Dorset Cottages with Pool

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Dorset Cottages with Pool

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Your Dorset search returned 25 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published
A house with a patio area and a wooden gazebo on a lawn at Royal Oak House in Motcombe
1 of 80
5
Motcombe, Dorset, SP7
  • Sleeps12
  • Bedrooms6
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Royal Oak House is a striking detached house with a heated swimming pool, barbecue, and 2-acre garden, located in the village of Motcombe in Dorset. Shaftesbury 3.3 miles; Stonehenge 22.9 miles; Salisbury 23.5 miles. (Ref. 1060629)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Games room


for 7 nights From £2186

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A two-story white house with a patio umbrella and outdoor furniture surrounded by a lawn and trees at Somerhill in Lyme Regis
1 of 33
5
Lyme Regis, Dorset, DT7
  • Sleeps10
  • Bedrooms5
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

An exceptional property close to Lyme Regis in Dorset. Swimming pool. Woodburning stove. Gardens. Sea views. Lyme Regis 0.7 miles; Bridport 10.5 miles; Branscombe 10.8 miles; Weymouth 29.3 miles. (Ref. 1106401)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £1831

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A brick house with a sloped roof and skylights with a gravel driveway at Baytree Lodge in Osmington
1 of 59
5
Osmington, Dorset, DT3
  • Sleeps12
  • Bedrooms5
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Luxurious 5 star contemporary property. Games room. Indoor swimming pool. WiFi. Stunning views. Five en-suite bedrooms, one family bathroom. Large sitting room and generous sitting/dining room/kitchen. (Ref. 993982)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights From £3510

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A fenced swimming pool with chairs and lawn in front of a brick and wood house at Manor Farm Barn in Dewlish
1 of 42
5
Dewlish, Dorset, DT2
  • Sleeps15
  • Bedrooms8
  • Pet FriendlyYes

    4.7★

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Wonderfully appointed barn conversion residing in the sleepy village of Dewlish in Dorset. Dog-friendly. Off-road parking. Shared outdoor heated pool. Dorchester 7 miles. (Ref. 1003646)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights From £2122

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A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
1 of 42
5
Dorchester, Dorset, DT2
  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. On-site facilities. Family-friendly. Lakeside views. Woodburning stove. Puddletown 5.3 miles; Dorchester 5.6 miles; Weymouth 10 miles. (Ref. 1138508)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £810

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Bredy Cottages - 1176478 - photo 1
1 of 52
5
Burton Bradstock, Dorset, DT6
  • Sleeps10
  • Bedrooms5
  • Pet FriendlyYes

    5.0★

    Perfect

  • Sykes rating

Bredy Cottages is an imaginatively extended 4-bedroom cottage with a handy open-plan living area, a snug with a woodburning stove, and pretty gardens. Bridport 4 miles; Weymouth 16.1 miles; Dorchester 14.2 miles; Yeovil 24.6 miles (Ref. 1176478)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights From £1271

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A brick and flint house with a slate roof and an outdoor patio area with wooden table and chairs surrounded by flowering plants at Churn House in Dewlish
1 of 15
5
Dewlish, Dorset, DT2
  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Beautiful barn conversion positioned in the lovely village of Dewlish in Dorset. Off-road parking. Shared outdoor heated pool. Pet-friendly. Shop 1.8 miles, pub 0.2 miles. (Ref. 1003641)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights From £792

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A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland
1 of 27
5
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

A well-positioned, fourth-floor apartment resting in Castletown, Dorset. Sea views. Close to amenities and the beach. Contemporary. Designated parking. Private balcony. Portland 1.9 miles; Weymouth 5.2 miles; Dorchester 12.6 miles. (Ref. 1119638)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine


for 7 nights From £561

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A white building with a stone wall and flowers in front and a lighthouse behind at Old Higher Lighthouse Stopes Cottage in Portland Bill
1 of 55
5
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Tourist Board rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £644

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A deck with chairs and a door at Chesil Beach Holiday Park - Holiday Accommodation 16933, Weymouth
1 of 12
5

