Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Winchester

2 bedrooms, WiFi, bed sheets
Cosy A-Frame cabin nestled in the chalk steams of Hampshire

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

Winchester
9.4 out of 10, Exceptional, (3)
"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.
$254 nightly
The price is $254
Nov 23 - Nov 24
Total with taxes and fees
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Front of property
room2 Southampton Hometel

room2 Southampton Hometel

4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1161)
"staff was very friendly and rooms we clean and comfortable "
Canada
Kathy
$89 nightly
The price is $106
Nov 23 - Nov 24
Total with taxes and fees
room2 Southampton Hometel
Studio, 1 Queen Bed | Private kitchen | Fridge, microwave, stovetop, dishwasher
Peartree Serviced Apartments

Peartree Serviced Apartments

3.5 star property
Salisbury
9.6 out of 10, Exceptional, (296)
"Enjoyable stay, handy to Salisbury landmarks."
Australia
Heather
$105 nightly
The price is $126
Dec 14 - Dec 15
Total with taxes and fees
Peartree Serviced Apartments
Marina
Daisy Haven in Southampton

Daisy Haven in Southampton

2.0 star property
Bassett Green
$176 nightly
The price is $212
Dec 7 - Dec 8
Total with taxes and fees
Daisy Haven in Southampton
Apartment | Private kitchen | Fridge, microwave, oven, stovetop
2 Bed Flat - Sleeps 4 - Parking - Wifi

2 Bed Flat - Sleeps 4 - Parking - Wifi

3.0 star property
The Polygon
10.0 out of 10, Exceptional, (1)
"Great apartment, super friendly host!"
United Kingdom
Amy
$202 nightly
The price is $243
Nov 21 - Nov 22
Total with taxes and fees
2 Bed Flat - Sleeps 4 - Parking - Wifi
Front of property
Gunwharf Quays Apartments

Gunwharf Quays Apartments

3.5 star property
Portsmouth
8.2 out of 10, Very Good, (64)
"Excellent apartment. Great location, great size, clean and good facilities. Great stay, will definitely stay again"
United Kingdom
Laura
Gunwharf Quays Apartments
Deluxe Room, 1 Double Bed, Harbor View | 1 bedroom, premium bedding, Select Comfort beds, desk
Pinnacle Suites

Pinnacle Suites

3.0 star property
Cowes
9.8 out of 10, Exceptional, (25)
"Great place to stay. Facilities are very nice and clean. Zoe is a very helpful and kind host. "
Denmark
Sebastian
$171 nightly
The price is $205
Nov 20 - Nov 21
Total with taxes and fees
Pinnacle Suites
Shared kitchen
Bayview Apartments

Bayview Apartments

2.0 star property
Southampton City Centre
8.0 out of 10, Very Good, (3)
"To be honest although the apartment was really nice we didn’t have hardly any knives and forks and spoons for 5 people, the fridge was filthy and the cooking equipment was old worn out and filthy. For nearly £300 for one night we expected better "
United Kingdom
Derek
$307 nightly
The price is $368
Nov 25 - Nov 26
Total with taxes and fees
Bayview Apartments
Balcony view
Southampton Serviced Apartment

Southampton Serviced Apartment

4.0 star property
Bassett
8.4 out of 10, Very Good, (176)
"Close to workplace. Nice heated apartment, has all the things you would need highly recommend. "
United Kingdom
Sheena
$163 nightly
The price is $196
Nov 24 - Nov 25
Total with taxes and fees
Southampton Serviced Apartment
Fridge, microwave, oven, dishwasher
Beautiful 2 bedroom full-furnished semi-detached house with parking

Beautiful 2 bedroom full-furnished semi-detached house with parking

Dibden Purlieu
9.4 out of 10, Exceptional, (6)
"Great location, xxx"
United Kingdom
Christopher K.
$243 nightly
The price is $243
Nov 24 - Nov 25
Total with taxes and fees
Beautiful 2 bedroom full-furnished semi-detached house with parking
Studio | Living area
Central Versatile Studio

