Title: Top 10 Hotels in Winchester, MD (from $58) 2026 - Competitive Prices | Expedia.com

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## Go beyond your typical stay in Winchester

Pool

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Maryland%2C+United+States+of+America&regionId=553248635975872164&latLong=39.670667%2C-75.86994&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-22&d2=2026-03-22&amenities=POOL)

Family friendly

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Maryland%2C+United+States+of+America&regionId=553248635975872164&latLong=39.670667%2C-75.86994&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-22&d2=2026-03-22&travelerType=family_friendly)

Pet friendly

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Maryland%2C+United+States+of+America&regionId=553248635975872164&latLong=39.670667%2C-75.86994&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-22&d2=2026-03-22&amenities=PETS)

Hot tub

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Maryland%2C+United+States+of+America&regionId=553248635975872164&latLong=39.670667%2C-75.86994&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-22&d2=2026-03-22&amenities=HOT_TUB)

Apart­ment

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Maryland%2C+United+States+of+America&regionId=553248635975872164&latLong=39.670667%2C-75.86994&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-22&d2=2026-03-22&lodging=APARTMENT)

Cottage

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Maryland%2C+United+States+of+America&regionId=553248635975872164&latLong=39.670667%2C-75.86994&adults=2&startDate=2026-03-20&d1=2026-03-20&endDate=2026-03-22&d2=2026-03-22&lodging=COTTAGE)

## Check prices for these dates

Tonight

[Mar 6 - Mar 7](https://www.expedia.com/Hotel-Search?regionId=553248635975872164&startDate=2026-03-06&endDate=2026-03-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Mar 7 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=553248635975872164&startDate=2026-03-07&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=553248635975872164&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=553248635975872164&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winchester hotels

![Vending machine](https://images.trvl-media.com/lodging/1000000/20000/11300/11260/c358a2a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, 2 Double Beds, Non Smoking, Kitchenette | Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/11300/11260/bca43f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11300/11260/01da12a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/11300/11260/8c4bdae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Red Roof Inn Perryville

[](https://www.expedia.com/Perryville-Hotels-Red-Roof-Inn-Perryville.h11260.Hotel-Information)

Perryville

8.8/10

Excellent

(139 reviews)

"This is an ok place to stay for the price"

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

Carla

$64 nightly

$72 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Perryville-Hotels-Red-Roof-Inn-Perryville.h11260.Hotel-Information)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/870000/861400/861316/2ade43db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/1000000/870000/861400/861316/bf528c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/870000/861400/861316/04e8b2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/870000/861400/861316/7a1b8834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Mendenhall

[](https://www.expedia.com/Exton-Hotels-Inn-At-Mendenhall.h861316.Hotel-Information)

Chadds Ford

9.0/10

Wonderful

(1,001 reviews)

"great place to stay if visiting Longwood"

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

barbara

$91 nightly

$101 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Exton-Hotels-Inn-At-Mendenhall.h861316.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/28f580ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/60ac8690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Accessible, Non Smoking | Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/a1ea31cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Queen Bed, Accessible, Non Smoking | Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/4911f85e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Woodspring Suites Wilmington Riverfront

[](https://www.expedia.com/Wilmington-Hotels-Woodspring-Suites-Wilmington-Riverfront.h119443969.Hotel-Information)

South Wilmington

8.2/10

Very Good

(125 reviews)

"clean, friendly "

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

Alex

$79 nightly

$87 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Wilmington-Hotels-Woodspring-Suites-Wilmington-Riverfront.h119443969.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/fd2dd5eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/a0c80d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/53ee3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Middletown

[](https://www.expedia.com/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information)

Middletown

9.2/10

Wonderful

(352 reviews)

"Consistently a good stay here with helpful staff and comfortable rooms. "

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

Mary

$99 nightly

$110 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information)