Holiday Park

Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

2x Bedroom Holiday Home at Chesil Beach Holiday Park with Veranda and Sea Views over the Beautiful Jurassic Coast in Dorset. (Ref. 1186144)

  • Wi-fi
  • Swimming pool


for 7 nights From £556

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An outdoor seating area with a table and chairs at Jurassic Discovery in Charmouth
Offer
1 of 30
5
Charmouth, Dorset, DT6
  • Sleeps6
  • Bedrooms2
  • Pet FriendlyYes

    5.0★

    Perfect

  • Sykes rating

A modern, pet-friendly static caravan in beautiful Charmouth, just steps from the Jurassic Coast. With flexible sleeping for up to six, great on-site facilities including a pool, sauna, café, and dog walking area. (Ref. 1193938)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Swimming pool
  • Ground floor bedroom
  • Washing machine

  • 10% off - Sun 28th Jun to 4th Jul 2026


for 7 nights From £410

Last booked 5 hours ago
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A lighthouse and white buildings with a stone wall and grassy area at Old Higher Lighthouse Branscombe Lodge Portland Bill
1 of 40
5
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Tourist Board rating

Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. Upside down accommodation with sensational sea views. Shared access to Lighthouse observatory. Shared use of heated pool and Jacuzzi. (Ref. 12497)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly


for 7 nights From £617

Last booked yesterday
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A white and gray prefab house with a small porch and steps surrounded by grass and pink flowers at Owls Nest in Furzehill
1 of 34
5
Furzehill, Dorset, BH21
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

A contemporary, lakeside lodge set in the village of Furzehill, Dorset. Open-plan living. Electric fire. Decking. Wimborne Minster 1.5 miles; Bournemouth 11.4 miles. (Ref. 1129123)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights From £648

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A house with ivy on one side a paved driveway and a porch with wooden furniture at Deer Leap House in Moreton
1 of 82
5
Moreton, Dorset, DT2
  • Sleeps15
  • Bedrooms7
  • Pet FriendlyYes

    4.2★

    Good

  • Sykes rating

A spacious holiday home resting in Moreton, Dorset. Woodburning stove. Ground-floor living. Shared outdoor pool and tennis court. Terrace with furniture. Dorchester 6 miles; Weymouth 10.5 miles; Blandford Forum 14.9 miles. (Ref. 1060785)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights From £2208

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A balcony with glass table and chairs overlooking buildings and a body of water at Panoramic View in Castletown Portland
Offer
1 of 22
5
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.2★

    Good

  • Sykes rating

A well-presented, modern apartment on the rugged Isle of Portland. Far reaching sea views. Open plan living. Balcony with seating. Access to indoor swimming pool and gym. Close to pub, beach and shop. WIFI and allocated parking. Weymouth within 6 miles. (Ref. 1034885)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Washing machine

  • 5% off - Mon 22nd Jun to 4th Sep 2026


for 7 nights From £519

Last booked yesterday
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An outdoor view of a stone building with a table and chairs at Apple Cottage in Whitchurch Canonicorum
1 of 30
5
Whitchurch Canonicorum, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    3.5★

    Good

  • Sykes rating

Apple Cottage is a charming one-bedroom cottage in Whitchurch Canonicorum, Dorset, with access to an indoor swimming pool. Bridport 5.4 miles. (Ref. 1192738)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom


for 7 nights From £378

Last booked 4 hours ago
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A beige mobile home with white railing and outdoor seating on a grassy area at Tri-Star House in Charmouth
1 of 27
5
Charmouth, Dorset, DT6
  • Sleeps6
  • Bedrooms2
  • Pet FriendlyYes

    4.4★

    Good

  • Sykes rating

Tri-Star House is a charming holiday lodge on Wood Farm Holiday Park, in the bustling seaside village of Charmouth, within the Dorset National Landscape. Lyme Regis 2.7 miles. Axminister 5.3 miles. Bridport 7.5 miles. (Ref. 1153199)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Washing machine


for 7 nights From £421

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a living room with a TV, coffee table, and view of a patio at Freshwater Beach Holiday Park - Holiday Accommodation 12281 in Burton Bradstock
Offer
1 of 11
5

