Winchester Vacation Rentals

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Check prices for these dates

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Winchester vacation rentals

Dining
Squirrel's Leap

Cottage in Winchester

Squirrel's Leap
3.0 star property
The price is P31,677
P38,012 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Squirrel's Leap
Terrace/patio
Peaceful Elevated Residential Area - Walk to City

Cottage in Winchester

Peaceful Elevated Residential Area - Walk to City
5.0 star property
The price is P21,078
P25,294 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Peaceful Elevated Residential Area - Walk to City
Property grounds
Rivergem - Riverside Coach House

Cottage in Winchester

Rivergem - Riverside Coach House
2.0 star property
The price is P57,153
P68,584 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Rivergem - Riverside Coach House
Private kitchen
Stonehenge Cottages

Cottage in Salisbury

Stonehenge Cottages
5.0 star property
9.8 out of 10, Exceptional, (105)
"Information, including a video, provided by the friendly owners before and during our stay was excellent. The beautifully appointed cottage was convenient for Salisbury and for the nearby pub which serves good food. We will definitely stay there again, if in the area."
United Kingdom
Fiona
The price is P12,488
P14,986 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Stonehenge Cottages
Front of property
room2 Southampton Hometel

Aparthotel in Southampton City Centre

room2 Southampton Hometel
4.0 star property
9.4 out of 10, Exceptional, (1180)
"Staff was great and the room was really nice. I was impressed by the design and it was spacious "
United States
Vanessa
The price is P4,959
P5,951 total
includes taxes & fees
Dec 30 - Dec 31
room2 Southampton Hometel
Balcony
Groomes Country House

Cottage in Bordon

Groomes Country House
3.5 star property
The price is P199,362
P239,235 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Groomes Country House
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.
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Top Winchester Hotel Reviews

Novotel Southampton

Novotel Southampton

10/10 Excellent
"None only cleanliness of hotel stay staff communication was limited "
David 1-night trip
Posted 2 days ago
Novotel Southampton

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we give you a choice of vacation rentals in Winchester close to Winchester Science Centre and Planetarium, or you can go with a more secluded option if you're looking for a relaxing stay. Visitors like the stunning cathedral and picturesque gardens in Winchester. The array of shops and festivals are some other things you might want to check out while you're here.

How many vacation rentals are there in Winchester?

Expedia has 40 vacation rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Winchester Science Centre and Planetarium and Marwell Zoo are a couple of family-friendly sights, whereas cultural attractions include Great Hall and Theatre Royal Winchester. While in the area, you can also visit popular places like Southampton Cruise Terminal and New Forest National Park.

What’s a vacation rental in Winchester like?

A vacation rental is a private property where you can stay for several days or longer in Winchester. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family getaway.