
Holiday rentals with a pool in Chesil Beach
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Top-rated rentals with a pool in Chesil Beach
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House rentals with a pool
Superhost

Home in Blandford Forum
5 out of 5 average rating, 22 reviewsLaunceston Farmhouse with swimming pool & sauna
ElizabethRating, 5 stars10 months ago
Gorgeous, well equipped house in peaceful surroundings. We wanted somewhere that we could unwind as a family after a busy few months with work and exams and this was perfect. Access to the pool was the cherry on the cake. Catherine and Sarah were great hosts.
Superhost

Home in Preston Road
4.84 out of 5 average rating, 112 reviewsSpacious Caravan near sea Weymouth Bay Haven
SuzanneRating, 5 stars4 months ago
This is our second time staying in this lovely caravan. It’s always pristine and lovely. I always felt like a home away from home there. The bedrooms are a good size and the extra full bathroom is a definite plus! I’d highly recommend staying here.
Superhost

Home in Somerset
5 out of 5 average rating, 4 reviews16th Century Grade II Listed Cottage for 5 People
LynseyRating, 5 stars8 months ago
We stayed for two nights and felt relaxed and calm. From star gazing to playing garden croquet, we filled our time. The pool was great but be warned it’s cold! Once you’re in you are fine but it takes a few minutes to get submerged. What was really thoughtful, and much appreciated, was the home-made scones on arrival. Maureen and William were very sociable and very kind. We would love to visit again.
Top Guest favourite

Home in Crossways
5 out of 5 average rating, 33 reviewsStunning Home with Roof Terrace at Silverlake
BarbaraRating, 5 stars1 month ago
The accommodation was spotlessly clean beautifully decorated, with luxuriously comfortable beds to sleep in, large fluffy thick towels. Kitchen equipment had everything Rhian’s accommodation is pure luxury.
Guest favourite

Home in Branscombe
5 out of 5 average rating, 26 reviewsIdyllic country house, organic swim pond, hot tub
DeborahRating, 5 stars3 weeks ago
We had the most amazing stay at Hill MIll. The house stands in the most beautiful grounds and is the most peaceful and calm setting we've ever stayed in. When we first arrived we just stood outside admiring the surroundings for almost 20 minutes before we even stepped inside. We had everything we needed and more. Our grandsons ages 2, 4, 5, 12, & 13 loved it. The natural swimming pond was so refreshing for a morning dip it certainly woke us all up!! You could walk directly from the house into Branscombe and on route stop for a drink at the Masons Arms (a beautiful pub) and then continue to join the coastal path to Beer. We would love to return and bring some other friends with us as we haven't stopped talking about it since we got back. Thank you Ian for being such a responsive and helpful host. See you again soon!!
Guest favourite

Home in Crewkerne
4.94 out of 5 average rating, 50 reviewsPerfect Country Home. Plenty of outdoor terraces
SharonRating, 5 stars2 days ago
We thoroughly enjoyed our stay. The stables were beautifully converted, peaceful and very comfortable.
Superhost

Home in Buckland Newton
5 out of 5 average rating, 3 reviewsPoacher's Cottage
AliceRating, 5 stars10 months ago
Our stay at Poachers cottage was really wonderful and exactly what we had wanted. The grounds are absolutely beautiful and the cottage was so thoughtfully and beautifully done. The facilities were incredible and we were very lucky to have the pool to ourselves with beautiful weather when we stayed. There was loads for our toddler to do and Adele had any bits we might need for him. I am pretty heavily pregnant and between the pool and the very comfortable beds I had a wonderfully relaxing stay and anytime I needed something, somehow it was already there in the cupboard or in the bedroom. We couldn’t have asked for more. Home made cake and local bits when we arrived and all. Honestly I’ve been so torn on whether to keep this place all to myself but I couldn’t help but rave about my holiday when I got home and have had 3 friends ask for the link to go and stay!
Superhost

Home in Chideock
4.84 out of 5 average rating, 62 reviewsEscape from it all at the Doghouse!
MeridithRating, 5 stars5 months ago
Fabulous country home walking distance to beach, pub and great hiking paths. Very cozy & warm. Our family loved our 3 nights and wished it was longer!
Condo rentals with a pool

Condo in Portland
4.64 out of 5 average rating, 58 reviewsSeascape Apartment
NadiaRating, 5 stars6 months ago
A lovely apartment, very bright, clean, spacious, very well equipped and very well-placed for visiting the surrounding area. The balcony and lovely views from every room were a highlight and the children were fascinated by the helicopters taking off and landing! 😊 Very clear instructions to check in/out by Philippa with excellent communication. The use of the swimming pool was an amazing bonus, the kids absolutely loved that and the times we used it we had it all to ourselves! 👍🏼 Thank you so much for a fabulous stay! 😀
Superhost

Condo in Woolland
5 out of 5 average rating, 6 reviewsCosy ground floor apartment for 4 below Bulbarrow
KateRating, 5 stars6 months ago
Beautiful and peaceful setting. The pool and activities room and playgrounds were wonderful. You could book private sessions in the pool although we also found the communal sessions generally weren’t busy and we often had the pool to ourselves. It was perfect for our daughter as it wasn’t too deep which really helped her build confidence at swimming. We loved playing table tennis and badminton with our older child while the plentiful toys (especially the pedal tractor) kept the little one very happy! Lots to do in the surrounding area, although the peaceful/remote location meant they were all a fair drive away. Apartment was as pictured. It had everything we needed and was always warm- important for October half term break!
Superhost

Condo in Woolland
4.8 out of 5 average rating, 5 reviewsRural hot tub retreat for 4 near Bulbarrow Hill
JamesRating, 5 stars6 months ago
A very nice location, that was as advertised. Great amenities and great staff. Thank you.

Condo in Portland
4.88 out of 5 average rating, 33 reviewsQuayside Apartment - Large and Spacious Duplex
GaryRating, 5 stars3 months ago
Lovely apartment. Had all equipment and items we required. Access to and from was simple and positioned well for local amenities and activities. Would stay again.
Top Guest favourite

Condo in Dorset
4.98 out of 5 average rating, 66 reviewsStudio in beautiful Charmouth
AnnRating, 5 stars4 weeks ago
The reason for our stay was so that we could help our daughter & her partner with some renovations to their house. So we already know this lovely area well, but for this visit, we were sanding down paintwork rather than enjoying the sand on the beach! We certainly appreciated the hot showers in this lovely clean chalet after a tiring day! There are lovely views of the countryside from the outside seating area - ideal place to sit with a glass of wine. Fortunately, we had lots of sunshine throughout our stay, and as it's the Easter holidays, we expected to see all the chalets occupied, but it was very quiet and we barely saw a soul. The adjacent hotel was also closed for refurbishment during our stay. The chalet is ideally placed for Charmouth, Lyme Regis and coastal walks. We only contacted the owners once during our stay (Netflix query) & Jules responded immediately. We happy to recommend Popple’s Nook and would certainly stay here again.
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- New Forest national park
- Weymouth Beach
- Bournemouth Beach
- Kimmeridge Bay
- Boscombe Beach
- Southbourne Beach
- Paultons Park Home of Peppa Pig World
- Stonehenge
- Tapnell Farm Park
- The Tank Museum
- Crealy Theme Park & Resort
- Preston Sands
- Torre Abbey
- Dartmouth Castle
- Sandy Bay Beach Blue Flag Winner 2019
- Charmouth Beach
- Hurst Castle
- Kilve Beach
- Poole Quay
- St Mary's Bay
- Oddicombe Beach
- Dawlish Warren Beach
- Watcombe Beach
- Highcliffe Beach