Title: 10 Best Hotels in Winchester-on-the-Severn, Annapolis for 2025 | Expedia.ca

  

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# Hotels in Winchester-on-the-Severn, Annapolis

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## Go beyond your typical stay in Winchester-on-the-Severn

House­boat

[](https://www.expedia.ca/Hotel-Search?destination=Winchester-on-the-Severn%2C+Annapolis%2C+Maryland%2C+United+States+of+America&regionId=553248635976475477&latLong=39.015549%2C-76.507143&adults=2&startDate=2025-10-25&d1=2025-10-25&endDate=2025-10-27&d2=2025-10-27&lodging=HOUSE_BOAT)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Winchester-on-the-Severn%2C+Annapolis%2C+Maryland%2C+United+States+of+America&regionId=553248635976475477&latLong=39.015549%2C-76.507143&adults=2&startDate=2025-10-25&d1=2025-10-25&endDate=2025-10-27&d2=2025-10-27&amenities=PETS)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Winchester-on-the-Severn%2C+Annapolis%2C+Maryland%2C+United+States+of+America&regionId=553248635976475477&latLong=39.015549%2C-76.507143&adults=2&startDate=2025-10-25&d1=2025-10-25&endDate=2025-10-27&d2=2025-10-27&lodging=COTTAGE)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Winchester-on-the-Severn%2C+Annapolis%2C+Maryland%2C+United+States+of+America&regionId=553248635976475477&latLong=39.015549%2C-76.507143&adults=2&startDate=2025-10-25&d1=2025-10-25&endDate=2025-10-27&d2=2025-10-27&travelerType=family_friendly)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Winchester-on-the-Severn%2C+Annapolis%2C+Maryland%2C+United+States+of+America&regionId=553248635976475477&latLong=39.015549%2C-76.507143&adults=2&startDate=2025-10-25&d1=2025-10-25&endDate=2025-10-27&d2=2025-10-27&amenities=HOT_TUB)

Condo

[](https://www.expedia.ca/Hotel-Search?destination=Winchester-on-the-Severn%2C+Annapolis%2C+Maryland%2C+United+States+of+America&regionId=553248635976475477&latLong=39.015549%2C-76.507143&adults=2&startDate=2025-10-25&d1=2025-10-25&endDate=2025-10-27&d2=2025-10-27&lodging=CONDO)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Winchester-on-the-Severn%2C+Annapolis%2C+Maryland%2C+United+States+of+America&regionId=553248635976475477&latLong=39.015549%2C-76.507143&adults=2&startDate=2025-10-25&d1=2025-10-25&endDate=2025-10-27&d2=2025-10-27&lodging=APARTMENT)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Winchester-on-the-Severn%2C+Annapolis%2C+Maryland%2C+United+States+of+America&regionId=553248635976475477&latLong=39.015549%2C-76.507143&adults=2&startDate=2025-10-25&d1=2025-10-25&endDate=2025-10-27&d2=2025-10-27&amenities=POOL)

## Check prices for these dates

Tonight

[Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976475477&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Recommended

Price (low to high)

Distance

Star rating

## Winchester-on-the-Severn hotels and places to stay

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Annapolis East-Kent Island by IHG

23.6 km from Winchester-on-the-Severn

9.2/10

Wonderful

(906)

"Nice Holiday Inn Express with great water views."

CA $167

CA $185 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/30000/23100/23043/b1b0ec95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/30000/23100/23043/033129c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/30000/23100/23043/a978e6f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23100/23043/d4f2e2ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Baltimore At The Stadiums by IHG

30.5 km from Winchester-on-the-Severn

8.6/10

Excellent

(338)

"Great Place Places to Stay "

CA $133

CA $156 total

includes taxes & fees

Oct 14 - Oct 15

[](https://www.expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-Baltimore-At-The-Stadiums.h23043.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9e72db94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/e60ed5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hyatt Place Kent Narrows & Marina

23.3 km from Winchester-on-the-Severn

9.4/10

Exceptional

(638)

"Great location and rooms. Great place!"

CA $202

CA $224 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/e17d8d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/66a1e121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/6468097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Kent Island Marina

23.6 km from Winchester-on-the-Severn

9.0/10

Wonderful

(1002)

"Hotel was great, beautiful location near the water"

CA $206

CA $228 total

includes taxes & fees

Oct 16 - Oct 17

[](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1155100/1155026/37cd357c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/2000000/1160000/1155100/1155026/5f4916ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1155100/1155026/2a2c48d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1155100/1155026/838f8140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Suites Columbia Gateway

29.8 km from Winchester-on-the-Severn

8.2/10

Very good

(1003)

"Staff at this place were very nice "

CA $125

CA $141 total

includes taxes & fees

Oct 12 - Oct 13

[](https://www.expedia.ca/Baltimore-Hotels-Comfort-Suites-Columbia-Gateway.h1155026.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Single Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kent Island Resort

