Annapolis Hotel Guide. Hotels in Winchester-on-the-Severn, Annapolis, United States of America

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Jul - 23 Jul
Tomorrow
23 Jul - 24 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Filter by

Guest rating
Guest rating
Property class

Top Trending Hotels Near Winchester-on-the-Severn, Annapolis

Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (963)
"Great spot with beautiful views. "
The price is €145
includes taxes & fees
28 Jul - 29 Jul
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (874)
"Great place"
The price is €132
includes taxes & fees
20 Aug - 21 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1006)
"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 €120
includes taxes & fees
18 Aug - 19 Aug
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (593)
"Great place to stay. "
The price is €145
includes taxes & fees
4 Aug - 5 Aug
Hyatt Place Kent Narrows & Marina
Mariners Motel
Marina

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 €147
includes taxes & fees
11 Aug - 12 Aug
Mariners Motel
Kent Island Resort
Aerial view

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 €228
includes taxes & fees
5 Aug - 6 Aug
Kent Island Resort
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (402)
"Staff was very polite and friendly. "
The price is €226
includes taxes & fees
20 Aug - 21 Aug
The Inn at Chesapeake Bay Beach Club
Village Inn
TV

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 €87
includes taxes & fees
31 Jul - 1 Aug
Village Inn
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1805)
"Loved the hotel-great location "
Historic Inns of Annapolis
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1003)
"Loved the location and the nautical decor "
The price is €151
includes taxes & fees
17 Aug - 18 Aug
Graduate by Hilton Annapolis
Hilton Garden Inn Annapolis Downtown
Suite, 1 Bedroom, Terrace | Living area

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1003)
"Really nice place to stay and enjoy Annapolis "
The price is €99
includes taxes & fees
17 Aug - 18 Aug
Hilton Garden Inn Annapolis Downtown
The Westin Annapolis
View from property

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 €155
includes taxes & fees
12 Aug - 13 Aug
The Westin Annapolis
Fairfield Inn & Suites By Marriott Annapolis
Property amenity

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (112)
"Wonderful stay. "
The price is €124
includes taxes & fees
3 Aug - 4 Aug
Fairfield Inn & Suites By Marriott Annapolis
Residence Inn By Marriott Annapolis
Property amenity

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 €132
includes taxes & fees
3 Aug - 4 Aug
Residence Inn By Marriott Annapolis
Anchored Inn at Hidden Harbour Marina
Front of property

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 €236
includes taxes & fees
27 Jul - 28 Jul
Anchored Inn at Hidden Harbour Marina
Holiday Inn Express & Suites Annapolis by IHG
Free daily buffet breakfast

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1006)
"Great hotel. No bar or restaurant onsite. If you stay there go to west end sports bar. Fantastic food and bartenders!!"
The price is €87
includes taxes & fees
30 Jul - 31 Jul
Holiday Inn Express & Suites Annapolis by IHG
Crowne Plaza Annapolis by IHG
Pool

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1002)
"Very clean and friendly staff. Best mattress and pillows have had in hotel."
The price is €87
includes taxes & fees
27 Jul - 28 Jul
Crowne Plaza Annapolis by IHG
Candlewood Suites Annapolis by IHG
Exterior

Candlewood Suites Annapolis by IHG

2.5 star property
8.8 out of 10, Excellent, (82)
"Great stay"
The price is €96
includes taxes & fees
29 Jul - 30 Jul
Candlewood Suites Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis
Garden

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1009)
"Excellent hospitable staff made the stay even better!"
The price is €99
includes taxes & fees
17 Aug - 18 Aug
DoubleTree by Hilton Hotel Annapolis
Best Western Annapolis
Exterior

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1011)
"Great hotel"
The price is €80
includes taxes & fees
29 Jul - 30 Jul
Best Western 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.

Where to stay in Winchester-on-the-Severn

Find the best Winchester-on-the-Severn areas for the activities you enjoy most.
Annapolis showing 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 garden and a house
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
"Loved the hotel-great location "
Lynn 1-night trip
Posted 1 day 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.