![Room #2 OF ELEVEN | Premium bedding, pillowtop beds, minibar, in-room safe](https://images.trvl-media.com/lodging/103000000/102740000/102739400/102739320/w1500h1180x0y20-625fb3fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/103000000/102740000/102739400/102739320/2b79390d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/103000000/102740000/102739400/102739320/a4e2953f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/103000000/102740000/102739400/102739320/0e0598f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Artelo 

[](https://www.expedia.com/Kennett-Square-Hotels-Artelo.h102739320.Hotel-Information)

Kennett Square

9.8/10

Exceptional

(101 reviews)

"Great place "

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

Justin

$139 nightly

$154 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Kennett-Square-Hotels-Artelo.h102739320.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/96caeac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/75af64ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/f15b0778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/f7bb1068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express North East by IHG

[](https://www.expedia.com/North-East-Hotels-Holiday-Inn-Express-North-East.h984873.Hotel-Information)

North East

8.4/10

Very Good

(559 reviews)

"The room the food the staff were all amazing Much better than other hotels we stayed in the area reasonable priced"

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

Gregory

$89 nightly

$100 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/North-East-Hotels-Holiday-Inn-Express-North-East.h984873.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/c9c370cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/8a6e6273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/90c843ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/06ec6f88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Newark - Wilmington

[](https://www.expedia.com/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information)

Newark

9.0/10

Wonderful

(1,075 reviews)

"This is my go to hotel always everytime I visit I love the free breakfast "

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

Latisha

$89 nightly

$99 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/4c3cf026.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/496ae4cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/c03fee2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, Private Bathroom (Chesapeake Haven) | Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/90041687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn At The Canal Bed & Breakfast

[](https://www.expedia.com/Chesapeake-City-Hotels-Inn-At-The-Canal-Bed-Breakfast.h15082750.Hotel-Information)

Chesapeake City

8.6/10

Excellent

(508 reviews)

"Ed was very welcoming and the location is amazing."

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

Jennifer

$157 nightly

$167 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Chesapeake-City-Hotels-Inn-At-The-Canal-Bed-Breakfast.h15082750.Hotel-Information)

![Classic Room, 1 King Bed | Down comforters, memory foam beds, individually decorated](https://images.trvl-media.com/lodging/101000000/100140000/100133900/100133805/d5b2216b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Suite, 1 King Bed with Sofa bed | Down comforters, memory foam beds, individually decorated](https://images.trvl-media.com/lodging/101000000/100140000/100133900/100133805/a52ddd50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Down comforters, memory foam beds, individually decorated](https://images.trvl-media.com/lodging/101000000/100140000/100133900/100133805/f66cca07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100140000/100133900/100133805/7b2f12ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Bookhouse Hotel

[](https://www.expedia.com/Kennett-Square-Hotels-The-Bookhouse-Hotel.h100133805.Hotel-Information)

Kennett Square

9.6/10

Exceptional

(45 reviews)

"Outstanding! Great Location, awesome room and extremely comfy bed!"

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

John

$189 nightly

$210 total

Mar 11 - Mar 12

Total with taxes and fees

[](https://www.expedia.com/Kennett-Square-Hotels-The-Bookhouse-Hotel.h100133805.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/700000/694500/694477/a965382f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, in-room safe, iron/ironing board](https://images.trvl-media.com/lodging/1000000/700000/694500/694477/a86d798c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, 1 King Bed | Living area | 37-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/700000/694500/694477/16145eea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/700000/694500/694477/02cbe693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Kennett Square

[](https://www.expedia.com/Exton-Hotels-Hilton-Garden-Inn-Kennett-Square.h694477.Hotel-Information)

Kennett Square

8.4/10

Very Good

(954 reviews)

"Excellent accommodations "

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

pat

$106 nightly

$117 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Exton-Hotels-Hilton-Garden-Inn-Kennett-Square.h694477.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/a4f6753f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/2ca9a3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/10fce65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/a3a44793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Newark/Christiana Inn

[](https://www.expedia.com/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information)

Bear

8.2/10

Very Good

(188 reviews)

