50 Best Dorset Self catering on Holiday Lettings - Cottages

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Dorset

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1,320 Vacation rentals

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(26) Excellent 

27

Vacation studio in Bradpole

Bridport / Bradpole

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Ask about pets
The Pressing room is all one level: Lounge with beams and stone floors throughout, double bed ,dining area, kitchen, and shower room with toilet and basin. Gas fired central heating, wood burning stove and laundry service. Outside there is a patio with furniture, parki  …see more

from $87 / night

$292 - $614 / week

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from $87 / night

(24) Excellent 

29

Cottage accommodation in Weymouth

Dorset / Weymouth

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
This Cottage is in a very central location of Weymouth only a short walk to the beach and radipole lake nature reserve, it's also a very short walk to the town centre and beautiful harbour, where you can sit and enjoy a drink at one of the local bars over looking  …see more

from $100 / night

$744 - $1054 / week

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from $100 / 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

$484 - $2108 / week

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from $100 / night

Featured properties

(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 $186 / night

$1730 - $3714 / week

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from $186 / night

(18) Excellent 

41

Vacation home rental

Lyme Regis / Uplyme

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
The Cedar House is a contemporary and highly comfortable 4 bedroom split level house. Walking over the contemporary glass, steel and wood bridge to the front door will set your expectations for the beautiful design and decoration of the house. The architect, Annie Mart  …see more

from $298 / night

$348 - $3100 / week

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from $298 / night

(78) Excellent 

33

Vacation apartment in Lyme Regis

Dorset / Lyme Regis

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Private garden
* Acorns Garden Apartment - privately situated - own Hot Tub * 2 nights minimum stay most of year * Enquire for short breaks of 3 & 4 nights May to Sept * Own use private Hot Tub - great in any weather - mood lighting * Includes a "Breakfast Basket" ample  …see more

from $149 / night

$868 - $1389 / week

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from $149 / 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

$472 - $1037 / week

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from $68 / night

(32) Excellent 

20

Vacation cottage in Corfe Castle

Isle of Purbeck / Corfe Castle

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
Quintessentially English thatched cottage in the heart of Purbecks and Thomas Hardy country set in a street so unspoilt it is used in period dramas.. 10 minutes from the Jurassic Coast and 10 minutes from the beautiful sandy beaches of Studland bay & Swanage. Romant  …see more

from $106 / night

$490 - $924 / week

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from $106 / night

4

Vacation home rental

Dorset / Ibberton

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
WELL LOCATED FOR WALKING, CYCLING, FISHING, HORSE RIDING AND GOLF The property nestles in the Dorset countryside and is surrounded by far reaching countryside views, offering couples a peaceful retreat. Approached through a private entrance shared with the owner  …see more

from $57 / night

$397 - $813 / week

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from $57 / 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 $230 / night

$1178 - $1550 / week

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from $230 / 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

$379 - $943 / week

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from $59 / night

(24) Excellent 

29

Vacation cottage in Shaftesbury

Dorset / Shaftesbury

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 45 mi
  • Child friendly
  • Car not necessary
Easter cottageA beautiful mews cottage in the heart of the historic part of Shaftesbury with it's own courtyard parking, perfect for enjoying the town's atmosphere, an interesting and lovely location to holiday for all seasons, with so much to see and  …see more

from $71 / night

$490 - $924 / week

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from $71 / night

(15) Excellent 

17

Vacation apartment in Poole Harbour

Poole / Poole Harbour

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Stunning panoramic sea and harbour views are available from this beautifully presented spacious first floor apartment. Fantastic balcony - only 50m from the Harbour shore, en-suite shower room, fully fitted kitchen/dining room and two parking spaces. A simply stunning p  …see more

from $112 / night

$620 - $1240 / week

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from $112 / night

(9) Excellent 

18

Vacation cottage in Okeford Fitzpaine

Blandford Forum / Okeford Fitzpaine

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 39 mi
  • Child friendly
  • Pet friendly
Netherway Farmhouse is a 17th century thatched cottage, one of 25 listed buildings in the conservation area of Okeford Fitzpaine, one of Dorset’s most attractive villages exhibiting rural charm and relaxed pace. Newly refurbished, the cottage is full of character  …see more

from $186 / night

$484 - $1278 / week

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from $186 / night

(24) Excellent 

18

Vacation apartment in Swanage Bay

Swanage / Swanage Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.002 mi
  • Child friendly
Situated on the end of an impressive Edwardian Parade, Bayview apartment is the ideal holiday accommodation with less than one minutes walk to either the beach, shops or various pubs, bars or restaurants. Stunning beach side location with breathtaking panoramic view ove  …see more

from $123 / night

$527 - $1209 / week

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from $123 / night

17

Piddletrenthide Vacation b&b rental

Dorchester / Piddletrenthide

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 18 mi
  • Private garden
Set in in the heart of Hardy country, in the picturesque village of Piddletrenthide, South House Retreat is a unique B and B offering accommodation to writers, artists, creative people, literary lovers and those who want to rest or just visit our beautiful County. Run b  …see more

from $75 / night

$521 / week

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from $75 / 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 $100 / night

