City of Winchester Vacation Rentals from CA $58: Short-Term Rentals for 2026

A cathedral at night with illuminated trees and a park with benches.

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Top cities in City of Winchester

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

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Our top choices for City of Winchester vacation rentals

A bedroom with a bed, a bedside table, a window, and a view of the outside.

1. Settle Winchester

Winchester City Center

CA $172 total

includes taxes & fees

Nov 19 - Nov 20

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

Waterlooville

CA $271 total

includes taxes & fees

Nov 20 - Nov 21

A modern black building with a wooden fence in front.

3. Suetts Farm Barns

Southampton

CA $1,782 total

includes taxes & fees

Nov 18 - Nov 19

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

Waterlooville

CA $249 total

includes taxes & fees

Nov 20 - Nov 21

A building with a gravel driveway, a door, and a window.

5. Barley Cottage

Alresford

CA $1,456 total

includes taxes & fees

Nov 23 - Nov 24

A bar area with stools, a counter with various items, and a patterned floor.

6. Second Nature Southampton

Southampton City Centre

Yahong Susan

CA $144 total

includes taxes & fees

Dec 13 - Dec 14

A balcony with wicker chairs, a table with a fruit basket and wine glasses, and a view of houses and trees.

7. Southampton Serviced Apartment

Bassett

Emma

CA $330 total

includes taxes & fees

Dec 13 - Dec 14

A wooden sign with "Horseshoe Cottage" and "The Bike Shed" labels.

8. Horseshoe Cottage

Romsey

Peter

CA $1,420 total

includes taxes & fees

Nov 20 - Nov 21

A modern bathroom with a freestanding bathtub, a round mirror, and a herringbone-patterned wall.

9. Pinnacle Suites

Cowes

Simon

CA $243 total

includes taxes & fees

Nov 15 - Nov 16

A traditional pub named "The Duke of Wellington" with a white facade, timber framing, and hanging flower baskets.

10. Beddoe Apartments

Eastleigh

Alan

CA $368 total

includes taxes & fees

Nov 15 - Nov 16

A room with a bed, a chair, a table, and a window with curtains.

11. Settle Southampton

Freemantle

Chris

CA $174 total

includes taxes & fees

Nov 15 - Nov 16

A grassy field with a wooden fence and a bush in the foreground.

12. Stone Circle Glamping

Durrington

Darnell

CA $102 total

includes taxes & fees

Nov 15 - Nov 16

A modern bathroom with a green wall, a white sink, and a grey sofa.

13. Peartree Serviced Apartments

Salisbury

Stephanie

CA $187 total

includes taxes & fees

Nov 15 - Nov 16

14. Caravan - Sleeps 6 With Parking and Terrace

Hayling Island

CA $316 total

includes taxes & fees

Dec 14 - Dec 15

A modern living room with a sofa, a dining table with chairs, a potted plant, and a painting on the wall.

15. Charles Hope Salisbury Centre

Salisbury

Theodros

CA $231 total

includes taxes & fees

Nov 23 - Nov 24

A round mirror with a woven frame reflecting a dining area with a table and chairs.

16. Hamilton House

Southsea

CA $192 total

includes taxes & fees

Nov 16 - Nov 17

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

Rushmoor District

John

CA $129 total

includes taxes & fees

Nov 22 - Nov 23

A swimming pool with a deck, lounge chairs, and a small building in the background.

18. Beam Cottage

Southampton

CA $4,847 total

includes taxes & fees

Nov 18 - Nov 19

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

Southsea

Claire

CA $118 total

includes taxes & fees

Nov 16 - Nov 17

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

Southsea

CA $66 total

includes taxes & fees

Nov 15 - Nov 16

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Top City of Winchester Hotel Reviews

A covered walkway with potted plants, a modern building with vertical wooden slats, and a glass entrance.

The Fox

Winchester

10/10 Excellent

sueann

The White Lion

Southampton

10/10 Excellent

David

The Old Vine

Winchester City Center

10/10 Excellent

I am a solo woman traveling from Canada and I am so happy I chose this hotel for a few days before my cruise out of Southampton. Everything was amazing, from the attentive and very helpful staff to the overall ambiance, my stay here was incredible! My room was so beautiful with views of the Winchester museum and the hotel just minutes away from the Cathedral. My bed was very comfy and I loved all the extra amenities included in the room! I also appreciated the towel warmer aftermy shower! I...

Chantelle

A cozy room with a stone fireplace, wooden beams, and framed pictures on the wall.

The White Hart, South Harting

Petersfield

10/10 Excellent

Ada

A hotel room with a bed, two bedside lamps, a wicker chair, a small round table, and a large mirror on the wall.

Westbury Lodge

Shanklin

10/10 Excellent

Laurie

A brick building with a sign for 'The White Star' dining, bar, and rooms.

The White Star Tavern

Southampton City Centre

10/10 Excellent

Maryann

A patio area with wicker chairs, a wooden pergola, and neatly trimmed hedges.

The White Horse

Chichester

10/10 Excellent

Jeffrey

A car park sign for hotel residents, a vintage car, and a brick building with outdoor seating.

Wykeham Arms

Winchester City Center

10/10 Excellent

Deborah

A large bed with a wooden headboard, a red throw blanket, and multiple pillows.

The Crown Inn

Southampton

10/10 Excellent

Brad

A large, historic building with a Tudor-style architecture, featuring multiple chimneys and a prominent tower.

Forest Park Country Hotel & Inn, Brockenhurst, New Forest

Brockenhurst

10/10 Excellent

Peter

A dining area with wooden furniture, a fireplace, and a chandelier.

The White Hart, Overton

Basingstoke

10/10 Excellent

John

Find out more about City of Winchester

Everything you need to know about City of 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 City of Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 City of Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

City of Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in City of 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 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.  The selection of City of Winchester vacation rentals we have selected for you start as low as CA $58 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on City of Winchester rentals

At Expedia, we put the best City of 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 City of 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 City of 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 City of 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.

City of Winchester Vacation Rentals

Change your mind

Treat yourself

Be picky

Top cities in City of Winchester

Southampton

Check prices for these dates

Our top choices for City of Winchester vacation rentals

1. Settle Winchester

2. The Shack Cabin Sleeps 3 With Enclosed Garden

3. Suetts Farm Barns

4. The Riley Stable- Cozy Getaway

5. Barley Cottage

6. Second Nature Southampton

7. Southampton Serviced Apartment

8. Horseshoe Cottage

9. Pinnacle Suites

10. Beddoe Apartments

11. Settle Southampton

12. Stone Circle Glamping

13. Peartree Serviced Apartments

14. Caravan - Sleeps 6 With Parking and Terrace

15. Charles Hope Salisbury Centre

16. Hamilton House

17. HQ Aparthotel Farnborough

18. Beam Cottage

19. ANG Apartments

20. Francis Avenue

Find vacation rentals that suit your style

Top City of Winchester Hotel Reviews

The Fox

10/10 Excellent

Find out more about City of Winchester

City of Winchester vacation rentals: An excellent choice for every season

How to find incredible deals on City of Winchester rentals