"Great location "

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

suzanne

$79 nightly

$88 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/98000000/97870000/97861600/97861549/a9d0f8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/98000000/97870000/97861600/97861549/72dd185b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/98000000/97870000/97861600/97861549/22ee9748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/98000000/97870000/97861600/97861549/29ca1e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard By Marriott New Castle

[](https://www.expedia.com/Courtyard-By-Marriott-New-Castle.h97861549.Hotel-Information)

New Castle

8.6/10

Excellent

(251 reviews)

"Check in was very friendly"

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

Ermelinda

$118 nightly

$131 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Courtyard-By-Marriott-New-Castle.h97861549.Hotel-Information)

![Suite, 2 Queen Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/a0122816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/f06ff3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Queen Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/8836fadd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/9cdfab37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wingate by Wyndham North East

[](https://www.expedia.com/North-East-Hotels-Best-Western-North-East-Inn.h1535860.Hotel-Information)

North East

8.0/10

Very Good

(961 reviews)

"Good stay. The room was clean, bed was super comfortable and the shower was great. "

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

DeAnda

$116 nightly

$130 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/North-East-Hotels-Best-Western-North-East-Inn.h1535860.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/9000000/8510000/8507200/8507156/4b168833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/9000000/8510000/8507200/8507156/cc699c6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/9000000/8510000/8507200/8507156/6b4faeec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/9000000/8510000/8507200/8507156/4b20ab4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites Wilmington New Castle

[](https://www.expedia.com/Wilmington-Hotels-Fairfield-Inn-Suites-Wilmington-New-Castle.h8507156.Hotel-Information)

New Castle

8.8/10

Excellent

(975 reviews)

"Nice, clean, staff is great!"

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

Arthur

$105 nightly

$116 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Wilmington-Hotels-Fairfield-Inn-Suites-Wilmington-New-Castle.h8507156.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/b66763a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6cc4a825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/7e87d5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn Middletown

[](https://www.expedia.com/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information)

Middletown

8.8/10

Excellent

(882 reviews)

"Clean room.breakfast was great.Staff.was helpful."

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

Susan

$95 nightly

$106 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/3cc8ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/6af27243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/b95d3d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express & Suites Middletown by IHG

[](https://www.expedia.com/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information)

Middletown

9.2/10

Wonderful

(668 reviews)

"Clean room and hotel. Breakfast was good, the fresh baked cookies at the front desk were delicious!"

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

Valerie

$109 nightly

$121 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/60000/50200/50134/0adbdd89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/60000/50200/50134/53e9ad31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50200/50134/640b7870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50200/50134/7d833cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites North East

[](https://www.expedia.com/North-East-Hotels-Comfort-Inn-And-Suites.h50134.Hotel-Information)

North East

7.8/10

Good

(662 reviews)

"Great stay"

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

Tina

$80 nightly

$90 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/North-East-Hotels-Comfort-Inn-And-Suites.h50134.Hotel-Information)

![Water park](https://images.trvl-media.com/lodging/104000000/103100000/103097900/103097849/31e21486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Waterslide](https://images.trvl-media.com/lodging/104000000/103100000/103097900/103097849/20587fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/104000000/103100000/103097900/103097849/1ef71864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/104000000/103100000/103097900/103097849/16cbcc8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Great Wolf Lodge Perryville

[](https://www.expedia.com/Perryville-Hotels-Great-Wolf-Lodge-Perryville.h103097849.Hotel-Information)

Perryville

8.6/10

Excellent

(179 reviews)

"Good experience ...very satisfying my family loved the place"

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

Mauricio

$199 nightly

$223 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Perryville-Hotels-Great-Wolf-Lodge-Perryville.h103097849.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/650ea886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Vending machine](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/a6e6b250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/0a422533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, soundproofing, rollaway beds](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/a39ec805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Super 8 by Wyndham Havre De Grace Aberdeen Area

[](https://www.expedia.com/Havre-De-Grace-Hotels-Super-8-By-Wyndham-Havre-De-Grace-Aberdeen-Area.h49890.Hotel-Information)

Havre De Grace

6.6/10

(975 reviews)

"There were no healthy options offered, not even hard-boiled eggs. I guess they haven't seen the new food pyramid!"

