Find hotels in Winchester-on-the-Severn, Annapolis from $85

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Discover 1,190 Winchester-on-the-Severn hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1048)
"Unique property, close to everything. Costly, but every hotel in the area is. "
The price is $195
$222 total
includes taxes & fees
May 27 - May 28
Graduate Annapolis
Pool
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1000)
"Parking limited on weekend evenings "
The price is $135
$154 total
includes taxes & fees
May 19 - May 20
Crowne Plaza Annapolis, an IHG Hotel
Lobby
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1001)
"Everything was great close to everything nice dining area walkable "
The price is $114
$130 total
includes taxes & fees
May 26 - May 27
DoubleTree by Hilton Hotel Annapolis
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Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Nice clean, large rooms. Thank you for an excellent stay. I would say the traffic around Annapolis is terrible as the only negative."
The price is $108
$123 total
includes taxes & fees
Jun 9 - Jun 10
Country Inn & Suites by Radisson, Annapolis, MD
Deluxe Studio Suite, 2 Double Beds, Non Smoking, Kitchen | Desk, laptop workspace, blackout drapes, iron/ironing board
Homestyle Suites
2.5 star property
5.6 out of 10, (722)
"It’s very quiet "
The price is $85
$97 total
includes taxes & fees
May 15 - May 16
Homestyle Suites
Exterior
Courtyard by Marriott Annapolis
3.0 star property
8.6 out of 10, Excellent, (856)
"Marriott rarely disappoints. Good, well maintained, comfortable hotel with a nice courtyard with a fireplace, seating areas, etc. Large enough room, comfortable, clean."
The price is $130
$148 total
includes taxes & fees
May 27 - May 28
Courtyard by Marriott Annapolis
Exterior
Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
8.8 out of 10, Excellent, (723)
"Great location, clean, "
The price is $97
$110 total
includes taxes & fees
May 20 - May 21
Microtel Inn & Suites by Wyndham Gambrills
Room, 2 Queen Beds, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
8.8 out of 10, Excellent, (710)
"I like everything about this property!"
The price is $247
$282 total
includes taxes & fees
May 27 - May 28
Annapolis Waterfront Hotel, Autograph Collection
Property amenity
Staybridge Suites Washington DC East - Largo, an IHG Hotel
3.0 star property
8.8 out of 10, Excellent, (417)
"Property and staff were outstanding! "
The price is $151
$171 total
includes taxes & fees
May 19 - May 20
Staybridge Suites Washington DC East - Largo, an IHG Hotel
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board
Hilton Garden Inn Annapolis
3.0 star property
8.4 out of 10, Very Good, (1000)
"The property is what you’d expect from a HGI, but it seemed overpriced, and what appeared to be a free buffet actually cost $10 per person. The signage for the breakfast should have been prominently placed before you entered the buffet area. Although it’s in a suburban area with plentiful parking, there are signs posted that parking is $8. For the location and cost of the hotel, I’d expect both breakfast and parking to be included. When I checked out, staff wouldn’t give me a printed...
The price is $116
$132 total
includes taxes & fees
May 26 - May 27
Hilton Garden Inn Annapolis
Suite, 1 Bedroom, Terrace | Living area | LED TV
Hilton Garden Inn Annapolis Downtown
3.0 star property
8.6 out of 10, Excellent, (846)
"Very close to shopping, dining, and night life. Parking was tight and we actually had to pay $25"
The price is $139
$158 total
includes taxes & fees
May 27 - May 28
Hilton Garden Inn Annapolis Downtown
Bar (on property)
Comfort Inn Conference Center
2.5 star property
9.0 out of 10, Wonderful, (1000)
"Had a handicapped room, however the bathroom was not set up for handicapped people. Just thought that was weird But loved my stay and will definitely come back. Thank You! "
The price is $109
$123 total
includes taxes & fees
Jun 9 - Jun 10
Comfort Inn Conference Center
Exterior
SpringHill Suites by Marriott Annapolis
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful , updated , modern and very clean. I like the space and the thoughtfulness that they brought into the rooms, they had a couple of plates, plastic forks and spoons in the microwavez Very quiet, comfy beds and good amount of parking spaces even on a busy weekend. Good distance to the town center, downtown and shopping area and very close to restaurants and fast food places, breakfast was pretty good as well. I would come back and stay here again. Thank you and keep it up. "
The price is $139
$158 total
includes taxes & fees
May 26 - May 27
SpringHill Suites by Marriott Annapolis
TV
Village Inn
2.0 star property
6.2 out of 10, (434)
"I have stayed here multiple times and have always enjoyed it"
The price is $86
$98 total
includes taxes & fees
May 15 - May 16
Village Inn
Exterior
Best Western Annapolis
2.5 star property
7.6 out of 10, Good, (1000)
"This property was convenient to the highway. The check in was easy and the receptionist was helpful and professional. The wifi connection was one of the best I have had in a hotel. I was able to work for a few hours without a dropped connection and with ease of access. Overall, a decent place to stay."
The price is $99
$113 total
includes taxes & fees
May 26 - May 27
Best Western Annapolis
Room, 1 King Bed, Non Smoking (Whirlpool) | In-room safe, desk, laptop workspace, blackout drapes
Holiday Inn Express & Suites Annapolis, an IHG Hotel
2.5 star property
8.2 out of 10, Very Good, (1000)
"Very Nice! "
The price is $113
$129 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Annapolis, an IHG Hotel
Egyptian cotton sheets, premium bedding, pillowtop beds, desk
Sonesta ES Suites Annapolis
3.0 star property
8.8 out of 10, Excellent, (617)
"Breakfast was surprisingly tasty. A few non-residents are helping themselves to breakfast but they caused no problems."
The price is $123
$140 total
includes taxes & fees
May 28 - May 29
Sonesta ES Suites Annapolis
Seasonal outdoor pool
Hampton Inn Bowie
2.5 star property
8.2 out of 10, Very Good, (1000)
"I always have a clean room and it’s quiet in the neighborhood and it’s so convenient to the shopping center"
The price is $110
$124 total
includes taxes & fees
May 26 - May 27
Hampton Inn Bowie
25-inch TV with cable channels
TownePlace Suites Bowie Town Center
2.5 star property
9.2 out of 10, Wonderful, (458)
"The best"
The price is $109
$123 total
includes taxes & fees
Jun 9 - Jun 10
TownePlace Suites Bowie Town Center
Premium bedding, pillowtop beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis
2.5 star property
8.2 out of 10, Very Good, (1001)
"The staff is exceptional. This is an older property so there is some wear and tear. Nothing that is any kind of a problem. We will definitely stay again. "
The price is $93
$106 total
includes taxes & fees
May 26 - May 27
Hampton Inn & Suites Annapolis
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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.

Frequently asked questions

What's it like in Winchester-on-the-Severn?

Travelers will be sure to enjoy their time in Annapolis's Winchester-on-the-Severn neighborhood.

Where is 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 traveler data.

If I need to cancel my hotel reservation in Winchester-on-the-Severn, will I receive a refund?

Yes! Most hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Add dates, click "Search", then you can use the "fully refundable" filter to view the best deals in Winchester-on-the-Severn.

Where can I learn more about changing or cancelling my trip to Winchester-on-the-Severn?

To access more information about picking new dates or cancelling your trip to Winchester-on-the-Severn, click here.

What is there to do in this Annapolis neighborhood?

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.