16.5 km from Winchester-on-the-Severn

9.2/10

Wonderful

(114)

"Great INN super nice staff"

CA $265

CA $346 total

includes taxes & fees

Oct 21 - Oct 22

[](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information)

![View from property](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/768e2886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/0684bd50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/04365757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Westin Annapolis

4.3 km from Winchester-on-the-Severn

8.6/10

Excellent

(1003)

"Would stay there again very soon "

CA $273

CA $311 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/19c3b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/58057ff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/a9a9ef59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Hotel & Conference Center

29.6 km from Winchester-on-the-Severn

7.8/10

Good

(1001)

"Great stay"

CA $150

CA $176 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7e58a966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/f531cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11100/11049/7f9539e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Annapolis

6 km from Winchester-on-the-Severn

8.6/10

Excellent

(1001)

"The room was great, and the staff was great. "

CA $153

CA $174 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/4cc768f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/c35aa4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/bd8b7105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott Baltimore Downtown/McHenry Row

29.1 km from Winchester-on-the-Severn

9.0/10

Wonderful

(674)

"Great location "

CA $177

CA $208 total

includes taxes & fees

Oct 19 - Oct 20

[](https://www.expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information)

![Egyptian cotton sheets, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/6846c015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/fbea7cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sonesta ES Suites Annapolis

6 km from Winchester-on-the-Severn

8.8/10

Excellent

(909)

"Had a great stay."

CA $122

CA $139 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/335c1120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room, 2 Double Beds, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/516c17a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee service](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/bf93fe2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/b510cc28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Village Inn Annapolis MD

3 km from Winchester-on-the-Severn

6.2/10

(502)

"The room was very nice, clean and quiet. Great location"

CA $116

CA $133 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Annapolis-Hotels-Village-Inn.h530229.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/cfbb67fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/w5759h3834x0y6-7304a3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/76f6e3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Crowne Plaza Annapolis by IHG

4.5 km from Winchester-on-the-Severn

8.8/10

Excellent

(1002)

"Good location"

CA $150

CA $171 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information)

![Suite, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/ead5e21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/028c45ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/48d9bd9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn

26.7 km from Winchester-on-the-Severn

7.8/10

Good

(839)

"Great place and great staff"

CA $137

CA $152 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information)

![1 bedroom, hypo-allergenic bedding, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/19214323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/6ea498fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Inn & Suites by Radisson, Annapolis, MD

5.4 km from Winchester-on-the-Severn

9.0/10

Wonderful

(1009)

"Great place to stay Friendly staff secure rooms Thank you "

CA $136

CA $155 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information)

![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business centre](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/cc651796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/068178f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Kent Narrows Inn

23.5 km from Winchester-on-the-Severn

8.0/10

Very good

(1009)

"Clean room and good location to biking trail."

CA $163

CA $181 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/9f06834f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ballroom](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b42a3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/cca95561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Inn at Chesapeake Bay Beach Club

16.2 km from Winchester-on-the-Severn

9.4/10

Exceptional

(421)

"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "

CA $271

CA $337 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/5575a0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/3952dad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DoubleTree by Hilton Hotel Annapolis

5 km from Winchester-on-the-Severn

8.6/10

Excellent

(1014)

"Comfortable place to stay, nice shopping area close by. "

CA $148

CA $169 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/be7252cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Historic Inns of Annapolis

Historic District, 4.3 km from Winchester-on-the-Severn

9.0/10

Wonderful

(1846)

"Perfect location…terrific staff…spacious room with a king sized bed! "

CA $145

CA $214 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/59d23d5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ffc728ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/8e8581bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Annapolis

5.3 km from Winchester-on-the-Severn

7.8/10

Good

(1008)

"Great place."

CA $111

CA $126 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.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.ca/Hotel-Search?startDate=2025-10-25&endDate=2025-10-26&regionId=553248635976475477&adults=2&sort=RECOMMENDED&openPlayBack=true)

## Where to stay in Winchester-on-the-Severn

Find the best Winchester-on-the-Severn areas and neighborhoods for the activities you enjoy most.