Holiday Park

Burton Bradstock, Dorset, DT6
  • Sleeps6
  • Bedrooms2
  • Pet FriendlyYes

  • Sykes rating

Freshwater Beach Holiday Park - Holiday Accommodation 12281 is a splendid caravan in Burton Bradstock, Dorset, boasting onsite swimming pools and bowling. Bridport 2.5 miles; Weymouth 17.5 miles; Dorchester 16.7 miles; Yeovil 21.8 miles (Ref. 1185175)

  • Pets go free
  • Wi-fi
  • Swimming pool
  • Ground floor bedroom
  • Baby-friendly

  • 20% off - Sat 27th Jun to 4th Jul 2026

  • 5% off - Sat 1st Aug to 30th Sep 2026


for 7 nights From £474

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A two story house with brick lower walls and pebble dash upper walls with multiple windows and a hedge in front at Deer Leap Cottage in Moreton
1 of 24
5
Moreton, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.2★

    Good

  • Sykes rating

A fantastic semi-detached house resting on the outskirts or Moreton, Dorset. Outdoor swimming pool. Open fire. Tennis court. Off-road parking. Dorchester 6 miles; Weymouth 10.7 miles; Blandford Forum 15.3 miles. (Ref. 1060768)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Washing machine
  • Baby-friendly


for 7 nights From £737

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Honeypot Cottage - 1193886 - photo 1
1 of 32
5
Whitchurch Canonicorum, Dorset, DT6
  • Sleeps3
  • Bedrooms2
  • Pet FriendlyYes

  • Sykes rating

Honeypot Cottage is a delightful, single‑storey, pet-friendly stone barn in Whitchurch Canonicorum, Dorset, with a woodburning stove and open-plan living. Bridport 5.5 miles. (Ref. 1193886)

  • Pets go free
  • Wi-fi
  • Swimming pool
  • Ground floor bedroom


for 7 nights From £581

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Map View

What could be more luxurious than a Dorset holiday cottage with a pool? Imagine yourself lounging by the pool during your staycation break. Dorset cottages with pools have a lot of advantages, one of which is that they provide you with a lot of independence. There's no need to book a sun lounger or brave the crowds on the beach; simply put on your swimsuit and dive in!

Why Dorset Holiday Cottages with a Pool?

Find a wide range of Dorset holiday cottages with indoor pools, ideal for adding a little something extra to your getaway. Whether you've spent the day exploring the verdant landscapes of Hardy Country or walking along the Jurassic Coast admiring some of the breath-taking natural wonders such as Lulworth Cove, Durdle Door and Old Harry Rocks, these holiday cottages in Dorset with indoor swimming pools are the ideal way to relax and unwind. Use our Dorset Travel Guide for even more holiday inspiration.

Places to Visit near Dorset Cottages with a Pool

Dorset Cottages with pools are in an ideal location to visit some of the county's most beautiful sights. Venture out to Kingston Lacy with its stunning formal gardens, Corfe Castle's evocative ruins, Cerne Abbas' famed giant, and the fossil-rich beaches of Lyme Regis, Charmouth, and Weymouth.

If you're travelling with children, there are several family-friendly attractions nearby, including Monkey World, Dorset Adventure Park, and Swanage Railway, as well as a variety of water sports and outdoor activities. The Isle of Purbeck is known for its biodiversity, natural beauty, and cliff-top treks. Dorset is the ideal spot for a UK holiday cottage break, with so much to see and do.

Types of Dorset Holidays

Alongside this collection of Dorset cottages with pools, you explore the spectacular Jurassic Coast from one of these Dorset coastal cottages. Bring the whole family to a large Dorset holiday cottage or arrange a last-minute Dorset break.

Alternatively, those of you looking to enjoy spending plenty of time in the great outdoors with a log cabin break in Dorset or a glamping break in Dorset.

With so many options, which also includes short breaks in Dorset, make sure you get the most out of your Dorset holiday.

Still undecided? Browse this larger collection of holiday cottages with indoor swimming pools, or these cottages with swimming pools.

If you're still searching, this wider range of Dorset cottages may contain the perfect break for you.