A large red brick building with a central entrance flanked by columns, a fountain in front, and trees on either side.

Winchester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Winchester holiday rentals

Iron/ironing board, free WiFi

Settle Winchester

Settle Winchester
2.0 star property
Winchester
The price is S$181
includes taxes & fees
12 Jul - 13 Jul
Settle Winchester
Dining

Squirrel's Leap

Squirrel's Leap
3.0 star property
Winchester
The price is S$852
includes taxes & fees
17 Jul - 18 Jul
Squirrel's Leap
Property grounds

Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester
The price is S$1,493
includes taxes & fees
7 Aug - 8 Aug
Rivergem - Riverside Coach House
Exterior

Hollington Park Glamping

Hollington Park Glamping
2.0 star property
Newbury
8.0 out of 10, Very good, (2 reviews)
"We had a lovely time here with our 2 year old for two nights. We stayed in the Bluebell Pod which was so cosy and comfortable. We had everything we needed and really enjoyed the woods and the animals. Many thanks. Hope to come again next year! "
United Kingdom
maria
The price is S$192
includes taxes & fees
13 Jul - 14 Jul
Hollington Park Glamping
Room

Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
9.0 out of 10, Wonderful, (6 reviews)
"The shepherds hut I stayed in for one night was so warm and cosy, it was like staying in a giant wendy house. I would have liked face to face contact with the host, but I guess thats a "sign of the times" Beautiful view of the countryside. "
United Kingdom
Deby
The price is S$107
includes taxes & fees
12 Jul - 13 Jul
Stone Circle Glamping
Free WiFi

The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
The price is S$237
includes taxes & fees
26 Jul - 27 Jul
The Riley Stable- Cozy Getaway
Iron/ironing board, free WiFi, bed sheets

QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
7.4 out of 10, Good, (3 reviews)
"Very comfortable and clean place! It had many amazing restaurants and shops nearby"
United Kingdom
Shiona
The price is S$232
includes taxes & fees
20 Jul - 21 Jul
QE2 Loft Apartments
Iron/ironing board, free WiFi

Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.4 out of 10, Very good, (6 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is S$165
includes taxes & fees
13 Jul - 14 Jul
Settle Southampton
Iron/ironing board, free WiFi

Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking

Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
2.0 star property
Gosport
8.0 out of 10, Very good, (4 reviews)
"The room was exactly as described. Communications with staff were clear and prompt. Check-in/Check-out was easy. Double bed was a nice firm mattress. Building was super quiet overnight. Location was very easy to access."
United Kingdom
Audrey
The price is S$124
includes taxes & fees
22 Jul - 23 Jul
Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
Premium bedding, Select Comfort beds, desk, laptop workspace

Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.2 out of 10, Wonderful, (33 reviews)
"Good location. Only 2 minutes walk from ferry terminal"
United Kingdom
harold
The price is S$295
includes taxes & fees
22 Jul - 23 Jul
Pinnacle Suites
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

8/10 Good
"Great location with parking. Good hotel with all the amenities you would need. Comfortable room with a view of the port."
Neil 1-night trip
Posted 3 hours ago
Leonardo Royal Southampton Grand Harbour

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Winchester Science Centre and Planetarium, or you can select 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 holiday rentals are there in Winchester?

Expedia has 39 holiday 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 the family-friendly sights, whereas cultural attractions include Great Hall and Horsepower The Museum Of The King's Royal Hussars. While in the area, you can also visit popular places such as Southampton Cruise Terminal and New Forest National Park.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.