Vacation Rentals in City of Winchester

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Top cities in City of Winchester

A sunset over a river with a bridge and buildings in the background.
Vacation Rentals

Southampton

Southampton

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for City of 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
Dec 13 - Dec 14
Total with taxes and fees
Settle Winchester
A green RV with a fire pit and outdoor seating area, surrounded by lanterns and plants.

2. The Shack Cabin Sleeps 3 With Enclosed Garden

The Shack Cabin Sleeps 3 With Enclosed Garden
2.0 star property
Waterlooville
$159 nightly
The price is $190
Nov 19 - Nov 20
Total with taxes and fees
The Shack Cabin Sleeps 3 With Enclosed Garden
An outdoor seating area with a table, chairs, and a bottle of wine.

3. Suetts Farm Barns

Suetts Farm Barns
3.0 star property
Southampton
$1,041 nightly
The price is $1,249
Nov 17 - Nov 18
Total with taxes and fees
Suetts Farm Barns
A bedroom with a wooden headboard, white bedding, two floral pillows, a bedside lamp, and a folded towel on the bed.

4. The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
$146 nightly
The price is $175
Nov 17 - Nov 18
Total with taxes and fees
The Riley Stable- Cozy Getaway
A building with a gravel driveway, a door, and two potted trees.

5. Barley Cottage

Barley Cottage
3.0 star property
Alresford
$851 nightly
The price is $1,021
Nov 17 - Nov 18
Total with taxes and fees
Barley Cottage
A modern interior with a red sofa, black chairs, and a patterned floor.

6. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,369 reviews)
"Nice staff, clean property. Close to restaurants. Nice park in front of the property. Overall very pleasant stay."
United States
Yahong Susan
$85 nightly
The price is $102
Nov 15 - Nov 16
Total with taxes and fees
Second Nature Southampton
A bedroom with a large bed, a nightstand, a wall-mounted lamp, and a window with blinds.

7. 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
$198 nightly
The price is $238
Nov 15 - Nov 16
Total with taxes and fees
Southampton Serviced Apartment
A bedroom with a bed, a bedside table with a lamp, a window with curtains, a mirror, and a wooden door with a metal handle.

8. Horseshoe Cottage

Horseshoe Cottage
3.0 star property
Romsey
10.0 out of 10, Exceptional, (1 review)
"Well presented and well equipped home. All the essentials plus more. Very family friendly."
United Kingdom
Peter
$830 nightly
The price is $996
Nov 17 - Nov 18
Total with taxes and fees
Horseshoe Cottage
A bedroom with a bed, a wooden bench, a staircase, and a wall-mounted light fixture.

9. Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.2 out of 10, Wonderful, (42 reviews)
"A great stay in this unique, cool venue."
United Kingdom
Simon
$142 nightly
The price is $170
Dec 13 - Dec 14
Total with taxes and fees
Pinnacle Suites
A kitchen counter with vegetables, a sink, and potted plants.

10. 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
$225 nightly
The price is $258
Nov 15 - Nov 16
Total with taxes and fees
Beddoe Apartments
A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

11. 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
$101 nightly
The price is $121
Nov 15 - Nov 16
Total with taxes and fees
Settle Southampton
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
8.8 out of 10, Excellent, (22 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 $71
Nov 15 - Nov 16
Total with taxes and fees
Stone Circle Glamping
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

13. Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (330 reviews)
"Great. They have everything you could need - well appointed kitchen, milk and breakfast provided, plenty of fluffy towels even down to non stick bath mats"
Australia
Stephanie
$108 nightly
The price is $130
Nov 15 - Nov 16
Total with taxes and fees
Peartree Serviced Apartments
A compact kitchenette with a stove, microwave, and cabinets.

14. Caravan - Sleeps 6 With Parking and Terrace

Caravan - Sleeps 6 With Parking and Terrace
3.0 star property
Hayling Island
$185 nightly
The price is $222
Dec 14 - Dec 15
Total with taxes and fees
Caravan - Sleeps 6 With Parking and Terrace
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.

15. 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
$135 nightly
The price is $162
Nov 23 - Nov 24
Total with taxes and fees
Charles Hope Salisbury Centre
A round mirror with a woven frame reflecting a dining area with a table and chairs.

16. Hamilton House

Hamilton House
Southsea
$112 nightly
The price is $135
Nov 14 - Nov 15
Total with taxes and fees
Hamilton House
A modern hotel room with a wooden floor, a bed with a grey blanket, a bedside table, and a desk with a laptop.

17. HQ Aparthotel Farnborough

HQ Aparthotel Farnborough
4.0 star property
Rushmoor District
9.2 out of 10, Wonderful, (484 reviews)
"I always stay here when visiting family nearby as I live in USA."
United States
John
$69 nightly
The price is $83
Nov 22 - Nov 23
Total with taxes and fees
HQ Aparthotel Farnborough
A dining area with a view of a swimming pool, a table with food, and a chair.

18. Beam Cottage

Beam Cottage
3.0 star property
Southampton
$2,831 nightly
The price is $3,397
Nov 17 - Nov 18
Total with taxes and fees
Beam Cottage
A view from a window overlooking a street with a bus, a pedestrian crossing, and a sign indicating a speed limit of 30.

19. ANG Apartments

ANG Apartments
2.0 star property
Southsea
9.0 out of 10, Wonderful, (6 reviews)
"Nice place to stay, lovely beach view and close to amenities"
United Kingdom
Claire
$83 nightly
The price is $83
Nov 17 - Nov 18
Total with taxes and fees
ANG Apartments
A hotel room with a wooden bed, white bedding, an orange throw blanket, a white nightstand, a red vase, and abstract wall art.

20. Francis Avenue

Francis Avenue
2.0 star property
Southsea
$39 nightly
The price is $46
Nov 15 - Nov 16
Total with taxes and fees
Francis Avenue
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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Find vacation rentals that suit your style

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Top City of Winchester Hotel Reviews

A restaurant with brick walls, wooden tables, and hanging spherical light fixtures.
The Fox

The Fox

The Fox
Winchester

10/10 Excellent

Unique place. Great stay for privacy and comfort
United States
Karin
Reviewed August 6, 2026
The Fox

Frequently Asked Questions

How many vacation rentals are available in City of Winchester?

Expedia has plenty of vacation rentals to choose from in and around City of Winchester, so you’re guaranteed to find the right one for you.


How much is a vacation rental in City of Winchester?

The selection of City of Winchester vacation rentals we have selected for you start as low as $71 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in City of Winchester?

Vacation rentals in City of Winchester come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of City of Winchester vacation rentals to suit everyone.


Why should I choose a vacation rental in City of Winchester?

Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A City of Winchester vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.


How do I find the best deal on a vacation rental in City of Winchester?

Find vacation rentals in City of Winchester by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in City of Winchester.


What amenities are available in a vacation rental in City of Winchester?

The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in City of Winchester vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in City of Winchester?

Everytime is a great time to head to City of Winchester! Staying in a City of Winchester vacation rentals you will always find lots going on to keep you entertained.


Why book a vacation rental with Expedia?

Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in City of Winchester. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect City of Winchester vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in City of Winchester, you can save even more.


Can I cancel my vacation rental through Expedia?

Yes, you can cancel or change your City of Winchester vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.