Vacation 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.

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Top guest favourite
Barn in Dinton
5 out of 5 average rating, 149 reviews

Unique, romantic luxury countryside retreat

Beautifully furnished, romantic and spacious ancient dovecote in a gorgeous peaceful countryside setting, the thick stone walls make it warm and cosy in winter, cool in summer as well as quiet and private. Upstairs there is a luxurious super kingsize bed, a rolltop bath, a huge velvet sofa and a 50" TV and downstairs is a shower room, kitchen and large dining area. Private swimming pool available, heated in summer. Lovely walks from the door and close to Salisbury, Longleat, Stonehenge and Bath

Guest favourite
A renovated barn exterior is framed by a charming garden with purple flowers. The entrance features a covered porch and large glass doors, leading to an inviting seating area with wicker furniture arranged around a table.
Farm stay in Plaitford
4.88 out of 5 average rating, 136 reviews

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.

Guest favourite
A scenic view showcases a lush green landscape surrounded by manicured hedges and diverse trees. Autumn colors are visible in the foliage, with muted yellows and greens punctuating the vast space. The cloudy sky creates a tranquil atmosphere over the serene setting.
Barn in West Sussex
4.95 out of 5 average rating, 131 reviews

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.

Guest favourite
A patio dining set features a dark woven table surrounded by four comfortable chairs with soft cushions. A vase of sunflowers sits at the center of the table, complemented by blue plates and glasses. The expansive lawn offers uninterrupted views of the Solent.
Bungalow in Warsash
4.92 out of 5 average rating, 173 reviews

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

Superhost
An indoor pool area is framed by large glass doors, allowing natural light to enhance the space. The pool features a vibrant blue color, surrounded by stylish loungers and illuminated by soft mood lighting. A spa area with textured tiles is visible at the far end.
Bungalow in Bosham
4.88 out of 5 average rating, 154 reviews

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

Top guest favourite
A modern guest lodge is showcased, featuring a distinctive curved roof and large glass windows that enhance the natural light. The surrounding outdoor area is paved, including a pool with a cover and seating arrangements for relaxation.
Place to stay in Hill Brow
4.99 out of 5 average rating, 103 reviews

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.

Top guest favourite
The shepherd's hut is nestled among greenery, featuring a light exterior and dark window frames. The entrance is adorned with flowing curtains, revealing glimpses of the contemporary interior. A small deck with chairs is positioned outside, surrounded by colorful wildflowers.
Shepherd’s hut in Winchester
4.96 out of 5 average rating, 399 reviews

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.

Superhost
The cottage is surrounded by lush greenery and a well-maintained garden. A gravel path leads to the entrance, framed by neatly trimmed hedges. Large windows reflect natural light, while bicycles are casually positioned nearby, suggesting an inviting outdoor environment.
Cottage in Hampshire
4.93 out of 5 average rating, 204 reviews

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.

Guest favourite
An outdoor space features a hot tub in the foreground, with jets gently bubbling. A swimming pool is visible in the background, surrounded by a stone patio and outdoor furniture. Lush greenery and a sunset sky create a serene backdrop.
Place to stay in Stroud
4.96 out of 5 average rating, 189 reviews

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.

Top guest favourite
A spacious bedroom features a comfortable bed dressed in light bedding. Large windows allow natural light to fill the room, with views of greenery outside. Artwork adorns the walls, and a cozy sitting area includes a chair and a television, enhancing the room's inviting atmosphere.
Guesthouse in West Sussex
4.96 out of 5 average rating, 163 reviews

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.

Top guest favourite
The exterior of a cottage features a mix of brick and flint walls, complemented by modern double-glazed windows. A spacious patio area with stone tiles is revealed, lined with potted greenery. The entrance showcases glass doors that open into the interior space.
Guesthouse in Aldingbourne
5 out of 5 average rating, 125 reviews

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.

Top guest favourite
The exterior of the charming guest house is illuminated by warm string lights. A private deck features a hot tub, surrounded by lush greenery. Cozy seating is provided nearby, enhancing the inviting atmosphere for a relaxing evening outdoors.
Tiny homes in Soberton
4.94 out of 5 average rating, 283 reviews

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

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 $56 CAD 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 and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Winchester vacation 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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