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

Carleen Lyden

$51 nightly

$58 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Havre-De-Grace-Hotels-Super-8-By-Wyndham-Havre-De-Grace-Aberdeen-Area.h49890.Hotel-Information)

![Cocktail bar](https://images.trvl-media.com/lodging/24000000/23090000/23089300/23089234/79ddc1c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, individually furnished](https://images.trvl-media.com/lodging/24000000/23090000/23089300/23089234/22921f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/24000000/23090000/23089300/23089234/015ae050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/24000000/23090000/23089300/23089234/6ad2d4bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SpringHill Suites by Marriott Newark Downtown

[](https://www.expedia.com/Wilmington-Hotels-SpringHill-Suites-By-Marriott-Newark-Downtown.h23089234.Hotel-Information)

Newark

9.4/10

Exceptional

(808 reviews)

"Very clean, staff was very cordial and the breakfast buffet is great. Definitely recommend! "

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

Patricia

$123 nightly

$137 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Wilmington-Hotels-SpringHill-Suites-By-Marriott-Newark-Downtown.h23089234.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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-20&endDate=2026-03-21&regionId=553248635975872164&adults=2&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

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## Top Winchester Hotel Reviews

![Quality Inn Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/30000/25100/25008/e605848f_y.jpg)

### Quality Inn Newark - Wilmington

10/10 Excellent

"My daughter and i have been staying here for awhile due to unforseen circumstances, the manager and staff are always helpful when needed, always say hi in passing. I am grateful for the help when needed. "

[](https://expedia.com/Wilmington-Hotels-Quality-Inn.h25008.Hotel-Information)

![Best Western Plus Newark/Christiana Inn](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/a4f6753f_y.jpg)

### Best Western Plus Newark/Christiana Inn

4/10 Poor

"Yes"

[](https://expedia.com/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information)

![Extended Stay America Suites Newark Christiana Wilmington](https://images.trvl-media.com/lodging/1000000/120000/119100/119061/02a2e620_y.jpg)

### Extended Stay America Suites Newark Christiana Wilmington

10/10 Excellent

"Ues"

[](https://expedia.com/Wilmington-Hotels-Extended-Stay-America-Suites-Newark-Christiana-Wilmington.h119061.Hotel-Information)

![Embassy Suites by Hilton Newark Wilmington South](https://images.trvl-media.com/lodging/1000000/330000/327600/327586/b7951f6a_y.jpg)

### Embassy Suites by Hilton Newark Wilmington South

8/10 Good

"Everything fine "

[](https://expedia.com/Wilmington-Hotels-Embassy-Suites-Newark-WilmingtonSouth.h327586.Hotel-Information)

![Red Roof Inn & Suites Newark - University](https://images.trvl-media.com/lodging/1000000/10000/8500/8462/72a36958_y.jpg)

### Red Roof Inn & Suites Newark - University

4/10 Poor

"I tried to give Red Roof another chance. We initially had to have our room changed, because we saw 2 roaches in the first room. And it wasn’t cleaned thoroughly. I did try, but I won’t be going back to Any locations. Unfortunately "

[](https://expedia.com/Wilmington-Hotels-Red-Roof-Inn-Suites-Newark-University.h8462.Hotel-Information)

![Staybridge Suites Wilmington Downtown by IHG](https://images.trvl-media.com/lodging/82000000/81880000/81875700/81875625/268c99c5_y.jpg)

### Staybridge Suites Wilmington Downtown by IHG

2/10 Terrible

"Location lost power for over 16 hours with no plan for guests and amenities non existent due to them having no power "