-   Historic District
-   Eastport
-   Murray Hill
-   Hillsmere
-   Cape Saint Claire

![Annapolis showing street scenes and a city as well as a small group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/146000/146977-Annapolis.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Annapolis showing street scenes and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/146000/146975-Annapolis.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Annapolis](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/253000/253200-Annapolis.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Annapolis which includes dining out, a city and signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/146000/146976-Annapolis.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Maryland State House which includes an administrative building, interior views and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/134000/134426-Annapolis.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976472706)

![Historic District map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:%7Bb%7ClF%7Cb%7DqMgJgEXiCaB%5BsJmPdDaLRaC%5BkA%7DEi%40gFmKrL%7DSuCsDlKcShDfDzEeJ%7CDvEnHoMfChCnMl%40v%40%7EBbAdNy%40bOhAnS%7ECbJ%3F%60FgArBK%60DwA%7CGyPkLeEMr%40zHoCx%40wByOaATuCjj%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=OqazwSPLvr5h-WgoH_Xe_qm6f6Y=)

### Historic District

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976472706)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976473127)

![Eastport map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:wowlFl%7DzqMkhAcXiOlHiDmH_Dr%40qAeFUgF%60B%7DJUoBcRsPwCaEMyBA%7DA%7EGkLrH%7BP%7EBsAnBHrBr%40%60P%60MbBpTtOtFtJpEvBvI%60JxDhUAtBlD%60GdPuA%60G%7E%40pGg%40bI&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=8C7j3Y4M9Ctt54PDCsHeBtpfKsY=)

### Eastport

While visiting Eastport, you might make a stop by sights like Annapolis Maritime Museum and Annapolis Harbor.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976473127)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976473392)

![Murray Hill map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:il%7BlF%7Cr%7DqMuMuu%40%7EFIp%40_GwE_Cs%40_B%7CAaDvBjBjBoFhCnB%60AaCdC%7CA%7C%40yCxDvAn%40fGnBfAt%40%7EEcAhHlDKvFbBUfE%7C%40pCOhEnAlGArBiA%60BKjBwA%7EDwBfAoFuH_CrBg%40_%40_DnB%7BG%7EG&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=jKOr6ipBt1dXnbT53EpyG6N8CsU=)

### Murray Hill

While visiting Murray Hill, you might make a stop by sights like Ballet Theater of Maryland and Spa Creek.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976473392)

![Maryland Quiet Waters Park showing a garden and a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/134000/134444-Annapolis.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Maryland Quiet Waters Park which includes a park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/134000/134443-Annapolis.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Maryland Quiet Waters Park featuring a garden as well as an individual male](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/135000/135020-Maryland-Quiet-Waters-Park.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Maryland Quiet Waters Park showing a statue or sculpture and a garden](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/135000/135023-Maryland-Quiet-Waters-Park.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

![Maryland Quiet Waters Park showing a park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/135000/135024-Maryland-Quiet-Waters-Park.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=553248635976473205)

![Hillsmere map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:%7DwtlF%7El%60rMuPwAwK%7DEeDeLmDwFmH%7CAsSs%40wBaKuK%7BDoq%40oBj%5C%7BObPeP%60Xej%40fFaZbFqRhFtBbU%7C%40XsKbKmPda%40mEtEaKjHdBvGxChFuBjQ%7BCxMn%5C%60T%7E%7C%40i%5E%7Eg%40aFxQoJ%7CEEp%5DoF%7EAsQmEqWbLaIrR&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=IJ7Xo8qRlQPWoO5oFb6yVBnP894=)

### Hillsmere

If you're spending some time in Hillsmere, Maryland Quiet Waters Park and Great Frogs Winery are top sights worth seeing.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=553248635976473205)

[](https://www.expedia.ca/Hotel-Search?pwaOverlay=map&regionId=3000440447)

![Cape Saint Claire map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:szgmFznvqMuFuCfAsB%60ADnDcC%7C%40cFYeAcByAyD%60KwGoOaD%7EAiCb%40eAa%40Co%40oBTyAo%40aCiCgKqPiFyDaBwI_KwOoC%7DG%7BFcUuf%40ecAhOy%5EdOuYhAsGvf%40k%40jPrBdLjDlR%60Dd%5C%7CITvAkBvM%60%40nDbBdCrC%60A%7ECJdEhE%7C%40vBErAnFhLvAJxA%7CBJ%7CIoB%60H_C%7EBeKrD_FbDqEvFwDhJ_BdJY%7CGB%7Cy%40%5DfQeKh%40gFrL&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=30TNaIuiYU_kf5r2dVaNSsZNNiY=)

### Cape Saint Claire

Boasting three marinas, multiple parks and beaches, Cape St. Claire offers a shopping center and various churches, with easy access to Annapolis and the Chesapeake Bay Bridge via U.S. Route 50.

[See properties](https://www.expedia.ca/Hotel-Search?regionId=3000440447)

## Top Winchester-on-the-Severn Hotel Reviews

![Red Roof Inn PLUS+ Baltimore-Washington DC/BWI Airport](//images.trvl-media.com/lodging/1000000/20000/14700/14697/cd71a232_y.jpg)

### Red Roof Inn PLUS+ Baltimore-Washington DC/BWI Airport

10/10 Excellent

"Room was clean and comfy!"

