Hotels in Winchester-on-the-Severn, Annapolis from CA $109

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Winchester-on-the-Severn hotels and places to stay

Chesapeake Suite
Flag House Inn
3.5 star property
9.8 out of 10, Exceptional, (48)
"Very close to downtown!"
The price is CA $408
CA $466 total
includes taxes & fees
May 15 - May 16
Flag House Inn
Beach nearby
Inn at Horn Point
3.0 star property
9.6 out of 10, Exceptional, (18)
"I booked the trip to celebrate an anniversary weekend away with my husband. The property came up through a Yelp review so I checked it out. I was impressed with the location, the detail to cleanliness, and the commitment to the environment. Once I booked the room, the innkeepers were very helpful in offering things to do and places to eat, as well as offering to help make our anniversary stay more memorable. Once we arrived, Cory took the time to greet us as we came in and share some of the...
The price is CA $443
CA $504 total
includes taxes & fees
May 15 - May 16
Inn at Horn Point
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1048)
"3-night business stay. Room was in excellent condition. All amenities worked as expected except ice machine on the floor did not work, so had to go up one floor. Great location for easy walk to downtown Annapolis and Naval Academy. Only critical comment is the lack of any documentation in the room on services, Wi-Fi, telephone how to use TV, etc. Learned by trial and error or calling front desk."
The price is CA $255
CA $291 total
includes taxes & fees
Jun 2 - Jun 3
Graduate Annapolis
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Desk, iron/ironing board, free cribs/infant beds, free WiFi
Courtyard by Marriott Bowie
3.0 star property
9.4 out of 10, Exceptional, (640)
"It was hassle free and the customer service was amazing 👏 "
The price is CA $238
CA $269 total
includes taxes & fees
May 26 - May 27
Courtyard by Marriott Bowie
Front of property
Anchored Inn at Hidden Harbour Marina
2.5 star property
9.4 out of 10, Exceptional, (363)
"Would stay here again "
The price is CA $306
CA $349 total
includes taxes & fees
May 15 - May 16
Anchored Inn at Hidden Harbour Marina
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (341)
"Beautiful property very kind staff and wonderful amenities..would highly recommend"
The price is CA $327
CA $397 total
includes taxes & fees
May 15 - May 16
The Inn at Chesapeake Bay Beach Club
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 CA $149
CA $168 total
includes taxes & fees
Jun 9 - Jun 10
TownePlace Suites Bowie Town Center
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 CA $147
CA $168 total
includes taxes & fees
Jun 9 - Jun 10
Country Inn & Suites by Radisson, Annapolis, MD
Bar (on property)
Comfort Inn Conference Center
2.5 star property
9.0 out of 10, Wonderful, (1000)
"It was a neat and quiet environment. Staff are friendly the breakfast was good just that some of the staff serving breakfast had some not so nice attitude "
The price is CA $149
CA $168 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)
"This was our first stay at the Springhill Suites while we were in town and we are definitely looking forward to staying again when we visit Annapolis again. "
The price is CA $190
CA $217 total
includes taxes & fees
May 26 - May 27
SpringHill Suites by Marriott 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 CA $197
CA $224 total
includes taxes & fees
May 19 - May 20
Crowne Plaza Annapolis, an IHG Hotel
Exterior
Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
8.8 out of 10, Excellent, (723)
"Great location, clean, "
The price is CA $132
CA $151 total
includes taxes & fees
May 20 - May 21
Microtel Inn & Suites by Wyndham Gambrills
Room, 2 Queen Beds, Balcony
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 CA $338
CA $385 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)
"No need to look any further! This place is everything you need or want. Friendly staff, so clean, close to Washington DC. "
The price is CA $206
CA $233 total
includes taxes & fees
May 19 - May 20
Staybridge Suites Washington DC East - Largo, 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)
"We had a great stay bad weather and all. The room was very comfortable and inviting. Enjoyed good eats from the local restaurant and had some drinks at the bar."
The price is CA $168
CA $191 total
includes taxes & fees
May 28 - May 29
Sonesta ES Suites Annapolis
Lobby
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1001)
"Beautiful and convenient suite. Very helpful staff. Thank you!"
The price is CA $156
CA $178 total
includes taxes & fees
May 26 - May 27
DoubleTree by Hilton Hotel Annapolis
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 CA $190
CA $217 total
includes taxes & fees
May 26 - May 27
Courtyard by Marriott Annapolis
Suite, 1 Bedroom, Terrace | Living area
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 CA $190
CA $217 total
includes taxes & fees
May 27 - May 28
Hilton Garden Inn Annapolis Downtown
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 CA $159
CA $181 total
includes taxes & fees
May 26 - May 27
Hilton Garden Inn Annapolis
Room, 1 King Bed, Non Smoking (Whirlpool)
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 CA $155
CA $176 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Annapolis, an IHG Hotel
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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.