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3,606 Holidays in Dorset, the South West of England

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House in West Bay, Dorset

House In West Bay, Dorset

West Bay, Dorset

15

Set within expansive private grounds, this stylish, detached property overlooks the Dorset countryside from its high vantage point. Accessed via country lanes, this spacious, bright and airy house is ideal for exploring the coast and town, which are within easy reach. Nearby…

  • Internet
  • Pub Nearby
  • Open Fire
Weekly from £3220
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
Wimborne House

Wimborne House

Wimborne, Dorset

16

Wimborne House holds a wonderful position on the outskirts of the market town of Wimborne Minster, set in a quiet spot which is just a quick stroll from the town square, the centre of all the action! For those looking to explore the beautiful country of Dorset, there is no…

  • Hot Tub / Jacuzzi
  • Internet
  • Open Fire
Weekly from £2972
Beach Side

Beach Side

Poole, Dorset

8

Welcome to Beach Side, a haven of tranquility with panoramic ocean views. Beach Side has been is an adored family home, owned by the same family for over 70 years. It has become a home away from home for not only them but guests that have been fortunate enough to stay. A perfect…

  • Pets Allowed
  • Internet
  • Pub Nearby
Weekly from £2927
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
Sherborne Cottage

Sherborne Cottage

Sherborne, Dorset

6

Sherborne Cottage holds a wonderful location in the heart of the popular Dorset town of Sherborne, where a variety of excellent pubs and restaurants as well as helpful supermarkets can be found within walking distance. The cottage is owned by the neighbouring hotel and so guests…

  • Hot Tub / Jacuzzi
  • Internet
  • Open Fire
Weekly from £2903
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
Wraxall Yard

Wraxall Yard

Dorchester, Dorset

21

Created to provide comfortable, elegant and attractive environments, Wraxall Yard is a development of five beautifully restored barns designed as a peaceful retreat for families including guests with disabilities. Set around a pretty shared courtyard garden and surrounded by…

  • Pets Allowed
  • Baby Friendly
Weekly from £2706
The Headlands

The Headlands

Weymouth, Dorset

6

A true coastal retreat situated on the stunning World Heritage Coastline between Chesil Beach and the Fleet nature Reserve, this well-designed property gives many opportunities to soak up the coastal views in comfort.   Up to six guests can enjoy the delights this…

  • Hot Tub / Jacuzzi
  • Internet
Weekly from £2652
Little Picket

Little Picket

Ringwood, Dorset

12

Ringwood 3 miles. Nestled within the New Forest National Park, on the outskirts of Ringwood in Hampshire is Little Picket, a fabulous, five-bedroom home. With an expansive garden, featuring a hot tub with swim spa, a private tennis court, and a bar, Little Picket also offers…

  • Pets Allowed
  • Baby Friendly
  • Internet
  • Open Fire
Weekly from £2646
Langton Barn

Langton Barn

Weymouth, Dorset

10

Nestled in the idyllic Dorset countryside, close to the seaside town of Weymouth, Langton Barn offers all the space and airy openness you’d expect from a lovely barn conversion! You’re surrounded by huge, open fields and the sea in the distance, and the interiors are…

  • Hot Tub / Jacuzzi
  • Internet
Weekly from £2606
Park House

Park House

Dorchester, Dorset

19

Situated within the grounds of the Came House Estate, Park House is a combination of our two handsome houses, The Garden House and The Courtyard House, which together can accommodate up to 19 guests in style. Dating from the mid 18th century, both properties enjoy the splendour…

  • Pets Allowed
  • Baby Friendly
Weekly from £2571
The Esplanade

The Esplanade

Weymouth, Dorset

18

The Esplanade is a stunning Georgian, Grade II listed, nine-bedroom holiday dwelling located in the beautiful seaside town of Weymouth, Dorset. Enjoy breathtaking sea views from the comfort of this spacious home, complete with a collection of en-suite bedrooms, free off-road…

  • Internet
  • Pub Nearby
  • Coast Nearby
Weekly from £2540
Number Twelve

Number Twelve

Poole, Dorset

8

Fabulous four bedroom, detached home located in Lilliput near Sandbanks overlooking Poole Harbour. The entire house is furnished to a very high standard, with carefully chosen pieces thoughtfully maintained by the owners. The kitchen is very well-equipped, with modern…

  • Pets Allowed
  • Hot Tub / Jacuzzi
  • Internet
  • Open Fire
Weekly from £2509
Beach View

Beach View

Poole, Dorset

8

We are delighted to add this wonderful, beach fronting home to our portfolio for 2023. Located in an elevated position above the beach and offers wonderful panoramic views across the bay stretching from the Isle of Wight to Old Harry Rocks on the Purbecks. With direct access to…

  • Internet
  • Pub Nearby
Weekly from £2509
Allure

Allure

Poole, Dorset

10

Located in the peaceful centre of Sandbanks peninsula, Allure is a bright, spacious and luxurious detached holiday home sleeping up to ten guests in five stunning bedrooms. The house is just a short walk from the famous blue flag beach that stretches eight miles along our…

  • Pets Allowed
  • Internet
  • Pub Nearby
Weekly from £2476
Stapleford Farm Cottages

Stapleford Farm Cottages

Beaminster, Dorset

20

The three individual cottages at Stapleford Farm are perfect for accommodating large families or groups and provide an ideal setting for gathering everyone together for a special occasion or holiday. The largest cottage, Drackenorth Lodge features a stunning dining hall which is…

  • Pets Allowed
  • Baby Friendly
Weekly from £2395
The Orchard Country House

The Orchard Country House

Rousdon, Dorset

26

Nestling in gardens complete with an impressive orchard, is this outstanding holiday home, The Orchard Country House in Rousdon, just outside Lyme Regis on the Devon/Dorset border. Perfect for large gatherings, The Orchard Country House is set within a former boutique hotel and…

  • Internet
  • Pub Nearby
  • Open Fire
Weekly from £2388
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
Coastguards

Coastguards

Poole, Dorset

6

Frontline property with direct access to a private beach and Poole Harbour This wonderful home is tucked away on Sandbanks in the most historic part of the Dorset coastline. Old Coastguards Road is one of the most historic parts of the peninsula which was well known to seafarers…

  • Internet
  • Pub Nearby
Weekly from £2349

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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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