[](https://expedia.ca/Baltimore-Hotels-Red-Roof-Inn-PLUS-Baltimore-Washington-DC-BWI-Airport.h14697.Hotel-Information)

![Aloft BWI Baltimore Washington International Airport](//images.trvl-media.com/lodging/3000000/2810000/2804100/2804098/12d1a93d_y.jpg)

### Aloft BWI Baltimore Washington International Airport

10/10 Excellent

"Easily accessible and the room was great. "

[](https://expedia.ca/Baltimore-Hotels-Aloft-BWI-Baltimore-Washington-International-Airport.h2804098.Hotel-Information)

![Hyatt Place Baltimore/BWI Airport](//images.trvl-media.com/lodging/1000000/50000/42100/42070/f6e5dc70_y.jpg)

### Hyatt Place Baltimore/BWI Airport

10/10 Excellent

"Attractive room with ample space"

[](https://expedia.ca/Baltimore-Hotels-Hyatt-Place-BaltimoreBWI-Airport.h42070.Hotel-Information)

![The Hotel at Arundel Preserve](//images.trvl-media.com/lodging/5000000/4550000/4542400/4542302/bd8bd966_y.jpg)

### The Hotel at Arundel Preserve

10/10 Excellent

"clean room, friendly check-in, great restaurant on premise"

[](https://expedia.ca/Baltimore-Hotels-The-Hotel-At-Arundel-Preserve.h4542302.Hotel-Information)

![Courtyard by Marriott Baltimore BWI Airport](//images.trvl-media.com/lodging/1000000/30000/22300/22275/98ab8a9c_y.jpg)

### Courtyard by Marriott Baltimore BWI Airport

10/10 Excellent

"Totally new spacious rooms; had 2 queen beds and a large TV with excellent cable. Bathroom with tub and great showhead. Price was so good compared to the other local properties; and I needed a 4:30am shuttle to the airport. This hotel was perfect for anyone needing convenience to BWI with early departure time."

[](https://expedia.ca/Baltimore-Hotels-Courtyard-By-Marriott-Baltimore-BWI-Airport.h22275.Hotel-Information)

![SpringHill Suites by Marriott Baltimore BWI Airport](//images.trvl-media.com/lodging/1000000/580000/574400/574327/c40dfb4d_y.jpg)

### SpringHill Suites by Marriott Baltimore BWI Airport

10/10 Excellent

"Room 238 was fine, but the sink & tub/shower were both slow to drain water when in use. "

[](https://expedia.ca/Baltimore-Hotels-SpringHill-Suites-By-Marriott-Baltimore-BWI-Airport.h574327.Hotel-Information)

![The Westin Baltimore Washington Airport - BWI](//images.trvl-media.com/lodging/2000000/1780000/1770700/1770627/13f895c7_y.jpg)

### The Westin Baltimore Washington Airport - BWI

10/10 Excellent

"Amazing "

[](https://expedia.ca/Baltimore-Hotels-The-Westin-Baltimore-Washington-Airport-BWI.h1770627.Hotel-Information)

![DoubleTree Hotel Baltimore - BWI Airport](//images.trvl-media.com/lodging/1000000/30000/26200/26137/0422878e_y.jpg)

### DoubleTree Hotel Baltimore - BWI Airport

10/10 Excellent

"Great location to the airport- staff was awesome and places down the street for food. Room was clean and nice. Water pressure was awesome!!!"

[](https://expedia.ca/Baltimore-Hotels-DoubleTree-Hotel-Baltimore-BWI-Airport.h26137.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Baltimore BWI Airport](//images.trvl-media.com/lodging/1000000/30000/25900/25898/941fbe1a_y.jpg)

### La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

10/10 Excellent

"Clean room!!"

[](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-BWI-Airport.h25898.Hotel-Information)

## Frequently asked questions

### What's it like in Winchester-on-the-Severn?

> Travelers will be sure to enjoy their time in Annapolis's Winchester-on-the-Severn neighborhood.

### If I need to cancel my hotel reservation in Winchester-on-the-Severn, will I receive a refund?

> Yes! Most hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Add dates, click "Search", then you can use the "fully refundable" filter to view the best deals in Winchester-on-the-Severn.

### What is there to do in this Annapolis neighborhood?

> A few places to visit in the area around Winchester-on-the-Severn include Maryland World War II Memorial, Jonas Green State Park, and Helen Avalynne Tawes Garden. When you're sightseeing in Annapolis, Navy-Marine Corps Memorial Stadium and Severna Park Golf Center are also worth a stop.

