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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Winchester vacation rentals

Smart TV

The Porterhouse - Residence II

The Porterhouse - Residence II
Winchester
$261 nightly
The price is $261
Aug 2 - Aug 3
Total with taxes and fees
The Porterhouse - Residence II
Exterior detail

The Porterhouse - Residence I

The Porterhouse - Residence I
Winchester
$274 nightly
The price is $274
Aug 2 - Aug 3
Total with taxes and fees
The Porterhouse - Residence I
Double Room | Iron/ironing board, free WiFi

Settle Winchester

Settle Winchester
2.0 star property
Winchester
$127 nightly
The price is $152
Jul 16 - Jul 17
Total with taxes and fees
Settle Winchester
Terrace/patio

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.
$314 nightly
The price is $314
Aug 3 - Aug 4
Total with taxes and fees
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
1 bedroom

Aethelred Annexe - New Build with Full Amenities

Aethelred Annexe - New Build with Full Amenities
Winchester
10.0 out of 10, Exceptional, (1 review)
"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.
$130 nightly
The price is $130
Jul 27 - Jul 28
Total with taxes and fees
Aethelred Annexe - New Build with Full Amenities
1 bedroom, iron/ironing board, WiFi, bed sheets

Garden room, central Winchester

Garden room, central Winchester
Winchester
$155 nightly
The price is $155
Jul 19 - Jul 20
Total with taxes and fees
Garden room, central Winchester
Iron/ironing board, travel crib, WiFi, bed sheets

Winchester City Centre Flat/Sleeps 6/Free Parking

Winchester City Centre Flat/Sleeps 6/Free Parking
Hampshire
$320 nightly
The price is $320
Aug 9 - Aug 10
Total with taxes and fees
Winchester City Centre Flat/Sleeps 6/Free Parking
Dining

Squirrel's Leap

Squirrel's Leap
3.0 star property
Winchester
$549 nightly
The price is $659
Jul 17 - Jul 18
Total with taxes and fees
Squirrel's Leap
Interior

Chic Home w/ Garden & Free On-Street Parking

Chic Home w/ Garden & Free On-Street Parking
Winchester
10.0 out of 10, Exceptional, (1 review)
"Perfect location and layout for a family!"
United States
Casye M.
$537 nightly
The price is $537
Jul 27 - Jul 28
Total with taxes and fees
Chic Home w/ Garden & Free On-Street Parking
Interior

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
$115 nightly
The price is $115
Aug 2 - Aug 3
Total with taxes and fees
Sunday Winchester Wessex Cathedral Hotel | Twin
Property grounds

Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester
$966 nightly
The price is $1,159
Jul 20 - Jul 21
Total with taxes and fees
Rivergem - Riverside Coach House
Tent, Courtyard View (Bell Tent )

Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
9.0 out of 10, Wonderful, (6 reviews)
"The shepherds hut I stayed in for one night was so warm and cosy, it was like staying in a giant wendy house. I would have liked face to face contact with the host, but I guess thats a "sign of the times" Beautiful view of the countryside. "
United Kingdom
Deby
$66 nightly
The price is $80
Jul 19 - Jul 20
Total with taxes and fees
Stone Circle Glamping
Deluxe Apartment | Iron/ironing board, free WiFi, bed sheets

QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.6 out of 10, (5 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
$150 nightly
The price is $180
Jul 14 - Jul 15
Total with taxes and fees
QE2 Loft Apartments
Apartment, Garden View | Free WiFi

The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
$154 nightly
The price is $185
Jul 26 - Jul 27
Total with taxes and fees
The Riley Stable- Cozy Getaway
Exterior

Radstock Road - Room 4a

Radstock Road - Room 4a
Southampton
$72 nightly
The price is $87
Aug 9 - Aug 10
Total with taxes and fees
Radstock Road - Room 4a
Smart TV

Highland Hideaway Southsea Stylish Coastal Stay

Highland Hideaway Southsea Stylish Coastal Stay
Southsea
$318 nightly
The price is $318
Jul 14 - Jul 15
Total with taxes and fees
Highland Hideaway Southsea Stylish Coastal Stay
Private kitchen

Centrally located double room

Centrally located double room
Freemantle
$42 nightly
The price is $50
Jul 20 - Jul 21
Total with taxes and fees
Centrally located double room
Deluxe Studio Suite, Garden View | Iron/ironing board, free WiFi

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
8.0 out of 10, Very Good, (4 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
$93 nightly
The price is $93
Jul 22 - Jul 23
Total with taxes and fees
Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
Deluxe Studio | Iron/ironing board, free WiFi

Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.4 out of 10, Very Good, (6 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
$105 nightly
The price is $126
Aug 12 - Aug 13
Total with taxes and fees
Settle Southampton
Exterior

Farm Cottage on a Secluded 9-acre Equestrian Small Holding

Farm Cottage on a Secluded 9-acre Equestrian Small Holding
Salisbury
10.0 out of 10, Exceptional, (14 reviews)
"Lovely 1 night stay in beautiful location. Louise very welcoming and property was perfect and very clean."
United Kingdom
Emily S.
$267 nightly
The price is $267
Jul 22 - Jul 23
Total with taxes and fees
Farm Cottage on a Secluded 9-acre Equestrian Small Holding
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

The Winchester Hotel & Spa

The Winchester Hotel & Spa

8/10 Good
"Rooms was absolutely spotless and very clean. Staff were also absolutely amazing. However I did find the spa facilities a little dated and also ali"
Emma 1-night trip
Posted 1 hour ago
The Winchester Hotel & Spa

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 $49 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?

MANSION WITH SWIMMING POOL, GAMES ROOM, SEA VIEWS, SANDY BEACHES 2 MINS WALK: This vacation home rental outside of Winchester is located on a lake and has a patio, a terrace, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Winchester?

Expedia has 38 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.