A large red brick building with a central entrance flanked by columns, a fountain in front, and trees on either side.

Holiday Rentals in Winchester

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester holiday 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
The price is €118
includes taxes & fees
4 Oct - 5 Oct
Settle Winchester
A bedroom with a large window, a bed with a blue and white checkered duvet, a grey headboard, and a small vase with flowers on a white shelf.

2. The Porterhouse - Residence I

The Porterhouse - Residence I
Winchester City Center
The price is €204
includes taxes & fees
27 Sept - 28 Sept
The Porterhouse - Residence I
A well-maintained garden with a patio area, a white chair, and a small table.

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

Garden room, central Winchester – self-contained, kitchenette & parking
Winchester
The price is €117
includes taxes & fees
27 Sept - 28 Sept
Garden room, central Winchester – self-contained, kitchenette & 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.

4. 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.
The price is €117
includes taxes & fees
30 Sept - 1 Oct
Aethelred Annexe - New Build with Full Amenities
A bed with a teal headboard, two pillows with tropical leaf patterns, and two folded towels on a yellow bedspread.

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

Winchester City Centre Flat/Sleeps 6/Free Parking
Hampshire
The price is €231
includes taxes & fees
22 Sept - 23 Sept
Winchester City Centre Flat/Sleeps 6/Free Parking
A two-story brick building with a sign for 'Wessex Hotel' and 'Wessex Hotel' written on the side. There are cars parked in front and a pedestrian walkway.

6. Winchester Wessex Hotel by Sunday Twin Room

Winchester Wessex Hotel by Sunday Twin Room
Winchester City Center
6.0 out of 10, (1 review)
"Didn’t have Kitchen like advertised, no fridge unfortunately "
United Kingdom
Hayden
The price is €122
includes taxes & fees
27 Sept - 28 Sept
Winchester Wessex Hotel by Sunday Twin Room

7. Calm 1 Bed Apartment with Parking, Winchester by At Hem

Calm 1 Bed Apartment with Parking, Winchester by At Hem
Winchester
10.0 out of 10, Exceptional, (1 review)
"Excellent location and property. The owner was very responsive and helpful "
Australia
Jayani
The price is €213
includes taxes & fees
28 Sept - 29 Sept
Calm 1 Bed Apartment with Parking, Winchester by At Hem
A wooden cabin with a sloped roof, a deck with two chairs, and a glass door leading inside.

8. 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.
The price is €257
includes taxes & fees
22 Sept - 23 Sept
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
A white, two-story building with a curved corner, a brick base, and a small balcony on the second floor.

9. Clifton Lodge

Clifton Lodge
2.0 star property
Winchester
The price is €676
includes taxes & fees
4 Oct - 5 Oct
Clifton Lodge
A living room with a flat-screen TV mounted on the wall displaying 'NETFLIX' in red letters, a white entertainment unit with a plant and decorative items, and a radiator on the wall.

10. The Porterhouse - Residence II

The Porterhouse - Residence II
Winchester City Center
The Porterhouse - Residence II
A canal with a wooden fence and a large terracotta pot with flowers.

11. Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester City Center
The price is €1,009
includes taxes & fees
29 Sept - 30 Sept
Rivergem - Riverside Coach House
A bedroom with a metal bed frame, a bedside table, a lamp, a nightstand, a framed picture, and a wall sign.

12. Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport

Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport
3.0 star property
Eastleigh
The price is €207
includes taxes & fees
4 Oct - 5 Oct
Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport
A modern interior with a red sofa, black chairs, and a patterned floor.

13. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,337 reviews)
"Great place to stay on the way to our cruise…would definitely recommend!!"
Canada
Shelly
The price is €95
includes taxes & fees
4 Oct - 5 Oct
Second Nature Southampton
A room with a bed, a chair, a table, and a window with curtains.

14. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.0 out of 10, Very good, (10 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is €127
includes taxes & fees
28 Sept - 29 Sept
Settle Southampton
A view from inside a room looking out onto a grassy field with trees and a fence.

15. 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.
The price is €128
includes taxes & fees
23 Sept - 24 Sept
Cosy Rural Cabin With Ensuite without Pergola
A dining table set with plates, cutlery, and a glass vase with yellow flowers.

16. 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.
The price is €236
includes taxes & fees
27 Sept - 28 Sept
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.

17. The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
The price is €154
includes taxes & fees
27 Sept - 28 Sept
The Riley Stable- Cozy Getaway
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
8.6 out of 10, Excellent, (13 reviews)
"Cozy place to stay, it is near a road but it didn’t bother me. It is as advertised"
Canada
Darnell
The price is €53
includes taxes & fees
28 Sept - 29 Sept
Stone Circle Glamping
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

19. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.0 out of 10, (12 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
The price is €193
includes taxes & fees
22 Sept - 23 Sept
QE2 Loft Apartments
A bedroom with a bed, a TV, and a window with curtains.

20. 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
The price is €327
includes taxes & fees
28 Sept - 29 Sept
Bayview Apartments
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

8/10 Good
"Great place to stay the night before your cruise!"
Robert 1-night trip
Posted 2 hours ago
voco Southampton by IHG

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €53 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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 holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Winchester Science Centre and Planetarium, or you can select 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 holiday rentals that Winchester has to offer?

Unique waterside home in stunning location.: This holiday 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 that you can cook with friends or family.

How many holiday rentals are there in Winchester?

Expedia has 37 holiday 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 the family-friendly sights, whereas cultural attractions include Great Hall and Theatre Royal Winchester. While in the area, you can also visit popular places such as Southampton Cruise Terminal and New Forest National Park.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.