50 Best Dorset Self catering on Holiday Lettings - Cottages

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1,549 Vacation rentals

(15) Very Good 

Certificate of Excellence

9

Isle of Portland Vacation home rental

Dorset / Isle of Portland

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Pebbles view is a Victorian Portland stone built mid terrace cottage in the village of Fortuneswell Portland offering stunning panoramic sea views of the Jurassic coasts Chesil beach from all floors The newly refurbished cottage arranged over three floors comprises …see more

Certificate of Excellence

from $99 / night

$655 - $787 / week

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Responds fast!
avg. 2 hours 3 minutes

from $99 / 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 $156 / night

$832 - $1755 / week

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avg. 2 hours 3 minutes

from $156 / night

(21) 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 $130 / night

$844 - $1923 / week

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from $130 / night

Featured properties

(38) 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 $169 / night

$845 - $2197 / week

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avg. 1 hour 23 minutes

from $169 / night

(29) Excellent 

12

Vacation home in Netherbury

Bridport / Netherbury

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Child friendly
Get away from it all in beautiful West Dorset and have a taste of the Good Life! Springfield House Annex offers a luxurious hideaway where you can enjoy absolute peace and quiet either outside in the large, enclosed garden or warming your toes indoors by the woodburne …see more

from $111 / night

$910 - $1001 / week

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Responds fast!
avg. 1 hour 52 minutes

from $111 / night

(12) 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 0.3 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, then the sandy beach is but a short walk away. The Jetty is fully equipped for a truly relaxing holid …see more

from $120 / night

$675 - $1950 / week

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avg. 3 hours 16 minutes

from $120 / night

(9) Excellent 

10

Swanage Bay Vacation apartment rental

Swanage / Swanage Bay

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
Spacious Maisonette Apartment on a clifftop position with Panoramic views over Swanage Bay, sleeps 7 comfortably, with access to both the beach and countryside on its doorstep. Free WIFI, Bedlinen, SkyTV, and Utilities all included in the price. Wake up to sunrise over …see more

from $254 / night

$1430 - $1560 / week

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avg. 1 hour 0 minutes

from $254 / night

(2) 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 $215 / night

$1229 - $2405 / week

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from $215 / night

(7) Very Good 

16

Bournemouth Vacation home rental

Dorset / Bournemouth

5 20 Min stay varies

  • 5 bedrooms
  • Sleeps 20
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
This quirky holiday property is a converted Old Brewery and features an original, listed, wooden lift in the hallway. The property is surrounded by local pubs, shops, bars and restaurants. Good connections to Bournemouth (around 13-15 minute taxi ride) to town centre …see more

from $520 / night

$2600 - $3250 / week

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from $520 / night

(77) 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 $117 / night

$780 - $1365 / week

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from $117 / night

(11) Excellent 

17

Vacation cottage in Sutton Poyntz

Weymouth / Sutton Poyntz

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly
Laurel Cottage is a charming 300 year old thatched cottage in the heart of the peaceful village of Sutton Poyntz on the outskirts of the seaside resort town of Weymouth. The interior has been refurbished to a high standard combining a modern kitchen and bathrooms with …see more

from $186 / night

$1300 - $1937 / week

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avg. 1 hour 58 minutes

from $186 / night

(5) Excellent 

45

Vacation cottage in Chesil Beach

Bridport / Chesil Beach

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly
Short House is a Purbeck stone and render cottage, part of the Long House small private country estate fronting Chesil Beach on Dorset's World Heritage Jurassic Coast, surrounded by National Trust farmland. Short House has recently been completely re-fitted with a la …see more

from $130 / night

$910 - $1892 / week

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avg. 2 hours 50 minutes

from $130 / night

(30) Very Good 

16

Vacation cottage in Wyke Regis

Weymouth / Wyke Regis

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Moonfleet is a two bedroom cottage located on the edge of Portland Harbour; the waters that hosted the 2012 Olmpic Sailing. Presented to a high standard this accommodation sleeps 5, with two double bedrooms (one with a double and single bed) a spacious lounge/diner and …see more

from $77 / night

$507 - $936 / week

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avg. 2 hours 44 minutes

from $77 / night

(16) 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 $149 / night

$838 - $2600 / week

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avg. 3 hours 16 minutes

from $149 / night

(8) 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 $55 / night

$426 - $965 / week

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avg. 1 hour 38 minutes

from $55 / night

(16) 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 for the 2016 season. New features include a stunning 50" fla …see more

from $104 / night

$650 - $1235 / week

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Responds fast!
avg. 23 minutes

from $104 / night

(3) Excellent 

20

Bournemouth Vacation apartment rental

Bournemouth / Southbourne

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Latutude West is located in the peaceful location of Southbourne-on-sea; perfect for easy access to the award winning blue flag beaches, just a 2 minute walk away! Local shops are just a 5-10 minute walk away with various restaurants and bars on Southbourne-on-sea highs …see more

