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

Winchester Vacation 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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winchester vacation rentals

Double Room | Iron/ironing board, WiFi (free)

1. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is AED 192
AED 496 total
includes taxes & fees
4 Oct - 5 Oct
Settle Winchester
Terrace/patio

2. Garden room, central Winchester – self-contained, kitchenette & parking

Garden room, central Winchester – self-contained, kitchenette & parking
Winchester
Garden room, central Winchester – self-contained, kitchenette & parking
1 bedroom

3. Aethelred Annexe - New Build with Full Amenities

Aethelred Annexe - New Build with Full Amenities
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Had a lovely stay at the Aethelred Annexe! Great amenities and an incredibly generous host. It felt very warm and cozy and the bed was super comfy. Great location for a quick drive/ bus into the city centre. Would absolutely recommend."
United States
Andrea W.
The price is AED 398
AED 477 total
includes taxes & fees
20 Sep - 21 Sep
Aethelred Annexe - New Build with Full Amenities
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

4. The Porterhouse - Residence I

The Porterhouse - Residence I
Winchester City Center
The Porterhouse - Residence I
2 bedrooms, iron/ironing board, travel crib, WiFi

5. Winchester City Centre Flat/Sleeps 6/Free Parking

Winchester City Centre Flat/Sleeps 6/Free Parking
Hampshire
Winchester City Centre Flat/Sleeps 6/Free Parking
Exterior

6. Winchester Wessex Hotel by Sunday Twin Room

Winchester Wessex Hotel by Sunday Twin Room
Winchester City Center
6.0 out of 10, (1 review)
"Didn’t have Kitchen like advertised, no fridge unfortunately "
United Kingdom
Hayden
The price is AED 513
AED 513 total
includes taxes & fees
20 Sep - 21 Sep
Winchester Wessex Hotel by Sunday Twin Room
Terrace/patio

7. Cosy A-Frame cabin nestled in the chalk steams of Hampshire

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Winchester
8.6 out of 10, Excellent, (7 reviews)
"Lovely cabin and outside kitchen plus garden. It's my second stay and I enjoyed my stay. Love the garden kitchen,. It's very pretty and relaxing ."
United Kingdom
Nicola H.
The price is AED 795
AED 1,050 total
includes taxes & fees
21 Sep - 22 Sep
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Exterior

8. Clifton Lodge

Clifton Lodge
2.0 star property
Winchester
The price is AED 2,369
AED 2,843 total
includes taxes & fees
1 Oct - 2 Oct
Clifton Lodge
Interior

9. The Porterhouse - Residence II

The Porterhouse - Residence II
Winchester City Center
The Porterhouse - Residence II
Property grounds

10. Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester City Center
The price is AED 3,537
AED 4,244 total
includes taxes & fees
24 Sep - 25 Sep
Rivergem - Riverside Coach House
Interior entrance

11. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,335 reviews)
"Great place to stay on the way to our cruise…would definitely recommend!!"
Canada
Shelly
The price is AED 347
AED 416 total
includes taxes & fees
4 Oct - 5 Oct
Second Nature Southampton
Deluxe Studio | Iron/ironing board, WiFi (free)

12. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.0 out of 10, Very good, (10 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is AED 285
AED 563 total
includes taxes & fees
5 Oct - 6 Oct
Settle Southampton
Tent, Courtyard View (Bell Tent )

13. Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
8.6 out of 10, Excellent, (13 reviews)
"Cozy place to stay, it is near a road but it didn’t bother me. It is as advertised"
Canada
Darnell
The price is AED 186
AED 223 total
includes taxes & fees
28 Sep - 29 Sep
Stone Circle Glamping
Outdoor dining

14. Stunning two Bedroom Apartment in The New Forest With Private Courtyard

Stunning two Bedroom Apartment in The New Forest With Private Courtyard
4.0 star property
Southampton
The price is AED 604
AED 1,049 total
includes taxes & fees
21 Sep - 22 Sep
Stunning two Bedroom Apartment in The New Forest With Private Courtyard
WiFi, bed sheets

15. Eastleigh Luxury Retreat with 4 Bedrooms | With Parking | Near Airport

Eastleigh Luxury Retreat with 4 Bedrooms | With Parking | Near Airport
Eastleigh
The price is AED 888
AED 1,006 total
includes taxes & fees
4 Oct - 5 Oct
Eastleigh Luxury Retreat with 4 Bedrooms | With Parking | Near Airport
Deluxe Apartment | Iron/ironing board, WiFi (free), bed sheets

16. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.6 out of 10, (10 reviews)
"No Air conditioning! Bar under with loud party all night long. Windows open for air. You book this room only if you want to party. Otherwise you will be kept up all night long. 90 degrees outside and hotter inside do to restaurant ovens directly under room. It was the worst experience. Jet lag turned into nightmare 😫"
United States
BRIAN
The price is AED 653
AED 784 total
includes taxes & fees
22 Sep - 23 Sep
QE2 Loft Apartments
Dining

17. 3 Bedrooms house ideal for long Stays!

3 Bedrooms house ideal for long Stays!
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"Great location, lovely clean property can recommend."
United Kingdom
Michael R.
3 Bedrooms house ideal for long Stays!
Interior

18. Cosy Rural Cabin With Ensuite without Pergola

Cosy Rural Cabin With Ensuite without Pergola
Chawton
10.0 out of 10, Exceptional, (9 reviews)
"The cabin has everything you need for a short stay, it's a great place for children and would easily for a family of three. Lovely surroundings for someone who loves nature and walks."
United States
NASTASSIA N.
The price is AED 540
AED 540 total
includes taxes & fees
20 Sep - 21 Sep
Cosy Rural Cabin With Ensuite without Pergola
Deluxe Studio Suite, Garden View | Iron/ironing board (on request), WiFi (free)

19. 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
7.8 out of 10, Good, (6 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 AED 302
AED 302 total
includes taxes & fees
28 Sep - 29 Sep
Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
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

Marwell Hotel Winchester South

Marwell Hotel Winchester South

8/10 Good
"only a quick one night stay, bed not the best hotel a little tired but good valve"
John 1-night trip
Posted 1 hour ago
Marwell Hotel Winchester South

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.

What are some of the best vacation home rentals in Winchester?

Unique waterside home in stunning location.: This vacation home rental outside of Winchester is located on the waterfront and has a balcony, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Winchester?

Expedia has 37 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 Horsepower The Museum Of The King's Royal Hussars. 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.