
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.

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.

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.

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.

Rural Isle of Wight cottage with woodburner
Escape to the Isle of Wight countryside in this peaceful, semi-detached cottage with three bedrooms, a large garden, wood burning stove and views across open fields. Rowborough Cottage is just 300m from our family farm. Guests can enjoy access with two other cottages to farm animals, playground, games room and heated indoor pool (Feb- Oct) - perfect for families 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.

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

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.

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 Cottage at The Dene - With Goodwood Healthclub
We have now completed a major renovation of the cottage and are taking bookings. The cottage combines chic luxury with a country touch, and provides a private location close to the amenities of Roman Chichester, Arundel with its impressive castle and quaint shops, and the facilities of the Goodwood estate. Guests (2 per visit) receive complimentary membership of the Goodwood Healthclub and Spa for the duration of their stay. See the cottage on the web for more details.

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

Luxe New Forest home with swim spa - Moonwood

Starfish Lodge Discounted ferry sailings available

Stunning 5BR Home with Pool - 5 min to Beach

Pet friendly 2 bed holiday home

Award winning architecture in a National Park

Marble Bridge Annexe | by The Butler Collection
Condo rentals with a pool

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

Bright, spacious annexe in beautiful Pewsey Vale.

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 vacation rentals with a pool

Self contained in New Forest, hot tub and pool

Cosy shepherd’s hut retreat in stunning garden

Cosy caravan in private woodland setting

Seaview three bedroom bungalow on holiday park

Amazing Lodge, edge of Forest with giant deck

Charming cottage with pool in the New Forest

Home Away From Home plus 25% off Ferries

Sleeps 2-4, heated indoor pool. Dog friendly.
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 ﺩ.ﺇ147 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
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Boscombe Beach
- Highclere Castle
- Winchester Cathedral
- Twickenham Stadium
- Chessington World of Adventures Resort
- Kimmeridge Bay
- Thorpe Park Resort
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- Goodwood Racecourse
- Highcliffe Beach
- Worthing Pier
- West Wittering Beach
- The Tank Museum
- Wentworth Golf Club
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- RHS Garden Wisley
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