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.

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Top guest favourite
A charming two-story lodge features a decorative timber facade and a welcoming entry. Lush greenery surrounds the home, with vibrant flower beds lining the pathway. A second-floor balcony offers an elevated view of the landscaped garden, and sunlight bathes the exterior in a warm glow.
Holiday home in Hawkley
4.98 out of 5 average rating, 186 reviews

Daily Red Kite Feeding/Pool - Countryside Lodge

JUNIPER HOUSE AIRBNB - 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: Provided upon arrival. - 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.

Guest favourite
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, 215 reviews

Beautiful S.Downs Cottage, pool and tennis

The private gate takes you directly onto the South Downs. Close to the beach and city, Chichester, Portsmouth, Goodwood, Cowdray and Witterings beaches are close by while the train takes you to Waterloo in an hour. Ripsley is a place to get away from it all. Great for cyclists, walkers, couples and families. There are garden games, a tree swing, tree house, firepit and football to enjoy while the pool and tennis court are available from late May until the end Sept/early Oct, Mon- Sat 9am - 1 pm.

Top guest favourite
Cottage in Steep
4.88 out of 5 average rating, 105 reviews

Secluded Country Cottage

Relax in this spacious, comfortable and serene cottage near Petersfield, and located in the South Downs National Park. The bright living room features a log fire, the generous bedroom a king-sized bed. The ensuite bathroom is airy and the kitchen well-equipped. All rooms have high ceilings, adding to the roomy feel. Outside is a seating area with table, chairs and parasol. Beautiful country setting with stunning views and exclusive stile to footpath leading up into the 'Hampshire Hangers'.

Top guest favourite
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 in Isle of Wight
4.94 out of 5 average rating, 237 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 favourite
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 in Plaitford
4.96 out of 5 average rating, 391 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 favourite
A patio table is set for dining, featuring blue plates and glasses. A vase of sunflowers adds a cheerful touch. In the background, a green lawn leads to a view of the sea and distant boats, showcasing the serene coastal setting.
Bungalow in Warsash
4.92 out of 5 average rating, 190 reviews

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

Top guest favourite
The lodge is presented with a spacious wraparound decking area, featuring ample seating. Large glass doors allow natural light to fill the interior, while the structure is set against a backdrop of greenery, providing a serene atmosphere.
Chalet in West Sussex
4.98 out of 5 average rating, 116 reviews

A spacious, light and airy luxury lodge

This stunning 45 x 20ft Tuscany style lodge is set in the tranquil grounds of Chichester Lakeside Holiday Park. The park boosts 10 fishing lakes, set in over 150 acres close to the historic town of Chichester, other local places nearby to explore are Bognor Regis, West Witterings beach, Portsmouth, South Downs, Brighton, Arundel Castle, Pagham Nature Reserve, Chichester golf course Goodwood racecourse. This is a great place to unwind, relax and explore what West Sussex has to offer.

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, 109 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.

Superhost
Home in Bosham
4.9 out of 5 average rating, 288 reviews

Cedar House - Pool & Spa Complex

Cedar House is a beautifully secluded 4 bedroom house in a private gated complex, with option to book the Spa Complex with Indoor Heated Pool & Hot Tub & Golf Simulator Room ✔ 4 bedrooms sleep 8 *PLEASE READ BELOW* ✔ Large garden set in the 3.5 acre grounds ✔ Onsite parking for 6 cars ✔ Indoor Pool & Spa Complex (extra) ✔ Fully Equipped Open Plan Kitchen ✔ Gas BBQ & Garden Furniture ✔ 20KW Highspeed 3 Phase EV Charging Point ✔ Pet Friendly ✔ Highspeed Wi-Fi See more below!

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, 227 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
The image showcases a spacious outdoor area featuring an 8-meter swimming pool and a private hot tub. A covered seating area with dining furniture is visible in the background, surrounded by well-maintained landscaping and clear blue skies.
Cabin in Portchester
4.99 out of 5 average rating, 116 reviews

Private Heated Pool & Hot Tub Escape

⚠️ Important: Neighbouring building works are currently underway on a property directly bordering Hillside Oasis. There may be daytime construction noise and occasional reduced privacy during working hours, so please consider this before booking. Prices have been reduced to reflect. Enjoy exclusive use of your heated pool, year-round hot tub and private accommodation for two. Inside is calm and comfortable, with a cosy lounge, restful bedroom and modern bathroom.

Top guest favourite
Tiny home in Soberton
4.94 out of 5 average rating, 324 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.

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