 2014. It boasts a view over the lakes from the large deck, which is equipped with seating for up to 8 plus glass topped table & cantilever parasol, or from inside the lodge through the fully glazed front. The main bedro …see more

from $159 / night

$1,049 - $6,357 / week

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from $159 / night

(29) Excellent 

19

Warmwell Vacation lodge rental

Weymouth / Warmwell

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Kingfisher Haven has it's own enclosed deck area, accessed from the lounge/diner via patio doors, for those warm summer days and nights. On the deck there is a large table, parasol and six chairs. There is a brand new colour TV/DVD player in each of the 3 bedrooms as …see more

from $140 / night

$840 - $2,543 / week

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from $140 / night

(6) Excellent 

16

Bridport Vacation cottage rental

Dorset / Bridport

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Rebuilt to a high specification in 2009 with views that literally take your breath away, the cottage is built in a stunning location surrounded by National Trust land and the Jurassic Coast. There are huge floor to ceiling windows in the vast kitchen/ diner/ sitting ro …see more

from $382 / night

$2,670 - $5,340 / week

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avg. 2 hours 26 minutes

from $382 / night

(8) Excellent 

16

Mudeford Vacation caravan/mobile home rental

Christchurch / Mudeford

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.15 mi
  • Swimming pool
LAZY DAZE ‘Lazy Daze’ plot 27 is a luxury caravan on the popular, small and exclusive Sandhills Holiday Park in Mudeford which is the perfect beachside location for a wonderful holiday. The caravan is a 2015 Pemberton Abingdon model which is situated on a quiet, sunny …see more

from $102 / night

$660 - $1,907 / week

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avg. 3 hours 56 minutes

from $102 / night

(47) 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 0.1 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 cottage …see more

from $191 / night

$763 - $1,399 / week

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Responds fast!
avg. 1 hour 18 minutes

from $191 / night

(9) Very Good 

6

Weymouth Vacation apartment rental

Dorset / Weymouth

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
If you are looking for a peaceful holiday in a high quality comfortable apartment close to the beach, harbour and town with on-site parking, then look no further than Tamarisk Court. The well regarded Tamarisk Hotel has been converted into seven luxury self-contained ap …see more

from $45 / night

$318 - $789 / week

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from $45 / night

(3) Excellent 

Certificate of Excellence

8

Vacation cottage rental

Gillingham / West Stour

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Marnhull Cottage is surrounded by fields and offers amazing views of the Blackmore Vale countryside. The accommodation has two bedrooms both with king size and single beds in each and will comfortably sleep up to six adults. There is a large living room with wifi availa …see more

Certificate of Excellence

from $128 / night

$890 / week

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Responds fast!
avg. 2 hours 21 minutes

from $128 / night

(50) Very Good 

22

Vacation cottage in Weymouth

Dorset / Weymouth

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Suitable for children age 5+
To have a great Holiday they say you only need 3 things sun, sea and sand but to find your perfect holiday base its all about Location Location Location and Duckling cottage is spot on. Just 70 yards to the left you will find the famous blue flag central beach and espla …see more

from $56 / night

$426 - $978 / week

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avg. 45 minutes

from $56 / night

(34) 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 $89 / night

$571 - $1,690 / week

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from $89 / night

(1) Excellent 

14

Vacation home in Bridport

Dorset / Bridport

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Situated next to the owner’s property with its own entrance,this impressive reverse level cottage has been refurbished to a high standard and is perfect for couples looking for a cosy break. Within walking distance of the popular town centre of Bridport,which has a c …see more

from $63 / night

$439 - $1,029 / week

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from $63 / night

(19) Excellent 

13

Swanage Bay Vacation cottage accommodation

Swanage / Swanage Bay

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly
Millpond Cottage is a traditional Purbeck stone cottage dating back to the early 18th century. It is set beside the tranquil Millpond in the heart of Swanage. It offers delightful accommodation for up to 7 people. It is a five minute walk to the town centre and beach. …see more

from $128 / night

$890 - $1,265 / week

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from $128 / night

(18) 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 ground floor, …see more

from $276 / night

$1,844 - $4,069 / week

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from $276 / night

(26) Excellent 

19

Vacation caravan/mobile home in Mudeford

Christchurch / Mudeford

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Luxury Holiday Home situated at Mudeford, Christchurch on Sandhills Holiday Park. The views of the harbour from the lounge and decking are amazing and ever changing, and the sandy beach is but a short level walk away. The Jetty is fully equipped for a truly relaxing h …see more

from $102 / night

$660 - $1,736 / week

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avg. 3 hours 56 minutes

from $102 / night

(92) Excellent 

23

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
WINNER OF TRIP ADVISOR CERTIFICATE OF EXCELLANCE PLEASE BE AWARE TAHT THE PAYMENT PROTECTION PLAN WILL ADD AN EXTRA 10% TO 15% TO THE COST OF YOUR HOLIDAY , THIS GOES TO TRIPADVISOR DIRECT AND ONLY COVERS YOU FOR NO ACCESS TO HOUSE. Which would not happen , do contact …see more

