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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
The price is P2,518
P7,498 total
includes taxes & fees
Oct 4 - Oct 5
Settle Winchester
A canal with a wooden fence and a large terracotta pot with flowers.

2. Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester City Center
The price is P59,660
P71,592 total
includes taxes & fees
Oct 4 - Oct 5
Rivergem - Riverside Coach House
A bedroom with a bed, a nightstand, a lamp, a window with a view, and a radiator.

3. Clifton Lodge

Clifton Lodge
2.0 star property
Winchester
The price is P39,961
P47,953 total
includes taxes & fees
Oct 4 - Oct 5
Clifton Lodge
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
The price is P3,849
P8,343 total
includes taxes & fees
Oct 5 - Oct 6
Settle Southampton
A modern interior with a red sofa, black chairs, and a patterned floor.

5. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,342 reviews)
"Great location and friendly staff!"
United States
Gary
The price is P5,847
P7,017 total
includes taxes & fees
Oct 4 - Oct 5
Second Nature Southampton
A tent with a bed inside, a colorful rug, and a sign on the ground.

6. 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 P3,209
P3,851 total
includes taxes & fees
Oct 2 - Oct 3
Stone Circle Glamping
A bedroom with a wooden headboard, white bedding, two floral pillows, a bedside lamp, and a folded towel on the bed.

7. The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
The price is P7,040
P10,931 total
includes taxes & fees
Oct 14 - Oct 15
The Riley Stable- Cozy Getaway
A room with a dartboard, a power outlet, a potted plant, and a curtain.

8. 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
Eastleigh Luxury Retreat With 4 Bedrooms With Parking Near Airport
A bedroom with two beds, a nightstand with a lamp, and wall art.

9. 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
The price is P5,363
P5,363 total
includes taxes & fees
Oct 4 - Oct 5
Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
A hotel room with a bed, a sofa, a small table, and a lamp.

10. Studio 24-Free Private Parking

Studio 24-Free Private Parking
2.0 star property
Southsea
The price is P6,570
P6,570 total
includes taxes & fees
Oct 12 - Oct 13
Studio 24-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

Leonardo Hotel Southampton

Leonardo Hotel Southampton

8/10 Good
"Nice place and will stay again"
Michael 1-night trip
Posted 22 hours ago
Leonardo Hotel Southampton

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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.

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.