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Check prices for these dates

This weekend
11 Sep - 13 Sep
Next weekend
18 Sep - 20 Sep

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

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

1. 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)
"Loved my stay!"
United States
Joshua
The price is ฿4,144
฿4,725 total
includes taxes & fees
10 Sept - 11 Sept
SpringHill Suites by Marriott Annapolis
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

2. 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, (1,025 reviews)
"Clean room Helpful staff Great breakfast"
United States
Cynthia
The price is ฿3,618
฿4,125 total
includes taxes & fees
13 Sept - 14 Sept
Crowne Plaza Annapolis by IHG
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

3. 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, (1,159 reviews)
"Nice hotel for decent price!"
United States
Chereis
The price is ฿2,729
฿3,111 total
includes taxes & fees
27 Sept - 28 Sept
DoubleTree by Hilton Hotel Annapolis
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

4. 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, (1,061 reviews)
"Great stay"
United States
Leslie
The price is ฿3,327
฿3,793 total
includes taxes & fees
27 Sept - 28 Sept
Country Inn & Suites by Radisson, Annapolis, MD
A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

5. 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, (1,004 reviews)
"Clean and comfortable. Close to where we needed to go. Good breakfast. Good value"
United States
Harold
The price is ฿3,454
฿3,937 total
includes taxes & fees
16 Sept - 17 Sept
Holiday Inn Express & Suites Annapolis by IHG
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

6. 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, (2,005 reviews)
"Great location and close to shops and restaurants. Very quiet/comfortable room with all the amenities and coffee available in the morning. Would definitely stay here again!"
United States
Amy
The price is ฿3,484
฿5,097 total
includes taxes & fees
27 Sept - 28 Sept
Historic Inns of Annapolis
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

7. 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, (1,001 reviews)
"Perfectly decent hotel for overnight stay during roadtrip."
United States
Phyllis
The price is ฿3,289
฿3,750 total
includes taxes & fees
27 Sept - 28 Sept
Courtyard by Marriott Annapolis
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

8. The Westin Annapolis

The Westin Annapolis
4.0 star property
4.3 km from Winchester-on-the-Severn
8.8 out of 10, Excellent, (1,000 reviews)
"Everything you want in a hotel.. kind service great restaurant and bar and featured amenities."
United States
susan greco
The price is ฿5,888
฿6,712 total
includes taxes & fees
13 Sept - 14 Sept
The Westin Annapolis
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, (1,013 reviews)
"Clean room, great location."
United States
Jeffrey
The price is ฿4,020
฿4,583 total
includes taxes & fees
27 Sept - 28 Sept
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, (1,011 reviews)
"Location, staff and cleanliness were above and beyond!"
United States
Patricia
The price is ฿5,099
฿5,813 total
includes taxes & fees
1 Oct - 2 Oct
Graduate by Hilton Annapolis
A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.

11. Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
15.7 km from Winchester-on-the-Severn
9.2 out of 10, Wonderful, (1,149 reviews)
"From check I. To check out it was a great stay. Staff is genuinely courteous and nice!"
United States
Mark
The price is ฿3,434
฿3,914 total
includes taxes & fees
13 Sept - 14 Sept
Microtel Inn & Suites by Wyndham Gambrills
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, (1,004 reviews)
"It had a wonderful breakfast and friendly staff"
United States
George
The price is ฿2,487
฿2,835 total
includes taxes & fees
27 Sept - 28 Sept
Best Western Annapolis
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

13. 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, (1,013 reviews)
"Room was big, staff was very nice, breakfast was good, would stay again."
United States
Philip
The price is ฿3,159
฿3,601 total
includes taxes & fees
28 Sept - 29 Sept
Sonesta ES Suites Annapolis
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

14. 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, (1,011 reviews)
"Great location, breakfast, room."
United States
Meghalee
The price is ฿3,237
฿3,690 total
includes taxes & fees
16 Sept - 17 Sept
Hampton Inn & Suites Annapolis
A modern lobby with a reception desk, seating area, and potted plants.

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 ฿2,972
฿3,388 total
includes taxes & fees
16 Sept - 17 Sept
Hilton Garden Inn Annapolis
A bar area with multiple seating options, including bar stools and tables, and a variety of bottles and glasses on shelves.

16. Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
19.6 km from Winchester-on-the-Severn
9.2 out of 10, Wonderful, (1,000 reviews)
"Good location, nice room, yummy breakfast. "
United States
Rachel
The price is ฿3,914
฿4,423 total
includes taxes & fees
13 Sept - 14 Sept
Comfort Inn Conference Center
A hotel room with a bed, a desk with a television, a chair, and a window with curtains.

17. Red Roof Inn Annapolis

Red Roof Inn Annapolis
2.0 star property
5.2 km from Winchester-on-the-Severn
7.2 out of 10, Good, (459 reviews)
"Air freshners in the room would possibly help. The room smelled musty. Staff was great and easy check in and out though."
United States
Melissa
The price is ฿2,434
฿2,775 total
includes taxes & fees
13 Sept - 14 Sept
Red Roof Inn Annapolis
A circular fire pit surrounded by outdoor seating with a brick wall and a multi-story building in the background.

18. 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, (128 reviews)
"It was AMAZING to stay there !!!"
United States
Nkusu Lauren
The price is ฿3,618
฿4,125 total
includes taxes & fees
16 Sept - 17 Sept
TownePlace Suites by Marriott Annapolis
A modern living room with a large window, a dining area, and a kitchen in the background.

19. 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, (309 reviews)
"Very nice stay"
United States
Javier
The price is ฿2,895
฿3,462 total
includes taxes & fees
27 Sept - 28 Sept
Candlewood Suites Annapolis by IHG
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, (932 reviews)
"It was a busy long line for check in, due to 2 conferences happening the same weekend, but the 2 front desk ladies handled it with grae and efficiency , the rooms were clean and the bathrooms too, it was a good stay with awesome customer service"
United States
Yolanda
The price is ฿4,559
฿5,151 total
includes taxes & fees
5 Oct - 6 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.

Admiral Heights

If you're looking for some top things to see and do in Admiral Heights and surrounding area, you can visit Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts.

Top Winchester-on-the-Severn Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great location with 20 min walk to stadium or USNA with friendly staff and clean rooms."
Daniel 1-night trip
Posted less than an hour ago
Graduate by Hilton Annapolis

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.