Find hotels in Winchester-on-the-Severn, Annapolis from CA $113

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Discover 1,234 Winchester-on-the-Severn hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (896)
"Great view"
The price is CA $148
CA $165 total
includes taxes & fees
Apr 1 - Apr 2
Hilton Garden Inn Kent Island Marina

Holiday Inn Express Annapolis - Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (820)
"Absolutely wonderful service from the time of check-in and request for adapting room from what I had apparently booked through a 3rd party site. Above and beyond what would have been received through many other customer service interactions. "
The price is CA $124
CA $138 total
includes taxes & fees
Apr 6 - Apr 7
Holiday Inn Express Annapolis - Kent Island by IHG

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Friendly staff"
The price is CA $128
CA $142 total
includes taxes & fees
Apr 2 - Apr 3
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (504)
"Loved the location on the waterfront and the views from the room. Our room had a small kitchen which was convenient. "
The price is CA $175
CA $194 total
includes taxes & fees
Apr 1 - Apr 2
Hyatt Place Kent Narrows & Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (88)
"Great location and very well cared for older motel. Updating extremely well done. We enjoyed the complimentary bikes, being so close to the water and the many good restaurants nearby. We will be back!"
The price is CA $205
CA $228 total
includes taxes & fees
Mar 31 - Apr 1
Mariners Motel

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (99)
"This is a really special property. A girlfriend and I got away for a night without the kids and found the historic property and the sprawling estate where it sits to be a perfect escape. The service was very friendly and attentive, the rooms lovely, the bar open at 12pm, and dinner delicious. We’ll definitely be back. "
The price is CA $282
CA $368 total
includes taxes & fees
Mar 30 - Mar 31
Kent Island Resort

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (375)
"Great spot!"
The price is CA $250
CA $314 total
includes taxes & fees
Apr 8 - Apr 9
The Inn at Chesapeake Bay Beach Club

Village Inn

2.0 star property
6.2 out of 10, (473)
"The road leading to the hotel was trashy and homely."
The price is CA $119
CA $135 total
includes taxes & fees
Mar 27 - Mar 28
Village Inn

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1727)
"Love the convenience that we valet parked the car and didn’t need it again until we checked out. Felt totally safe as we walked around to first class shops and restaurants. The property was clean and comfortable. We had an issue with the pillows on the bed. Too new and full. Called to the desk and had different pillows brought up and like Goldie locks, they were just right. Check in was in another building but that didn’t matter. Really enjoyed the historic ambiance. Would stay there again our...
The price is CA $184
CA $257 total
includes taxes & fees
Mar 31 - Apr 1
Historic Inns of Annapolis

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1003)
"Great location in Annapolis. Beds very comfortable. Quiet."
The price is CA $217
CA $248 total
includes taxes & fees
Apr 20 - Apr 21
Graduate by Hilton Annapolis

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1000)
"Beautiful room. Staff was great. "
The price is CA $120
CA $137 total
includes taxes & fees
Apr 13 - Apr 14
Hilton Garden Inn Annapolis Downtown

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1000)
"I loved it "
The price is CA $213
CA $242 total
includes taxes & fees
Apr 6 - Apr 7
The Westin Annapolis

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.2 out of 10, Wonderful, (83)
"Very easy to access and close to many attractions"
The price is CA $182
CA $207 total
includes taxes & fees
Apr 1 - Apr 2
Fairfield Inn & Suites By Marriott Annapolis

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (425)
"Water pressure is great. Hot water is abundant. Mattress was comfortable. Late check-in was effortless. Early check-out was a breeze. We would have preferred that the bar next door serve food...only liquor, no food."
The price is CA $269
CA $306 total
includes taxes & fees
Mar 30 - Mar 31
Anchored Inn at Hidden Harbour Marina

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1000)
"Breakfast "
The price is CA $133
CA $151 total
includes taxes & fees
Mar 31 - Apr 1
Holiday Inn Express & Suites Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1002)
"Recommend"
The price is CA $157
CA $179 total
includes taxes & fees
Apr 2 - Apr 3
Crowne Plaza Annapolis by IHG

Candlewood Suites Annapolis by IHG

2.5 star property
6.0 out of 10, (830)
"Clean hotel, polite staff. The shower took quite a while to warm up, but no other complaints. It was a nice quiet stay. "
The price is CA $121
CA $138 total
includes taxes & fees
Mar 31 - Apr 1
Candlewood Suites Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1003)
"My stay was very enjoyable with a friendly staff, clean room with a variety of shopping and dining options. Thank you."
The price is CA $145
CA $165 total
includes taxes & fees
Mar 30 - Mar 31
DoubleTree by Hilton Hotel Annapolis

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1000)
" Very clean rooms and property "
The price is CA $120
CA $136 total
includes taxes & fees
Apr 2 - Apr 3
Best Western Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very good, (1003)
"Lack of staff"
The price is CA $113
CA $129 total
includes taxes & fees
Mar 31 - Apr 1
Hampton Inn & Suites 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.
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Find out more about Winchester-on-the-Severn

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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?
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.