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-   [Romantic Hotels in Maryland](https://www.expedia.ca/Destinations-In-Maryland-Romantic-Hotel.0-0-d222-tRomanticHotel.Hotel-Filter-Destinations)
-   [Ski Hotels in Maryland](https://www.expedia.ca/Destinations-In-Maryland-Ski-Hotel.0-0-d222-tSkiHotel.Hotel-Filter-Destinations)
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-   [Eastport Hotels](https://www.expedia.ca/Eastport-Annapolis-Hotels.0-n553248635976473127-0.Travel-Guide-Filter-Hotels)
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-   [Historic District Hotels](https://www.expedia.ca/Historic-District-Annapolis-Hotels.0-n553248635976472706-0.Travel-Guide-Filter-Hotels)
-   [Homewood Hotels](https://www.expedia.ca/Homewood-Annapolis-Hotels.0-n553248635976468944-0.Travel-Guide-Filter-Hotels)
-   [Apartments in Maryland](https://www.expedia.ca/Maryland-Apartments.d222-aaApartments.Travel-Guide-Accommodation)
-   [B&B in Maryland](https://www.expedia.ca/Maryland-Bed-And-Breakfast.d222-aaBedAndBreakfast.Travel-Guide-Accommodation)
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-   [Cottages in Maryland](https://www.expedia.ca/Maryland-Cottages.d222-aaCottages.Travel-Guide-Accommodation)
-   [Cruise Ships in Maryland](https://www.expedia.ca/Maryland-Cruise-Ships.d222-aaCruiseShips.Travel-Guide-Accommodation)
-   [Hotels near Maryland Hall for Creative Arts](https://www.expedia.ca/Maryland-Hall-For-Creative-Arts-Hotels.0-l553248621580159031-0.Travel-Guide-Filter-Hotels)
-   [Hostels in Maryland](https://www.expedia.ca/Maryland-Hostels.d222-aaHostels.Travel-Guide-Accommodation)
-   [Motels in Maryland](https://www.expedia.ca/Maryland-Motels.d222-aaMotels.Travel-Guide-Accommodation)
-   [Vacation Homes in Maryland](https://www.expedia.ca/Maryland-Private-Vacation-Homes.d222-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Hotels near Maryland Quiet Waters Park](https://www.expedia.ca/Maryland-Quiet-Waters-Park-Hotels.0-l6172639-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Maryland State House](https://www.expedia.ca/Maryland-State-House-Hotels.0-l6077394-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Navy-Marine Corps Memorial Stadium](https://www.expedia.ca/Navy-Marine-Corps-Memorial-Stadium-Hotels.0-l6091645-0.Travel-Guide-Filter-Hotels)
-   [Parole Hotels](https://www.expedia.ca/Parole-Hotels.d553248634999151929.Travel-Guide-Hotels)
-   [Severna Park Hotels](https://www.expedia.ca/Severna-Park-Hotels.d156680.Travel-Guide-Hotels)
-   [Apartments in Sherwood Forest](https://www.expedia.ca/Sherwood-Forest-Apartments.d553248635975871192-aaApartments.Travel-Guide-Accommodation)
-   [Sherwood Forest Hotels](https://www.expedia.ca/Sherwood-Forest-Hotels.d553248635975871192.Travel-Guide-Hotels)
-   [Hotels near St John's College](https://www.expedia.ca/St-Johns-College-Hotels.0-l553248621533116848-0.Travel-Guide-Filter-Hotels)
-   [Hotels near U.S. Naval Academy](https://www.expedia.ca/US-Naval-Academy-Hotels.0-l6077390-0.Travel-Guide-Filter-Hotels)
-   [Adults Only Resorts & in West Annapolis](https://www.expedia.ca/West-Annapolis-Annapolis-Hotels-Adults-Only-Resorts.0-n553248635976472135-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
-   [Boutique Hotels in West Annapolis](https://www.expedia.ca/West-Annapolis-Annapolis-Hotels-Boutique-Hotel.0-n553248635976472135-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels)
-   [Hotels with a Pool in West Annapolis](https://www.expedia.ca/West-Annapolis-Annapolis-Hotels-Hotel-With-Pool.0-n553248635976472135-0-tHotelwithPool.Travel-Guide-Filter-Hotels)
-   [Hotels with Bar in West Annapolis](https://www.expedia.ca/West-Annapolis-Annapolis-Hotels-Hotels-With-Bar.0-n553248635976472135-0-tHotelswithBar.Travel-Guide-Filter-Hotels)
-   [Hotels with Tennis Courts in West Annapolis](https://www.expedia.ca/West-Annapolis-Annapolis-Hotels-Hotels-With-Tennis-Courts.0-n553248635976472135-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels)
-   [Pet-Friendly Hotels in West Annapolis](https://www.expedia.ca/West-Annapolis-Annapolis-Hotels-Pet-Friendly-Hotel.0-n553248635976472135-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
-   [Romantic Hotels in West Annapolis](https://www.expedia.ca/West-Annapolis-Annapolis-Hotels-Romantic-Hotel.0-n553248635976472135-0-tRomanticHotel.Travel-Guide-Filter-Hotels)
-   [West Annapolis Hotels](https://www.expedia.ca/West-Annapolis-Annapolis-Hotels.0-n553248635976472135-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Westfield Annapolis Mall](https://www.expedia.ca/Westfield-Annapolis-Mall-Hotels.0-l6172637-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Wild Bird Center](https://www.expedia.ca/Wild-Bird-Center-Hotels.0-l553248621532662329-0.Travel-Guide-Filter-Hotels)

