Holiday rentals with a pool in Chesil Beach

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Top-rated rentals with a pool in Chesil Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite

Shepherd’s hut in Lyme Regis

4.99 out of 5 average rating, 106 reviews

Headland Hideaway Shepherd's Hut in Lyme Regis

SHEPHERDS HUT An opulent hideaway retreat nestled on the Lyme Bay headland with uninterrupted ocean views, perfect for romantics & family adventurers. With an expansive sundeck, fire pit & swimming pool & endless expanse of garden. Embark on the most charming private adventure from bedroom shepherd's hut & adjacent shower room to the architectural wonder of the glass framed kitchen, diner & sitting room with freestanding log burner & stylish interior. Sit and wonder at the expanse of ocean views

Top guest favourite

Chalet in Dorset

4.97 out of 5 average rating, 36 reviews

Our Plaice by the Sea

'Our Plaice by the Sea' is a 2 bedroom caravan, on the flagship Littlesea Haven holiday park. Our Plaice feels like a home from home, reminding us of a beach hut with its pale- blue cladding, decking out front and stunning views of Chesil Beach; it stands out, giving a relaxed seaside vibe. There’s plenty to do on-site with an indoor and outdoor pool, adventure golf, arcade, day and night entertainment (Haven passes to be purchased) fabulous coastal path walks and near to the Jurassic coastline.

Guest favourite

Home in Somerset

4.91 out of 5 average rating, 239 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

Group Gatherings Host your own event Exclusive use 10-16 guests (6-16 winter) Jacuzzi All year Outdoor Pool (heated in summer; cold in winter!) Sun Deck Garden Kitchen/Bar Games room: Music/Karaoke system Wood burner TV Communal eating space, shower/wc Escape Room Somerset Evening -pork roast cider tasting welly wanging Large peaceful grounds BBQ Fire Pit Annexe (sole use): kitchen lounge bathroom 2 bedrooms 2 sofa beds House (part use): 4 bedrooms 3 bathrooms Glamping Trailer

Superhost

Cottage in Woolland

4.86 out of 5 average rating, 7 reviews

Escape to the country! hot tub retreat for 7

Welcome to The Victorian Barn Countryside Estate & Farm in Dorset. Set in 65 acres of lush green parkland The Victorian Barn Estate offers the perfect retreat for your Dorset escape. Explore the rural footpaths and fishing lakes, take a dip in the warm indoor pool, enjoy your bubbly private hot tub, have fun with the kids in the games rooms and outdoor play area or simply relax in your comfortable accommodation. Perfect for any occasion and within easy drive of the historic Jurassic Coast.

Guest favourite

Barn in Long Sutton

4.87 out of 5 average rating, 312 reviews

Somerset Threshing Barn w/ Pool, Hot Tub & Sauna

Discover the Threshing Barn, an ideal spot for family or group gatherings. Enjoy the spacious double-height kitchen and the cozy lounge with woodburner. Unwind in the covered hot tub and sauna, take a dip in the heated pool (open May to Sept) or play table tennis, pool, and table football. Explore nearby footpaths leading to three excellent pubs. We can help organise catering, pampering, and a wide range of activities, from archery and shooting to cider tasting, both on-site and off-site.

Superhost

Campervan/Motorhome in Furzehill

4.92 out of 5 average rating, 13 reviews

Wilksworth Holiday Park - 2 Bed - Pool Access

Escape to our charming 2 bedroom home nestled in the serene Wilksworth Holiday Park near Dorset’s picturesque countryside and stunning golden beaches. Perfect for families or couples, our home offers a cozy retreat with modern amenities. Enjoy shared access to a refreshing pool, perfect for unwinding after a day of exploration. Discover nearby scenic trails, quaint villages, and breathtaking coastal views. Your ideal getaway awaits, combining relaxation and adventure in a beautiful setting.

Guest favourite

Guest house in Iwerne Minster

4.97 out of 5 average rating, 61 reviews

One bed Lodge in AONB Dorset with shared pool area

Fully refurbished ,Brook Lodge sits in the grounds of the main house in the village of Iwerne Minster. One bedroom , king sized bed. Bathroom with free standing bath and separate walk in shower. Open plan living area downstairs with sofa , dining area for 4, new fitted kitchen ,separate cloakroom and entrance hall. Small outdoor semi private seating area.Free WiFi .TV. Welcome pack. NB Outdoor heated pool OPEN beginning JUNE to SEPTEMBER ONLY .NB Pool use is shared with property owners.

Superhost

Cabin in Dorset

4.88 out of 5 average rating, 17 reviews

Bay View Holiday Home With Sea Views

Spacious two bedroom holiday home with a Balcony/Sun deck. Situated on a wide sunny plot in the most desirable Bay Hollow which has a splendid sea views over the bay at the award winning "Rockley Park" in Dorset.. The holiday home is 'Platinum' graded and benefits from central heating and double glazing. It is a short walk from the amenities and 150yds walk to the lovely sandy beach, with cafe and water sports. Haven passes are available at an extra cost for swimming and entertainment.

Guest favourite

Home in Harpford

5 out of 5 average rating, 6 reviews

The Pool House

Set within the grounds of our old rectory, The Pool House provides a wonderful retreat for those looking to escape to the country whilst being a short drive from the seaside town of Sidmouth and nearby city of Exeter. The Pool House has been renovated to a high specification providing spacious contemporary accommodation with use of heated outdoor swimming pool (mid May to mid September) during the day, and exclusive use of the courtyard in the evening. We also provide fast WiFi.

Top guest favourite

Home in Lyme Regis

5 out of 5 average rating, 24 reviews

Your Own Private Indoor Pool. Rural Seaside

Up to 30% discount on Mon-Fri bookings in May and June 2025. Coombehayes Barn. Beautifully appointed, self-contained, spacious. A mile from the sea. Super warm, private indoor pool - for your exclusive use. Perfect for relaxed family/friends get-togethers and celebrations. Tranquil yet convenient location. Lyme Regis, Jurassic Coastline. Beaches, footpaths, fossils. Lots for kids to do: PS5, table football, table tennis. Large, safe, enclosed garden. Super fast wifi.

Top guest favourite

Cottage in Dorset

4.98 out of 5 average rating, 348 reviews

The Condo (Indoor Pool available May- end Sept)

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

Top guest favourite

Home in Margaret Marsh

5 out of 5 average rating, 29 reviews

Charming thatched farmhouse, heated pool & cottage

Lose yourself in the peaceful hideaway in the middle of nature, yet only 10 minutes from the ever popular town of Shaftesbury, and less than an hour to the beach. Wonderful grounds and expansive open views in the great British countryside. Main house + cottage. Pool is outdoors and will be available from the end of April until end of September.