Title: Winchester Vacation Rentals from $67: Search Short-Term Rentals | Expedia.com

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![Winchester showing heritage architecture as well as a small group of people](https://images.trvl-media.com/place/5477/36ffd968-a708-44fd-a530-107c0f9501f1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/5477/36ffd968-a708-44fd-a530-107c0f9501f1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=5477&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=5477&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=5477&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=5477&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester vacation rentals

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118470000/118466000/118465980/w1024h680x0y0-2826f4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118470000/118466000/118465980/02e121d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118470000/118466000/118465980/ae156521.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118466000/118465980/w378h683x323y0-94174cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cosy A-Frame cabin nestled in the chalk steams of Hampshire

[](https://www.expedia.com/Winchester-Hotels-Cosy-A-Frame-Cabin-Nestled-In-The-Chalk-Steams-Of-Hampshire.h118465980.Hotel-Information)

Winchester

9.0/10

Wonderful

(4 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](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Nicola H.

$282 nightly

$282 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Cosy-A-Frame-Cabin-Nestled-In-The-Chalk-Steams-Of-Hampshire.h118465980.Hotel-Information)

![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125550000/125549900/125549894/af7201b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/126000000/125550000/125549900/125549894/1858649a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/126000000/125550000/125549900/125549894/0864efae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125550000/125549900/125549894/29437efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Winchester City Centre Flat/Sleeps 6/Free Parking

[](https://www.expedia.com/Winchester-Hotels-Winchester-City-Centre-FlatSleeps-6Free-Parking.h125549894.Hotel-Information)

Hampshire

$251 nightly

$251 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Winchester-City-Centre-FlatSleeps-6Free-Parking.h125549894.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/76a834c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/e08259e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/375b1564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/f5fcb3b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunday Winchester Wessex Cathedral Hotel | Twin

[](https://www.expedia.com/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Twin.h116100858.Hotel-Information)

Winchester

6.0/10

(1 review)

"Didn’t have Kitchen like advertised, no fridge unfortunately "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Hayden

$124 nightly

$124 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Twin.h116100858.Hotel-Information)

![1 bedroom](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/a7917cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/33100fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/ac1dd699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/94bb2b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aethelred Annexe - New Build with Full Amenities

[](https://www.expedia.com/Winchester-Hotels-Aethelred-Annexe-New-Build-With-Full-Amenities.h121578063.Hotel-Information)

Winchester

10/10

Exceptional

(1 review)

"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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrea W.

$131 nightly

$131 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Aethelred-Annexe-New-Build-With-Full-Amenities.h121578063.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119350000/119340100/119340066/bb8bbe76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/120000000/119350000/119340100/119340066/b3bbd15d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/120000000/119350000/119340100/119340066/w2245h1500x4y0-f616be12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119350000/119340100/119340066/7c6a2147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Garden room, central Winchester

[](https://www.expedia.com/Winchester-Hotels-Garden-Room.h119340066.Hotel-Information)

Winchester

$143 nightly

$143 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Garden-Room.h119340066.Hotel-Information)

![4 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/b263005b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/64ec86b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/600c976e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/d3c67c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Piping House 4bedroom

[](https://www.expedia.com/Winchester-Hotels-Piping-House-4bedroom.h76882122.Hotel-Information)

Colden Common

$386 nightly

$386 total

Feb 25 - Feb 26

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Piping-House-4bedroom.h76882122.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882133/8af8844f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882133/b9f804d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882133/b48ff27b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882133/d2f5b779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Birdsong House

[](https://www.expedia.com/Winchester-Hotels-Birdsong-House.h76882133.Hotel-Information)

Winchester

10/10

Exceptional

(1 review)

"We had a wonderful stay at Birdsong house. The owner was always available and the house was so cozy and comfortable! Thank you"

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Judith D.

