
Holiday rentals with a pool in Winchester
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winchester
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Spacious house and garden in Itchenor
Located in Shipton Green, Itchenor, The Willows is surrounded by large gardens with tennis court and heated swimming pool. Close to W. Wittering Beach and Itchenor Harbour, and with easy access to local walks, bike rides and waterside pubs. Near Chichester and Goodwood. 'WOW. The house is absolutely fantastic, we couldn't have asked for a better setting to celebrate Christmas. If you are looking for a spacious, beautiful property then this is a must book house. We will 100% be back'. Dec 2021

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 immediate access to numerous picturesque country walks right outside the barn doors. The property comes with a wood burner making Autumn and 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.

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.

Panoramic Sea Views, quiet, relaxed, Cozy, 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

Rural cottage with pool at Cheverton Farm Holidays
Escape to the Isle of Wight countryside in this peaceful, semi-detached cottage with a large garden, wood burning stove, BBQ area and views across open fields. Rowborough Cottage is just 300m from our family farm, guests enjoy shared access (with one other cottage) to a heated indoor pool, children’s playground, and games room - perfect for families or couples seeking a rural break. With EV charging at the farm and plenty of space to unwind, it’s an ideal base for exploring the island.

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.

Shepherd's Hut with Hot Tub near Winchester
Traditional shepherd's hut with a contemporary interior and private hot tub 3 miles from Winchester. En-suite shower, kitchenette, deck with table and chairs, bbq and brazier. The hut has a private location in the grounds of a country house. Guests can use the owner’s tennis court and heated outdoor pool (open May to end of September). Explore Winchester, Portsmouth, the New Forest and Hampshire’s beaches. This year-round retreat has a heated towel rail, electric radiator and WiFi.

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.

Beautiful S.Downs Cottage, pool and tennis
A private gate takes you directly onto the South Downs with some lovely foot and cycle paths on your doorstep. Close to the beach and city, Chichester, Portsmouth, Southhampton, Winchester, Goodwood and Witterings beaches are in easy reach while Liphook station takes you to Waterloo in an hour. Ripsley is a place to get away from it all. Great for cyclists, walkers, couples and families. The pool and tennis court are available from May to end Sept/early Oct, Mon- Sat 9am - 1 pm.

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.

Comfortable 1-Bedroom Guest Suite in rural setting
Quietly situated on the side of Blackdown in the South Downs National Park, 2 miles from Haslemere and convenient for visiting Chichester and Goodwood, The Barn is a well-appointed guest suite which offers comfortable accommodation for two. Convenient for exploring the local area, with immediate access to numerous public footpaths including the Sussex Border Path and Blackdown Hill. Ideally situated for animal lovers with an abundance of wildlife plus our own pet alpacas.

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

Copse Farm Cottage

Starfish Lodge Discounted ferry sailings available

Award winning architecture in a National Park

Villa @London Rd

6-Bedroom Retreat w/ Pool, Sauna, Garden & Bar

Stunning forest cottage

Stunning beachside holiday home with heated pool
Apartment rentals with a pool

Beautiful 3-bed flat by the sea with use of pool

Luxury Penthouse: Spacious & Stylish

Seafront Serenity - FREE Car Ferry 3+ nights

Balcony On The Bay - FREE Car Ferry 3+ nights

The Palms Apartment 16 with Balcony

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

Beach Lookout - FREE Car Ferry 3+ nights

The Palms, Apartment 19
Other holiday rentals with a pool

Self contained in New Forest, hot tub and pool

The Annex - Forest View

Cosy shepherd’s hut retreat in stunning garden

Private Spa Cabin- Cosy Hot Tub Under Stars

Seaview three bedroom bungalow on holiday park

The Barn at Holly Cottage. Indoor Pool and tennis

Home Away From Home plus 25% off Ferries

Charming cottage with pool in the New Forest
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 $52 SGD per night before taxes and fees

Verified guest reviews
Over 2,050 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 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!
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- New Forest national park
- Paultons Park Home of Peppa Pig World
- Oxford University
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