
House holiday rentals in Winchester
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Top-rated house rentals in Winchester
Guests agree: these houses are highly rated for location, cleanliness and more.

Bay Tree, fabulous, modern 4 bed house, Winchester
Bay Tree is a spacious house in a quiet semi-rural location close to Winchester. Please do not book for a party or loud gathering. There are four bedrooms (six beds) two with ensuites, a downstairs shower wet room, well equipped kitchen, separate utility room and a large lounge/diner. The house has an enclosed private garden with decking & bbq. There is a trampoline for children to play on in the next garden. Towels and linen provided for guest use. On drive parking for two standard cars.

Stride’s Barn
A newly restored and beautifully refurbished oak framed barn conversion bordering the New Forest National Park . With spectacular far reaching views Stride’s Barn is situated 9 miles from the Cathedral City of Salisbury and 15 miles from Southampton . An ideal base to explore the local areas including many walks, pubs , restaurants, golf clubs and other tourist attractions such as Stonehenge and Paultons Park/Peppa Pig World . Can be rented with additional listing ‘The Cowshed’ (sleeps 2) .

4 Bed City House with Private Garden and Parking
Discover our beautifully decorated four-bedroom home in Winchester's historic city centre. Enjoy the convenience of two rare parking spaces and a courtyard garden to unwind in. Indulge in the city's amenities that are just a stone's throw away, from artisan coffee shops to chic restaurants. Winchester Cathedral is only a leisurely five-minute stroll away! Whether for leisure or business, our spacious home offers comfort and convenience. Experience Winchester's charm and book your stay today!

The Piggery: with tennis court and games barn
The Piggery is a secluded flint built hideaway, with lots of period charm, set in the grounds of a manor house. Converted to a high standard it has it’s own private garden, access to the owners tennis court & a large barn with table tennis, table football & pool, wider house grounds including an island, surrounded by the river Meon. Numerous walks direct from The Piggery and a number of local vineyards are nearby. 5/10mins walk away are two super pubs and the very well stocked village shop.

Oak Framed Barn with Tennis Court
A stylish secluded, two storey, oak framed barn with tennis court, 4 miles from Winchester. Homely space with two bedrooms plus a sofa bed (upon request) and ground floor open plan living area. Super fast WiFi. The Barn adjoins the Watercress Way and stands separately in the grounds with views over open Hampshire fields. Nearest neighbour c.1 mile away but there is loads to do in the area with an abundance of country pubs, one or two within walking distance and beaches within 50 minutes

Homely and Comfortable in a quiet location
A pretty, well-equipped and homely two bedroom terraced property situated in a quiet and lovely area of Chandler's Ford. Marwell Zoo, the New Forest, Paulton's Park/Peppa Pig World, Beaulieu, Isle of Wight ferry links and south coast beaches are a short drive away with excellent motorway and rail links. Ideal for contractor/business stays as well as families, couples and friends. Walk to the local shops and take a stroll to the beautiful Hiltingbury Lakes and local nature reserve.

Annex for couple or solo stay.
The Beehive, is a separate building with private access. It's part of our home in Headbourne Worthy and set in a peaceful semi-rural retreat. It is perfect for solo visitors or couples but not suitable for young children. We have lovely views, with great access to the rural footpaths and only a 15-20 minute walk to Winchester. It is a bright and airy space, with modern features and neutral décor. We are a 5 minute drive from the City of Winchester and mainline train station to London.

Central Winchester 1 Bedroom Home with own parking
Welcome to your lovely detached one bedroom home in a quiet leafy private road on the edge of St Giles Hill - just above medieval Winchester and on the edge of beautiful the South Downs Way. Your self-contained home includes parking on the drive, a stylish double bedroom, shower room, living area (with full double-width sofa bed) incorpoating a full kitchen/washing machine. Its an easy 10 minute downhill stroll across the park (lovely for a sunset picnic) to historic Winchester.

