50 Best Dorset Self catering on Holiday Lettings - Cottages

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287 properties
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Estates Shaftesbury
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Dorset

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1,480 Vacation rentals

(11) Excellent 

27

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' atmospher …see more

from $140 / night

$833 - $1626 / week

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from $140 / 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 and c …see more

from $194 / night

$504 - $1329 / week

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from $194 / night

(22) Excellent 

35

Vacation cottage with tennis court in Tincleton

Dorchester / Tincleton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 16 mi
  • Child friendly
TINCLETON LODGE is a luxury self-catering accommodation awarded both with 5 Star and coveted with English Tourist Board GOLD award and the M3a Disability for 2016. Free Wi-FI. Offering spacious accommodation for up to 10 with 5 bedrooms and 4 bathrooms. Secure garde …see more

from $320 / night

$1284 - $3090 / week

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from $320 / 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 $136 / night

$807 - $1419 / week

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from $136 / night

(13) 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 0.3 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 $148 / night

$831 - $2580 / week

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from $148 / night

(40) Very Good 

17

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 $55 / night

$422 - $958 / week

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from $55 / night

(5) Excellent 

17

Weymouth Vacation cottage rental

Dorset / Weymouth

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0.1 mi
  • Child friendly
  • Car not necessary
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 Dormouse cottage is spot on. Just 70 yards to the left you will find the famous blue flag central beach and espla …see more

from $54 / night

$419 - $950 / week

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from $54 / night

(30) 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 $91 / night

$390 - $1268 / week

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from $91 / night

(37) Excellent 

19

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. Romantic, …see more

from $109 / night

$634 - $954 / week

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from $109 / night

(42) 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
Due to a cancellation AUGUST WEEK available HOLIDAY HOUSE SWANAGE is an end of terrace Victorian house full of charm and character. Downstairs there is a cosy comfortable living room with dining area,plenty of seating. T.V., DVD Player,WI-FI .The kitchen has everythi …see more

from $130 / night

$780 - $1430 / week

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from $130 / 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 cottage A 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 do, or jus …see more

from $74 / night

$510 - $962 / week

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from $74 / night

(1) Very Good 

15

Vacation apartment in Bournemouth

Dorset / Bournemouth

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Our family run apartment makes for a wonderful base when staying in Bournemouth or visiting the wider area. You may be looking for a short break to get away from it all and enjoy the tranquillity of Bournemouth's famous gardens and beach, a more energetic long weekend …see more

from $74 / night

$620 / week

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from $74 / 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 $96 / night

$429 - $1103 / week

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from $96 / 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 $155 / night

$826 - $1742 / week

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from $155 / night

(1) Excellent 

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 after Sydney. …see more

from $213 / night

$1220 - $2322 / week

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from $213 / night

(37) 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 $168 / night

$891 - $2129 / week

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from $168 / night

(2) Excellent 

10

Vacation apartment in Bournemouth

Dorset / Bournemouth

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
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 $387 / night

$1935 / week

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from $387 / night

34

Poole Harbour Vacation townhouse rental

Poole / Poole Harbour

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Private garden
This three bedroom, two storey town house is situated in a quiet residential close on Poole Quay. The property hosts a perfect location for a holidaymakers in a tasteful setting just a few minutes stroll from the beach; offering gorgeous panoramic sea views. Its easy tr …see more

from $215 / night

$920 - $1789 / week

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from $215 / night

(33) 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 $120 / night

$535 - $1457 / week

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from $120 / night

(11) Good 

21

Vacation home in West Lulworth

Dorset / West Lulworth

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Family holiday home in West Lulworth village near beautiful Lulworth Cove on the UNESCO Jurassic Coast of Dorset. Great house and location for family holidays, coastal walking or short breaks in this stunning coastal region .End of terrace in quiet residential area on …see more

from $117 / night

$742 - $915 / week

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from $117 / night

(6) Very Good 

23

Vacation cottage rental

Corfe Castle / Kingston, Dorset

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
19th Century Purbeck stone cottage and summer house(sleeps 6 + 4) with breath-taking views of Corfe Castle. Perfect location for a bucket and spade beach holiday or a large family get together. Perfect for walkers too as 1 mile from the South West Coast Path. The cotta …see more

