
Vacation rentals with a pool in Weymouth
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Top-rated rentals with a pool in Weymouth
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Unique, romantic luxury countryside retreat
Unique luxury cottage for two, an ancient dovecote with a fabulous swimming pool. Beautifully furnished, romantic and spacious, in gorgeous peaceful countryside, the thick stone walls make it warm and cosy in winter, cool in summer as well as quiet and private. Upstairs there is a very comfortable super kingsize bed, a rolltop bath, a huge velvet sofa and a 50" TV. Downstairs is a shower room, kitchen and large dining area. Lovely walks from the door and close to Salisbury, Longleat & Stonehenge

Shepherd's Hut (wood-fired hot tub/sauna optional)
Get away from it all and create romantic memorable moments in your rustic Acorn Hut. Step outside and be enveloped by nature and enjoy sitting in front of a fire pit or have a BBQ or a relaxing hot tub (EXTRA CHARGE). Acorn Hut has everything you need to stay comfortably and is particularly suited for nature lovers. Its small Hobbit wood burner will keep you snug and warm on a cold evening. Toilet/shower. Other cabins on site/ Horton Road which can be noisy at times. Hut is not fully fenced in.

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.

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

Shepherds Pye - Lakeside Retreat In The New Forest
Shepherd's Pye is a unique, 1920's Railway Carriage. Rescued from a local farm as a neglected frame, it has been lovingly restored by ourselves into a cosy, modern retreat on the edge of the New Forest. The hut is set in a secluded, private spot on our farm overlooking a lake. It is self contained and finished to a high standard; including a comfy double bed, heating, mains electrics and a fully equipped kitchen and en-suite bathroom, supplying all you need for rural yet comfortable stay.

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

Heated Pool, Hot Tub, Sauna, Games - Upton Bourn
Welcome to Upton Bourn Lodge, where unforgettable memories await for families and friends celebrating, or reuniting. Enjoy meals in the spacious double height dining room with seating for all. Take a dip in your heated pool, relax in the hot tub and sauna, and enjoy various games like table tennis, football, and pool. Explore nearby footpaths to visit three pubs offering superb food, beer, and cider. Catering, pampering or a host of on and offsite activities available to guests.

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.

Piilopirtti - a traditional Finnish log cabin
Spend your days in a traditional Finnish log cabin with a grass roof. Step outside and be enveloped by rhododendrons and enjoy sitting in front of a fire pit or a BBQ amongst trees and nature. The main room is for sleeping and living with a super-king size bed, table, TV, 2 easy chairs. The cabin has a fully equipped kitchen and a bathroom. Cabin is not fenced in. Adjacent to Ringwood Forest where you will find a cycle trail, Moors Valley Country Park, a golf course and a lake.

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.
Popular amenities for Weymouth rentals with a pool
House rentals with a pool

Silvermere, Silverlake in Dorset

Launceston Farmhouse with swimming pool & sauna

Coastal, New Forest 3 Bed Home Facilities Included

Susie's Caravan in Dorset

Fontwood Cottage – Woodland Hideaway with Hot Tub

Country House - Pool Jacuzzi Escape Room Karaoke

The Beach House Bournemouth

6-Bedroom Retreat w/ Pool, Sauna, Garden & Bar
Condo rentals with a pool

Seascape Apartment

Holiday apartment own heated indoor pool & sauna

Flat 10 Pelican House

The Palms, Apartment 15

The Palms Apartment 16 with Balcony

Bournemouth 2 Bedroom Apartment 22

2-BR Penthouse Apt. close to Beach with Pool*.

The Palms, Apartment 19
Other vacation rentals with a pool

Modern Spacious Holiday Home With Sea Views

Self contained in New Forest, hot tub and pool

Gardener's Cottage

Charming cottage with pool in the New Forest

Entire house with large garden.

Cosy Cabin in the New Forest at Sandy Balls

Kingfisher Lodge with Sea Views

Dorset Coastal Holiday Home
When is the best time to visit Weymouth?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$28,237 GYD | G$28,237 GYD | G$24,890 GYD | G$27,400 GYD | G$30,119 GYD | G$28,237 GYD | G$36,603 GYD | G$40,368 GYD | G$26,354 GYD | G$26,563 GYD | G$22,380 GYD | G$21,544 GYD |
| Avg. temp | 7°C | 7°C | 8°C | 9°C | 12°C | 15°C | 17°C | 17°C | 16°C | 13°C | 10°C | 8°C |
Quick stats about vacation rentals with a pool in Weymouth

Total vacation rentals
Explore 50 vacation rentals in Weymouth

Nightly prices starting at
Weymouth vacation rentals start at G$12,550 GYD per night before taxes and fees

Verified guest reviews
Over 2,100 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Weymouth vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Weymouth rentals

4.8 Average rating
Weymouth stays are highly rated by guests—averaging 4.8 out of 5!
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- New Forest National Park
- Paultons Park Home of Peppa Pig World
- Stonehenge
- Weymouth Beach
- Bournemouth Beach
- Boscombe Beach
- Brixham Harbour
- Lyme Regis Beach
- Bournemouth International Centre
- Southbourne Beach
- The Tank Museum
- Kimmeridge Bay
- Torquay Beach
- Crealy Theme Park & Resort
- Beer Beach
- Mudeford Quay
- Mendip Hills
- Mudeford Sandbank
- Shorefield Country Park
- Preston Sands
- Weymouth Pavilion
- West Bay Beach
- Longleat Safari Park
- Man O'War Beach





