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Holiday rentals with a pool in Chesil Bank

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Top-rated rentals with a pool in Chesil Bank

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

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Guest favourite
An expansive wooden deck is featured, with a modern round fire pit positioned among lush greenery and vibrant flowers. Large glass doors allow views into the interior space, which is visible beyond the deck. The natural landscape extends in the background under a clear sky.
Shepherd’s hut in Lyme Regis
4.99 out of 5 average rating, 133 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

Guest favourite
A gravel driveway leads to a charming white house surrounded by lush greenery. The property features a two-story structure and an annexe, both set within spacious grounds. Noticeable are the well-maintained gardens and outdoor seating areas, perfect for gatherings.
Home in Somerset
4.91 out of 5 average rating, 268 reviews

Country House - Pool Jacuzzi Escape Room Karaoke

Group Gatherings Host your own event Exclusive use 10-16 guests Min 2 off peak 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 -pulled pork 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

Guest favourite
A light-colored caravan is positioned on a grassy area with a paved pathway leading up to it. The exterior features multiple windows, and a ramp provides accessible entry. The surrounding trees create a natural ambiance, with a partially cloudy sky adding to the setting.
Holiday park in Dorset
4.89 out of 5 average rating, 70 reviews

3 Bedroomed Abi Trieste Bronze Caravan 8 Berth

Well Presented, 3 Bed, Abi Trieste Caravan, situated on Haven Littlesea Complex, 10 minute Drive from Weymouth Town Centre and Seafront. Amenities on the Park include:- Bar/Restaurant, Showbar, Arcade, Tennis Court, Indoor/Outdoor Swimming Pools, Launderette, Golf, Shop, Chip Shop & Papa Johns, 2 Childrens Parks and Play Area. Entertainment Passes & Towels not included. Please purchase Passes from Reception on arrival. Contact Haven for Prices. Bed Linen Provided. Max 2 Pets Welcome.

Guest favourite
The interior features two twin beds with colorful bedding arranged against wooden walls. A dining table is set with two glasses of red wine, a bottle, and a small vase of flowers. A window offers views of the surrounding greenery.
Shepherd’s hut in Dorset
4.89 out of 5 average rating, 194 reviews

Everdene shepherd's hut

Lovely views of the Blackmore Vale (amazing sunsets weather permitting!) Our huts are in a secluded area of the farm. Kingsize bed/twin beds opposite ends with curtains for privacy. Woodburner, hot/cold running water, fridge, hob, microwave, wardrobe. Picnic bench & fire pit outside. Wonderful walks, only 10 minutes on foot to village shop and pub. Great for families. Short walk to luxury wetrooms, w/m, drier. Fishing on farm. Indoor exercise pool payable locally. (Subject to availability)

Guest favourite
A serene outdoor seating area is highlighted, featuring two wicker armchairs with soft cushions and a glass-topped table. Beyond, the tranquil Fleet Lagoon reflects sunlight, providing picturesque views, while colorful flowers add a touch of warmth to the setting.
Chalet in Weymouth
4.95 out of 5 average rating, 222 reviews

Summer Lodge

The Summer Lodge boasts uninterrupted views of the Fleet Lagoon and world famous Chesil Beach from its elevated position on the South West Coast Path (Jurassic Coast). 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. Our sea view lodge sleeps 6 people. There are 2 double bedrooms and a small double sofa bed.

Top Guest favourite
A green yurt is nestled among lush grass and trees, with a spacious wooden terrace visible nearby. The landscape features rolling hills in the background, under a bright blue sky illuminated by rays of sunshine. The area offers a serene rural setting.
Yurt in Colyton
4.98 out of 5 average rating, 184 reviews

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) Hot tub (can be advance booked by EITHER Kingfisher or Buzzard yurt). Dog friendly, footpaths. Kid heaven! By booking you take responsibility for safety of your group. Check-in form /waiver on arrival please.

Guest favourite
An indoor pool is surrounded by sleek gray tiling and illuminated by recessed lighting. The pool's inviting turquoise water reflects the ceiling lights. A cozy seating area with cushions is visible in the corner, providing a relaxed atmosphere.
Cottage in Osmington
4.86 out of 5 average rating, 174 reviews

A luxury unique home spa - White Stones Retreats.

Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

Guest favourite
A rectangular freshwater pool is framed by a wooden deck, surrounded by a landscaped garden. Lush greenery and rolling hills are visible in the background, offering a serene and expansive view of the countryside.
Bungalow in Charmouth
4.94 out of 5 average rating, 226 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

Top Guest favourite
Train in Axminster
4.99 out of 5 average rating, 304 reviews

Clover Carriage with pool, sauna and 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 heate pool & sauna (located in the pool house), beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and a romantic outdoor bath

Guest favourite
A charming barn conversion features natural stone walls and large windows that invite ample sunlight. The surrounding landscape includes lush greenery and a clear blue sky, creating a serene rural atmosphere. The driveway leads to the entrance, providing easy access to the property.
Cottage in Dorset
4.79 out of 5 average rating, 193 reviews

Stunning Barn conversion with heated swimming pool

Courage Cottage is a two bedroom detached barn conversion in a Georgian farmyard.The barn was converted in 2013 so has all modern conveniences including underfloor heating. It is very individual and situated in a quiet , rural setting. It has two bedrooms with en-suite bathrooms. The village of Martinstown has an excellent pub and shop. Dorchester is 2 miles away and has every facility including good rail connections in all directions.Swimming pool (shared ) open May 15th-Sept 15th

Guest favourite
A charming cottage is set amidst a lush garden, featuring well-tended greenery and colorful shrubs. The building's white exterior is complemented by a slate roof, with trees casting gentle shadows over the expansive, manicured lawn under a clear sky.
Apartment in Whitchurch Canonicorum
4.93 out of 5 average rating, 288 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

Guest favourite
The entrance of the cottage is framed by vibrant greenery and blooming flowers. A wooden deck leads to a welcoming door, which is complemented by a classic lantern. A decorative sailboat can be seen through the window, adding a touch of charm to the exterior.
Cottage in Charmouth
4.9 out of 5 average rating, 162 reviews

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.

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