from $150 / night

$637 - $1411 / week

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from $150 / night

(11) Excellent 

32

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 $195 / night

$780 - $2340 / week

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avg. 2 hours 43 minutes

from $195 / night

(14) Excellent 

14

Vacation apartment in Swanage Bay

Swanage / Swanage Bay

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Springhill House sits in the heart of Swanage with the Beaches,Restaurants and local amenities on your doorstep. Recently updated this split level apartment benefits from one large master suite, one large sized twin bedroom and a single box bedroom, lounge with access t …see more

from $140 / night

$975 - $1261 / week

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avg. 2 hours 40 minutes

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 $195 / night

$507 - $1339 / week

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from $195 / night

(26) 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 $104 / night

$559 - $839 / week

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avg. 3 hours 17 minutes

from $104 / night

(6) 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 $325 / night

$961 - $2183 / week

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from $325 / night

28

Townhouse rental in Bournemouth

Bournemouth / Lansdowne

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Carlton Road is a newly completed three bedroom semi-detached holiday property, offering a modern and contemporary finish, this property is ideal for families. The ground floor facilities include a dinning area, spacious lounge and an enclosed private garden/patio area …see more

from $124 / night

$868 - $1304 / week

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from $124 / 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 $111 / night

$644 - $2074 / week

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from $111 / night

(16) Excellent 

23

Home rental in Swanage Bay

Swanage / Swanage Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
This is a detached house in an elevated position in Swanage with wonderful views overlooking Swanage Bay, Old Harry Rocks and the Isle of Wight. The garden in the front and to the side of the house is laid to lawn and at the back of the house is a Purbeck stone patio b …see more

from $121 / night

$845 - $1625 / week

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from $121 / 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

21

Vacation apartment in Bournemouth

Bournemouth / West Cliff

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Flat B Durley Chine Road South is a beautiful attic apartment, the newly refurbished (Feb, 2015) two bedroom apartment offers great convenience and finds the perfect mix of comfort and convenience. Situated in the very popular location of Westcliff, guest can truly make …see more

from $146 / night

$617 - $1246 / week

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from $146 / night

(34) 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 $130 / night

$780 - $1430 / week

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avg. 2 hours 28 minutes

from $130 / night

(16) Excellent 

21

Vacation caravan/mobile home with golf nearby in Mudeford

Christchurch / Mudeford

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
If you love the great British seaside but prefer to keep it simple, Mudeford could well be your place. And if you want to stay in comfort just 200 yards from a long sandy beach that isn't too busy, then the Bolt Hole could be a great base for you. Tucked into wo …see more

from $180 / night

$754 - $1248 / week

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avg. 3 hours 20 minutes

from $180 / night

(19) 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 $137 / night

$813 - $1430 / week

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Responds fast!
avg. 1 hour 0 minutes

from $137 / night

(6) Excellent 

Certificate of Excellence

27

Vacation caravan/mobile home in West Bay

Bridport / West Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Child friendly
A six berth static caravan with stunning views across the river towards the Jurassic cliffs and West Bay in one direction and the bustling market town of Bridport in the other direction. Ten minute walk to the harbour where fishing boats still come and sell their catch, …see more

Certificate of Excellence

from $94 / night

$734 - $885 / week

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Responds fast!
avg. 30 minutes

from $94 / night

(34) Excellent 

34

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 $111 / night

$403 - $1112 / week

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Responds fast!
avg. 2 hours 48 minutes

from $111 / night

(32) 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 - $1333 / week

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avg. 1 hour 35 minutes

from $91 / 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 $390 / night

$1950 / week

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from $390 / night

(7) 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 $254 / night

$1144 - $2145 / week

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Responds fast!
avg. 3 hours 49 minutes

from $254 / night

(9) Excellent 

39

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 $293 / night

$1560 - $2145 / week

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Responds fast!
avg. 3 hours 32 minutes

from $293 / night

(69) Excellent 

23

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 $86 / night

$519 - $1278 / week

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Responds fast!
avg. 1 hour 1 minutes

from $86 / night

(32) Excellent 

Certificate of Excellence

28

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 $98 / night

$358 - $644 / week

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Responds fast!
avg. 48 minutes

from $98 / night

(16) 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
  • Child friendly
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 love …see more

from $143 / night

$1001 - $2093 / week

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Responds fast!
avg. 1 hour 22 minutes

from $143 / night

(20) Excellent 

24

Apartment rental in Swanage Bay

Swanage / Swanage Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
'Island View' offers light, spacious and newly refurbished accommodation over 2 floors with spectacular views of the coastline from all main rooms and is fully equipped for all your holiday needs. Watch the boats in the bay and the comings and goings from the pier thro …see more

from $98 / night

$553 - $878 / week

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Responds fast!
avg. 2 hours 53 minutes

from $98 / night