
Vacation 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.

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

Family friendly & comfortable 2 Bed Holiday Home
Family friendly 2-bed holiday home (sleeps 6), centrally heated & double glazed throughout. Located in a quiet cul-de-sac close to all park amenities & adjoining beach. Price includes Wi-Fi. Open plan living space with large L shaped sofa/bed, 43" TV, & fully equipped integrated kitchen. Family shower room, & an en-suite to the Master bedroom, which also has a fitted double wardrobe, 32” TV & king-size bed. The twin bedroom has two single beds. The patio doors lead to a wraparound veranda.

A luxurious modern 3-bedroom Swift Bordeaux
A luxurious modern 3-bedroom Swift Bordeaux Silver Prestige. This fabulous caravan is situated at Haven Littlesea Holiday Park in Weymouth in a spacious plot with views of the Fleet Lagoon and Chesil Beach. Sleeps up to 6 people. 1.5 bathrooms Linen and towels supplied. Parking spaces for 2 cars. Outside decking and seating area. Onsite restaurant, laundrette and local shop. For use of swimming pool, entertainment venue and booking activities you can purchase Play Passes from Haven

Secluded hideaway, heated pool, walks, fossils
The Annex is bright, comfortable and cosy with a wood burner for winter. The public footpath crossing our garden next to the river Char links with many others - great for dog walkers. We are close to Charmouth beach and Lyme Regis – renowned for their fossil treasures. Love swimming? our freshwater pool is generally heated to a very cosy 29 - 30 degrees (warm bath temperature) and can be used from April to October With advance notice, the twin beds can be connected to form a king size bed

Buzzard Yurt - A unique eco holiday in East Devon
Unique and comfortable yurt (sleeps 5+), large terrace, stunning views - also you could check out Kingfisher yurt (bigger kitchen) by the swimming pond. Private kitchen, chill-out cabin, shower, rustic flushing loo, compost loo with a view, campfire area. Wild swimming pond (fenced) Bookable woodfired hot tub. Dog friendly, footpaths. Kid heaven! Late check-out negotiable. By booking you take full responsibility for the safety of your group. Check-in form /waiver on arrival please.

Breathtaking sea views from this light, cosy lodge
Seascape is a bright, airy lodge down its own drive at the edge of Swanage Bay View. Adjoining Townsend Nature Reserve it enjoys utter tranquillity and spectacular views over the bay, as seen on 'A Place in the Sun'. With its tasteful modern furnishings, central heating and double glazing, Seascape is cosy in winter, while outside, the large deck offers a panoramic view all the way to Corfe Castle. In addition, guests enjoy the amenities of SBV - all within a 15 min walk of the seafront!

Spacious Caravan near sea Weymouth Bay Haven
Our holiday home is spacious with a well equipped kitchen. Located 12-15min flat walk (buggy friendly) from the seaside. The Haven park offers a swimming pool, live entertainment and play areas for kids until 14th November (access to indoor complex is an additional fee on a first come first serve basis) We are opposite the activity field. One car parking space next to the caravan.. CHANGEOVER DAYS ARE MONDAY OR FRIDAY. Please contact us to make a shorter booking or with any questions.

Secluded Stargazing Romantic Shepherds hut&hot tub
Shepherds hut on the Blackdown hills on the rural Somerset/Devon border over looking countryside in secluded spot, own Wood fired hot tub with views of farmland and animals. Wood burning stove in hut with fire pit outside. Private parking, bicycles available to borrow to explore the surrounding AONB. 1mile from village with pub and shop. Hut includes large shower, toilet and heated towel rail. Kitchen area has fridge, Belfast sink, and induction hob. Great for stargazing and relaxing.

Foxglove Carriage with pool, sauna & outdoor bath
Nestled into our working farm, this lovingly restored railway carriage is the perfect spot for a romantic stay away. The views are out of this world and all viewable from the large glass doors so you can stay tucked up in bed or on the sofa in front of the fire, with great wifi, free access to our beautiful heated pool and sauna in the pool house, beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and romantic outdoor bath.

Daisy Cottage on the Jurassic Coast
A cosy and stylish, dog-friendly cottage, set amid the beautiful fields and woodlands of the Fernhill Estate with easy walking access to the coastal village of Charmouth and only 2 miles to Lyme Regis. The South West Coastal Path runs opposite our front door and our guests have seasonal access to a heated outdoor pool. Our cottage sleeps four and is furnished and equipped to a very high standard with everything you need for a relaxing holiday on the Jurassic Coast in West Dorset.

The Duck House. A child/dog friendly rural chalet
The Duck House is a lovely child/dog friendly chalet nestling in the orchard at Plenty Cottage. Quiet and peaceful it's the perfect retreat for a family - and dogs are especially welcome! Open plan living it’s a comfortable and home from home. A wonderful rambling garden, summerhouse, BBQ and a (free) heated swimming pool (1st April - 31st Sept). The mantra is 'No Stress'. Ample parking, dog/child friendly pub 7 mins walk away. Wonderful NT beaches just five min drive.

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!
Popular amenities for Chesil Beach rentals with a pool
House rentals with a pool

Cider Barn

Luxury 5 Bedroom House - Games Room & Hot Tub/Pool

Stunning Home with Roof Terrace at Silverlake

Your Own Private Indoor Pool. Rural Seaside

Idyllic country house, organic swim pond, hot tub

Country House - Pool Jacuzzi Escape Room Karaoke

Dog Friendly, 2 miles from coast, sleeps 2-4, Owl

Rooks Orchard Annexe
Other vacation rentals with a pool

Seascape Apartment

Luxurious holiday home at Weymouth Bay

3 bedrooms, stunning seaview, wrap around decking

A homely seaside static caravan

Sleeps 6 with wild swimming & woodburner

Luxury barn conversion with indoor pool

Kingfisher Lodge with Sea Views

Dorset Coastal Holiday Home
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