
Vacation 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.

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

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

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.

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)

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.

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.

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

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

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

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.

Kingfisher yurt, A unique eco holiday in Devon
Unique yurt (sleeps 5+) surrounded by oak trees, next to the wild swimming pond (shared /gated.) Also check out Buzzard yurt with its terrace / views /pizza oven /rustic flush loo. Private large, rustic, open plan kitchen (+ games, maps and books), shower, compost loo and fire pit. The shared games/music cabin adjoins your kitchen. Dog friendly. Bookable hot tub. The safety of your group is your responsibility. Check-in form /waiver to sign on arrival please.
Popular amenities for Chesil Bank rentals with a pool
House rentals with a pool

Silvermere, Silverlake in Dorset

Susie's Caravan in Dorset

Fontwood Cottage – Woodland Hideaway with Hot Tub

Your Own Private Indoor Pool. Rural Seaside

Stunning Home with Roof Terrace at Silverlake

Charming & cosy thatched farmhouse with fireplace

Large Airy Barn, 5 bedrooms, dog friendly

Greenhill Cottage Sea Views Thatched Charm
Other vacation rentals with a pool

The Woodlark Lodge with Harbour Views

Bay View Holiday Home With Sea Views

One bed Lodge in AONB Dorset with shared pool area

Warmwell Luxury Lodge near Dry Ski Slope

Kingfisher Lodge with Sea Views

5star Beachside Park & Spa | Jurassic Coast Luxury

Dorset Coastal Holiday Home

Pet Friendly Holiday Home by Ally Cat Breaks
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- New Forest National Park
- Paultons Park Home of Peppa Pig World
- Stonehenge
- Weymouth Beach
- Boscombe Beach
- Bournemouth Beach
- Brixham Harbour
- Bournemouth International Centre
- Lyme Regis Beach
- The Tank Museum
- Kimmeridge Bay
- Torquay Beach
- Highcliffe Beach
- Southbourne Beach
- Crealy Theme Park & Resort
- Beer Beach
- Preston Sands
- Mudeford Quay
- Mudeford Sandbank
- West Bay Beach
- Man O'War Beach
- Charmouth Beach
- Longleat Safari Park
- Torre Abbey




