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159 Holiday Cottages with a Swimming Pool in Dorset, the South West of England

Accommodation sleeping any number of people

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The Downwood

The Downwood

Blandford Forum, Dorset

16

The Downwood is a truly breath-taking detached holiday home nestled in Dorset’s picturesque countryside on the edge of Blandford Forum. This fabulous, dog friendly holiday home benefits from a fun-filled outdoor area including an outdoor pool, a tennis court, a badminton and…

  • Pets Allowed
  • Swimming Pool
  • Internet
  • Pub Nearby
Weekly from £5964
Branksome Wood House

Branksome Wood House

Poole, Dorset

10

Branksome Wood House, an architect-designed, detached house is set on a private road within Poole, Dorset. centred around one acre of gated gardens. Featuring an indoor pool, hot tub, sauna and pizza oven, as well as en-suite bedrooms and a study, Branksome Wood House provides…

  • Pets Allowed
  • Swimming Pool
  • Baby Friendly
  • Internet
  • Pub Nearby
  • Coast Nearby
Weekly from £4374
House in Bridport, Dorset

House In Bridport, Dorset

Bridport, Dorset

17

Just half a mile from an idyllic village with its friendly local pub, and only three miles from the Jurassic Coast. The local village provides shops with local produce including fresh bread, pastries, cheese and local beer, gin and wine you won t have to go far for these tasty…

  • Swimming Pool
  • Hot Tub / Jacuzzi
  • Pub Nearby
  • Coast Nearby
  • Open Fire
  • Sky TV
Weekly from £4080
Tamarisk

Tamarisk

Poole, Dorset

9

We are delighted to introduce this amazing property to the Rumsey Bespoke portfolio. Located in a private and elevated position on the edge of Poole Harbour, Tamarisk is flooded with crisp seaside light and boasts panoramic sea views across the harbour and over to Brownsea…

  • Pets Allowed
  • Swimming Pool
  • Hot Tub / Jacuzzi
  • Internet
  • Pub Nearby
Weekly from £3117
Baytree Lodge

Baytree Lodge

Osmington, Dorset

10

This exquisite holiday home, tucked away in the village of Osmington (less than a mile from the sea) and backing onto countryside, ticks all the boxes for a perfect memorable family holiday. From the moment you walk into this modern spacious property you will be wowed with its…

  • Swimming Pool
  • Internet
  • Pub Nearby
Weekly from £2920
Cottage in Highcliffe, Dorset

Cottage In Highcliffe, Dorset

Highcliffe, Dorset

12

Highcliffe is a small coastal town boasting both beautiful beaches and superb views. Take a walk through the nature reserve, where wildlife abounds, or visit the historic clifftop castle, which overlooks the beach. You will find a good variety of shops, cafes, and restaurants in…

  • Swimming Pool
  • Internet
  • Pub Nearby
  • Coast Nearby
Weekly from £2767
Panorama 39

Panorama 39

Poole, Dorset

8

Wake up to a beautiful harbour view in this luxurious, contemporary holiday home. Situated on Sandbanks Peninsula and just a short walk away from the world famous Blue Flag Sandbanks beach, Rick Stein's Restaurant and the yacht clubs. Panorama 39 has been extensively and…

  • Pets Allowed
  • Swimming Pool
  • Hot Tub / Jacuzzi
  • Internet
  • Pub Nearby
Weekly from £2349
Royal Oak House

Royal Oak House

Motcombe, Dorset

14

Royal Oak House is an incredible high-end property, meticulously converted from a former pub to an exceptional standard. Situated on two acres on the picturesque Dorset-Wiltshire border in Motcombe, Dorset, this period property dates back to 1875. With off-road parking, this…

  • Swimming Pool
  • Internet
  • Pub Nearby
Weekly from £2319
Manor Farm Barn

Manor Farm Barn

Dewlish, Dorset

15

Set in the pretty Dorset village of Dewlish, Manor Farm Barn is a beautiful conversion of an 18th century barn that faces into a courtyard. With large flagstone floors, a farmhouse kitchen with a table big enough for everyone and spacious rooms, this is the perfect place for the…

  • Swimming Pool
  • Baby Friendly
  • Internet
  • Pub Nearby
Weekly from £2013
House in Minterne Magna, Dorset

House In Minterne Magna, Dorset

Minterne Magna, Dorset

10

The village of Minterne Magna is steeped in history and home to the beautiful Minterne gardens, which host a mass of flowering plants, nestled in a unique Himalayan valley and surrounded by wonderful views of the Dorset landscape. It is famous for an important collection of…

  • Swimming Pool
  • Internet
  • Open Fire
Weekly from £1796
Somerhill

Somerhill

Lyme Regis, Dorset

10

Offering truly outstanding accommodation complete with a stunning outdoor heated swimming pool, is this spacious, detached property, Somerhill. The perfect location for large gatherings of family and friends, Somerhill has everything needed for a relaxing and enjoyable stay. The…

