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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winchester vacation rentals

Double Room

1. Settle Winchester

Settle Winchester
2.0 star property
Winchester
$114 nightly
The price is $136
Sep 6 - Sep 7
Total with taxes and fees
Settle Winchester
Room

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

Garden room, central Winchester – self-contained, kitchenette & parking
Winchester
$146 nightly
The price is $146
Aug 31 - Sep 1
Total with taxes and fees
Garden room, central Winchester – self-contained, kitchenette & parking
Interior

3. The Porterhouse - Residence I

The Porterhouse - Residence I
Winchester
$250 nightly
The price is $250
Sep 6 - Sep 7
Total with taxes and fees
The Porterhouse - Residence I
Interior

4. Sunday Winchester Wessex Cathedral Hotel | Twin

Sunday Winchester Wessex Cathedral Hotel | Twin
Winchester
6.0 out of 10, (1 review)
"Didn’t have Kitchen like advertised, no fridge unfortunately "
United Kingdom
Hayden
$134 nightly
The price is $134
Sep 13 - Sep 14
Total with taxes and fees
Sunday Winchester Wessex Cathedral Hotel | Twin
Room

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

Winchester City Centre Flat/Sleeps 6/Free Parking
Hampshire
$275 nightly
The price is $275
Sep 27 - Sep 28
Total with taxes and fees
Winchester City Centre Flat/Sleeps 6/Free Parking
Terrace/patio

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

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Winchester
8.8 out of 10, Excellent, (5 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.
$290 nightly
The price is $290
Sep 2 - Sep 3
Total with taxes and fees
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Room

7. Clifton Lodge

Clifton Lodge
2.0 star property
Winchester
$654 nightly
The price is $784
Sep 7 - Sep 8
Total with taxes and fees
Clifton Lodge
Interior

8. The Porterhouse - Residence II

The Porterhouse - Residence II
Winchester
$260 nightly
The price is $260
Sep 6 - Sep 7
Total with taxes and fees
The Porterhouse - Residence II
Property grounds

9. Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester
$976 nightly
The price is $1,171
Sep 6 - Sep 7
Total with taxes and fees
Rivergem - Riverside Coach House
Deluxe Studio

10. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.8 out of 10, Excellent, (8 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
$101 nightly
The price is $121
Aug 31 - Sep 1
Total with taxes and fees
Settle Southampton
Private kitchen

11. Property

Property
3.0 star property
Bevois Valley
$173 nightly
The price is $207
Sep 1 - Sep 2
Total with taxes and fees
Property
Interior entrance

12. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,311 reviews)
"Great place to stay on the way to our cruise…would definitely recommend!!"
Canada
Shelly
$113 nightly
The price is $135
Aug 31 - Sep 1
Total with taxes and fees
Second Nature Southampton
Apartment, Garden View

13. The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
$149 nightly
The price is $179
Sep 1 - Sep 2
Total with taxes and fees
The Riley Stable- Cozy Getaway
Tent, Courtyard View (Bell Tent )

14. Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
8.4 out of 10, Very Good, (10 reviews)
"Cozy place to stay, it is near a road but it didn’t bother me. It is as advertised"
Canada
Darnell
$52 nightly
The price is $62
Aug 31 - Sep 1
Total with taxes and fees
Stone Circle Glamping
Dining

15. 3 Bedrooms house ideal for long Stays!

3 Bedrooms house ideal for long Stays!
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"Great location, lovely clean property can recommend."
United Kingdom
Michael R.
$289 nightly
The price is $289
Sep 9 - Sep 10
Total with taxes and fees
3 Bedrooms house ideal for long Stays!
Exterior

16. 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.
$152 nightly
The price is $152
Sep 2 - Sep 3
Total with taxes and fees
Cosy Rural Cabin With Ensuite without Pergola
Miscellaneous

17. Beddoe Apartments

Beddoe Apartments
3.0 star property
Eastleigh
7.8 out of 10, Good, (20 reviews)
"Ideal for couple of nights stay. Easy parking was a bonus. "
United Kingdom
Alan
$467 nightly
The price is $548
Aug 30 - Aug 31
Total with taxes and fees
Beddoe Apartments
Deluxe Apartment

18. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
6.4 out of 10, (8 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
$172 nightly
The price is $206
Aug 30 - Aug 31
Total with taxes and fees
QE2 Loft Apartments
Private kitchen

19. 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.
$249 nightly
The price is $249
Aug 31 - Sep 1
Total with taxes and fees
Adorable 2-bedroom apartment in Southampton
Room

20. 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
$773 nightly
The price is $928
Sep 3 - Sep 4
Total with taxes and fees
Horseshoe Cottage
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

Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

10/10 Excellent
"Stay was great. Very close to port for cruise. Only one issue, but it was not with the hotel. Concierge scheduled us a taxi for travel to port, literally 6 blocks away. Taxi charged us $20. It was 2 people & 2 medium suitcases, and 2 backpacks that we kept with us. Definitely would recommend using Uber."
Karen 2-night trip
Posted 12 hours ago
Leonardo Royal Southampton Grand Harbour

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $62 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Redwood Escape - Stylish New Forest Stay | Sleep 4 | Near Paultons Park | Free Parking: This vacation home rental outside of Winchester has laundry facilities and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Winchester?

Expedia has 39 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.