$1,077 nightly

$1,077 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Birdsong-House.h76882133.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/d22e552e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/b1fc34ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/178af1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/0f155587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Piping Green 4Bedroom House

[](https://www.expedia.com/Winchester-Hotels-Piping-Green-4Bedroom-House.h89183237.Hotel-Information)

Colden Common

$410 nightly

$410 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Piping-Green-4Bedroom-House.h89183237.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/81ff3273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/0fb958ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/2ca8078e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/7f31934a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Birdsong Mansion sleeps 12 Twyford Winchester

[](https://www.expedia.com/Winchester-Hotels-Birdsong-Mansion-Sleeps-12-Twyford-Winchester.h76882120.Hotel-Information)

Winchester

$1,363 nightly

$1,363 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Birdsong-Mansion-Sleeps-12-Twyford-Winchester.h76882120.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/61d2ed89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/ffa00035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/4087c90b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/334cfc10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Squirrel's Leap

[](https://www.expedia.com/Winchester-Hotels-Squirrels-Leap.h114092093.Hotel-Information)

Winchester

$541 nightly

$650 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Squirrels-Leap.h114092093.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/b283f83d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/3de5128c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/5433d693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/e7adf6ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunday Winchester Wessex Cathedral Hotel | Compact

[](https://www.expedia.com/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Compact.h116099531.Hotel-Information)

Southampton

$95 nightly

$95 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Compact.h116099531.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/b1bfbc14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/07ad8319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/a82d468b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/ad63c2bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sunday Winchester Wessex Cathedral Hotel | Classic

[](https://www.expedia.com/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Classic.h114476100.Hotel-Information)

Winchester

6.0/10

(1 review)

"Carpets and sofa in room were noticeably stained. Otherwise the view was great, bed was comfortable and clean. Staff were very helpful and professional "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Cathy

$109 nightly

$109 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Classic.h114476100.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114343400/114343350/4d3192ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/115000000/114350000/114343400/114343350/c8883c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, individually decorated, individually furnished, free WiFi](https://images.trvl-media.com/lodging/115000000/114350000/114343400/114343350/f2203821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114343400/114343350/efb6cc86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rivergem - Riverside Coach House

[](https://www.expedia.com/Winchester-Hotels-Rivergem-Riverside-Coach-House.h114343350.Hotel-Information)

Winchester

$953 nightly

$1,143 total

Feb 27 - Feb 28

Total with taxes and fees

[](https://www.expedia.com/Winchester-Hotels-Rivergem-Riverside-Coach-House.h114343350.Hotel-Information)

![Spa](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/b4dd21bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/f5936e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/4b86d2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/a32d826a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 4 Berth Boat on the Isle of Wight for the Ultimate Relaxation

[](https://www.expedia.com/Newport-Hotels-Beautiful-4-Berth-Boat-On-The-Isle-Of-Wight-For-The-Ultimate-Relaxation.h95045482.Hotel-Information)

Binfield

10/10

Exceptional

(1 review)

"Best stay! Very new experience of staying in a boat. Amazing location for public services as well. "

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

srini k.

$256 nightly

$256 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Newport-Hotels-Beautiful-4-Berth-Boat-On-The-Isle-Of-Wight-For-The-Ultimate-Relaxation.h95045482.Hotel-Information)

![Bell Tent](https://images.trvl-media.com/lodging/124000000/123160000/123150700/123150677/7924290d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bell Tent](https://images.trvl-media.com/lodging/124000000/123160000/123150700/123150677/921ec2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Basic Cabin | Garden](https://images.trvl-media.com/lodging/124000000/123160000/123150700/123150677/w746h1598x0y1-3da5f877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room](https://images.trvl-media.com/lodging/124000000/123160000/123150700/123150677/0404605f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stone Circle Glamping

[](https://www.expedia.com/Salisbury-Hotels-Stonehenge-Inn-Glamping-Touring-Park.h123150677.Hotel-Information)

Durrington

$59 nightly

$70 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Salisbury-Hotels-Stonehenge-Inn-Glamping-Touring-Park.h123150677.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108400000/108398400/108398396/649a6a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/109000000/108400000/108398400/108398396/805a33d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/109000000/108400000/108398400/108398396/184a6efb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108400000/108398400/108398396/3002a450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool

[](https://www.expedia.com/Eastleigh-Hotels-Romantic-Swiss-Cabin-Hideaway-Hot-Tub-Spa-Pool.h108398396.Hotel-Information)

