Book Holiday Homes in Winchester

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Winchester

Two Bare Feet

Two Bare Feet

3.5 out of 5
15a Parchment Street, Winchester, England
The price is NZ$211 per night from 17 Nov to 18 Nov
NZ$211
includes taxes & fees
17 Nov - 18 Nov
Stay at this 3.5-star vacation home in Winchester. Enjoy free WiFi, parking (surcharge), and bathrobes. Popular attractions Winchester Cathedral and Theatre ...
Two Bare Feet
Lovely dog friendly 2 bed bungalow with parking

Lovely dog friendly 2 bed bungalow with parking

Sway
Stay at this vacation home in Lymington. Enjoy free WiFi, a garden, and patios. Popular attractions New Forest National Park and St. Nicholas Church are located ...
Lovely dog friendly 2 bed bungalow with parking
Squirrels Drey

Squirrels Drey

Fareham
Stay at this vacation home in Fareham. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Titchfield Abbey and Hamble Common Beach are located ...
Squirrels Drey
Save an average of 15% on thousands of hotels when you're signed in
Beautiful 2-bed Apart in Southampton

Beautiful 2-bed Apart in Southampton

3 out of 5
Southampton
Stay at this 3-star vacation home in Southampton. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Southampton Cruise Terminal ...
Beautiful 2-bed Apart in Southampton
Charming 2 bedroom cottage in Lymington, very close to town, marina & sea walks

Charming 2 bedroom cottage in Lymington, very close to town, marina & sea walks

Lymington
Stay at this vacation home in Lymington. Enjoy a garden and in-room fireplaces. Our guests praise the property condition in our reviews. Popular attractions ...
Charming 2 bedroom cottage in Lymington, very close to town, marina & sea walks
Unique waterside home in stunning location.

Unique waterside home in stunning location.

Hythe
Stay at this vacation home in Southampton. Enjoy a garden and balconies. Popular attractions Southampton Cruise Terminal and WestQuay Shopping Centre are located ...
Unique waterside home in stunning location.
Spacious semi-detached Southsea House

Spacious semi-detached Southsea House

Portsmouth
Stay at this vacation home in Portsmouth. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Gunwharf Quays and Portsmouth Historic Dockyard ...
Spacious semi-detached Southsea House
Luxury home in the New Forest featuring a year-round heated swimming pool.

Luxury home in the New Forest featuring a year-round heated swimming pool.

Boldre
Stay at this vacation home in Lymington. Enjoy a garden, concierge services, and an in-room coffeemaker. Popular attractions New Forest National Park and Beaulieu ...
Luxury home in the New Forest featuring a year-round heated swimming pool.
Rampart View -  a house that sleeps 6 guests  in 3 bedrooms

Rampart View - a house that sleeps 6 guests in 3 bedrooms

Gosport
Stay at this vacation home in Gosport. Enjoy free WiFi and a garden. Popular attractions Gunwharf Quays and Portsmouth Historic Dockyard are located nearby.
Rampart View - a house that sleeps 6 guests in 3 bedrooms
Don't see what you're looking for?
See all available properties in Winchester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Winchester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winchester vacation homes are the perfect way for you to wing it.

Holiday houses in Winchester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winchester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winchester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winchester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winchester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winchester Holiday Homes essential information

Accommodation
462 Holiday Homes
Lowest Price
NZ$192
Highest Price
NZ$211
Popular accommodation
Two Bare Feet, Lovely dog friendly 2 bed bungalow with parking, Squirrels Drey, Beautiful 2-bed Apart in Southampton, Charming 2 bedroom cottage in Lymington, very close to town, marina & sea walks, Unique waterside home in stunning location., Spacious semi-detached Southsea House, Luxury home in the New Forest featuring a year-round heated swimming pool., Rampart View - a house that sleeps 6 guests in 3 bedrooms

Top trending hotels in Winchester

The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane, Winchester, England
Fully refundableReserve now, pay when you stay
The price is NZ$200 per night from 17 Nov to 18 Nov
NZ$200
includes taxes & fees
17 Nov - 18 Nov
Stay at this 4-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
The Winchester Hotel & Spa
Winchester Royal Hotel

Winchester Royal Hotel

4 out of 5
St Peter Street, Winchester, England
Fully refundableReserve now, pay when you stay
The price is NZ$199 per night from 15 Dec to 16 Dec
NZ$199
includes taxes & fees
15 Dec - 16 Dec
Stay at this hotel in Winchester. Enjoy breakfast (surcharge), 24-hour room service, and parking (surcharge). Our guests praise the breakfast and the bar in ...
Winchester Royal Hotel
Norton Park Hotel, Spa & Manor House

Norton Park Hotel, Spa & Manor House

4 out of 5
Sutton Scotney, Winchester, England
Fully refundableReserve now, pay when you stay
The price is NZ$192 per night from 15 Dec to 16 Dec
NZ$192
includes taxes & fees
15 Dec - 16 Dec
Stay at this 4-star spa hotel in Winchester. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in ...
Norton Park Hotel, Spa & Manor House
Save an average of 15% on thousands of hotels when you're signed in
Mercure Wessex Winchester Hotel

Mercure Wessex Winchester Hotel

4 out of 5
Paternoster Row, Winchester, England
Fully refundableReserve now, pay when you stay
The price is NZ$192 per night from 17 Nov to 18 Nov
NZ$192
includes taxes & fees
17 Nov - 18 Nov
Stay at this 4-star business-friendly hotel in Winchester. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
Mercure Wessex Winchester Hotel
Don't see what you're looking for?
See all available properties in Winchester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.