-   [Flights to Annapolis](https://www.expedia.ca/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights)
-   [Flights to Arnold](https://www.expedia.ca/Cheap-Flights-To-Arnold.d74829.Travel-Guide-Flights)
-   [Flights to Maryland](https://www.expedia.ca/Destinations-In-Maryland.d222.Flight-Destinations)
-   [Flights from Maryland](https://www.expedia.ca/lp/flights/222/flights-from-maryland)

-   [Visit Epping Forest](https://www.expedia.ca/Annapolis-Epping-Forest.dx553248635976473158)
-   [Visit Annapolis](https://www.expedia.ca/Annapolis.dx6034082)
-   [Visit Arnold](https://www.expedia.ca/Arnold.dx74829)
-   [Hammond-Harwood House](https://www.expedia.ca/Hammond-Harwood-House-Historic-District.d6077396.Vacation-Attraction)
-   [Maryland Vacations](https://www.expedia.ca/Maryland.d222.Destination-Travel-Guides)
-   [Visit Maryland](https://www.expedia.ca/Maryland.dx222)
-   [U.s. Naval Academy](https://www.expedia.ca/US-Naval-Academy-Annapolis.d6077390.Vacation-Attraction)
-   [Golf Vacation Packages Maryland](https://www.expedia.ca/lp/theme-vacations/golf-vacations/222/Maryland)

-   [Car rentals in Alamo Rent A Car 9020 Aviation Blvd](https://www.expedia.ca/Alamo-Rent-A-Car-at-9020-Aviation-Blvd-Los-Angeles-California-USA.v222.Car-Rental-Guide-Location)
-   [Car rental Arnold](https://www.expedia.ca/Car-Rentals-In-Arnold.d74829.Car-Rental-Guide)
-   [Car rentals near Maryland](https://www.expedia.ca/Destinations-In-Maryland.d222.Car-Rental-Destinations)
-   [Enterprise Rental Cars in Maryland](https://www.expedia.ca/Enterprise-Destinations-In-Maryland.d222-c15.Car-Rental-Destination-Suppliers)

-   [Arnold Vacation Rentals](https://www.expedia.ca/Arnold-Vacation-Rentals.d74829.Travel-Guide-VacationRentals)
-   [Maryland Vacation Rentals](https://www.expedia.ca/Destinations-In-Maryland.d222.Vacation-Rental-Destinations)

-   [Things to do in Annapolis](https://www.expedia.ca/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)
-   [Things to do in Anne Arundel County](https://www.expedia.ca/Things-To-Do-In-Anne-Arundel-County.d553248635083910990.Travel-Guide-Activities)
-   [Things to do in Maryland](https://www.expedia.ca/Things-To-Do-In-Maryland.d222.Travel-Guide-Activities)

-   [Book Hotels in Winchester-on-the-Severn on Expedia.com](https://www.expedia.com/Winchester-On-The-Severn-Annapolis-Hotels.0-n553248635976475477-0.Travel-Guide-Filter-Hotels)

-   Explore a world of travel with Expedia

### Hotels in top Annapolis neighborhoods

-   [Hotels in Historic District](https://expedia.ca/Historic-District-Annapolis-Hotels.0-n553248635976472706-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Eastport](https://expedia.ca/Eastport-Annapolis-Hotels.0-n553248635976473127-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Murray Hill](https://expedia.ca/Murray-Hill-Annapolis-Hotels.0-n553248635976473392-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Hillsmere](https://expedia.ca/Hillsmere-Annapolis-Hotels.0-n553248635976473205-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Cape Saint Claire](https://expedia.ca/Cape-Saint-Claire-Annapolis-Hotels.0-n3000440447-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Admiral Heights](https://expedia.ca/Admiral-Heights-Annapolis-Hotels.0-n903582789788700672-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Homewood](https://expedia.ca/Homewood-Annapolis-Hotels.0-n553248635976468944-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Epping Forest](https://expedia.ca/Epping-Forest-Annapolis-Hotels.0-n553248635976473158-0.Travel-Guide-Filter-Hotels)
-   [Hotels in West Annapolis](https://expedia.ca/West-Annapolis-Annapolis-Hotels.0-n553248635976472135-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Arundel on the Bay](https://expedia.ca/Arundel-On-The-Bay-Annapolis-Hotels.0-n553248635976475949-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Oyster Harbor](https://expedia.ca/Oyster-Harbor-Annapolis-Hotels.0-n553248635976482330-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Annapolis Cove](https://expedia.ca/Annapolis-Cove-Annapolis-Hotels.0-n903583391744937984-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Hunt Meadows](https://expedia.ca/Hunt-Meadows-Annapolis-Hotels.0-n553248635976470840-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Anchorage](https://expedia.ca/Anchorage-Annapolis-Hotels.0-n553248635976473602-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Downs on the Severn](https://expedia.ca/Downs-On-The-Severn-Annapolis-Hotels.0-n553248635976473924-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Cape St. John](https://expedia.ca/Cape-St-John-Annapolis-Hotels.0-n553248635976473538-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Winchester-on-the-Severn](https://expedia.ca/Winchester-On-The-Severn-Annapolis-Hotels.0-n553248635976475477-0.Travel-Guide-Filter-Hotels)
-   [Hotels in Atlantis](https://expedia.ca/Atlantis-Annapolis-Hotels.0-n553248635976472610-0.Travel-Guide-Filter-Hotels)