Central Versatile Studio

2.0 star property
Portsmouth
6.0 out of 10, (1)
"property just down rd from the hard. Hard to find without prior knowledge. Entry was difficult becuase the entry system at first took a lot of doing. It is on a safe system that needs imput from the owners and a no to get the small safe to drop and reveal the key to apt. Not able to get TV or internet until landlady came on sun morning. Phone conversation was not good at all. Frequently breaking down when asking questions. No instructions at all in apt to get started. No hot water...
United Kingdom
Leslie
$142 nightly
The price is $171
Dec 10 - Dec 11
Total with taxes and fees
Central Versatile Studio
Family Apartment | Living area | Flat-screen TV
Charles Hope Salisbury Centre

Charles Hope Salisbury Centre

3.5 star property
Salisbury
9.6 out of 10, Exceptional, (4)
"Great location and well appointed apartment"
Australia
Greg
Charles Hope Salisbury Centre
Cottage | Interior
Aquanaut

Aquanaut

3.5 star property
Cowes
$3,469 nightly
The price is $4,163
Nov 22 - Nov 23
Total with taxes and fees
Aquanaut
Apartment, 1 Bedroom, Patio, Garden View | Living area | 42-inch Smart TV with digital channels, Netflix, streaming services
Rudley Ranch

Rudley Ranch

2.5 star property
Waterlooville
$171 nightly
The price is $205
Nov 19 - Nov 20
Total with taxes and fees
Rudley Ranch
Fridge, dishwasher, electric kettle, cookware/dishes/utensils
Bailey Cottage

Bailey Cottage

3.0 star property
Southampton
$1,600 nightly
The price is $1,920
Dec 1 - Dec 2
Total with taxes and fees
Bailey Cottage
Marina
Superyacht on 5* Town Quay Marina, Southampton

Superyacht on 5* Town Quay Marina, Southampton

Southampton City Centre
9.6 out of 10, Exceptional, (9)
"The yacht Ohana is a great place to stay with excellent facilities and in a fab location close to bars and restaurants.A very helpful owner made our weekend perfect! "
United States
Helen D.
$379 nightly
The price is $379
Nov 19 - Nov 20
Total with taxes and fees
Superyacht on 5* Town Quay Marina, Southampton
Marina
40 foot luxury yacht on 5* Ocean Village Marina

40 foot luxury yacht on 5* Ocean Village Marina

Southampton City Centre
10.0 out of 10, Exceptional, (2)
"We decided to try something new instead of hotel so booked the yacht. Great experience. Marina and boat were lovely. Lots of restaurants and easy to walk around and explore. Steve and Miros went over and above to make sure our stay was great and even picked us up from cruise port and drove us to airport hotel the next day. Would highly recommend . "
Canada
Sheila
$276 nightly
The price is $276
Nov 19 - Nov 20
Total with taxes and fees
40 foot luxury yacht on 5* Ocean Village Marina
Superior Studio | 1 bedroom, premium bedding, individually decorated
The Madison

The Madison

3.0 star property
Banister's Park
9.6 out of 10, Exceptional, (28)
"Clean, modern, quiet and great communication from company before and during my stay - very helpful. "
United Kingdom
Sabrina
The Madison
Outdoor spa tub
Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool

Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool

Chandler's Ford
$125 nightly
The price is $125
Nov 25 - Nov 26
Total with taxes and fees
Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool
Children's play area - outdoor
Mill Rythe Coastal Village

Mill Rythe Coastal Village

2.0 star property
Hayling Island
9.4 out of 10, Exceptional, (48)
"First time staying here and it was excellent, from checking in at reception to the property with every facility you could want and, more importantly, cleanliness throughout. "
United Kingdom
India
Mill Rythe Coastal Village
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

Meon Valley Hotel, Golf & Country Club

Meon Valley Hotel, Golf & Country Club

10/10 Excellent
"Room was clean, staff very helpful as we needed additional pillows and amenities great. We stayed for 1 night to attend a party locally and found it to be the perfect stay "
Julie 1-night trip
Posted 3 days ago
Meon Valley Hotel, Golf & Country Club

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 $106 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?

Purple Cloud Cottage: This vacation home rental outside Winchester is located in the city center and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a full-sized fridge, a stovetop, and a microwave, so you can cook with friends or family.

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 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.