
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) .

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

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.

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.

Romantic 17th Century Paper Mill on The Meon River
Enchanting converted 17th Century Paper Mill over the River Meon in Warnford, Hampshire. Quirky interior with original Japanese features. Trout anglers will have a ball. There are swans, herons, kingfishers and mallards and, if you're really lucky, you might see an otter. As you can see from the photo, the Mill is just by our cottage, but we're not always there so often you'd have the whole garden to yourself. My place is good for couples and solo adventurers.

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, it’s a guest favourite—“an iconic beachfront stay” and “perfect relaxing getaway.” 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.

The Granary Annex at Worthy Barn.
Ideal location for visiting the beautiful & historic Winchester in Hampshire. The Granary is 2 miles from Winchester, opposite a farm shop & lovely country pub is a 10 minute walk away. The main bedroom has a kingsize bed and views across watercress beds, the adjoining bedroom has bunk beds. The Granary is self contained with private 24 hour, access via key safe. There are many local walks and a variety of local food delivery options available.

Martyr Worthy Home with a View
Situated at the end of a lane with the river as your neighbour, the accommodation is set in beautiful cottage gardens. With walks on your doorstep and local village pubs just a stroll across the fields, you have the benefit of a peaceful rural location and the convenience of being close to the historic city of Winchester and the attractive Georgian town of Alresford.
Popular amenities for house rentals in Winchester
House rentals with a pool

Coastal, New Forest 3 Bed Home Facilities Included

A holiday home in New Forest with pool & hot tub

Copse Farm Cottage

Flint Cottage for two with indoor pool & sauna

Award winning architecture in a National Park

Stunning forest cottage with sauna and hot tub

Luxury Cedar House - Private Garden, Pool & Spa

Eden Cottage, your home away
Weekly house rentals

Luxury Rural Retreat with Hot Tub set in 3 acres

Weaver's Cottage

Charming cottage less than 5 minutes from the sea

House in the heart of Winchester

Grove Place, Winchester (2 parking spaces)

Stunning House in Central Winchester

Betty the Bedford + Outdoor Jacuzzi Bath!

Delightful 2 Bed Lodge In Downland Village
Private house rentals

Cosy annex escape within the South Downs!

Winchester Cottage, Easton

Stylish house in Central Winchester

Highbury house

Cosy cottage in stunning village

Beautiful townhouse in central Winchester

Quirky home in winchester 2 bedrooms entire unit

Stunning peaceful base to explore Hampshire
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $205 SGD | $233 SGD | $222 SGD | $232 SGD | $225 SGD | $218 SGD | $228 SGD | $290 SGD | $274 SGD | $258 SGD | $242 SGD | $255 SGD |
| 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 130 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $26 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 – averaging 4.8 out of 5!
Destinations to explore
- Flat rentals Winchester
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- House rentals Hampshire
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- New Forest National Park
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Bracklesham Bay
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Lower Mill Estate
- Highclere Castle
- Boscombe Beach
- Winchester Cathedral
- Chessington World of Adventures Resort
- Thorpe Park Resort
- Bournemouth Beach
- Kimmeridge Bay
- Goodwood Racecourse
- Highcliffe Beach
- The Tank Museum
- Worthing Pier
- West Wittering Beach
- Southbourne Beach
- Wentworth Golf Club
- RHS Garden Wisley




