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

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for 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 $58
CA $172 total
includes taxes & fees
Nov 8 - Nov 9
Settle Winchester
A hotel room with a bed, a desk with a chair, a dresser, a television, and a mirror.

2. Winchester Wessex Hotel by Sunday Twin Room

Winchester Wessex Hotel by Sunday Twin Room
Winchester City Center
9.4 out of 10, Exceptional, (40 reviews)
"Didn’t have Kitchen like advertised, no fridge unfortunately "
United Kingdom
Hayden
The price is CA $194
CA $194 total
includes taxes & fees
Oct 14 - Oct 15
Winchester Wessex Hotel by Sunday Twin Room
A bedroom with a skylight, a bed, a dresser, a sofa, and a view of the garden through a sliding door.

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

Garden room, central Winchester – self-contained, kitchenette & parking
Winchester
The price is CA $177
CA $207 total
includes taxes & fees
Oct 25 - Oct 26
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.

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

Winchester City Centre Flat/Sleeps 6/Free Parking
Hampshire
The price is CA $194
CA $364 total
includes taxes & fees
Nov 12 - Nov 13
Winchester City Centre Flat/Sleeps 6/Free Parking
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.

5. 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 $170
CA $200 total
includes taxes & fees
Oct 25 - Oct 26
Aethelred Annexe - New Build with Full Amenities
A wooden cabin with a sloped roof, a deck with two chairs, and a glass door leading inside.

6. 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 $226
CA $311 total
includes taxes & fees
Nov 3 - Nov 4
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
A modern interior with a red sofa, black chairs, and a patterned floor.

7. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,355 reviews)
"Great location and friendly staff!"
United States
Gary
The price is CA $122
CA $146 total
includes taxes & fees
Nov 10 - Nov 11
Second Nature Southampton
A room with a dartboard, a power outlet, a potted plant, and a curtain.

8. 4 Bedrooms - The Family Haven With Parking Near Airport

4 Bedrooms - The Family Haven With Parking Near Airport
3.0 star property
Eastleigh
The price is CA $255
CA $306 total
includes taxes & fees
Nov 4 - Nov 5
4 Bedrooms - The Family Haven With Parking Near Airport
A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

9. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.0 out of 10, Very good, (12 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is CA $92
CA $195 total
includes taxes & fees
Nov 8 - Nov 9
Settle Southampton
A calm lake with ducks and a swan, a boat docked on the left, and a building in the background.

10. Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton

Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
Portswood
10.0 out of 10, Exceptional, (1 review)
"We had a great time, lovely neighborhood, location is easy access to needed items. Marvin is an excellent host. He responds right away with all questions. For a home that is 140 years old it is in excellent shape. Beautifully decorated. Everything we needed was there. Big plus to be on the water. Thank you Marvin!"
United States
Terri M.
The price is CA $221
CA $275 total
includes taxes & fees
Oct 22 - Oct 23
Perfect 2-bedroom house, Albert cottage with WiFi in charming Southampton
A modern kitchen with a large island, wooden beams, and a view to the outside.

11. 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 $859
CA $859 total
includes taxes & fees
Oct 16 - Oct 17
The Stables, Wickham - a barn conversion that sleeps 2 guests in 1 bedroom
A bedroom with a bed, a TV, and a window with curtains.

12. Bayview Apartments

Bayview Apartments
2.0 star property
Southampton City Centre
7.8 out of 10, Good, (7 reviews)
"The apartment was reasonably priced, conveniently located to our destination and perfectly adequate for our needs."
United States
Donald
The price is CA $440
CA $528 total
includes taxes & fees
Oct 15 - Oct 16
Bayview Apartments
A tent with a bed inside, a colorful rug, and a sign on the ground.

13. Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
8.8 out of 10, Excellent, (16 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 $69
CA $83 total
includes taxes & fees
Oct 24 - Oct 25
Stone Circle Glamping
A cozy attic bedroom with a wooden ceiling, a sofa, a bed, and a wardrobe.

14. Wigwam Holidays Cabin With Ensuite without Pergola

Wigwam Holidays 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 CA $207
CA $207 total
includes taxes & fees
Oct 19 - Oct 20
Wigwam Holidays Cabin With Ensuite without Pergola
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

15. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.8 out of 10, (17 reviews)
"They sent me an email at the last minute saying that it was double booked and they canceled my reservation that was already prepaid"
United States
kia
The price is CA $240
CA $288 total
includes taxes & fees
Oct 14 - Oct 15
QE2 Loft Apartments
A modern kitchen with a central island, bar stools, hanging plants, and a variety of appliances.

16. Adorable 2-bedroom apartment in Southampton

Adorable 2-bedroom apartment in Southampton
Freemantle
9.0 out of 10, Wonderful, (4 reviews)
"Apartment was in great condition, no complaints!"
United Kingdom
Bethany M.
The price is CA $267
CA $348 total
includes taxes & fees
Oct 25 - Oct 26
Adorable 2-bedroom apartment in Southampton
A bedroom with a bed, a bedside table with a lamp, a window with curtains, a mirror, and a wooden door with a metal handle.

17. Horseshoe Cottage

Horseshoe Cottage
3.0 star property
Romsey
10.0 out of 10, Exceptional, (1 review)
"Well presented and well equipped home. All the essentials plus more. Very family friendly."
United Kingdom
Peter
The price is CA $1,077
CA $1,293 total
includes taxes & fees
Oct 24 - Oct 25
Horseshoe Cottage
A corner room with a large window overlooking a city street and buildings.

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

Ocean Quay Luxury - Stylish 2 Bed - Has Parking
3.0 star property
Southampton City Centre
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

19. Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (327 reviews)
"Great. They have everything you could need - well appointed kitchen, milk and breakfast provided, plenty of fluffy towels even down to non stick bath mats"
Australia
Stephanie
The price is CA $183
CA $220 total
includes taxes & fees
Nov 9 - Nov 10
Peartree Serviced Apartments
A view from a window overlooking a street with a bus, a pedestrian crossing, and a sign indicating a speed limit of 30.

20. ANG Apartments

ANG Apartments
2.0 star property
Southsea
9.0 out of 10, Wonderful, (6 reviews)
"Nice place to stay, lovely beach view and close to amenities"
United Kingdom
Claire
The price is CA $116
CA $116 total
includes taxes & fees
Oct 22 - Oct 23
ANG Apartments
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

ibis Southampton Centre

ibis Southampton Centre

8/10 Good
"Room was clean. I liked that there was a bath as well as a shower, Only stayed for one night,but overall An enjoyable night."
Sonia 1-night trip
Posted 11 hours ago
ibis Southampton Centre

Find out more about Winchester

Everything you need to know about 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 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 Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in 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 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 Winchester vacation rentals we have selected for you start as low as CA $83 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best 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 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 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 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. 

Explore a world of travel with Expedia

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 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.