Chandler's Ford

$128 nightly

$128 total

Mar 2 - Mar 3

Total with taxes and fees

[](https://www.expedia.com/Eastleigh-Hotels-Romantic-Swiss-Cabin-Hideaway-Hot-Tub-Spa-Pool.h108398396.Hotel-Information)

![Deluxe Studio Suite, Garden View | Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/122000000/121390000/121380200/121380135/ad869ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio Suite, Garden View | Private kitchen](https://images.trvl-media.com/lodging/122000000/121390000/121380200/121380135/4f6ec6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio Suite, Garden View | Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/122000000/121390000/121380200/121380135/60a89242.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/122000000/121390000/121380200/121380135/7031afdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking

[](https://www.expedia.com/Gosport-Hotels-Ground-Floor-Family-Studio-Apartment-With-Double-And-Single-Beds-Free-Parking.h121380135.Hotel-Information)

Gosport

$77 nightly

$93 total

Mar 3 - Mar 4

Total with taxes and fees

[](https://www.expedia.com/Gosport-Hotels-Ground-Floor-Family-Studio-Apartment-With-Double-And-Single-Beds-Free-Parking.h121380135.Hotel-Information)

![Chalet, Garden View | Free WiFi](https://images.trvl-media.com/lodging/121000000/120400000/120393800/120393715/b9b0417c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120400000/120393800/120393715/d0bae57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Chalet, Garden View | Living area](https://images.trvl-media.com/lodging/121000000/120400000/120393800/120393715/a575fd20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/121000000/120400000/120393800/120393715/0fd77111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hugo Stable- Cozy get away

[](https://www.expedia.com/Waterlooville-Hotels-The-Hugo-Stable-Cozy-Get-Away.h120393715.Hotel-Information)

Waterlooville

$161 nightly

$193 total

Feb 24 - Feb 25

Total with taxes and fees

[](https://www.expedia.com/Waterlooville-Hotels-The-Hugo-Stable-Cozy-Get-Away.h120393715.Hotel-Information)

![Apartment, Garden View | Free WiFi](https://images.trvl-media.com/lodging/121000000/120620000/120614400/120614312/7f7f074c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120620000/120614400/120614312/ae3aa445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Garden View | Living area](https://images.trvl-media.com/lodging/121000000/120620000/120614400/120614312/998d98eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120620000/120614400/120614312/c558d149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Riley Stable- Cozy Getaway

[](https://www.expedia.com/Waterlooville-Hotels-The-Riley-Stable-Cozy-Getaway.h120614312.Hotel-Information)

Waterlooville

$171 nightly

$205 total

Mar 26 - Mar 27

Total with taxes and fees

[](https://www.expedia.com/Waterlooville-Hotels-The-Riley-Stable-Cozy-Getaway.h120614312.Hotel-Information)

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

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=APARTMENT)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CABIN)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=VACATION_HOME)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CHALET)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=HOUSE_BOAT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=VILLA)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=CONDO)

Residences

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-05-24&d1=2026-05-24&endDate=2026-05-27&d2=2026-05-27&lodging=RESIDENCE)

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## Top Winchester Hotel Reviews

![The Winchester Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/26100/26080/4127003a_y.jpg)

### The Winchester Hotel & Spa

10/10 Excellent

"Had a great stay! Was lucky enough to get upgraded, which was a lovely touch. Spa facilities very enjoyable, nice room, great breakfast! "

[](https://expedia.com/Winchester-Hotels-The-Winchester-Hotel-Spa.h26080.Hotel-Information)

![The Langstone Quays](https://images.trvl-media.com/lodging/1000000/10000/8600/8541/952fcd26_y.jpg)

### The Langstone Quays

10/10 Excellent

"Staff friendly and helpful. The Dyson hot cold fan was brilliant. We enjoyed using the pool and steam room. Dinner in the restaurant was amazing!"

[](https://expedia.com/Hayling-Island-Hotels-The-Langstone-Quays.h8541.Hotel-Information)

![voco Winchester Hotel & Spa by IHG](https://images.trvl-media.com/lodging/4000000/3440000/3430900/3430824/bec3fe8c_y.jpg)

### voco Winchester Hotel & Spa by IHG

10/10 Excellent

"Friendly staff all round. Room spotless. Nice bar area. Plenty of parking. Can't fault at this price point."

