
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.

Spacious and Stylish Home in Heart of Top Village
A stylish and spacious recently renovated recording studio, which has been finished to a high spec with exposed timber beams, brickwork and a stunning log burner perfect for relaxing after exploring all that Hampshire and West Sussex have to offer. There is a large double bedroom with king sized bed and ensuite bathroom, and an open plan living area with sofa beds and log burner that can accommodate up to 3 further guests. There are 3 fantastic pubs within walking distance - one only 50m away!

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.

Strideโs Barn
A newly restored and beautifully refurbished oak framed barn conversion bordering the New Forest National Park . With spectacular far reaching views Strideโs 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 โThe Cowshedโ (sleeps 2) .

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 itโs 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.

Spacious one bedroom annex in Hampshire village
Little Ashbrook is a newly renovated annex adjacent to our main home, on the edge of the pretty Hampshire village of Abbotts Ann. Just 5 minutes walk to 2 village pubs and an excellent award-winning, well stocked village shop and post office. Conveniently located to explore Iron Age forts, Stonehenge, Avebury, the bustling market town of Stockbridge, the Cathedral cities of Winchester and Salisbury, the New Forest and the South Coast. London Waterloo is an hour by train. A perfect escape!

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

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 dรฉcor. 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.

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.

The Old Stables, Derrydown Farm
A spacious cottage - two bedroom, three bathroom - converted from old stables - part of a 15th century traditional Hampshire farmstead in a tranquil edge-of-village setting in the iconic Bourne Valley. Two local pubs and village shop plus historic 12th century church within a 10 minute walk along flat footpaths. One guest described St Mary Bourne as a "Miss Marple village". Anyway it's perfect for a get-away-from-it-all weekend or midweek break.

Iconic Beach Front Stay | The Watch House, Lepe
A standout seafront landmark on Lepe Beach, The Watch House is a lovingly restored former lifeboat and coastguard station, once used to combat smuggling across the Solent. With original features, a modern kitchen, wood burner, cosy window seat over the water, and views to the Isle of Wight, itโs a guest favouriteโโan iconic beachfront stayโ and โperfect relaxing getaway.โ Pet-friendly with parking for two, perfect for families, couples, or friends.

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.
Popular amenities for house rentals in Winchester
House rentals with a pool

Perfect family getaway in the stunning Test Valley

Granary Cottage with access to indoor pool & spa

Coastal, New Forest 3 Bed Home Facilities Included

A holiday home in New Forest with pool & hot tub

Copse Farm Cottage

Award winning architecture in a National Park

Stunning forest cottage with sauna and hot tub

Eden Cottage, your home away
Weekly house rentals

Lovely 2BR Cottage Spacious with Garden

Cosy annex escape within the South Downs!

Winchester Cottage, Easton

Stylish house in Central Winchester

Highbury house

Waterfront. River Hamble. Private Pontoon. Hot Tub

4 Bed City House with Private Garden and Parking

Beautiful townhouse in central Winchester
Private house rentals

The Garden Wing is a very special tranquil place

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

Home in the Heart of Whitchurch

Coombe Cottage

Walsingham House Winchester

Idyllic countryside 3 Bedroom Cottage

Idyllic Dovecote Cottage in Jane Austen's Chawton

Charming Coach House with Hot Tub
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $207 SGD | $235 SGD | $223 SGD | $234 SGD | $226 SGD | $220 SGD | $230 SGD | $292 SGD | $276 SGD | $259 SGD | $244 SGD | $257 SGD |
| Avg. temp | 5ยฐC | 5ยฐC | 7ยฐC | 9ยฐC | 12ยฐC | 15ยฐC | 17ยฐC | 17ยฐC | 15ยฐC | 11ยฐC | 8ยฐC | 5ยฐC |
Quick stats about house rentals in Winchester

Total holiday rentals
Explore 130 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $26ย SGD per night before taxes and fees

Verified guest reviews
Over 6,410 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
130 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 โ averaging 4.8 out of 5!
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- South Downs National Park
- New Forest National Park
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Stonehenge
- Bracklesham Bay
- Windsor Castle
- Hampton Court Palace
- Highclere Castle
- Lower Mill Estate
- Boscombe Beach
- Chessington World of Adventures Resort
- Thorpe Park Resort
- Bournemouth Beach
- Winchester Cathedral
- Bournemouth International Centre
- Goodwood Racecourse
- The Tank Museum
- Kimmeridge Bay
- Southbourne Beach
- West Wittering Beach
- Highcliffe Beach
- Worthing Pier




