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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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OLD HIGHER LIGHTHOUSE STOPES COTTAGE, with pool in Portland Bill

Old Higher Lighthouse Stopes Cottage, with Pool …

Portland, Dorset

4

This semi detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms. Stopes Cottage is a semi detached cottage next to a lighthouse on the tip of Portland Bill near to Weymouth in Dorset. The cottagesleeps four people in one…

  • Swimming Pool
  • Hot Tub / Jacuzzi
  • Baby Friendly
  • Internet
  • Coast Nearby
Weekly from £1246
Lakeside family friendly property (OI24)

Lakeside Family Friendly Property (oi24)

Warmwell, Dorset

6

OverviewOverton Island 24 is the perfect lakeside hideaway for any couple or group of friends with a cosy log burner and lakeside views. This property is brand new to the Habitat Escapes portfolio at Silverlake! It’s the perfect property for you to enjoy all that Dorset and…

  • Swimming Pool
  • Baby Friendly
  • Internet
Weekly from £1246
Luxury property with spa access on a nature reserve

Luxury Property with Spa Access On a …

Warmwell, Dorset

4

Silverlake is a true jewel located in West Dorset. Opportunity for adventure abounds at every turn with a heated infinity pool, a stunning private spa, roof bar, water sports, a private beach, tennis, table tennis and forest playgrounds. Step inside this cosy, mid-terrace cottage…

  • Swimming Pool
  • Internet
Weekly from £1232
Beautiful Country Cottage in Burley -  the Heart of the New Forest National Park

Beautiful Country Cottage in Burley …

Burley, Dorset

6

In the event of government restricting travel , refunds will be given 100% refund of amount paid if you cancel 60 days beore . 50% refund if cancelled 1 month before ( minute service fee) No refund if you cancel after 30 days before stay This is our Simply Owners family…

  • Swimming Pool
  • Baby Friendly
  • Internet
  • Coast Nearby
  • Open Fire
Weekly from £1225
Lakeside property with spa access on a nature reserve

Lakeside Property with Spa Access On a …

Dorset

6

Silverlake is a true jewel located in West Dorset. Opportunity for adventure abounds at every turn with a heated infinity pool, a stunning private spa, roof bar, water sports, a private beach, tennis, table tennis and forest playgrounds. ACCOMMODATIONOnce you’ve prepared…

  • Swimming Pool
  • Internet
  • Open Fire
Weekly from £1218
3 bedroom accommodation in Wareham

3 Bedroom Accommodation in Wareham

Wareham, Dorset

6

A spacious property with plenty to do inside and a fantastic base to stay to explore all of Dorset’s many wonders.. Ground Floor:Living/dining room: With coal-effect electric fire, 43" Freeview TV and patio doors leading to garden. Kitchen: With breakfast area, electric oven,…

  • Swimming Pool
  • Baby Friendly
  • Internet
Weekly from £1197
'Serendipity' - by the beach on Sandhills Holiday Park, Mudeford

'serendipity' - by the Beach On Sandhills …

Christchurch, Dorset

4

Serendipity:Serendipity is our spacious lodge on Sandhills Holiday Park in Mudeford, under two minutes' walk from the seafront promenade overlooking the beach. The property is well equipped to a high standard with everything you will need for comfortable stay by the sea. The…

  • Swimming Pool
  • Internet
Weekly from £1162
Baabara - Shepherds Hut - in Paddock with Alpacas & Sheep - Spa & Indoor Pool

Baabara - Shepherds Hut - in Paddock …

Nr Lyme Regis, Dorset

2

Baabara is an original Shepherds Hut renovated and ready for a peaceful get away from it all stay. It's situated by the pond, 200m from the complex with our ducks and moorhens in our paddock with alpacas, sheep, chickens and the odd bunny, pheasant, deer etc…. Baabara is fully…

  • Swimming Pool
  • Hot Tub / Jacuzzi
  • Internet
Weekly from £1092
Skydeck Holiday home with fabulous views over Chesil Beach and Portland Harbour

Skydeck Holiday Home with Fabulous Views Over …

Weymouth, Dorset

6

Our Sky Deck holiday home is situated on the award winning 5* Chesil Beach Holiday Park. Chesil Beach Holiday Park is part of the Waterside Holiday Group and is situated at the lower end of Wyke Regis, conveniently located near Weymouth, the national sailing academy and…

  • Pets Allowed
  • Swimming Pool
  • Internet
  • Coast Nearby
Weekly from £1085
Fern Cottage - Two Bedroom House, Sleeps 4

Fern Cottage - Two Bedroom House, Sleeps …

Fernhill, Dorset

4

A two bedroom, two bathroom property in a secluded development between Lyme Regis and Charmouth, with access to a communal pool, BBQ with beautiful lake and woodlands walks. Size: sleeps 4 in 2 bedrooms Beds:  1 x king size and 2 x singles Rooms: Living/dining room,…

  • Swimming Pool
  • Internet
Weekly from £1057
‘Everglade’ - a cosy coastal retreat by sea and by forest

