Vacation rentals with a pool in Chesil Beach

Find and book unique homes with a pool on Airbnb

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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Guest favorite

Yurt in Colyton

4.98 out of 5 average rating, 126 reviews

Buzzard Yurt - A unique eco holiday in East Devon

Unique and comfortable yurt (sleeps 5) with large terrace and stunning views of Devon Exclusive use of a separate kitchen, hut, shower, compost loo and campfire area. Homegrown produce available from our organic smallholding Wild swimming in our natural swimming pond. Woodfired hot tub available (£50 a day) Dog friendly with great footpaths straight from the field. Use of our 26 acre rewilding woodland a 30 minute hike away, forest school activities, games, maps and books. Kid heaven!

Apr 8 – 15

G$25,589 GYD per night

Guest favorite

Bungalow in Dorset

4.96 out of 5 average rating, 193 reviews

Cosy Chesil Beach Getaway

Welcome to our beautiful static caravan, situated on the 5* award wining Chesil Beach Holiday Park. You can enjoy views across Chesil beach towards to the Isle of Portland. Ideal for making the most of all that Weymouth has to offer, as well as Portland and the Jurassic Coast. It is also perfectly located for walking the infamous South West Coast Path, which runs along the bottom end of the site. One dog per booking welcome. **PLEASE NOTE : BED LINEN PROVIDED FOR AN ADDITIONAL CHARGE**

Feb 7 – 14

G$45,321 GYD per night

Guest favorite

Bungalow in Charmouth

4.94 out of 5 average rating, 179 reviews

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

Jan 6 – 13

G$53,872 GYD per night

Guest favorite

Train in Axminster

4.99 out of 5 average rating, 186 reviews

Clover Carriage, sauna, underfloor heat, log fire

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 sauna in the pool house (pool closed for winter!), beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights. It's a winter dream.

Mar 21 – 28

G$22,948 GYD per night

Superhost

Home in Preston Road

4.83 out of 5 average rating, 108 reviews

Haven Weymouth Bay Holiday Park

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.

Aug 19 – 26

G$42,218 GYD per night

Guest favorite

Shepherd’s hut in Churchstanton

4.97 out of 5 average rating, 169 reviews

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.

Jul 5 – 12

G$25,364 GYD per night

Superhost

Home in Dorset

4.81 out of 5 average rating, 119 reviews

Deluxe caravan & decking Littlesea Haven Resort

12ft wide caravan. 2 bedroom sleeps up to 6. Spacious open plan lounge/kitchen/dinning area. L shape sofa with separate eating area. Modern style kitchen. Fridge and microwave Ample double bedroom. 2 double wardrobes and dressing table, with a large mirror. own WC and basin. twin bedroom with single wardrobe. Gas fire in lounge, fan heaters in the bedrooms. Gas, water and electricity included Shower room & WC 52 inch TV in the lounge Decking, outside table and chairs, free Wifi

Oct 7 – 14

G$18,745 GYD per night

Guest favorite

Apartment in Whitchurch Canonicorum

4.94 out of 5 average rating, 235 reviews

The Duck Wing, quirky dog friendly apartment

The Duck Wing is a quirky, self contained apartment on the first floor within Plenty Cottage. It's beautifully appointed for a relaxed, carefree stay in a wonderfully rural environment. Nothing is too much trouble. It sleeps two in double bed in a pretty bedroom and has a double sofa bed too. Own bathroom/shower, a separate WC and a warm spacious living area. The pub is 7 mins walk away and the beaches a 5 mins drive. The private, heated swimming is available 1st April - 31 Sept

Jan 26 – Feb 2

G$27,273 GYD per night

Guest favorite

Chalet in Weymouth

4.93 out of 5 average rating, 120 reviews

Bowleaze Cove with a view

Modern, 3 bed static in an elevated position on the beautifully kept Bowleaze Cove Holiday Park & Spa on the Jurassic Coast! 1 double, 2 twins & sofabed.2 bathrooms,1 with power shower.Large gated deck area with seating & sea views.Parking for 2 cars. Site facilities: spa/gym/restaurant/sports bar/soft-play/kids park/pool (indoor & outdoor). Prices include park passes. Sorry no single sex groups or dogs. For off peak bookings, contact us directly to discuss flexible stays.

Sep 5 – 12

G$32,922 GYD per night

Guest favorite

Cottage in Dorset

4.98 out of 5 average rating, 313 reviews

The Condo (Indoor Pool available May-Oct only)

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!

Mar 12 – 19

G$26,936 GYD per night

Superhost

Cabin in Forton

4.89 out of 5 average rating, 149 reviews

Woodpecker Lodge - Log Cabin with Private Hot Tub

Each solid wood log cabin is encircled by trees for your privacy yet open enough to let sunlight through. We aim to give you that cosy, romantic log cabin retreat experience with a solid wood burner, private hot tub and free access to our seasonal outdoor heated pool (end May - Sept). If the dates you require are already booked, please look at our other cabins: Nuthatch Lodge, Tawny Owl Lodge, Hedgehog Lodge (all with private hot tubs) or Roe Deer Lodge.

Jan 24 – 31

G$27,388 GYD per night

Guest favorite

Chalet in Weymouth

4.95 out of 5 average rating, 168 reviews

Summer Lodge

The Summer Lodge boasts uninterrupted and unrivaled views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the Jurassic Coast path. Located just one mile from the Isle of Portland, the home of the 2012 Olympic sailing events and a short drive from Weymouth town centre and harbour, our stunning holiday home is perfectly situated for anyone wanting a coastal escape.

Sep 7 – 14

G$64,347 GYD per night