Vacation rentals with a pool in City of Winchester

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Top-rated rentals with a pool in City of Winchester

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Top guest favorite

An indoor swimming pool is set within a spacious enclosure, featuring a clear roof that allows natural light to filter through. The water is calm and inviting, surrounded by tiled flooring. Lush greenery is visible through the transparent walls, adding a natural element to the setting.

Vacation home

4.99 out of 5 average rating, 116 reviews

Daily Red Kite Feeding/Pool - Countryside Lodge

Peaceful, getaway lodge in the heart of Hampshire’s beautiful Hangars. We offer: - Daily Red Kite & Badger feeding, viewed from inside comfortable conservatory, with tea, coffee and refreshments! 30-90 Red Kites during each feeding/up to 10+ badgers! - Milk, bread, spread, tea, wine, sweets and soaps provided with each stay! - Indoor swimming pool, with full access; no permission required, 24/7. - Thirty acres of private garden/woodland to explore! - Free, on-site parking; multiple spaces.

Top guest favorite

The private swimming pool is surrounded by a well-maintained terrace featuring loungers and plantings. The clear water reflects the bright sky, while lush greenery provides a serene backdrop. The pool area offers a stylish and private space for relaxation.

Barn

5 out of 5 average rating, 125 reviews

Unique, romantic luxury retreat with swimming pool

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. Private heated swimming pool available in summer. 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. Lovely walks from the door and close to Salisbury, Longleat, Stonehenge and Bath

Top guest favorite

An indoor heated swimming pool is showcased, surrounded by large glass windows that provide views of the surrounding woodland. Comfortable seating is arranged nearby, and wooden beams create a warm ambiance throughout the space.

Tiny home

4.93 out of 5 average rating, 175 reviews

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.

Top guest favorite

A tranquil outdoor space features a heated swimming pool surrounded by a stone patio. Lush greenery and colorful flower beds enhance the setting, with an inviting barn structure visible in the background under a clear blue sky.

Barn

4.95 out of 5 average rating, 115 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.

Top guest favorite

A clear blue swimming pool is framed by a spacious patio featuring sun loungers and wooden dining furniture. The dark wooden loft conversion is visible in the background, surrounded by leafy greenery and potted plants, creating a serene outdoor atmosphere.

Barn

4.99 out of 5 average rating, 143 reviews

Luxurious getaway on rural Surrey/Sussex border.

Redwood is a charming loft conversion with views overlooking a garden, swimming pool, and farmland fields in the perfect location for both the South Downs and the Surrey Hills Area of Outstanding Natural Beauty, with several nearby pubs. Situated within the quaint village of Loxwood, you can enjoy the enchanting Surrey/Sussex countryside and rich wildlife. Enjoy a drink as the sun sets over our swimming pool or a picnic looking over the stunning nearby views. Continental Breakfast included.

Guest favorite

A tranquil view of the hut by a calm lake, surrounded by lush greenery and tall grasses. The serene water reflects the clear sky and distant trees, creating a peaceful atmosphere. The wooden fence encloses the property, highlighting the retreat's seclusion.

Shepherd’s hut

4.96 out of 5 average rating, 351 reviews

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.

Guest favorite

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

4.92 out of 5 average rating, 159 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

Guest favorite

Bungalow

4.91 out of 5 average rating, 127 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 favorite

The outdoor area features a rectangular pool covered with a blue tarp, bordered by a stone deck. Decorative planters are positioned along the edge, and lush greenery surrounds the space, with tall trees visible in the background.

Shepherd’s hut

4.96 out of 5 average rating, 387 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.

Top guest favorite

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

4.97 out of 5 average rating, 172 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 favorite

The Barn is showcased with a well-maintained outdoor swimming pool, surrounded by landscaped grass and trees. The inviting structure features large glass doors that open onto the patio area, creating a seamless connection between indoor and outdoor spaces.

Guesthouse

4.96 out of 5 average rating, 146 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 favorite

A charming wooden guest house is surrounded by lush greenery. Featuring a wooden deck with seating and a private hot tub, the structure has large glass doors that invite natural light. Sun loungers are positioned nearby, creating a serene outdoor space.

Tiny home

4.94 out of 5 average rating, 254 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.