Vacation rentals with a pool in City of Winchester

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Top-rated rentals with a pool in City of Winchester

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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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 in Hawkley

4.98 out of 5 average rating, 126 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

A private swimming pool is set within a stone patio, surrounded by lush greenery. The water exhibits a bright blue hue, and steps lead gracefully into the pool. Nearby seating areas and the exterior of the barn can be glimpsed in the background.

Barn in Wroxall

4.99 out of 5 average rating, 118 reviews

Idyllic, private & unique countryside holiday

Our Granary is a stylish, sustainable barn conversion set in idyllic countryside at the end of a quiet country lane, surrounded by a horseshoe of downs and near wonderful beaches. It truly is a picturesque spot, and all just 3 hours from London. The Granary has just been renovated from two agricultural buildings. With two comfy bedrooms, a large kitchen diner to inspire a great meal, a lounge with a wood burner and a huge window seat in which to gaze out at the garden, courtyard and the pool.

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 in West Sussex

4.98 out of 5 average rating, 101 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

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 in Dinton

5 out of 5 average rating, 135 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. 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

Guest favorite

The exterior of the luxury period property showcases a charming combination of brick and wood. A graceful conservatory with large glass windows opens onto the landscaped gardens. Lush greenery surrounds the home, emphasizing its spacious outdoor setting beneath a partly cloudy sky.

Home in Tiptoe

4.9 out of 5 average rating, 161 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.

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 in West Sussex

4.95 out of 5 average rating, 116 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 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 in Warsash

4.92 out of 5 average rating, 162 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

A spacious indoor pool area is featured with large windows that provide abundant natural light and views of the surrounding gardens. Comfortable lounge seating is visible along one side, complementing the serene atmosphere of the heated pool.

Home in Bosham

4.91 out of 5 average rating, 242 reviews

Luxury Cedar House - Private Garden, Pool & Spa

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 private 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!

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 in Winchester

4.96 out of 5 average rating, 391 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.

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 in Hampshire

4.94 out of 5 average rating, 196 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

The Pool House is set against a twilight backdrop, featuring warm lights that highlight its modern design. The spacious patio area is adorned with seating and a large pool, surrounded by greenery, offering an inviting outdoor space for relaxation.

Place to stay in Stroud

4.97 out of 5 average rating, 175 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 in West Sussex

4.96 out of 5 average rating, 151 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.