
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.

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.

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.

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'.

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.

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

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.

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.

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

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.

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.

Oak House Annexe in the New Forest
Welcome to Oak House Annexe a beautiful new property in the New Forest and 5 minutes from the gorgeous seaside town of Lymington. The moment you drive through the large oak gates you know you are somewhere special. The Property is set in 10 Acres of land and sits alongside the beautiful Oak House. Only 25 minutes from Bournemouth & Christchurch, 35 minutes from Southampton. Escape from everything and experience something special.

Luxurious Lodge on Lake at Chichester with Hot Tub
Our Lodge is situated right on a lake. It has a lovely large decking with sunken hot tub. The new entertainment centre has a clubhouse, bar and restaurant open April to October It has a large decked terrace overlooking the lake, heated indoor pool and shop with seasonal hours. Nearby, Goodwood, Fontwell, Arundel Bognor Regis and West Wittering Beach. Chichester Station 2.2miles
Popular amenities for Winchester rentals with a pool
House rentals with a pool

Coastal, New Forest 3 Bed Home Facilities Included

Copse Farm Cottage

Starfish Lodge Discounted ferry sailings available

Award winning architecture in a National Park

The Beach House Bournemouth

Dive in at Deco Beach - Heated Pool and Hot Tub

Stunning forest cottage with pool, sauna & hot tub

Hidden Gem in the South Downs
Other holiday rentals with a pool

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

Rural retreat for two very near Winchester

Piilopirtti - a traditional Finnish log cabin

Lodge by the sea to cater for all ages

Bright beachside home with far reaching sea view.

Lovely 'Seaside Lodge’ Hoburne Naish Nr New Forest

5* waterside luxury boathouse - pool & log-burner

The Lodge
Destinations to explore
- Fitness-friendly rentals Winchester
- Rentals with a washing machine and dryer Winchester
- Smoking-friendly rentals Winchester
- Hotel rooms Winchester
- Rentals with outdoor seating Winchester
- Pet-friendly rentals Winchester
- Flat rentals Winchester
- Family-friendly rentals Winchester
- Waterfront rentals Winchester
- Townhouse rentals Winchester
- House rentals Winchester
- Apartment rentals Winchester
- Shepherd’s hut rentals Winchester
- Cabin rentals Winchester
- Rentals with breakfast Winchester
- Rentals with lake access Winchester
- Private suite rentals Winchester
- Rentals with beach access Winchester
- Rentals with a hot tub Winchester
- Rentals with an EV charger Winchester
- Guest house rentals Winchester
- Rentals with a patio Winchester
- Barn rentals Winchester
- Cottage rentals Winchester
- Rentals with a fireplace Winchester
- Serviced apartment rentals Winchester
- Bungalow rentals Winchester
- Bed and breakfasts Winchester
- Tiny house rentals Winchester
- Rentals with a firepit Winchester
- Nature eco lodge rentals Winchester
- Rentals with pools Hampshire
- Rentals with pools England
- Rentals with pools United Kingdom
- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Stonehenge
- Thorpe Park Resort
- South Downs National Park
- Chessington World of Adventures Resort
- Longleat Safari Park
- Windsor Castle
- Southbourne Beach
- LEGOLAND® Windsor Resort
- Bracklesham Bay
- Hampton Court Palace
- Highclere Castle
- Boscombe Beach
- Mudeford Quay
- Goodwood Racecourse
- The Tank Museum
- Winchester Cathedral
- Ascot Racecourse
- Twickenham Stadium
- Things to do Winchester
- Things to do Hampshire
- Art and culture Hampshire
- Nature and outdoors Hampshire
- Things to do England
- Wellness England
- Nature and outdoors England
- Sightseeing England
- Food and drink England
- Tours England
- Entertainment England
- Art and culture England
- Sports activities England
- Things to do United Kingdom
- Food and drink United Kingdom
- Entertainment United Kingdom
- Sports activities United Kingdom
- Wellness United Kingdom
- Nature and outdoors United Kingdom
- Tours United Kingdom
- Sightseeing United Kingdom
- Art and culture United Kingdom







