
Holiday rentals with a pool in Winchester
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Top-rated rentals with a pool in Winchester
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

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

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.

Blackberry Pye, Riverside Escape in The New Forest
Nestled on the edge of the New Forest National Park; Blackberry Pye is a beautiful, converted 1920's railway carriage. Set in a secluded spot on our family-run farm overlooking rolling fields, it is perfect for stargazing and getting away from it all! The decking area outside is 'suspended' above the river, creating a truly unique experience. This bespoke, handmade carriage provides you with all the luxuries you need for a rural, relaxing break in the great British countryside.

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.

Sea Views, Seaside, Quiet,Relaxing, Beach,Cliffs,
A beautifully presented Chalet Bungalow based on the edge of Solent Breezes Holiday park. 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 sofas or on the 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.

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.

Sandy Balls Holiday Village New Forest Hampshire
Spacious and well equipped holiday home located in a quiet spot at Sandy Balls Holiday Village. Bed linen & WIFI are included. Facilities: Indoor/outdoor pools, gym, jacuzzi, 2 adventure play areas, soft play, arcade, restaurants, Starbucks coffee shop and a village store. Enjoy evening entertainment and family activities, bike hire & alpaca walks. Sandy Balls is the perfect location for exploring the New Forest and surrounding areas. Paulton’s Park is 25 minutes away.

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.

Martyr Worthy Home with a View
Situated at the end of a lane with the river as your neighbour, the accommodation is set in beautiful cottage gardens. With walks on your doorstep and local village pubs just a stroll across the fields, you have the benefit of a peaceful rural location and the convenience of being close to the historic city of Winchester and the attractive Georgian town of Alresford.
Popular amenities for Winchester rentals with a pool
House rentals with a pool

Coastal, New Forest 3 Bed Home Facilities Included

Copse Farm Cottage

Shorefield Country Park-Free entertainment passes

Starfish Lodge Discounted ferry sailings available

5* Luxury dog friendly lodge @ Hoburne Bashley

Hoburne Holiday Park Home by the beach in Dorset

Koda’s Luxury 40x16 ft Lodge Shorefield New Forest

Dog friendly family home in The New Forest
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

Seafront Serenity - FREE Car Ferry 3+ nights

Balcony On The Bay - FREE Car Ferry 3+ nights
Other holiday rentals with a pool

Pete's Pad - Whitecliff Bay - Isle of Wight

Stylish Modern Caravan Stay

Self contained in New Forest, hot tub and pool

Holiday Home with Private Hot Tub near the beach.

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
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 $60 AUD 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 and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Winchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
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