Winchester-on-the-Severn Hotels, Annapolis

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18 July - 19 July
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19 July - 20 July
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18 July - 20 July
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25 July - 27 July

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1270 Cheap Hotels in Winchester-on-the-Severn - Specials, Reviews, & Last Minute Deals

Hilton Garden Inn Kent Island Marina
Relax on the outdoor terrace with a view of the marina, surrounded by wicker furniture and beautiful flowers.

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (960)
"Great spot with beautiful views. "
The price is AU$260
includes taxes & fees
28 July - 29 July
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Welcome to the Holiday Inn Express, where guests can check in and enjoy a convenient stay.

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (873)
"Great place"
The price is AU$217
includes taxes & fees
24 July - 25 July
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
Two single beds with white linens and dark wood headboard, flat-screen TV, and a dresser with drawers.

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1004)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is AU$215
includes taxes & fees
10 Aug - 11 Aug
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Relax by the fire pit in this scenic waterfront seating area, overlooking the marina with boats docked.

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (587)
"Great place to stay. "
The price is AU$260
includes taxes & fees
4 Aug - 5 Aug
Hyatt Place Kent Narrows & Marina
Mariners Motel
Docked in the marina, a sleek yacht awaits your arrival.

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is AU$265
includes taxes & fees
20 July - 21 July
Mariners Motel
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
The price is AU$451
includes taxes & fees
20 July - 21 July
Inn at Haven Harbour
Kent Island Resort
Surrounded by lush greenery and a serene lake, this historic property offers a picturesque setting with a spacious parking area and a circular driveway.

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (105)
"Welcoming and well-staffed property, in a lovely and tranquil setting. Staff was friendly and helpful. Restaurant/bar service and food were outstanding. Great quiet getaway weekend spot. "
The price is AU$452
includes taxes & fees
4 Aug - 5 Aug
Kent Island Resort
The Inn at Chesapeake Bay Beach Club
Welcome to our hotel, featuring a modern entrance with a covered area and lush greenery.

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (401)
"Staff was very polite and friendly. "
The price is AU$407
includes taxes & fees
22 July - 23 July
The Inn at Chesapeake Bay Beach Club
Village Inn
Relax in a spacious room with a large bed, nightstand, and comfortable armchair.

Village Inn

2.0 star property
6.2 out of 10, (488)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is AU$147
includes taxes & fees
24 July - 25 July
Village Inn
Historic Inns of Annapolis
Relax in the serene outdoor patio, surrounded by trees and equipped with comfortable seating and tables.

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1790)
"Great location close to bars, restaurants a s shops."
Historic Inns of Annapolis
Graduate by Hilton Annapolis
Enjoy serene sailing and stunning views of the marina, surrounded by historic landmarks.

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1000)
"Great stay! Would come here again."
The price is AU$272
includes taxes & fees
3 Aug - 4 Aug
Graduate by Hilton Annapolis
Hilton Garden Inn Annapolis Downtown
Relax in a serene space with a comfortable seating area, flat-screen TV, and sliding glass door to a patio.

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1000)
"Really nice place to stay and enjoy Annapolis "
The price is AU$177
includes taxes & fees
17 Aug - 18 Aug
Hilton Garden Inn Annapolis Downtown
The Westin Annapolis
Experience the grandeur of this classic hotel, featuring a symmetrical facade with a central entrance and evenly spaced windows.

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1002)
"Easy downtown location, walkable to waterfront and great restaurants "
The price is AU$279
includes taxes & fees
10 Aug - 11 Aug
The Westin Annapolis
Fairfield Inn & Suites By Marriott Annapolis
Hotel exterior with outdoor seating areas and decorative lighting.

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (108)
"Wonderful stay. "
The price is AU$222
includes taxes & fees
3 Aug - 4 Aug
Fairfield Inn & Suites By Marriott Annapolis
Residence Inn By Marriott Annapolis
Hotel exterior with outdoor seating areas and large windows.

Residence Inn By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (39)
"The hotel staff and accommodations were exceptional."
The price is AU$237
includes taxes & fees
3 Aug - 4 Aug
Residence Inn By Marriott Annapolis
Anchored Inn at Hidden Harbour Marina
Stunning hotel with a symmetrical facade and landscaped gardens.

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (440)
"The staff specifically Victoria was impeccable! "
The price is AU$423
includes taxes & fees
28 July - 29 July
Anchored Inn at Hidden Harbour Marina
Holiday Inn Express & Suites Annapolis by IHG
Indulge in a diverse selection of international cuisine at our buffet, featuring omelets, cheese, and more.

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1004)
"Great hotel. No bar or restaurant onsite. If you stay there go to west end sports bar. Fantastic food and bartenders!!"
The price is AU$162
includes taxes & fees
24 July - 25 July
Holiday Inn Express & Suites Annapolis by IHG
Crowne Plaza Annapolis by IHG
Relax by the pool surrounded by lounge chairs and a skylight.

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1000)
"Very clean and friendly staff. Best mattress and pillows have had in hotel."
The price is AU$190
includes taxes & fees
22 July - 23 July
Crowne Plaza Annapolis by IHG
Candlewood Suites Annapolis by IHG
Relax in a spacious room with a dining area, seating area, and desk, perfect for work and relaxation.

Candlewood Suites Annapolis by IHG

2.5 star property
8.8 out of 10, Excellent, (81)
"Great stay"
The price is AU$171
includes taxes & fees
24 July - 25 July
Candlewood Suites Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis
Welcome to DoubleTree by Hilton, featuring a traditional brick facade and a distinctive peaked roof.

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1007)
"Excellent hospitable staff made the stay even better!"
The price is AU$179
includes taxes & fees
17 Aug - 18 Aug
DoubleTree by Hilton Hotel Annapolis
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.

Our guide on where to stay in Winchester-on-the-Severn

Find the best Winchester-on-the-Severn areas for the activities you enjoy most.
Annapolis featuring street scenes and a city as well as a small group of people
Historic District map

Historic District

1 out of top 10 points of interest in this area

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

Eastport map

Eastport

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

Murray Hill map

Murray Hill

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

Cape Saint Claire map

Cape Saint Claire

Though Cape Saint Claire may not have many top sights, you can venture to the surrounding area to see attractions like Sandy Point State Park and Chesapeake Bay Bridge.

Maryland Quiet Waters Park featuring a house and a park
Hillsmere map

Hillsmere

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

Top Winchester-on-the-Severn Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Stayed at the Historic Inns of Annapolis - Governor Calvert House. The front desk receptionist was friendly and helpful. Check in was easy and efficient. Valet parked the car and due to being centrally located, we didn't use the car for the two days we were in Annapolis. The room was clean and the bed was comfortable. Very quiet. We would definitely stay here again! "
Mary 2-night trip
Posted 19 hours ago
Historic Inns of 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.

What's the best hotel for a stay in Winchester-on-the-Severn?

For your stay in Winchester-on-the-Severn, PRIVATE BEACH & magnificent views of the Severn River. Lovely & Spacious Severn River Waterfront - Beautifully furnished and fully equipped 4BR/4FB home with private beach is one of the top choices based on our traveller data.

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.