from $252 / night

$1136 - $2129 / week

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from $252 / night

(13) 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 $140 / night

$598 - $977 / week

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from $140 / night

(3) Excellent 

47

Bournemouth Vacation apartment rental

Dorset / Bournemouth

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
NB I do not normally take bookings more than 6 months in advance. Please contact me if you wish to make such a booking so that I can quote availability and price. A bright, clean apartment close to miles of sandy beach and Bournemouth town centre. Parking right in …see more

from $116 / night

$1024 - $1741 / week

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from $116 / night

(31) Excellent 

20

Vacation cottage in Tolpuddle

Dorchester / Tolpuddle

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 24 mi
  • Child friendly
  • Pet friendly
Adjacent to a bridle path so ideal for walkers and dog owners, West Lane Cottage is a modern cottage built using reclaimed materials and furnished to reflect it's Country setting. Piddlehinton is a delightful village which has a pub and a children's play area both of w …see more

from $104 / night

$542 - $1103 / week

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from $104 / night

(24) Very Good 

Certificate of Excellence

33

Langton Herring Vacation cottage rental

Weymouth / Langton Herring

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Private garden
Far from the madding crowds, set down its own private leafy driveway nestled in 8 acres of fields and woodland. The old cottage dates back to the early Victorian age and is full of charm and character. It has an open fire, oil fired central heating, and has a warm ho …see more

Certificate of Excellence

from $154 / night

$576 - $1024 / week

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from $154 / night

(33) Excellent 

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

from $84 / night

$491 - $800 / week

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from $84 / night

(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 benefits of t …see more

from $162 / night

$1065 / week

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from $162 / night

(10) 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 $280 / night

$1871 - $3741 / week

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from $280 / night

(34) Excellent 

30

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 combines rustic …see more

from $123 / night

$504 - $1278 / week

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from $123 / night

(73) 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 , An attractive cottage built from Purbeck. Stone , full of character,situated in the oldest part of Swanage. Just 5 mins walk from the town centre, beach and Steam Railway. The house is perfect for families or coup …see more

from $117 / night

$774 - $1355 / week

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from $117 / night

(31) 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 cottage …see more

from $129 / night

$774 - $1419 / week

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from $129 / night

(34) Excellent 

31

Apartment rental in Sandbanks

Bournemouth / Sandbanks

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Shore Point is situated in the heart of the prestigious Sandbanks peninsular. The property is in Brownsea Road, a quiet and peaceful location yet just a minute or two's walk from the award winning Sandbanks beaches and is at the entrance of one of the world's largest na …see more

from $234 / night

$1281 - $2295 / week

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from $234 / night

(30) Very Good 

31

Vacation home in Lyme Regis

Dorset / Lyme Regis

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Teal House is an 18th Century property in the heart of Lyme Regis split over 3 floors, sleeping up to 8 people in 4 bedrooms plus bathroom, shower room and outside toilet. The house has recently been refurbished to a high standard. Oak flooring throughout the gro …see more

from $194 / night

$1155 - $2058 / week

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from $194 / night

(59) Excellent 

19

Cottage rental in Bradpole

Bridport / Bradpole

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Daisy Cottage is situated in a quiet and peaceful location, and not too far away from amenities. Within a 5 minute drive you can reach the market town of Bridport and with 10 minutes the Beautiful Jurassic coastline. Daisy cottage has a modern spacious open plan …see more

from $142 / night

$516 - $1226 / week

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from $142 / night

(12) 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 $71 / night

$491 - $1079 / week

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from $71 / night

(29) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $97 / night

$355 - $639 / week

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from $97 / night

(12) 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
  • Private garden
Booking fee included in Price with Weymouth Harbour View! Video Tour: https://youtu.be/sWvEXoH02p4 32" Smart LCD TV's IN ALL BEDROOMS WITH SKY MOVIES AND FIBRE BROADBAND!!! LOCATION Directly on Weymouth's Old Harbour this 200 year old character house with uninte …see more

from $162 / night

$903 - $2116 / week

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from $162 / 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 panoramic …see more

from $429 / night

$1980 - $4940 / week

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from $429 / night

(31) Excellent 

25

Bridport Vacation bungalow rental

Dorset / Bridport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Sunnybrook is situated in a quiet cul-de-sac only three minutes level walk from Bridport town centre. This comfortable and spacious two-bedroomed bungalow offers visitors all the facilities of a medium sized Dorset market town, combined with the stunning scenery of the …see more

from $104 / night

$645 - $968 / week

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from $104 / night

(27) 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 $61 / night

$391 - $973 / week

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from $61 / night

1