[](https://expedia.com/Wilmington-Hotels-Staybridge-Suites-Wilmington-Downtown.h81875625.Hotel-Information)

![DoubleTree by Hilton Downtown Wilmington - Legal District](https://images.trvl-media.com/lodging/1000000/30000/20900/20863/3de63e00_y.jpg)

### DoubleTree by Hilton Downtown Wilmington - Legal District

4/10 Poor

"Front desk staff were great, however, rooms weren’t ready at check in time and the room wasn’t stocked with items that are usually provided. "

[](https://expedia.com/Wilmington-Hotels-DoubleTree-By-Hilton-Downtown-Wilmington-Legal-District.h20863.Hotel-Information)

![Hyatt Place Wilmington Riverfront](https://images.trvl-media.com/lodging/35000000/34930000/34927700/34927626/5d36bf4b_y.jpg)

### Hyatt Place Wilmington Riverfront

10/10 Excellent

"We enjoyed our visit. The room was clean. Good breakfast. The menu for lunch and dinner could be improved. The staff was extra nice! "

[](https://expedia.com/Wilmington-Hotels-Hyatt-Place-Wilmington-Riverfront.h34927626.Hotel-Information)

![Holiday Inn Express & Suites Wilmington-Newark by IHG ](https://images.trvl-media.com/lodging/1000000/20000/14200/14182/0462a60c_y.jpg)

### Holiday Inn Express & Suites Wilmington-Newark by IHG 

10/10 Excellent

"excellent staff, clean rooms convenient location"

[](https://expedia.com/Wilmington-Hotels-Holiday-Inn-Express-Hotel-Suites-Wilmington-Newark.h14182.Hotel-Information)

## More cheap stays in Winchester

![Quality Inn Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/30000/25100/25008/e605848f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn Newark - Wilmington

65 Geoffrey Dr Newark DE

$66 nightly

$73 total

Mar 13 - Mar 14

Total with taxes and fees

5.4/10 (1,012 reviews)

[](https://expedia.com/Wilmington-Hotels-Quality-Inn.h25008.Hotel-Information)

![Red Roof Inn & Suites Newark - University](https://images.trvl-media.com/lodging/1000000/10000/8500/8462/72a36958_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Red Roof Inn & Suites Newark - University

1119 S College Avenue Newark DE

$69 nightly

$77 total

Mar 8 - Mar 9

Total with taxes and fees

5.4/10 (1,007 reviews)

[](https://expedia.com/Wilmington-Hotels-Red-Roof-Inn-Suites-Newark-University.h8462.Hotel-Information)

![Extended Stay America Suites Newark Christiana Wilmington](https://images.trvl-media.com/lodging/1000000/120000/119100/119061/02a2e620_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Extended Stay America Suites Newark Christiana Wilmington

333 Continental Dr Newark DE

$77 nightly

$85 total

Mar 8 - Mar 9

Total with taxes and fees

6/10 (1,007 reviews)

[](https://expedia.com/Wilmington-Hotels-Extended-Stay-America-Suites-Newark-Christiana-Wilmington.h119061.Hotel-Information)

![Woodspring Suites Wilmington Riverfront](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/44b1f889_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Woodspring Suites Wilmington Riverfront

600 A Street Wilmington DE

$79 nightly

$87 total

Mar 8 - Mar 9

Total with taxes and fees

8.2/10 Very Good! (125 reviews)

[](https://expedia.com/Wilmington-Hotels-Woodspring-Suites-Wilmington-Riverfront.h119443969.Hotel-Information)

![Best Western Plus Newark/Christiana Inn](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/a4f6753f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Best Western Plus Newark/Christiana Inn

875 Pulaski Highway Bear DE

$79 nightly

$88 total

Mar 15 - Mar 16

Total with taxes and fees

8.2/10 Very Good! (188 reviews)

[](https://expedia.com/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information)

