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Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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Our top choices for Winchester-on-the-Severn hotels

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

1. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
4.5 km from Winchester-on-the-Severn
8.8 out of 10, Excellent, (1,005 reviews)
"Great location"
United States
Jose
The price is ฿3,521
฿4,014 total
includes taxes & fees
25 Oct - 26 Oct
Crowne Plaza Annapolis by IHG
A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

2. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
4.7 km from Winchester-on-the-Severn
8.4 out of 10, Very good, (1,001 reviews)
"We stayed for 3 nights and we had a good experience."
Canada
Omer
The price is ฿3,185
฿3,631 total
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn Express & Suites Annapolis by IHG
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

3. The Westin Annapolis

The Westin Annapolis
4.0 star property
4.3 km from Winchester-on-the-Severn
8.8 out of 10, Excellent, (1,002 reviews)
"This is a fabulous resort! Very clean, great location and the staff is great!"
United States
Bobbi
The price is ฿6,672
฿7,607 total
includes taxes & fees
11 Oct - 12 Oct
The Westin Annapolis
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

4. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
5 km from Winchester-on-the-Severn
8.8 out of 10, Excellent, (1,243 reviews)
"My favorite place to stay in Annapolis"
United States
Michele
The price is ฿3,712
฿4,231 total
includes taxes & fees
19 Oct - 20 Oct
DoubleTree by Hilton Hotel Annapolis
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

5. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
6 km from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (1,000 reviews)
"The breakfast had a nice variety of food"
United States
Lisa
The price is ฿3,990
฿4,549 total
includes taxes & fees
1 Nov - 2 Nov
SpringHill Suites by Marriott Annapolis
An outdoor patio with tables, chairs, and a fire feature.

6. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
4 km from Winchester-on-the-Severn
8.8 out of 10, Excellent, (244 reviews)
"Nice hotel"
United States
Imola
The price is ฿3,319
฿3,784 total
includes taxes & fees
13 Oct - 14 Oct
Fairfield Inn & Suites By Marriott Annapolis
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

7. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District, 4.3 km from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (2,039 reviews)
"Would stay again"
United States
Ashley
The price is ฿3,114
฿4,697 total
includes taxes & fees
1 Nov - 2 Nov
Historic Inns of Annapolis
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

8. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
5.4 km from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (1,043 reviews)
"Clean room, friendly staff, convenient location for our road trip!"
United States
Catherine
The price is ฿3,058
฿3,486 total
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Annapolis, MD
A modern lobby with a seating area, a fireplace, and a bookshelf.

9. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
4.3 km from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1,000 reviews)
"Loved everything about it but especially the staff was so friendly and accommodating!"
United Kingdom
petra
The price is ฿3,547
฿4,043 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Annapolis Downtown
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

10. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
4.3 km from Winchester-on-the-Severn
9.4 out of 10, Exceptional, (1,000 reviews)
"Great Hotel in a very central location"
United States
Mark
The price is ฿4,922
฿5,611 total
includes taxes & fees
26 Oct - 27 Oct
Graduate by Hilton Annapolis
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

11. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
5.7 km from Winchester-on-the-Severn
8.2 out of 10, Very good, (1,000 reviews)
"Friendly staff, clean room, great breakfast"
United States
Courtney
The price is ฿3,272
฿3,730 total
includes taxes & fees
18 Oct - 19 Oct
Hampton Inn & Suites Annapolis
A modern hotel kitchen with a central island, seating area, and various kitchen appliances.

12. Best Western Annapolis

Best Western Annapolis
2.5 star property
5.3 km from Winchester-on-the-Severn
7.8 out of 10, Good, (1,005 reviews)
"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."
United States
Silvia
The price is ฿2,656
฿3,027 total
includes taxes & fees
13 Oct - 14 Oct
Best Western Annapolis
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

13. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
6 km from Winchester-on-the-Severn
8.6 out of 10, Excellent, (1,000 reviews)
"The staff were super friendly."
United States
Jim
The price is ฿3,364
฿3,835 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Annapolis
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

14. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
6 km from Winchester-on-the-Severn
8.8 out of 10, Excellent, (1,003 reviews)
"Room was big, staff was very nice, breakfast was good, would stay again."
United States
Philip
The price is ฿3,051
฿3,478 total
includes taxes & fees
1 Nov - 2 Nov
Sonesta ES Suites Annapolis
A hotel room with a flat-screen TV, a desk with a chair, a framed picture on the wall, a lamp, and an air conditioning unit.

15. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
6.1 km from Winchester-on-the-Severn
8.2 out of 10, Very good, (1,000 reviews)
"Nice place to stay friendly service"
United States
Glenn
The price is ฿3,107
฿3,541 total
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Annapolis
A circular fire pit surrounded by outdoor seating with a brick wall and a multi-story building in the background.

16. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
3.0 star property
5.9 km from Winchester-on-the-Severn
9.0 out of 10, Wonderful, (137 reviews)
"It was AMAZING to stay there !!!"
United States
Nkusu Lauren
The price is ฿3,822
฿4,358 total
includes taxes & fees
19 Oct - 20 Oct
TownePlace Suites by Marriott Annapolis
A modern living room with a large window, a dining area, and a kitchen in the background.

17. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
5.8 km from Winchester-on-the-Severn
8.8 out of 10, Excellent, (320 reviews)
"The property was very clean and staff was friendly."
United States
Darren
The price is ฿3,118
฿3,720 total
includes taxes & fees
25 Oct - 26 Oct
Candlewood Suites Annapolis by IHG
A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.

18. Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton
2.0 star property
15.7 km from Winchester-on-the-Severn
9.2 out of 10, Wonderful, (1,156 reviews)
"A great hotel with a great staff!"
United States
paul
The price is ฿3,078
฿3,509 total
includes taxes & fees
25 Oct - 26 Oct
Microtel Inn & Suites by Wyndham Gambrills/Odenton
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

19. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
16.2 km from Winchester-on-the-Severn
9.4 out of 10, Exceptional, (500 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is ฿6,863
฿8,473 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Chesapeake Bay Beach Club
An outdoor patio area with seating arrangements and a fire feature.

20. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
3.0 star property
18.6 km from Winchester-on-the-Severn
9.4 out of 10, Exceptional, (945 reviews)
"Great staff and hospitality, we will definitely be back again! Best experience we’ve had!"
United States
Halima
The price is ฿4,496
฿5,081 total
includes taxes & fees
26 Oct - 27 Oct
Courtyard by Marriott Bowie
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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Where to stay in Winchester-on-the-Severn

Find the best Winchester-on-the-Severn areas for the activities you enjoy most.
An aerial view of a coastal town with a prominent church, dense residential area, and a marina with boats.

Historic District

While visiting Historic District, you might make a stop by sights like Maryland State House and William Paca House.

A marina with numerous sailboats docked, surrounded by residential houses and a backdrop of trees and a distant shoreline.

Eastport

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

A cityscape with historic buildings, a river, and a bridge in the background.

Murray Hill

If you're spending some time in Murray Hill, Spa Creek and Ballet Theater of Maryland are top sights worth seeing.

A large suspension bridge spanning a wide river at sunset.

Hillsmere

While visiting Hillsmere, you might make a stop by sights like Maryland Quiet Waters Park and Great Frogs Winery.

A suspension bridge over a body of water with a sunset in the background.

Cape Saint Claire

While visiting Cape Saint Claire, you might make a stop by sights like Northern Chesapeake Bay and Chesapeake Bay.

Top Winchester-on-the-Severn Hotel Reviews

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

10/10 Excellent
"C"
Luis 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

Frequently asked questions

What's it like in Winchester-on-the-Severn?
Travellers will be sure to enjoy their time in Annapolis's Winchester-on-the-Severn neighbourhood.
If I need to cancel my hotel reservation in Winchester-on-the-Severn, will I receive a refund?
Yes! The majority of hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and get a refund within a 24-hour period of booking. Put your dates in and click on "Search", then filter by "fully refundable" to get the best deals in Winchester-on-the-Severn.
What is there to do in this Annapolis neighbourhood?
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.