
Holiday rentals with a pool in Winchester
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Winchester

Total holiday rentals
Explore 40 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 2,210 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Winchester holiday rentals include wifi access

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

4.9 Average rating
Winchester stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with a pool in Winchester
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Daily Red Kite Feeding/Pool - Countryside Lodge
JUNIPER HOUSE AIRBNB - Peaceful, getaway lodge in the heart of Hampshire’s beautiful Hangars. We offer: - Daily Red Kite & Badger feeding, viewed from inside comfortable conservatory, with tea, coffee and refreshments! 30-90 Red Kites during each feeding/up to 10+ badgers! - Milk, bread, spread, tea: Provided upon arrival. - Indoor swimming pool, with full access; no permission required, 24/7. - Thirty acres of private garden/woodland to explore! - Free, on-site parking; multiple spaces.

Beautiful S.Downs Cottage, pool and tennis
The private gate takes you directly onto the South Downs. Close to the beach and city, Chichester, Portsmouth, Goodwood, Cowdray and Witterings beaches are close by while the train takes you to Waterloo in an hour. Ripsley is a place to get away from it all. Great for cyclists, walkers, couples and families. There are garden games, a tree swing, tree house, firepit and football to enjoy while the pool and tennis court are available from late May until the end Sept/early Oct, Mon- Sat 9am - 1 pm.

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.

Secluded Country Cottage
Relax in this spacious, comfortable and serene cottage near Petersfield, and located in the South Downs National Park. The bright living room features a log fire, the generous bedroom a king-sized bed. The ensuite bathroom is airy and the kitchen well-equipped. All rooms have high ceilings, adding to the roomy feel. Outside is a seating area with table, chairs and parasol. Beautiful country setting with stunning views and exclusive stile to footpath leading up into the 'Hampshire Hangers'.

Panoramic Sea Views, quiet, relaxed, cliffs, Beach
A beautifully presented Chalet Bungalow based on the edge of Solent Breezes Holiday park. Full Sea views over the Solent from the comfort of the open plan kitchen diner and lounge. Light airy building ideal for relaxing either on the large leather sofa or on the rattan furniture in the garden. In all weathers there is always something to see out of the large patio doors. Stony beach and slipway for boats only metres from the property. Ideal for long walks watching the sunset and relaxing

Delightful one bedroom barn with beautiful views
Our beautiful rustic one bedroom barn is attached to the end of our family home. Situated in the popular Surrey Hills an area of outstanding beauty surrounded by many local award winning pubs and to numerous picturesque country walks right outside the barn doors. The property comes with a wood burner making winter particularly lovely with board games available. Guests are also welcome to use the house facilities which include a heated swimming pool and tennis court. Dogs are very welcome

The Pool House (for 2 Adults & 2 Children)
This unique, Architect designed self contained building, has a style all of its own. With an open plan kitchenette and island unit, including an oven, microwave, hob and fridge freezer, you can dine in or go out to the Market Town of Petersfield. The lounge area has a 72" TV with a full sky package and spare HDMI leads. There is a walk in shower wet room and a separate cloakroom. The bedroom is cosy, with a king size bed. There is a separate area with bunkbeds, for smaller children.

The Pool House: Contemporary country escape
Enjoy a relaxing time in the heart of the South Downs. Have a dip in the pool to cool off or warm up in the hot tub. Consisting of 2 king size beds, double sofa bed, open plan kitchen, dining room and living space. Open up the bi fold doors onto a large patio area with bbq, pizza oven and eating area. Situated 1 mile from the market town of Petersfield. Country walks on the doorstep and 500m from the local pub. Only 20 mins drive to the beach its a great spot for a break.

Cedar Lodge - Pool & Spa Complex
A Luxurious Retreat in the Heart of Nature Nestled within the scenic South Downs, a short stroll from Bosham Harbour, Cedar Lodge is a new development offering luxury & tranquility. Less than 6 miles from Goodwood & 9 miles from West Wittering Beach, this retreat is close to the historic city of Chichester, contained within a vast 3.5-acre garden amid peaceful fields & woodlands. Key Highlights: ✔ VAT Friendly ✔ Indoor Pool & Spa Complex (extra) ✔ Spectacular Grounds

Grayswood Cowshed in stunning Grounds
A beautifully converted Cowshed in a rustic style with luxurious Super King bed in a studio suite with added double bunk room for up to four extra guests. Studio has a galley kitchen with hob and oven for basic cooking. Well fitted bathroom facilities including powerful shower and roll top bath and underfloor heating. Relaxing Sofa in main space with Flatscreen TV and wifi throughout. Underfloor heating throughout. Large french windows overlooking an orchard.

Heated Pool & Hot Tub – Couples Retreat
⚠️ Important: Neighbouring building works are currently underway on a property directly bordering Hillside Oasis. There may be daytime construction noise and occasional reduced privacy during working hours, so please consider this before booking. Prices have been reduced to reflect. Enjoy exclusive use of your heated pool, year-round hot tub and private accommodation for two. Inside is calm and comfortable, with a cosy lounge, restful bedroom and modern bathroom.

The Guest House, Five Trees
The Guest House is a perfect rural get away. It is set in the classic English country garden of a 16th century thatched house in the Meon Valley. It has a private deck with a hot tub. The grounds contain a swimming pool and tennis court for guest use upon request. The pool is open in summer. The River Meon, multiple footpaths and a lovely local pub are within a few steps of the property. Use of pool, hot tub and tennis court are at your own risk.
Popular amenities for Winchester rentals with a pool
House rentals with a pool

Coastal, New Forest 3 Bed Home Facilities Included

Starfish Lodge Discounted ferry sailings available

Award winning architecture in a National Park

The Beach House Bournemouth

Stunning forest cottage with pool, sauna & hot tub

Stunning beachside holiday home with heated pool

Surrey Cottage with indoor heated swimming pool

Beautiful countryside home with indoor heated pool
Apartment rentals with a pool

The Palms, Apartment 20

Guest house in Pewsey Vale with pool

Luxury Penthouse: Spacious & Stylish

Flat 10 Pelican House

Seafront Serenity - FREE Car Ferry 3+ nights

Balcony On The Bay - FREE Car Ferry 3+ nights

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

Beach Lookout - FREE Car Ferry 3+ nights
Other holiday rentals with a pool

Luxurious Lodge on Lake at Chichester with Hot Tub

Piilopirtti - a traditional Finnish log cabin

‘Stag Cottage’ New Forest Romantic Hideaway

Bright beachside home with far reaching sea view.

Lodge by the sea to cater for all ages

Lovely 'Seaside Lodge’ Hoburne Naish Nr New Forest

5* waterside luxury boathouse - pool & log-burner

Oak House Annexe in the New Forest
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- Rentals with pools Hampshire
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- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Stonehenge
- Thorpe Park Resort
- South Downs National Park
- Chessington World of Adventures Resort
- Longleat Safari Park
- Windsor Castle
- Southbourne Beach
- LEGOLAND® Windsor Resort
- Bracklesham Bay
- Hampton Court Palace
- Highclere Castle
- Boscombe Beach
- Mudeford Quay
- Goodwood Racecourse
- The Tank Museum
- Winchester Cathedral
- Ascot Racecourse
- Kimmeridge Bay
- Things to do Winchester
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