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 favorite
A clear view of the spacious backyard features a heated swimming pool in the foreground, surrounded by a wooden deck. A grassy area extends toward the house, which is designed with large windows and a patio with outdoor seating, providing a serene outdoor environment.
Home
4.98 out of 5 average rating, 107 reviews

Spacious house and garden in Itchenor

Located in Shipton Green, Itchenor, The Willows is surrounded by large gardens with tennis court and heated swimming pool. Close to W. Wittering Beach and Itchenor Harbour, and with easy access to local walks, bike rides and waterside pubs. Near Chichester and Goodwood. 'WOW. The house is absolutely fantastic, we couldn't have asked for a better setting to celebrate Christmas. If you are looking for a spacious, beautiful property then this is a must book house. We will 100% be back'. Dec 2021

Guest favorite
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
4.89 out of 5 average rating, 140 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 favorite
The exterior of a luxury period property is showcased, featuring a large garden area with lush green grass. The house displays a blend of brick and greenery, including a charming conservatory with numerous windows. Trees frame the property, enhancing the serene outdoor setting.
Home
4.9 out of 5 average rating, 176 reviews

Arnewood Rise, a holiday home in New Forest & pool

Arnewood Rise is a luxury period property located in the heart of the New Forest. It is the perfect holiday home for big groups of all ages and fully equipped for fun times indoors and out. The grounds span 5.5 acres, including 1.5 acres of landscaped gardens with a heated outdoor swimming pool, a tennis court and 4 acres of fields complete with two ponies. It is ideally located within walking distance of the open national park and a short drive from the coastline and the many pretty villages.

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
4.94 out of 5 average rating, 204 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.

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, 176 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
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
4.89 out of 5 average rating, 166 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
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
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 favorite
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
4.96 out of 5 average rating, 400 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
The image captures a log cabin with a green grass roof adorned with seasonal bluebells. A chimney emits smoke, indicating warmth within. A wooden hot tub is positioned on the deck, surrounded by trees and nature, inviting a serene outdoor experience.
Cabin
4.94 out of 5 average rating, 277 reviews

Piilopirtti - a traditional Finnish log cabin

Spend your days in a traditional Finnish log cabin with a grass roof. Step outside and be enveloped by rhododendrons and enjoy sitting in front of a fire pit or a BBQ amongst trees and nature. The main room is for sleeping and living with a super-king size bed, table, TV, 2 easy chairs. The cabin has a fully equipped kitchen and a bathroom. Cabin is not fenced in. Adjacent to Ringwood Forest where you will find a cycle trail, Moors Valley Country Park, a golf course and a lake.

Guest favorite
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
4.93 out of 5 average rating, 205 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.

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
4.96 out of 5 average rating, 197 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 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 home
4.94 out of 5 average rating, 287 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 € 34 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 & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Winchester vacation rentals include wi-fi 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!

Destinations to explore

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