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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
$102 nightly
The price is $122
Nov 8 - Nov 9
Total with taxes and fees
Settle Winchester
A modern interior with a staircase, seating area, and a green wall.

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
$123 nightly
The price is $123
Nov 15 - Nov 16
Total with taxes and fees
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
$132 nightly
The price is $132
Nov 8 - Nov 9
Total with taxes and fees
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
$269 nightly
The price is $269
Nov 29 - Nov 30
Total with taxes and fees
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.
$134 nightly
The price is $134
Nov 10 - Nov 11
Total with taxes and fees
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.
$201 nightly
The price is $201
Nov 10 - Nov 11
Total with taxes and fees
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, (1,365 reviews)
"Great location and friendly staff!"
United States
Gary
$85 nightly
The price is $101
Dec 6 - Dec 7
Total with taxes and fees
Second Nature Southampton
A historic stone building with a round tower and a rectangular structure with arched windows.

8. 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
$189 nightly
The price is $214
Nov 8 - Nov 9
Total with taxes and fees
Beddoe Apartments
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
8.2 out of 10, Very good, (14 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
$99 nightly
The price is $119
Nov 10 - Nov 11
Total with taxes and fees
Settle Southampton
A bedroom with a large bed, a nightstand, a wall-mounted lamp, and a window with blinds.

10. Southampton Serviced Apartment

Southampton Serviced Apartment
4.0 star property
Bassett
8.6 out of 10, Excellent, (188 reviews)
"Clean rooms, spacious enough for two for a weekend/long weekend. Easy access to Southampton City centre on the No1 bus, which runs right past the front door. Plenty of parking front and rear to service all the apartments."
United Kingdom
Emma
$189 nightly
The price is $227
Dec 6 - Dec 7
Total with taxes and fees
Southampton Serviced Apartment
A green RV with a fire pit and outdoor seating area, surrounded by lanterns and plants.

11. The Shack Cabin Sleeps 3 With Enclosed Garden

The Shack Cabin Sleeps 3 With Enclosed Garden
2.0 star property
Waterlooville
$161 nightly
The price is $193
Nov 20 - Nov 21
Total with taxes and fees
The Shack Cabin Sleeps 3 With Enclosed Garden
A tent with a bed inside, a colorful rug, and a sign on the ground.

12. Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
8.6 out of 10, Excellent, (21 reviews)
"Cozy place to stay, it is near a road but it didn’t bother me. It is as advertised"
Canada
Darnell
$60 nightly
The price is $73
Nov 12 - Nov 13
Total with taxes and fees
Stone Circle Glamping
A dining area with a view of a swimming pool, a table with food, and a chair.

13. Beam Cottage

Beam Cottage
3.0 star property
Southampton
$2,947 nightly
The price is $3,536
Nov 17 - Nov 18
Total with taxes and fees
Beam Cottage
A dining table set with plates, cutlery, and a glass vase with yellow flowers.

14. 3 Bedrooms house ideal for long Stays!

3 Bedrooms house ideal for long Stays!
Southampton
10.0 out of 10, Exceptional, (5 reviews)
"Great location, lovely clean property can recommend."
United Kingdom
Michael R.
$204 nightly
The price is $204
Nov 29 - Nov 30
Total with taxes and fees
3 Bedrooms house ideal for long Stays!
A bedroom with a wooden headboard, white bedding, two floral pillows, a bedside lamp, and a folded towel on the bed.

15. The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
$148 nightly
The price is $177
Nov 9 - Nov 10
Total with taxes and fees
The Riley Stable- Cozy Getaway
A wooden cabin with an open door, surrounded by lush greenery.

16. 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.
$148 nightly
The price is $148
Nov 6 - Nov 7
Total with taxes and fees
Wigwam Holidays Cabin With Ensuite without Pergola
A bedroom with a bed, a chair, a TV, and a window.

17. Orchard Road

Orchard Road
2.0 star property
Southsea
$49 nightly
The price is $59
Dec 5 - Dec 6
Total with taxes and fees
Orchard Road
A historic building with timber framing, a stone facade, and a covered passageway with purple wisteria.

18. Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.

Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"This cottage was absolutely charming and exactly what our family needed for a safe comfortable place to stay."
United States
Grace O.
Charming 3 bed Thatched cottage in rural village near Stockbridge Winchester.
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.

19. Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (10 reviews)
"Clean modern room, well equipped and great locaton"
United Kingdom
Theodros
$137 nightly
The price is $164
Nov 17 - Nov 18
Total with taxes and fees
Charles Hope Salisbury Centre
Exterior

20. The South Coast Snug

The South Coast Snug
2.0 star property
Fareham
7.4 out of 10, Good, (6 reviews)
"Fantastic place great location everything close by"
United Kingdom
Nikki
$62 nightly
The price is $75
Nov 9 - Nov 10
Total with taxes and fees
The South Coast Snug
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

Novotel Southampton

Novotel Southampton

10/10 Excellent
"Easy walking distance from train station. Also easy walking distance to port. Ideal for cruisers who would like to arrive the day prior to their departure."
Daniel 1-night trip
Posted 16 hours ago
Novotel Southampton

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 $73 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.