Boxwood, Owslebury, Winchester
Boxwood is on the edge of Owslebury, a picturesque village outside Winchester (15 minutes drive) in the South Downs National Park . It has a large open planning living space and 1 bedroom on the ground floor level alongside a cloak/shower room. Upstairs there are 3 bedrooms 1 twin, 1 double and 1 king with ensuite and a bathroom with bath and separate shower. There are 2 terraces and parking for 3 cars at the end of a shared drive. Note there are steps down to the door for access.

Stable Cottage Beauworth Southdowns Hampshire
Welcome to Stable Cottage, your idyllic getaway. Our newly built cottage is designed to the highest standard for your comfort and enjoyment. The cozy atmosphere is enhanced by super-insulated walls and a log-burning stove that keep you warm during colder months. In summer, the sliding patio doors let in sunshine and stunning views of the Hampshire countryside. Stay connected with super-fast fibre broadband and a Smart TV. Your stay at Stable Cottage will be unforgettable.

Secluded and peaceful home in beautiful village
A delightful detached two storey property in the grounds of Whitethorn cottage, in the picturesque village of Crawley near the historic city of Winchester. Secluded and quiet with pleasant garden views. Nicely furnished to a high standard throughout. Crawley is a beautiful classic English village with an excellent gastro pub, within easy walking distance. We will be available to offer help and advice on the many places to visit in the local area.

Charming period home in historic Newbury
Welcome to our cosy home in central Newbury. Perfect for Highclere castle and Just a 3-min walk to the town centre and Train station, walking distance to Newbury racecourse, ideal for exploring local shops, cafes, and the River Kennett. Enjoy countryside walks, cycling, and shopping nearby. Two bedrooms, 2 Bathrooms, Dining room, Private garden, Fast Wi-Fi. Pets welcome. Easy rail access to London, Oxford, Cotswolds. easy access to the M4.
Popular amenities for house rentals in Winchester
House rentals with a pool

Stunning Lodge, St Helens IOW. Beach Access & Pool

Coastal, New Forest 3 Bed Home Facilities Included

Award winning architecture in a National Park

Old Wharf Cottage

Eden Cottage, your home away

Stable Cottage with Hot Tub near Winchester

Surrey Cottage with indoor heated swimming pool

South Wing of Country House
Weekly house rentals

Spacious family home with garden

2BR Lovely Cottage Spacious with Private Garden

Weaver's Cottage

Stunning House in Central Winchester

Stylish house in Central Winchester

The Bowie is a David Bowie themed Smart Home + EV

Summer Riverside Escape Near Winchester

Beautiful townhouse in central Winchester
Private house rentals

Barn Annexe, Sleeps 4, Garden, Parking spaces

Racecourse Marina Lodge | Hot tub | Parking | EV

Grove Place, Winchester (2 parking spaces)

Boutique Retreat in Central Winchester

4 Bedroom Winchester Town House (central, parking)

4 BR House Winchester,Town-4 mins, 2X Free Parking

Coombe Cottage

Stunning Beachhouse with Sea Views | Pass the Keys
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £127 | £133 | £126 | £136 | £131 | £127 | £133 | £169 | £160 | £150 | £142 | £149 |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 15°C | 11°C | 8°C | 5°C |
Quick stats about house rentals in Winchester

Total holiday rentals
Explore 140 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at £15 per night before taxes and fees

Verified guest reviews
Over 6,480 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
140 of Winchester holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.8 Average rating
Winchester stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Cabin rentals Winchester
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- Rentals with a washing machine and dryer Winchester
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- Family-friendly rentals Winchester
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- House rentals Hampshire
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- House rentals United Kingdom
- South Downs National Park
- New Forest National Park
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Windsor Castle
- Stonehenge
- Bracklesham Bay
- Bournemouth Beach
- Thorpe Park Resort
- Lower Mill Estate
- Highclere Castle
- Hampton Court Palace
- Chessington World of Adventures Resort
- Boscombe Beach
- Winchester Cathedral
- Southbourne Beach
- Bournemouth International Centre
- Goodwood Racecourse
- The Tank Museum
- West Wittering Beach
- St Mary's Stadium
- Kimmeridge Bay
- Worthing Pier





