The Best Hotels in Winchester-on-the-Severn, Annapolis - 2026 Updated Prices

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

Holiday Inn Express Baltimore at the Stadiums by IHG

30.5 km from Winchester-on-the-Severn

GEORGI

Rp2.047.423 total

includes taxes & fees

12 Jul - 13 Jul

Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

26.7 km from Winchester-on-the-Severn

Carol

Rp1.993.893 total

includes taxes & fees

12 Jul - 13 Jul

Best Western Kent Narrows Inn

23.5 km from Winchester-on-the-Severn

Brenda

Rp2.496.138 total

includes taxes & fees

8 Jul - 9 Jul

Kent Island Resort

16.5 km from Winchester-on-the-Severn

Sue

Rp3.866.973 total

includes taxes & fees

9 Jul - 10 Jul

Anchored Inn at Hidden Harbour Marina

26.1 km from Winchester-on-the-Severn

BENNY

Rp4.957.679 total

includes taxes & fees

6 Jul - 7 Jul

Microtel Inn & Suites by Wyndham Gambrills

15.7 km from Winchester-on-the-Severn

Erin

Rp2.001.707 total

includes taxes & fees

3 Aug - 4 Aug

Hyatt Place Kent Narrows & Marina

23.3 km from Winchester-on-the-Severn

Richard

Rp3.549.130 total

includes taxes & fees

19 Jul - 20 Jul

Hilton Garden Inn Kent Island Marina

23.6 km from Winchester-on-the-Severn

Sandy

Rp2.926.635 total

includes taxes & fees

2 Aug - 3 Aug

Historic Inns of Annapolis

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

Randy

Rp2.460.686 total

includes taxes & fees

12 Jul - 13 Jul

DoubleTree by Hilton Hotel Annapolis

5 km from Winchester-on-the-Severn

Diane

Rp2.277.170 total

includes taxes & fees

6 Jul - 7 Jul

Holiday Inn Express Annapolis East-Kent Island by IHG

23.6 km from Winchester-on-the-Severn

Michele

Rp2.771.512 total

includes taxes & fees

23 Jul - 24 Jul

The Inn at Chesapeake Bay Beach Club

16.2 km from Winchester-on-the-Severn

Damika

Rp4.955.389 total

includes taxes & fees

4 Aug - 5 Aug

Hilton Garden Inn Annapolis Downtown

4.3 km from Winchester-on-the-Severn

Victoria

Rp2.166.144 total

includes taxes & fees

19 Jul - 20 Jul

Holiday Inn Baltimore BWI Airport by IHG

25.2 km from Winchester-on-the-Severn

Shaqauelia

Rp2.600.683 total

includes taxes & fees

12 Jul - 13 Jul

Live! Casino & Hotel Maryland

24.7 km from Winchester-on-the-Severn

Gregory

Rp3.574.174 total

includes taxes & fees

12 Jul - 13 Jul

Hilton Baltimore BWI Airport

25 km from Winchester-on-the-Severn

Anthony

Rp2.166.143 total

includes taxes & fees

12 Jul - 13 Jul

Wingate by Wyndham Baltimore BWI Airport

25.5 km from Winchester-on-the-Severn

Rp1.824.574 total

includes taxes & fees

6 Jul - 7 Jul

Hilton Garden Inn Annapolis

6.1 km from Winchester-on-the-Severn

Paul

Rp2.042.662 total

includes taxes & fees

12 Jul - 13 Jul

The Hotel at Arundel Preserve

25.4 km from Winchester-on-the-Severn

Carl

Rp2.604.815 total

includes taxes & fees

12 Jul - 13 Jul

Comfort Inn Conference Center

19.6 km from Winchester-on-the-Severn

Francis

Rp2.225.696 total

includes taxes & fees

26 Jul - 27 Jul

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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.

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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.

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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.

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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.

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Cape Saint Claire

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

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Top Winchester-on-the-Severn Hotel Reviews

Live! Casino & Hotel Maryland

10/10 Excellent

"I loved everything about my stay. 10/10"

The Hotel at Arundel Preserve

8/10 Good

"We were only here for one night. Had a handicap accessible room. This was by far the best accessible room we have ever stayed in. There was no carpeting (which make getting around in a wheelchair much easier), the bathroom was incredibly well appointed for handicap use. The shower was perfect with grab bars and both handheld wand or regular shower head and large! The transition from bathroom floor to shower was perfect! Grab bars around toilet spot on! Only issue was the sink faucet handle. Very sharp. The bed was a bit old? and worn at the edges. Meaning, when you sat on the edge of the bed, there was no support (it gave way to the bottom of the mattress). Lighting was good (a lot of switches to figure out). The window covering did not fit the window well at the edges, light streamed in in the morning. The extra towels and blanket in the closet were appreciated. The restaurant in the lobby was very nice. Good food and staff was great. Parking was expensive but convenient. All in all, we would stay here again."

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.

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

Holiday Inn Express Baltimore at the Stadiums by IHG

Quality Inn Grasonville near Kent Island

Best Western Kent Narrows Inn

Kent Island Resort

Anchored Inn at Hidden Harbour Marina

Microtel Inn & Suites by Wyndham Gambrills

Hyatt Place Kent Narrows & Marina

Hilton Garden Inn Kent Island Marina

Historic Inns of Annapolis

DoubleTree by Hilton Hotel Annapolis

Holiday Inn Express Annapolis East-Kent Island by IHG

The Inn at Chesapeake Bay Beach Club

Hilton Garden Inn Annapolis Downtown

Holiday Inn Baltimore BWI Airport by IHG

Live! Casino & Hotel Maryland

Hilton Baltimore BWI Airport

Wingate by Wyndham Baltimore BWI Airport

Hilton Garden Inn Annapolis

The Hotel at Arundel Preserve

Comfort Inn Conference Center

Where to stay in Winchester-on-the-Severn

Historic District

Eastport

Murray Hill

Hillsmere

Cape Saint Claire

Top Winchester-on-the-Severn Hotel Reviews

Live! Casino & Hotel Maryland

Frequently asked questions

Explore a world of travel with Expedia