‘everglade’ - a Cosy Coastal Retreat by …

Christchurch, Dorset

5

Everglade Holiday Home is a cosy seaside retreat situated on 5* Hoburne Park in Christchurch, Dorset, nestled between The New Forest & the spectacular Dorset Coast. Our beautiful 5 year old, 2 bedroom static caravan, sleeping 4 guests plus one infant, is a perfect retreat for…

  • Swimming Pool
  • Baby Friendly
  • Internet
  • Coast Nearby
Weekly from £1050
OLD HIGHER LIGHTHOUSE BRANSCOMBE LODGE, with pool in Portland Bill

Old Higher Lighthouse Branscombe Lodge, with Pool …

Portland, Dorset

4

This detached cottage is located on the tip of Portland Bill in Dorset and can sleep four people in two bedrooms. Brancombe Lodge is a detached cottage next to a lighthouse on the tip of Portland Bill near to Weymouth in Dorset. The cottage sleeps four people in one double…

  • Swimming Pool
  • Baby Friendly
  • Internet
  • Coast Nearby
Weekly from £1036
Family friendly property on a nature reserve with spa access

Family Friendly Property On a Nature Reserve …

Crossways, Dorset

4

Silverlake is a true jewel located in West Dorset. Opportunity for adventure abounds at every turn with a heated infinity pool, a stunning private spa, roof bar, water sports, a private beach, tennis, table tennis and forest playgrounds. Cosy mid-terrace two bed cottage nestled…

  • Pets Allowed
  • Swimming Pool
  • Baby Friendly
  • Internet
  • Open Fire
Weekly from £1022
Family friendly property in a nature reserve with spa. Swan Cottage (BV32)

Family Friendly Property in a Nature Reserve …

Warmwell, Dorset

4

Silverlake is a true jewel located in West Dorset. Opportunity for adventure abounds at every turn with a heated infinity pool, a stunning private spa, roof bar, water sports, a private beach, tennis, table tennis and forest playgrounds. Situated at the peak of the crescent in…

  • Pets Allowed
  • Swimming Pool
  • Internet
Weekly from £1001
Dorset - Freshwater Beach Holiday Home ...with its own private beach!

Dorset - Freshwater Beach Holiday Home ...with …

Bridport, Dorset

6

Freshwater Beach Holiday Home is a 2021 model 2 bedroom, 6 berth ( King size double in Main bedroom, Twin single beds in 2nd bedroom, Fold down double sofa bed in lounge.) with family bathroom and en suite toilet with sink in main bedroom, integrated lounge, dining and kitchen…

  • Swimming Pool
  • Internet
  • Coast Nearby
Weekly from £1001
Cosy Farm Cottage in the Heart of Dorset

Cosy Farm Cottage in the Heart of …

Blandford Forum, Dorset

5

Cosy Victorian farm lodge full of character, with its own private garden and broad horizon views over the downs. Newly and lovingly renovated and redecorated throughout. Located on a working family farm in the heart of the Dorset countryside, but also just 30 minutes from the…

  • Swimming Pool
  • Baby Friendly
  • Internet
  • Open Fire
Weekly from £910
Spectacular Views of Swanage Bay and Downs

Spectacular Views of Swanage Bay and Downs

Swanage, Dorset

4

Superb location for walking the Jurassic Coastal Path. Spacious accommodation and Balcony to enjoy a quiet and relaxing stay whilst taking in the beautiful views of Swanage Bay. Club House offering entertainment, refreshments, Gym and Heated Pool. Located in Swanage, this…

  • Swimming Pool
  • Internet
  • Coast Nearby
  • Open Fire
Weekly from £903
Honeysuckle Large Modern Luxury Caravan on Award Winning Rockley Park

Honeysuckle Large Modern Luxury Caravan On Award …

Poole, Dorset

4

Our high-quality luxury caravan, Honeysuckle, occupies an elevated sunny plot on Pine Ridge with magnificent panoramic views over Poole Harbour. The caravan is large modern and furnished to a very high standard. It is double glazed, central heated and has a front veranda where…

  • Swimming Pool
  • Baby Friendly
  • Coast Nearby
Weekly from £833
2 bedroom accommodation in Charmouth

2 Bedroom Accommodation in Charmouth

Charmouth, Dorset

6

28 x 12ft caravan with one double and one twin. Fridge/freezer. Shower. Double glazed and fully heated. No pets.. Just 15 minutes’ walk from the famous fossil beach and village of Charmouth, this family run park on the beautiful Jurassic coast, offers you the ideal base for…

  • Swimming Pool
  • Internet
  • Coast Nearby
Weekly from £777
2 bedroom accommodation in Cricket St Thomas, near Chard

2 Bedroom Accommodation in Cricket St Thomas …

Cricket St Thomas, Near Chard, Dorset

4

This beautiful lodge ticks all the boxes for your next break in the Somerset countryside.. All on the ground floor. Open plan living space. Living area: With wood burner and Smart TV. Dining area. Kitchen area: With breakfast bar, electric oven, induction hob, microwave,…

  • Swimming Pool
  • Internet
  • Open Fire
Weekly from £763

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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