### Hotels near popular Annapolis Attractions

-   [Hotels near Chesapeake Bay](https://expedia.ca/Chesapeake-Bay-Hotels.d6056980.Travel-Guide-Hotels)
-   [Hotels near Arundel Mills Mall](https://expedia.ca/Arundel-Mills-Mall-Hotels.0-l6125242-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Baltimore Cruise Terminal](https://expedia.ca/Baltimore-Cruise-Terminal-Hotels.0-l6306104-0.Travel-Guide-Filter-Hotels)
-   [Hotels near U.S. Naval Academy](https://expedia.ca/US-Naval-Academy-Hotels.0-l6077390-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Maryland Live Casino](https://expedia.ca/Maryland-Live-Casino-Hotels.0-l6223052-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Six Flags America](https://expedia.ca/Six-Flags-America-Hotels.0-l6091683-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Horseshoe Casino Baltimore](https://expedia.ca/Horseshoe-Casino-Baltimore-Hotels.0-l553248621558141317-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Chesapeake Bay Bridge](https://expedia.ca/Chesapeake-Bay-Bridge-Hotels.0-l6077400-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Sandy Point State Park](https://expedia.ca/Sandy-Point-State-Park-Hotels.0-l6163398-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Annapolis City Dock](https://expedia.ca/Annapolis-City-Dock-Hotels.0-l553248633992240262-0.Travel-Guide-Filter-Hotels)

### More Accommodation Types in Winchester-on-the-Severn

-   [Vacation Homes in Annapolis](https://expedia.ca/Annapolis-Private-Vacation-Homes.d6034082-aaPrivateVacationHomes.Travel-Guide-Accommodation)
-   [Apartments in Annapolis](https://expedia.ca/Annapolis-Apartments.d6034082-aaApartments.Travel-Guide-Accommodation)
-   [Cottages in Annapolis](https://expedia.ca/Annapolis-Cottages.d6034082-aaCottages.Travel-Guide-Accommodation)
-   [Condo Rentals in Annapolis](https://expedia.ca/Annapolis-Condos.d6034082-aaCondos.Travel-Guide-Accommodation)
-   [B&B in Annapolis](https://expedia.ca/Annapolis-Bed-And-Breakfast.d6034082-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Houseboats in Annapolis](https://expedia.ca/Annapolis-Houseboats.d6034082-aaHouseboats.Travel-Guide-Accommodation)
-   [Guest Houses in Annapolis](https://expedia.ca/Annapolis-Guest-Houses.d6034082-aaGuestHouses.Travel-Guide-Accommodation)
-   [Motels in Annapolis](https://expedia.ca/Annapolis-Motels.d6034082-aaMotels.Travel-Guide-Accommodation)

### Hotels Close to Nearby Airports

-   [Hotels near Baltimore Washington Intl. Thurgood Marshall Airport](https://expedia.ca/Baltimore-Washington-Intl-Thurgood-Marshall-Airport-Hotels.0-aBWI-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Ronald Reagan Washington National Airport](https://expedia.ca/Ronald-Reagan-Washington-National-Airport-Hotels.0-aDCA-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Martin State Airport](https://expedia.ca/Martin-State-Airport-Hotels.0-aMTN-0.Travel-Guide-Filter-Hotels)

### Winchester-on-the-Severn Hotels by Star Rating

-   [2 Star Hotels in Winchester-on-the-Severn](https://expedia.ca/2Star-Winchester-On-The-Severn-Annapolis-Hotels.s20-n553248635976475477-0.Travel-Guide-Filter-Hotels)
-   [3 Star Hotels in Winchester-on-the-Severn](https://expedia.ca/3Star-Winchester-On-The-Severn-Annapolis-Hotels.s30-n553248635976475477-0.Travel-Guide-Filter-Hotels)
-   [4 Star Hotels in Winchester-on-the-Severn](https://expedia.ca/4Star-Winchester-On-The-Severn-Annapolis-Hotels.s40-n553248635976475477-0.Travel-Guide-Filter-Hotels)
-   [5 Star Hotels in Winchester-on-the-Severn](https://expedia.ca/5Star-Winchester-On-The-Severn-Annapolis-Hotels.s50-n553248635976475477-0.Travel-Guide-Filter-Hotels)