$589 - $961 / week

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from $100 / night

(26) 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 5 star rated, large, four bedroomed detached property ideal for 1 or 2 week holidays and weekend breaks throughout the year. It offers comfortable accommodation for up to 8 people. The property is particularly well positioned in a quiet cul-de sac i  …see more

from $149 / night

$794 - $1674 / week

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from $149 / night

(10) 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 0.1 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  …see more

from $142 / night

$799 - $2480 / week

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from $142 / night

(31) Excellent 

21

Corfe Castle Vacation cottage rental

Isle of Purbeck / Corfe Castle

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
Wissett Cottage is the quintessential, traditional Dorset stone cottage. Steeped in period character such as exposed stonework, ancient timbers and a partly thatched roof, this 300 year old cottage provides a cosy and welcoming 'home away from home' that combi  …see more

from $93 / night

$484 - $1228 / week

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from $93 / night

4

Vacation home in West Lulworth

Dorset / West Lulworth

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
1 OF 6 PROPERTIES SET ALONG THE JURASSIC COASTLINE AT DURDLE DOOR WITH OUTDOOR SWIMMING POOL, SLEEPS 4+1 Set on the Dorset coast these converted farm buildings have been beautifully renovated and furnished. Each property is named after its original use and retain muc  …see more

from $95 / night

$664 - $1792 / week

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from $95 / night

(2) Excellent 

20

Vacation home in Puncknowle

Dorset / Puncknowle

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Large victorian cottage set in a quiet edge of village location with a large garden and views over surrounding countryside. Located just 1.5 miles from the sea and the well known Jurassic coast with its stunning scenery. The village is close to Weymouth to the east and  …see more

from $106 / night

$484 - $1333 / week

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from $106 / night

(37) Very Good 

17

West Bexington Vacation chalet rental

Dorset / West Bexington

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Chesil Lodge Cottage is situated in the beautiful coastal hamlet of West Bexington, one of Dorset's best kept secrets, and just a stone's throw from the spectacular Chesil beach. The cottage itself is a comfortably appointed wooden chalet with its own private  …see more

from $49 / night

$248 - $862 / week

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from $49 / night

(3) Excellent 

19

Vacation apartment in Bournemouth

Bournemouth / Sandbanks

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Lower rates available when booking directly through 'Smart Holiday Rentals' website. Please enter the following reference in the quick search box: 3 Seahaven Seahaven is located on Banks Road, Sandbanks; the perfect location for a lovely family holiday in a t  …see more

from $158 / night

$609 - $1529 / week

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from $158 / night

(11) Excellent 

26

Vacation home in Langton Matravers

Swanage / Langton Matravers

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Kilderkin Cottage provides contemporary living in a Purbeck stone cottage. Set in a quiet conservation area its open plan and spacious rooms are newly fitted with comfortable furnishings and modern day conveniences. The cosy and welcoming 'home away from home'  …see more

from $134 / night

$589 - $1563 / week

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from $134 / night

(4) Excellent 

18

Charminster Vacation cottage rental

Dorset / Charminster

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Pet friendly
The Wagon House holiday cottage is the old converted Wagon House with a galleried ceiling exposing oak beams. Suitable for families or couples, this cottage is all on one level and has a large sitting room with a woodburner in an inglenook fireplace. It has a separate  …see more

from $106 / night

$519 - $1054 / week

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from $106 / night

(21) Excellent 

19

Vacation apartment rental

Dorset / Weymouth

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Car not necessary
Little Gem - uninterruptable front line sea views positioned only 30 meters from sea and overlooking Portland Harbour the 2012 Olympic venue, and the remains of Sandsfoot castle. Off road dedicated parking within property boundary. Quite and tranquil location and only a  …see more

