Holiday rentals with a pool in Chickerell

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chickerell

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, 108 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, 37 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, 240 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, 313 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/RV in Furzehill

4.87 out of 5 average rating, 15 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

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.

Top Guest favourite

Home in Lyme Regis

5 out of 5 average rating, 24 reviews

Your Own Private Indoor Pool. Rural Seaside

OFFER 4 NIGHTS FOR THE PRICE OF 3! 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, 349 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 Westbourne

4.97 out of 5 average rating, 72 reviews

Incredible sea views and heated outdoor pool

“With its incredible sea views, contemporary open-plan living and heated outdoor pool, this Airbnb is like something out of a Hollywood film” according to Good Housekeeping May 2024. The designer garden with hard and soft landscaping features a heated private endless pool (available April to December) and amazing sea views that draw you to the cliff top deck. Powerboat charter available on prior request.

Guest favourite

Bungalow in Saint Leonards

4.88 out of 5 average rating, 56 reviews

Forest views in secluded location, swimming pools

Beautiful forest views! Family holiday home on Oakdene Forest Park, situated in a peaceful location directly overlooking the forest. Minutes from The New Forest & Dorset beaches - perfect for a family holiday. The park has a leisure complex which includes pools, sauna, jacuzzi, steam room & gym as well as entertainments, bars/restaurant & kids activities.

Superhost

Apartment in Horton

4.8 out of 5 average rating, 49 reviews

Peaceful 2-Bed Escape | Hot Tub • Pool • Sauna

Rivendell park: Stylish 2-bedroom flat with private entrance, set within a peaceful holiday park. This bright, self-contained space is perfect for a relaxing escape from everyday life. Guests enjoy shared access to the seasonal heated pool, large hot tub, sauna and beautifully maintained gardens — ideal for unwinding or exploring the outdoors.