### Winchester-on-the-Severn Hotels by Brand

-   [Best Western Hotels](https://expedia.ca/Winchester-On-The-Severn-Annapolis-Hotels-Best-Western.0-n553248635976475477-0--bBestWestern.Travel-Guide-Filter-Hotels)
-   [Independent Hotels](https://expedia.ca/Winchester-On-The-Severn-Annapolis-Hotels-Independent.0-n553248635976475477-0--bIndependent.Travel-Guide-Filter-Hotels)
-   [La Quinta Inn & Suites Hotels](https://expedia.ca/Winchester-On-The-Severn-Annapolis-Hotels-La-Quinta-Inn-Suites.0-n553248635976475477-0--bLaQuintaInnSuites.Travel-Guide-Filter-Hotels)
-   [Motel 6 Hotels](https://expedia.ca/Winchester-On-The-Severn-Annapolis-Hotels-Motel-6.0-n553248635976475477-0--bMotel6.Travel-Guide-Filter-Hotels)
-   [Red Roof Inn Hotels](https://expedia.ca/Winchester-On-The-Severn-Annapolis-Hotels-Red-Roof-Inn.0-n553248635976475477-0--bRedRoofInn.Travel-Guide-Filter-Hotels)

### Explore more hotels

-   [The Hotel at Arundel Preserve](https://expedia.ca/Baltimore-Hotels-The-Hotel-At-Arundel-Preserve.h4542302.Hotel-Information)
-   [DoubleTree Hotel Baltimore - BWI Airport](https://expedia.ca/Baltimore-Hotels-DoubleTree-Hotel-Baltimore-BWI-Airport.h26137.Hotel-Information)
-   [Comfort Suites Columbia Gateway](https://expedia.ca/Baltimore-Hotels-Comfort-Suites-Columbia-Gateway.h1155026.Hotel-Information)
-   [Courtyard by Marriott Baltimore BWI Airport](https://expedia.ca/Baltimore-Hotels-Courtyard-By-Marriott-Baltimore-BWI-Airport.h22275.Hotel-Information)
-   [Best Western Plus Hotel & Conference Center](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information)
-   [Wingate by Wyndham Baltimore BWI Airport](https://expedia.ca/Baltimore-Hotels-Wingate-By-Wyndham-Baltimore-BWI-Airport.h12658.Hotel-Information)
-   [Embassy Suites by Hilton Baltimore at BWI Airport](https://expedia.ca/Baltimore-Hotels-Embassy-Suites-By-Hilton-Baltimore-At-BWI-Airport.h16467.Hotel-Information)
-   [Hyatt Place Baltimore/BWI Airport](https://expedia.ca/Baltimore-Hotels-Hyatt-Place-BaltimoreBWI-Airport.h42070.Hotel-Information)
-   [Hyatt House BWI Airport Baltimore](https://expedia.ca/Baltimore-Hotels-Hyatt-House-BWI-Airport-Baltimore.h103174233.Hotel-Information)
-   [Holiday Inn Columbia East-Jessup by IHG](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Columbia-East-Jessup.h15724.Hotel-Information)
-   [Graduate by Hilton Annapolis](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)
-   [Holiday Inn Express Baltimore At The Stadiums by IHG](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-Baltimore-At-The-Stadiums.h23043.Hotel-Information)

[See a list of all hotels in Annapolis](https://expedia.ca/All-Annapolis-Hotels.d6034082.Travel-Guide-City-All-Hotels)

### More ways to book

-   [Book Hotels in Winchester-on-the-Severn on Expedia.com](https://www.expedia.com/Winchester-On-The-Severn-Annapolis-Hotels.0-n553248635976475477-0.Travel-Guide-Filter-Hotels)

### Expedia's Latest Trends

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-   [Visit Downtown Washington D.C.](https://expedia.ca/Washington-Downtown-Washington-DC.dx800144)
-   [Visit Old Town Alexandria](https://expedia.ca/Washington-Old-Town-Alexandria.dx6163859)
-   [Visit Downtown Baltimore](https://expedia.ca/Baltimore-Downtown-Baltimore.dx6057529)
-   [Visit Fells Point](https://expedia.ca/Baltimore-Fells-Point.dx6197112)
-   [Visit Foggy Bottom](https://expedia.ca/Washington-Foggy-Bottom.dx6284985)
-   [Visit Capitol Hill](https://expedia.ca/Washington-Capitol-Hill.dx800142)
-   [Visit Georgetown](https://expedia.ca/Washington-Georgetown.dx107820)