Search Hotels in Winchester-on-the-Severn, Annapolis

Start date: Check-in selected.
To Date
End date: Check-out
    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
30 Sep - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Filter by

Guest rating
Guest rating
Star rating

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

Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (633)
"Great location and rooms. Great place!"
The price is 3.936.431 ₫
4.369.438 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Hotel was great, beautiful location near the water"
The price is 4.159.001 ₫
4.616.491 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Baltimore At The Stadiums by IHG
Free daily buffet breakfast

Holiday Inn Express Baltimore At The Stadiums by IHG

2.5 star property
8.4 out of 10, Very good, (332)
"Great Place Places to Stay "
The price is 2.613.897 ₫
3.071.461 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Baltimore At The Stadiums by IHG
Comfort Suites Columbia Gateway
Front of property

Comfort Suites Columbia Gateway

2.5 star property
8.2 out of 10, Very good, (1004)
"Staff at this place were very nice "
The price is 2.352.507 ₫
2.658.334 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Comfort Suites Columbia Gateway
The Westin Annapolis
View from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1009)
"Would stay there again very soon "
The price is 5.653.666 ₫
6.445.179 ₫ total
includes taxes & fees
26 Oct - 27 Oct
The Westin Annapolis
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is 4.993.191 ₫
6.534.740 ₫ total
includes taxes & fees
21 Oct - 22 Oct
Kent Island Resort
Best Western Plus Hotel & Conference Center
Lobby

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1001)
"Nice hotel "
The price is 3.289.430 ₫
3.865.079 ₫ total
includes taxes & fees
23 Oct - 24 Oct
Best Western Plus Hotel & Conference Center
Courtyard by Marriott Annapolis
Exterior

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1000)
"The room was great, and the staff was great. "
The price is 3.009.942 ₫
3.431.334 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Courtyard by Marriott Annapolis
Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (832)
"Great place and great staff"
The price is 2.718.981 ₫
3.018.069 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Quality Inn
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very good, (1004)
"Excellent location"
The price is 3.337.867 ₫
3.705.032 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Best Western Kent Narrows Inn
Courtyard by Marriott Baltimore Downtown/McHenry Row
Property amenity

Courtyard by Marriott Baltimore Downtown/McHenry Row

3.0 star property
9.0 out of 10, Wonderful, (667)
"I liked that it was conveniently next to a grocery store. I also liked that the rooms were spacious and appeared to be soundproof. "
The price is 3.540.642 ₫
4.160.253 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Courtyard by Marriott Baltimore Downtown/McHenry Row
Sonesta ES Suites Annapolis
Egyptian cotton sheets, premium bedding, pillow-top beds, desk

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (901)
"Had a great stay."
The price is 2.735.687 ₫
3.118.498 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Sonesta ES Suites Annapolis
Hampton Inn & Suites Annapolis
Premium bedding, pillow-top beds, in-room safe, individually furnished

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very good, (1016)
"Nice location and staff was friendly and helpful."
The price is 2.976.365 ₫
3.393.056 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Hampton Inn & Suites 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, (455)
"The view from the balcony is the best, whether at night or the day time. The outside bar everyone is so friendly. I have stayed here a few times and every time I come to the area, I will only stay here. I highly recommend it !"
The price is 4.731.643 ₫
5.394.232 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Anchored Inn at Hidden Harbour Marina
Country Inn & Suites by Radisson, Annapolis, MD
1 bedroom, hypo-allergenic bedding, desk, blackout curtains

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1024)
"Great place to stay. The pool and hot tub are great amenities. "
The price is 2.670.663 ₫
3.044.556 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Country Inn & Suites by Radisson, Annapolis, MD
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, (420)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is 5.415.895 ₫
6.683.743 ₫ total
includes taxes & fees
26 Oct - 27 Oct
The Inn at Chesapeake Bay Beach Club
Crowne Plaza Annapolis by IHG
Indoor pool

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1020)
"Good location"
The price is 2.747.576 ₫
3.132.237 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Crowne Plaza Annapolis by IHG
Capital O Village Inn Annapolis MD US 50
TV

Capital O Village Inn Annapolis MD US 50

2.0 star property
6.2 out of 10, (502)
"The room was very nice, clean and quiet. Great location"
The price is 3.326.778 ₫
3.792.526 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Capital O Village Inn Annapolis MD US 50
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1861)
"Perfect location…terrific staff…spacious room with a king sized bed! "
Historic Inns of Annapolis
Best Western Annapolis
Exterior

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1027)
"Great place."
The price is 2.186.168 ₫
2.492.232 ₫ total
includes taxes & fees
7 Oct - 8 Oct
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.
View all properties

Where to stay in Winchester-on-the-Severn

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

Historic District

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

Eastport

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

Murray Hill

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

Maryland Quiet Waters Park showing a garden and a house

Hillsmere

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

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.

Top Winchester-on-the-Severn Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.