
Vacation 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

Cottage Pye - Beautiful Barn In The New Forest
Robert & Claire welcome you to Cottage Pye - a lovely renovated barn on the edge of the New Forest, which is renowned for its wild ponies & scenery. Located on our family farm within an idyllic courtyard of converted barns, beautifully decorated & furnished to a high standard. Accommodating between 6-8 guests + infants. Situated within the charming Hampshire countryside close to historic Romsey, Salisbury & Winchester, there are plenty of places to visit. 10 MINUTE DRIVE TO PEPPER PIG WORLD.

Arnewood Rise, a holiday home in New Forest & pool
Arnewood Rise is a luxury period property located in the heart of the New Forest. It is the perfect holiday home for big groups of all ages and fully equipped for fun times indoors and out. The grounds span 5.5 acres, including 1.5 acres of landscaped gardens with a heated outdoor swimming pool, a tennis court and 4 acres of fields complete with two ponies. It is ideally located within walking distance of the open national park and a short drive from the coastline and the many pretty villages.

Delightful Chalet Bungalow with a Spa
This beautifully presented chalet is within an old vineyard in a woodland area on the outskirts of Ryde ,with stunning views around the property. Although secluded, it is just a short distance to Ryde town centre & beaches . The property boasts a living/dining room with a smart tv and dining table and chairs , one being a double sofa bed.. Walk in shower in bathroom.. The kitchen has everything you need including dishwasher… The bedroom can be made up as 2 singles or kingsize upon request.

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

Chic Bungalow Retreat - Serene Garden, Pool & Spa
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 ✔ Newly Developed Location ✔ Ultimate Privacy & Security ✔ Spectacular Grounds

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.

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

Stunning Lodge, St Helens IOW. Beach Access & Pool

Coastal, New Forest 3 Bed Home Facilities Included

Copse Farm Cottage

Starfish Lodge Discounted ferry sailings available

Koda’s Luxury 40x16 ft Lodge Shorefield New Forest

Award winning architecture in a National Park

Villa @London Rd

Stunning forest cottage
Condo rentals with a pool

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

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

Beach Lookout - FREE Car Ferry 3+ nights

Luxury Penthouse: Spacious & Stylish

Seafront Serenity - FREE Car Ferry 3+ nights

Balcony On The Bay - FREE Car Ferry 3+ nights
Other vacation 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

Seaview three bedroom bungalow on holiday park

The Barn at Holly Cottage. Indoor Pool and tennis

Charming cottage with pool in the New Forest

Home Away From Home plus 25% off Ferries

Acer Double Shepherd's Hut
Quick stats about vacation rentals with a pool in Winchester

Total vacation rentals
Explore 40 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at € 34 per night before taxes and fees

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

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Winchester vacation rentals include wi-fi 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
- Goodwood Motor Circuit
- Paultons Park Home of Peppa Pig World
- Oxford University
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Boscombe Beach
- Highclere Castle
- Winchester Cathedral
- Twickenham Stadium
- Chessington World of Adventures Resort
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- Thorpe Park Resort
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- Worthing Pier
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