A cathedral at night with illuminated trees and a park with benches.

City of Winchester Vacation Rentals

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Top Cities in City of Winchester

A large stone castle with multiple towers and battlements.
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Southampton

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

Winchester

Our top choices for City of Winchester vacation rentals

A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

1. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is CA $57
CA $169 total
includes taxes & fees
Oct 4 - Oct 5
Settle Winchester
A neatly made bed with a grey quilt, two pillows, and rolled towels on the side. There is a bedside table with a lamp and a small decorative item.

2. 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 CA $169
CA $199 total
includes taxes & fees
Oct 4 - Oct 5
Aethelred Annexe - New Build with Full Amenities
Dining

3. Calm 1 Bed Apartment with Parking, Winchester by At Hem

Calm 1 Bed Apartment with Parking, Winchester by At Hem
Winchester
10.0 out of 10, Exceptional, (1 review)
"Excellent location and property. The owner was very responsive and helpful "
Australia
Jayani
Calm 1 Bed Apartment with Parking, Winchester by At Hem
A wooden cabin with a sloped roof, a deck with two chairs, and a glass door leading inside.

4. 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 CA $303
CA $397 total
includes taxes & fees
Oct 1 - Oct 2
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
A bedroom with a bed, a nightstand, a lamp, a window with a view, and a radiator.

5. Clifton Lodge

Clifton Lodge
2.0 star property
Winchester
The price is CA $904
CA $1,085 total
includes taxes & fees
Oct 2 - Oct 3
Clifton Lodge
A bedroom with a skylight, a bed, a dresser, a sofa, and a view of the garden through a sliding door.

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

Garden room, central Winchester – self-contained, kitchenette & parking
Winchester
The price is CA $176
CA $206 total
includes taxes & fees
Oct 4 - Oct 5
Garden room, central Winchester – self-contained, kitchenette & parking
A bed with a teal headboard, two pillows with tropical leaf patterns, and two folded towels on a yellow bedspread.

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

Winchester City Centre Flat/Sleeps 6/Free Parking
Hampshire
The price is CA $205
CA $374 total
includes taxes & fees
Sep 30 - Oct 1
Winchester City Centre Flat/Sleeps 6/Free Parking
A hotel room with a bed, a desk with a chair, a dresser, a television, and a mirror.

8. 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 CA $172
CA $172 total
includes taxes & fees
Sep 30 - Oct 1
Winchester Wessex Hotel by Sunday Twin Room
A bedroom with a wooden headboard, white bedding, two floral pillows, a bedside lamp, and a folded towel on the bed.

9. The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
The price is CA $153
CA $240 total
includes taxes & fees
Oct 12 - Oct 13
The Riley Stable- Cozy Getaway
A modern kitchen with a large island, wooden beams, and a view to the outside.

10. The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom

The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom
Shedfield
9.6 out of 10, Exceptional, (15 reviews)
"Fabulous place to stay."
United States
CHRISTOPHER S.
The price is CA $853
CA $853 total
includes taxes & fees
Oct 2 - Oct 3
The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom
A rustic outdoor setting with a fire pit, a table, and a vintage camper van in the background.

11. Out in the countryside,Retreat away@The Box

Out in the countryside,Retreat away@The Box
Denmead
The price is CA $167
CA $234 total
includes taxes & fees
Oct 1 - Oct 2
Out in the countryside,Retreat away@The Box
A modern kitchen with a built-in toaster, a microwave, and a coffee maker.

12. The Porterhouse - Residence I

The Porterhouse - Residence I
Winchester City Center
The price is CA $228
CA $378 total
includes taxes & fees
Oct 4 - Oct 5
The Porterhouse - Residence I
A canal with a wooden fence and a large terracotta pot with flowers.

13. Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester City Center
The price is CA $1,350
CA $1,620 total
includes taxes & fees
Oct 2 - Oct 3
Rivergem - Riverside Coach House
A building with a gravel driveway, a door, and two potted trees.

14. Barley Cottage

Barley Cottage
3.0 star property
Alresford
The price is CA $1,264
CA $1,517 total
includes taxes & fees
Oct 5 - Oct 6
Barley Cottage
An outdoor seating area with a table, chairs, and a bottle of wine.

15. Suetts Farm Barns

Suetts Farm Barns
2.0 star property
Southampton
The price is CA $1,341
CA $1,609 total
includes taxes & fees
Oct 4 - Oct 5
Suetts Farm Barns
A wooden table with a round top, a hot tub, and a patio umbrella in a garden setting.

16. Coppice Hill House

Coppice Hill House
3.0 star property
Southampton
The price is CA $1,949
CA $2,339 total
includes taxes & fees
Oct 25 - Oct 26
Coppice Hill House
A modern interior with a red sofa, black chairs, and a patterned floor.

17. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,341 reviews)
"Great location and friendly staff!"
United States
Gary
The price is CA $133
CA $159 total
includes taxes & fees
Oct 4 - Oct 5
Second Nature Southampton
A compact kitchen with wooden cabinets, a built-in washing machine, a gas stove, and a tiled backsplash.

18. Ocean Quay Luxury - Stylish 2 Bed - Has Parking

Ocean Quay Luxury - Stylish 2 Bed - Has Parking
3.0 star property
Southampton City Centre
The price is CA $189
CA $227 total
includes taxes & fees
Oct 6 - Oct 7
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
A tent with a bed inside, a colorful rug, and a sign on the ground.

19. 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 CA $73
CA $87 total
includes taxes & fees
Oct 2 - Oct 3
Stone Circle Glamping
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 City of Winchester Hotel Reviews

voco Southampton by IHG

voco Southampton by IHG

10/10 Excellent
"A great stay as usual, rooms are lovely and dinner and breakfast excellent. Staff are friendly and helpful, we always stay here when we are in Southampton"
Edward 1-night trip
Posted 7 hours ago
voco Southampton by IHG

Find out more about City of Winchester

Everything you need to know about City of Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the City of Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect City of Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

City of Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in City of Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A City of Winchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of City of Winchester vacation rentals we have selected for you start as low as CA $87 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on City of Winchester rentals

At Expedia, we put the best City of Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top City of Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream City of Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around City of Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.