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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
$98 nightly
The price is $118
Nov 8 - Nov 9
Total with taxes and fees
Settle Winchester
A bedroom with a bed, a nightstand, a lamp, a window with a view, and a radiator.

2. Clifton Lodge

Clifton Lodge
2.0 star property
Winchester
$639 nightly
The price is $766
Oct 25 - Oct 26
Total with taxes and fees
Clifton Lodge
A modern interior with a red sofa, black chairs, and a patterned floor.

3. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,354 reviews)
"Great location and friendly staff!"
United States
Gary
$87 nightly
The price is $105
Nov 8 - Nov 9
Total with taxes and fees
Second Nature Southampton
A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

4. 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
$116 nightly
The price is $139
Oct 11 - Oct 12
Total with taxes and fees
Settle Southampton
A corner room with a large window overlooking a city street and buildings.

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

Ocean Quay Luxury - Stylish 2 Bed - Has Parking
3.0 star property
Southampton City Centre
$137 nightly
The price is $165
Nov 9 - Nov 10
Total with taxes and fees
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
A building with a gravel driveway, a door, and two potted trees.

6. Barley Cottage

Barley Cottage
3.0 star property
Alresford
$775 nightly
The price is $930
Nov 2 - Nov 3
Total with taxes and fees
Barley Cottage
A bedroom with a bed, a wooden bench, a staircase, and a wall-mounted light fixture.

7. Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.2 out of 10, Wonderful, (41 reviews)
"Very friendly host with modern suites"
United Kingdom
Samuel
$140 nightly
The price is $168
Oct 11 - Oct 12
Total with taxes and fees
Pinnacle Suites
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

8. 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
$154 nightly
The price is $184
Oct 12 - Oct 13
Total with taxes and fees
QE2 Loft Apartments
A bedroom with a bed, a TV, and a window with curtains.

9. 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
$308 nightly
The price is $370
Oct 15 - Oct 16
Total with taxes and fees
Bayview Apartments
A view from a window overlooking a street with a bus, a pedestrian crossing, and a sign indicating a speed limit of 30.

10. ANG Apartments

ANG Apartments
2.0 star property
Southsea
9.0 out of 10, Wonderful, (6 reviews)
$81 nightly
The price is $81
Oct 14 - Oct 15
Total with taxes and fees
ANG Apartments
A bedroom with two beds, a nightstand with a lamp, and wall art.

11. 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
$83 nightly
The price is $83
Oct 21 - Oct 22
Total with taxes and fees
Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

12. 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
$132 nightly
The price is $158
Nov 8 - Nov 9
Total with taxes and fees
Peartree Serviced Apartments
A living room with a dark blue sofa, a round wooden coffee table, a dining table with chairs, a large abstract painting, a round mirror, and a window with curtains.

13. Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (10 reviews)
$125 nightly
The price is $150
Oct 11 - Oct 12
Total with taxes and fees
Charles Hope Salisbury Centre
A building with multiple windows and doors, illuminated by green and white lights.

14. Ground-Floor Super King or Twin Studio Apartment with Free Private Parking

Ground-Floor Super King or Twin Studio Apartment with Free Private Parking
2.0 star property
Southsea
$70 nightly
The price is $84
Oct 15 - Oct 16
Total with taxes and fees
Ground-Floor Super King or Twin Studio Apartment with Free Private Parking
A kitchen with grey cabinets, a microwave, an oven, a sink, and a wooden countertop.

15. Stunning 2-bed Apt, Sleeps 6 in The New Forest

Stunning 2-bed Apt, Sleeps 6 in The New Forest
4.0 star property
Southampton
$250 nightly
The price is $300
Oct 11 - Oct 12
Total with taxes and fees
Stunning 2-bed Apt, Sleeps 6 in The New Forest
A narrow stream with clear water, surrounded by lush greenery and wildflowers.

16. Roslyn

Roslyn
2.0 star property
Romsey
$570 nightly
The price is $684
Oct 21 - Oct 22
Total with taxes and fees
Roslyn
A building with multiple windows and doors, illuminated by green and white lights.

17. Ground-Floor Queen Bed Studio Apartment with Free Parking

Ground-Floor Queen Bed Studio Apartment with Free Parking
2.0 star property
Southsea
$79 nightly
The price is $79
Oct 15 - Oct 16
Total with taxes and fees
Ground-Floor Queen Bed Studio Apartment with Free Parking
A tent with a bed inside, a colorful rug, and a sign on the ground.

18. 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
$48 nightly
The price is $58
Oct 10 - Oct 11
Total with taxes and fees
Stone Circle Glamping
A beach with a clear sky, calm sea, and a distant ship.

19. Loft 2bed Appartment with EVCharger

Loft 2bed Appartment with EVCharger
2.0 star property
Southsea
$126 nightly
The price is $126
Nov 4 - Nov 5
Total with taxes and fees
Loft 2bed Appartment with EVCharger
A hotel room with a bed, a desk, a chair, a television, and a window.

20. Studio 32-Free Private Parking

Studio 32-Free Private Parking
2.0 star property
Southsea
$86 nightly
The price is $86
Oct 20 - Oct 21
Total with taxes and fees
Studio 32-Free Private 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.
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Top Winchester Hotel Reviews

voco Southampton by IHG

voco Southampton by IHG

10/10 Excellent
"close to cruise port and food for short stay"
JULIE 1-night trip
Posted 1 hour ago
voco Southampton by IHG

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 $58 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?

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.