![Holiday Inn Express & Suites Wilmington-Newark by IHG ](https://images.trvl-media.com/lodging/1000000/20000/14200/14182/0462a60c_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Holiday Inn Express & Suites Wilmington-Newark by IHG 

1201 Christiana Rd Newark DE

$99 nightly

$110 total

Mar 31 - Apr 1

Total with taxes and fees

9.4/10 Exceptional! (1,007 reviews)

[](https://expedia.com/Wilmington-Hotels-Holiday-Inn-Express-Hotel-Suites-Wilmington-Newark.h14182.Hotel-Information)

## Hotels in Winchester with star-rating

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

6 properties

[](https://expedia.com/4Star-Winchester-Hotels.s40-0-d553248635975872164.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

46 properties

[](https://expedia.com/3Star-Winchester-Hotels.s30-0-d553248635975872164.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

211 properties

[](https://expedia.com/2Star-Winchester-Hotels.s20-0-d553248635975872164.Travel-Guide-Filter-Hotels)

## Frequently asked questions

### What is the best area to stay in Winchester?

> This area is highly walkable and characterized by its unique architecture and tree-lined streets. You'll find many local shops, restaurants, and historical markers along the Loudoun Street Walking Mall, a pedestrian-only thoroughfare. The area is also home to landmarks like the Handley Regional Library and the Old Court House Civil War Museum.
> 
>   
> Couples will find downtown Winchester particularly appealing for a relaxing getaway. The pedestrian mall provides a pleasant setting for strolls, and there are many dining options from casual eateries to upscale restaurants. The proximity to historical sites and local boutiques makes it easy to fill a day with activities without needing a car.
> 
>   
> For those interested in history, staying downtown provides direct access to Winchester's rich past.

### When is the best time to go to Winchester?

> Spring brings blooming flowers and comfortable temperatures, great for outdoor activities like walking tours of the historic downtown or visiting nearby orchards. The average daytime temperatures range from the low 60s to mid-70s Fahrenheit, making it enjoyable to spend time outside without extreme heat or cold.
> 
>   
> Fall provides crisp air, colorful foliage, and a variety of harvest-themed events. Temperatures typically range from the mid-50s to upper 60s Fahrenheit. This season is particularly appealing for couples looking for scenic drives through the Shenandoah Valley or visiting local wineries and cideries.

### Can I cancel my hotel reservation on Expedia?

### How can I save on a Winchester hotel booking with Expedia?

> \*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

### How much is the nightly rate at a Winchester hotel?

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- [North East Hotels ](https://www.expedia.com/North-East-Hotels.d139151.Travel-Guide-Hotels)
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- [Flights to Elk Mills ](https://www.expedia.com/Cheap-Flights-To-Elk-Mills.d3000347868.Travel-Guide-Flights)
- [Flights to Elkton ](https://www.expedia.com/Cheap-Flights-To-Elkton.d7834.Travel-Guide-Flights)
- [Flights from Elkton ](https://www.expedia.com/lp/flights/7834/flights-from-elkton)
- [Flights from Cecil County ](https://www.expedia.com/lp/flights/553248635976434204/flights-from-cecil-county)
- [Flights to North East ](https://www.expedia.com/Cheap-Flights-To-North-East.d139151.Travel-Guide-Flights)
- [Dallas to North East ](https://www.expedia.com/lp/flights/178253/139151/dallas-to-north-east)