from $159 / night

$763 - $1,431 / week

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from $159 / night

(3) Very Good 

14

Vacation caravan/mobile home rental

Weymouth / Chickerell

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0.5 mi
  • Child friendly
  • Car not necessary
This carefully maintained 2014 Burgundy Swift caravan is located within a two minute walk of the Jurassic Coastline, in the highly rated Littlesea Holiday Park. A mere 15 minute cycle from the seaside town of Weymouth, the combination of privacy provided by its serene …see more

from $108 / night

$757 / week

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avg. 1 hour 6 minutes

from $108 / night

(14) Excellent 

21

Vacation caravan/mobile home with shared pool in Hamworthy

Poole / Hamworthy

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
2017 Willerby, Aspen 2 bedroom Lodge - 40 foot long and 13 feet wide, it is an exceptionally presented holiday home with seaviews from this corner plot. This also gives access to wheelchair uses via the ramp and a small step into the holiday home. This Aspen Lodge is c …see more

from $128 / night

$890 / week

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avg. 1 hour 44 minutes

from $128 / night

(56) Excellent 

20

Vacation home in Swanage Bay

Swanage / Swanage Bay

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
Late Deal !!1 week in August available £800 ( should be (£1100) PLEASE BE AWARE THAT THE PAYMENT PROTECTION PLAN WILL ADD AN EXTRA 10% -15% to your holiday cost this goes to trip adviser direct and only covers you for no access to house , which would not happen , do …see more

from $169 / night

$763 - $1,431 / week

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from $169 / night

(45) Excellent 

Certificate of Excellence

12

Vacation apartment in Piddlehinton

Dorchester / Piddlehinton

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 21 mi
  • Child friendly
  • Private garden
Private and modern annexe that has been recently refurbished to a high standard and provides a wonderful rural retreat for couples, young families or friends. The bedroom is a stylish sanctuary with a king size bed, sumptuous duvet and selection of pillows. There is a …see more

Certificate of Excellence

from $77 / night

$407 - $789 / week

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Responds fast!
avg. 3 hours 40 minutes

from $77 / night

16

Vacation apartment in Studland

Swanage / Studland Bay

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
New beautiful, stylish 2 bedroom apartment located within an exclusive development. Individually designed and fitted out to the highest standard for ultimate comfort and relaxation; the apartment is just moments from the award winning beach at Shore Road. Swanage is the …see more

from $166 / night

$1,157 / week

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from $166 / night

(21) Excellent 

24

Vacation cottage in Swanage Bay

Swanage / Swanage Bay

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Only five minutes from a Blue Flag beach in beautiful Swanage, this Grade II listed cottage is full of character with a farmhouse kitchen complete with Aga, sitting room with a woodburning stove, an outside sundeck and BBQ. On three floors, the cottage sleeps up to 7 p …see more

from $178 / night

$1,244 - $1,404 / week

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avg. 3 hours 55 minutes

from $178 / night

(10) Excellent 

Certificate of Excellence

18

Sherborne Vacation barn rental

Dorset / Sherborne

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Private garden
The Tack Room And Middle Stable is a barn converson. It is a lovely light and airy space with wood floors throughout, it has it's own secluded patio gardens with ample room for a family of four. Want to bring the grandparents as well? Please see our property The Hay Bar …see more

Certificate of Excellence

from $105 / night

$656 - $984 / week

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Responds fast!
avg. 3 hours 2 minutes

from $105 / night

37

Vacation home in Isle of Portland

Dorset / Isle of Portland

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 3 mi
  • Child friendly
Set in a stunning location with magnificent views over Portland Bill and the lighthouse, this detatched cottage for 4 with decked patio, offers a great holiday location where one can watch time go by with the passing ships and boating activity around Portland Bill. Ther …see more

from $115 / night

$476 - $1,297 / week

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Responds fast!
avg. 57 minutes

from $115 / night

(32) Excellent 

15

Home rental in Rousdon Estate

Lyme Regis / Rousdon Estate

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
St Pancras is the lovingly restored old church situated on the beautiful Rousdon Country Estate, near Lyme Regis set amidst 350 acres of parkland. A Grade ll listed building formally the church for the estate. There are lovely amenity walks for the residents, in …see more

from $159 / night

$827 - $1,526 / week

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from $159 / night

(33) 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 $172 / night

$1,441 - $1,462 / week

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avg. 44 minutes

from $172 / night

29

Vacation home rental

Christchurch / Mudeford

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0.7 mi
  • Child friendly
  • Car not necessary
BEDROOMS: Double Bedroom - Twin Bedroom (with bunk beds) - Twin Bedroom. Lounge/diner with TELEVISION - DVD - FREEVIEW - FREE WIFI (subject to availability from Internet Service Provider). Conservatory with doors leading to the garden. Fitted kitchen with GAS HOB - EL …see more

from $117 / night

$819 / week

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avg. 2 hours 33 minutes

from $117 / night

(2) Excellent 

16

Vacation home with indoor pool in Whitchurch Canonicorum

Dorset / Whitchurch Canonicorum

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Swimming pool
Baabara is an original Shepherds Hut renovated and ready for a peaceful 'get away from it all' stay. It's situated by the pond with our ducks and moorhens in our paddock with alpacas, sheep and the odd bunny, pheasant, deer etc…. Baabara in fully insulated and has a cos …see more

from $159 / night

$578 / week

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Responds fast!
avg. 2 hours 22 minutes

from $159 / night