  • Swimming Pool
  • Internet
  • Pub Nearby
  • Coast Nearby
  • Open Fire
Weekly from £1778
Deer Leap House

Deer Leap House

Moreton, Dorset

15

Nestled on the outskirts of the village of Moreton in Dorset and set on beautiful grounds is Deer Leap House, aptly named for the wild, roaming deer you may spot while here. This wonderfully spacious holiday home welcomes up to 15 guests across seven spacious and well-appointed…

  • Swimming Pool
  • Internet
  • Pub Nearby
Weekly from £1767
Dominey's Yard

Dominey's Yard

Buckland Newton, Dorset

18

Collectively called Dominey's Yard, the delightful cottages of GardenerÕs, PoacherÕs, WoodcutterÕs and GamekeeperÕs sit side by side. They offer splendid accommodation for individual families or larger gatherings. Each cottage is beautifully furnished and well-equipped and…

  • Swimming Pool
  • Baby Friendly
  • Pub Nearby
Weekly from £1674
House in Poole, Dorset

House In Poole, Dorset

Poole, Dorset

8

This property enjoys a sought after location in the village of Canford Cliffs close to the Sandbanks peninsula. The village beach with its golden sands, is a short walk away, allowing guests to enjoy a true seaside holiday. A little way down the beach is the Sandbanks peninsula…

  • Swimming Pool
  • Internet
  • Pub Nearby
  • Coast Nearby
  • Open Fire
Weekly from £1587
Swandown, 14 Goldenhaye

Swandown, 14 Goldenhaye

Cricket St. Thomas Near Chard, Dorset

6

Set within the 1,000-acre Swandown Lodges Estate, in Cricket St. Thomas in Somerset, is this opulent three-bedroom lodge, 14 Goldenhaye. Offering access to a variety of on-site facilities, including an exclusive spa for adults and a child-friendly adventure trail, whilst…

  • Swimming Pool
  • Internet
  • Pub Nearby
Weekly from £1080
Cottage in Charmouth, Dorset

Cottage In Charmouth, Dorset

Charmouth, Dorset

10

Situated in the traditional Dorset seaside village of Charmouth, this gated holiday complex offers a selection of well thought out, purpose built accommodation within these converted former farm buildings. With onsite leisure facilities for all ages, the property is also…

  • Swimming Pool
  • Internet
  • Pub Nearby
  • Coast Nearby
Weekly from £1074
Swandown, 12A Goldenhaye

Swandown, 12A Goldenhaye

Cricket St. Thomas Near Chard, Dorset

6

Tucked away within the breath-taking parkland of the renowned Swandown Lodges Estate in Cricket St. Thomas, Somerset, is this luxury three-bedroom lodge, 12A Goldenhaye. Enjoying a superb location with access to on-site facilities, an exclusive spa for adults and a…

  • Swimming Pool
  • Internet
  • Pub Nearby
Weekly from £1070
Cottage in Charmouth, Dorset

Cottage In Charmouth, Dorset

Charmouth, Dorset

8

This gated holiday complex is just a short stroll from the traditional Dorset seaside village of Charmouth. Here you will find an array of shops and pubs, ideal for picking up the morning paper or enjoying a hearty meal at the end of a long walk. If you re looking for stunning…

  • Swimming Pool
  • Internet
  • Pub Nearby
  • Coast Nearby
Weekly from £834
Swandown, 19 Poldon

Swandown, 19 Poldon

Cricket St. Thomas Near Chard, Dorset

6

19 Poldon is a stunning, reverse-level lodge set on the renowned Swandown Lodges Estate in Cricket St. Thomas, Somerset. Surrounded by breath-taking parkland on the 1,000-acre estate, this stylish lodge has a contemporary interior, off-road parking, a private garden with hot…

  • Swimming Pool
  • Internet
  • Pub Nearby
Weekly from £813
Swandown, 20 Poldon

Swandown, 20 Poldon

Cricket St. Thomas, Dorset

6

Settled within a stunning 1,000-acres of parkland on the renowned Swandown Lodges Estate at Cricket St. Thomas, Somerset, is this luxury reverse-level lodge, 20 Poldon. Offering access to a variety of on-site facilities, including an exclusive spa for adults and a child-friendly…

  • Swimming Pool
  • Internet
  • Pub Nearby
Weekly from £813

We've found 159 properties

Explore the South West of England

Big fields, rolling countryside and the stunning Jurassic coast, rich with fossils, make Dorset a beautiful and fascinating place to visit. With abundant wildlife, ancient woodlands and the South West Coast Path National Trail running through, it's a great place for walkers and naturalists. Lots of historic houses and gardens to visit too.

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