- [Visit Elk Mills ](https://www.expedia.com/Elk-Mills.dx3000347868)
- [Fair Hill State Natural Resources Management Area ](https://www.expedia.com/Fair-Hill-State-Natural-Resources-Management-Area-Elkton.d6187511.Vacation-Attraction)
- [Union Hospital ](https://www.expedia.com/Union-Hospital-Elkton.d6288957.Vacation-Attraction)
- [Cow Pond ](https://www.expedia.com/Cow-Pond-Elkton.d553248621532663259.Vacation-Attraction)
- [East Meadow Park ](https://www.expedia.com/East-Meadow-Park-Elkton.d553248621532663261.Vacation-Attraction)
- [Visit Elkton ](https://www.expedia.com/Elkton.dx7834)
- [Historical Society of Cecil County ](https://www.expedia.com/Historical-Society-Of-Cecil-County-Elkton.d553248621561879715.Vacation-Attraction)
- [Elkton Vacations ](https://www.expedia.com/Elkton.d7834.Destination-Travel-Guides)
- [Milburn Stone Theater ](https://www.expedia.com/Milburn-Stone-Theater-North-East.d553248621532662925.Vacation-Attraction)
- [Elkton Golf and Batting Center ](https://www.expedia.com/Elkton-Golf-And-Batting-Center-Elkton.d553248621532663258.Vacation-Attraction)
- [West Meadow Park ](https://www.expedia.com/West-Meadow-Park-Elkton.d553248621532663260.Vacation-Attraction)
- [North East Vacations ](https://www.expedia.com/North-East.d139151.Destination-Travel-Guides)
- [Visit North East ](https://www.expedia.com/North-East.dx139151)

- [Car rentals near Childs ](https://www.expedia.com/Car-Rentals-In-Childs.d3000347838.Car-Rental-Guide)
- [Car rentals near Fair Hill ](https://www.expedia.com/Car-Rentals-In-Fair-Hill.d553248635975847229.Car-Rental-Guide)
- [Car rentals near Elk Mills ](https://www.expedia.com/Car-Rentals-In-Elk-Mills.d3000347868.Car-Rental-Guide)
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- [Enterprise Rental Cars in Elkton ](https://www.expedia.com/Enterprise-Car-Rentals-In-Elkton.d7834-c15.Car-Rental-Guide-Suppliers)
- [Van Car Rentals in Elkton ](https://www.expedia.com/Van-Car-Rentals-In-Elkton.d7834-tVan.Car-Rental-Guide-Class)
- [Avis Rental Cars in Elkton ](https://www.expedia.com/Avis-Car-Rentals-In-Elkton.d7834-c41.Car-Rental-Guide-Suppliers)
- [Hertz Rental Cars in Elkton ](https://www.expedia.com/Hertz-Car-Rentals-In-Elkton.d7834-c40.Car-Rental-Guide-Suppliers)
- [Suv Car Rentals in Elkton ](https://www.expedia.com/SUV-Car-Rentals-In-Elkton.d7834-tSUV.Car-Rental-Guide-Class)
- [Payless Rental Cars in Elkton ](https://www.expedia.com/Payless-Car-Rentals-In-Elkton.d7834-c38.Car-Rental-Guide-Suppliers)
- [Convertible Car Rentals in Elkton ](https://www.expedia.com/Convertible-Car-Rentals-In-Elkton.d7834-tConvertible.Car-Rental-Guide-Class)
- [Sixt Rental Cars in Elkton ](https://www.expedia.com/Sixt-Car-Rentals-In-Elkton.d7834-c35.Car-Rental-Guide-Suppliers)
- [Minivan Car Rentals in Elkton ](https://www.expedia.com/Minivan-Car-Rentals-In-Elkton.d7834-tMinivan.Car-Rental-Guide-Class)
- [Car rentals near Milburn Stone Theater ](https://www.expedia.com/Car-Rentals-In-Milburn-Stone-Theater.d553248621532662925.Car-Rental-Guide)
- [Car rentals near Westminister ](https://www.expedia.com/Car-Rentals-In-Westminister.d553248635975868995.Car-Rental-Guide)
- [Car rentals near North East ](https://www.expedia.com/Car-Rentals-In-North-East.d139151.Car-Rental-Guide)

- [Elkton Vacation Rentals ](https://www.expedia.com/Elkton-Vacation-Rentals.d7834.Travel-Guide-VacationRentals)
- [North East Vacation Rentals ](https://www.expedia.com/North-East-Vacation-Rentals.d139151.Travel-Guide-VacationRentals)

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