Holiday rentals with a pool in Winchester

Find and book unique homes with a pool on Airbnb

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 $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,210 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Winchester holiday 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!

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, 182 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, 212 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.

Guest favourite
A rustic Acorn Hut, clad in green, is surrounded by lush foliage and blooming flowers. A hot tub sits on a wooden deck, while a wood burner is positioned nearby, enhancing the natural setting. The entrance to the hut is inviting, framed by greenery.
Shepherd’s hut in Ashley Heath
4.95 out of 5 average rating, 460 reviews

Shepherd's Hut (wood-fired hot tub/sauna optional)

Get away from it all and create romantic memorable moments in your rustic Acorn Hut. Step outside and be enveloped by nature and enjoy sitting in front of a fire pit or have a BBQ or a relaxing hot tub (EXTRA CHARGE). Acorn Hut has everything you need to stay comfortably and is particularly suited for nature lovers. Its small Hobbit wood burner will keep you snug and warm on a cold evening. Toilet/shower. Other cabins on site/ Horton Road which can be noisy at times. Hut is not fully fenced in.

Top guest favourite
Cottage in Steep
4.88 out of 5 average rating, 100 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'.

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, 187 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
Barn in West Sussex
4.94 out of 5 average rating, 152 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 to numerous picturesque country walks right outside the barn doors. The property comes with a wood burner making 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. Dogs are very welcome

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, 108 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
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
4.97 out of 5 average rating, 225 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.

Superhost
A spacious indoor swimming pool is highlighted by bright LED mood lighting and expansive windows providing views of the surrounding landscape. Luxurious loungers and seating areas are positioned nearby, enhancing the serene ambiance of the space.
Bungalow in Bosham
4.87 out of 5 average rating, 199 reviews

Cedar Lodge - Pool & Spa Complex

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 ✔ Indoor Pool & Spa Complex (extra) ✔ Spectacular Grounds

Top guest favourite
Guest house in Grayswood
4.97 out of 5 average rating, 346 reviews

Grayswood Cowshed in stunning Grounds

A beautifully converted Cowshed in a rustic style with luxurious Super King bed in a studio suite with added double bunk room for up to four extra guests. Studio has a galley kitchen with hob and oven for basic cooking. Well fitted bathroom facilities including powerful shower and roll top bath and underfloor heating. Relaxing Sofa in main space with Flatscreen TV and wifi throughout. Underfloor heating throughout. Large french windows overlooking an orchard.

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, 113 reviews

Heated Pool & Hot Tub – Couples Retreat

⚠️ 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, 320 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

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