from $100 / night

$534 - $800 / week

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from $100 / night

(61) Excellent 

24

Vacation apartment rental

Dorset / Bournemouth

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly
A charming small block of four apartments in the very heart of Bournemouth, just a short walk to the beach or shops. The Farthings are charming and each of the apartments has their own charm and character, they are fitted out to a high standard with quality fittings and  …see more

from $82 / night

$495 - $1154 / week

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from $82 / night

(10) Excellent 

34

Vacation townhouse in Lyme Regis

Dorset / Lyme Regis

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
General Info Number 6 Church Street (DT7 3BS), dates back to 1600 and can be found a short distance from the middle of town near the Tourist Information Office and Theatre. The property is only a few steps from the sea and middle of town. Lyme has a variety of pubs and  …see more

from $186 / night

$682 - $2232 / week

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from $186 / night

(13) Excellent 

24

Vacation home with golf nearby in Poole Harbour

Poole / Poole Harbour

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Car not necessary
A beautiful one bedroom house located in the Harbourside Park area of Poole, just a five minute walk to the quay front and its many wonderful restaurants, bars. Lander also benefits from a landscaped decked patio area ideal for alfresco dinning. A well presented house  …see more

from $124 / night

$757 - $893 / week

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from $124 / night

4

Vacation cottage in Wareham

Dorset / Wareham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Pet friendly
CHARMING COTTAGE QUIETLY LOCATED WITHIN THE WALLS OF WAREHAM Located a short walk from the historic town centre this character cottage, dating back to 1750, still retains a lot of its original charm yet benefits from complete modernisation throughout. The traditio  …see more

from $81 / night

$565 - $1178 / week

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from $81 / night

(27) Excellent 

24

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 $87 / night

$372 - $1209 / week

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from $87 / 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 $116 / night

$514 - $1400 / week

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from $116 / night

(28) Excellent 

24

Home rental in Rodwell

Weymouth / Rodwell

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
A wonderful self contained and well equipped self catering house with all of the modern amenities to make your stay a memorable one and just a stones throw from the sea. Perfectly located for the beach, town and habour. It sleeps 5 with 1 main bedroom with a double bed  …see more

from $195 / night

$1364 / week

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from $195 / night

4

Vacation home in Buckhorn Weston

Dorset / Buckhorn Weston

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
LOVELY BARN CONVERSION WITH GARDEN AND USE OF HOT TUB, CLOSE TO ATTRACTIONS SLEEPS 4+2 REDUCED PRICE FOR COUPLES DURING OFF PEAK SEASON - PLEASE CALL FOR DETAILS SPRING BREAKS - STAY WITH U  …see more

from $78 / night

$546 - $1154 / week

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from $78 / night

4

Vacation cottage in Charmouth

Bridport / Charmouth

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
1 OF 16 CHARMING PROPERTIES A STROLL FROM THE POPULAR WORLD HERITAGE JURASSIC COASTLINE REGRET NO BABIES OR CHILDREN UNDER 18 YEARS IN THIS PROPERTY OR FOSSIL COTTAGE, AMBER COTTAGE AND JURASSIC TIDE LINE. WELCOME IN ALL OTHER PROPERTIES ON SITE This gated holiday  …see more

from $62 / night

$434 - $924 / week

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from $62 / night

4

Vacation home in Charmouth

Charmouth / Fernhill

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
SINGLE LEVEL PROPERTY SET WITHIN 30 ACRES WITH BREATHTAKING SURROUNDINGS REGRET NO CHILDREN OR BABIES The compact accommodation has been renovated with great care and is a perfect location for enjoying the countryside and makes the perfect touring base for discove  …see more

from $57 / night

$397 - $813 / week

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from $57 / night

19

Vacation home in Sherborne

Dorset / Sherborne

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 27 mi
  • Child friendly
  • Car not necessary
Detached spacious 3 bed cottage. Offers parking, short walk to the beautiful Abbey town of Sherborne. The cottage offers all the facilities to make your stay comfortable, including Towels, bedding.. It is lovely & Warm & spacious . Short walk to the main Waterl  …see more

from $106 / night

$738 / week

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from $106 / 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 $137 / night

$955 - $1997 / week

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from $137 / night

(28) Excellent 

44

Vacation apartment in Bournemouth

Bournemouth / Sandbanks

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
A bright modern child friendly 1st floor apartment on the exclusive Sandbanks peninsula. This 2 bedroom 2 bathroom apartment is a 2 minute walk from the award winning blue flag sandy beaches, beautiful sunsets over Poole harbour, Brownsea Island and Studland peninsula.  …see more

from $168 / night

$924 - $1389 / week

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from $168 / night