[](https://expedia.com/Winchester-Hotels-Holiday-Inn-Winchester.h3430824.Hotel-Information)

![Leonardo Hotel Southampton ](https://images.trvl-media.com/lodging/2000000/1180000/1178300/1178290/0c96afed_y.jpg)

### Leonardo Hotel Southampton 

10/10 Excellent

"The check in staff were friendly and helpful as were the restaurant staff. The room was clean but hot at night."

[](https://expedia.com/Southampton-Hotels-Jurys-Inn-Southampton.h1178290.Hotel-Information)

![Village Hotel Southampton Eastleigh](https://images.trvl-media.com/lodging/65000000/64270000/64264800/64264792/67cc524a_y.jpg)

### Village Hotel Southampton Eastleigh

10/10 Excellent

"Great chilled hotel with easy self-service check in. Room was clean with lots of tea/coffee facilities and gym is big with lots of machines and weights."

[](https://expedia.com/Eastleigh-Hotels-Village-Hotel-Southampton-Eastleigh.h64264792.Hotel-Information)

![Royal Maritime Hotel](https://images.trvl-media.com/lodging/16000000/15090000/15086700/15086665/8c64c9ac_y.jpg)

### Royal Maritime Hotel

10/10 Excellent

"Great room, quiet and warm. All you need."

[](https://expedia.com/Portsmouth-Hotels-The-Royal-Maritime-Club.h15086665.Hotel-Information)

![Norton Park Hotel, Spa & Manor House](https://images.trvl-media.com/lodging/3000000/2780000/2773900/2773823/757d6db6_y.jpg)

### Norton Park Hotel, Spa & Manor House

10/10 Excellent

"The room was clean, well resourced and the pool is lovely. Breakfast is fantastic."

[](https://expedia.com/Winchester-Hotels-Norton-Park.h2773823.Hotel-Information)

![Leonardo Royal Southampton Grand Harbour](https://images.trvl-media.com/lodging/1000000/20000/20000/19955/662fccb6_y.jpg)

### Leonardo Royal Southampton Grand Harbour

10/10 Excellent

"The room was clean and spacious, the amenities were great, housekeeping staff were excellent and only did what we asked if them. Location was perfect for what we needed."

[](https://expedia.com/Southampton-Hotels-Leonardo-Royal-Southampton-Grand-Harbour.h19955.Hotel-Information)

![Moxy Southampton](https://images.trvl-media.com/lodging/43000000/42110000/42101700/42101688/92beb57c_y.jpg)

### Moxy Southampton

10/10 Excellent

"Staff fantastic, very clean and enjoyed 💯 "

[](https://expedia.com/Southampton-Hotels-Moxy-By-Marriott-Southampton.h42101688.Hotel-Information)

## 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 $67 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

- Trending destinations on Expedia.com
- All accommodation types in Winchester

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- [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals)
- [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals)
- [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals)
- [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals)
- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Apartments in Winchester ](https://expedia.com/Winchester-Apartments.d5477-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.com/Winchester-Cottages.d5477-aaCottages.Travel-Guide-Accommodation)
- [Vacation Homes in Winchester ](https://expedia.com/Winchester-Private-Vacation-Homes.d5477-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Inns in Winchester ](https://expedia.com/Winchester-Inns.d5477-aaInns.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.com/Winchester-Bed-And-Breakfast.d5477-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Condo Rentals in Winchester ](https://expedia.com/Winchester-Condos.d5477-aaCondos.Travel-Guide-Accommodation)
- [Houseboats in Winchester ](https://expedia.com/Winchester-Houseboats.d5477-aaHouseboats.Travel-Guide-Accommodation)
- [Holiday Park Resorts in Winchester ](https://expedia.com/Winchester-Holiday-Parks.d5477-aaHolidayParks.Travel-Guide-Accommodation)
- [Castles in Winchester ](https://expedia.com/Winchester-Castles.d5477-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Winchester?

### What are some of the best vacation home rentals in Winchester?

### How many vacation rentals are there in Winchester?

### What’s there to see and do in Winchester?

### What’s a vacation rental in Winchester like?

### Expedia's Latest Trends

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General

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