Hillsmere Hotels, Annapolis

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8 Dec - 9 Dec
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12 Dec - 14 Dec
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1304 Cheap Hotels in Hillsmere - Specials, Reviews, & Last Minute Deals

Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
22.9 km from Hillsmere
9.2 out of 10, Wonderful, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is NZ$152
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
22.9 km from Hillsmere
9.0 out of 10, Wonderful, (1004)
"We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us. "
United States
Anthony
The price is NZ$198
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
5.9 km from Hillsmere
8.6 out of 10, Excellent, (1010)
"Great place!"
United States
Tawnya
The price is NZ$163
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Annapolis
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
22.6 km from Hillsmere
9.6 out of 10, Exceptional, (673)
"Great view, good ambiance all around"
United States
Dianne
The price is NZ$223
includes taxes & fees
14 Dec - 15 Dec
Hyatt Place Kent Narrows & Marina
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 star property
6.2 km from Hillsmere
8.8 out of 10, Excellent, (1007)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is NZ$191
includes taxes & fees
15 Dec - 16 Dec
Crowne Plaza Annapolis by IHG
Premium bedding, pillow-top beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
5.5 km from Hillsmere
8.2 out of 10, Very good, (1001)
"I had a great experience at my stay at Hampton "
United States
Idris O
The price is NZ$171
includes taxes & fees
17 Dec - 18 Dec
Hampton Inn & Suites Annapolis
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3.0 star property
5.9 km from Hillsmere
8.6 out of 10, Excellent, (1001)
"Wonderful stay. "
United States
Angela
The price is NZ$191
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Annapolis
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
4 km from Hillsmere
8.6 out of 10, Excellent, (1002)
"Spectacular "
United States
Dennis
The price is NZ$304
includes taxes & fees
14 Dec - 15 Dec
The Westin Annapolis
Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
6.8 km from Hillsmere
9.0 out of 10, Wonderful, (1006)
"Clean room, friendly staff"
United States
Jodi
The price is NZ$164
includes taxes & fees
28 Dec - 29 Dec
Country Inn & Suites by Radisson, Annapolis, MD
Room, 2 Queen Beds, Balcony
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District, 4.2 km from Hillsmere
8.8 out of 10, Excellent, (880)
"Great location, nice and clean "
United States
Micah
The price is NZ$351
includes taxes & fees
15 Dec - 16 Dec
Annapolis Waterfront Hotel, Autograph Collection
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District, 4.4 km from Hillsmere
9.0 out of 10, Wonderful, (1905)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Suite, 1 Bedroom, Terrace | Living area
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3.0 star property
4.1 km from Hillsmere
8.6 out of 10, Excellent, (1003)
"Great value for stay with breakfast included "
United States
Aisling
The price is NZ$156
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Annapolis Downtown
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
5.7 km from Hillsmere
8.2 out of 10, Very good, (1000)
"Clean room and friendly staff! "
United States
Silvia
The price is NZ$158
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn Express & Suites Annapolis by IHG
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
16 km from Hillsmere
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is NZ$306
includes taxes & fees
11 Dec - 12 Dec
Kent Island Resort
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3.0 star property
5.5 km from Hillsmere
8.8 out of 10, Excellent, (960)
"Nice breakfast, clean room, great parking"
United States
Amy
The price is NZ$180
includes taxes & fees
28 Dec - 29 Dec
Sonesta ES Suites Annapolis
Hypo-allergenic bedding, down duvets, in-room safe, desk
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
5.9 km from Hillsmere
8.2 out of 10, Very good, (1005)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is NZ$147
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Annapolis
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4.0 star property
28 km from Hillsmere
8.4 out of 10, Very good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is NZ$239
includes taxes & fees
2 Jan - 3 Jan 2026
Rod 'N' Reel Resort
Free daily self-service breakfast
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
5.4 km from Hillsmere
9.0 out of 10, Wonderful, (1000)
"Friendly staff and comfortable rooms. We love staying here when we visit the area as a family."
United States
Jennifer
The price is NZ$200
includes taxes & fees
14 Dec - 15 Dec
SpringHill Suites by Marriott Annapolis
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
4.2 km from Hillsmere
9.4 out of 10, Exceptional, (1001)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is NZ$253
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
15.9 km from Hillsmere
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is NZ$397
includes taxes & fees
14 Dec - 15 Dec
The Inn at Chesapeake Bay Beach Club
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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Our guide on where to stay in Hillsmere

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

Historic District

While visiting Historic District, you might make a stop by sights like Thurgood Marshall Memorial and Maryland State 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, Spa Creek and Ballet Theater of Maryland are top sights worth seeing.

Cape Saint Claire

While visiting Cape Saint Claire, you might make a stop by sights like Northern Chesapeake Bay and Chesapeake Bay.

Admiral Heights

If you're looking for some top things to see and do in Admiral Heights and surrounding area, you can visit Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts.

Top Hillsmere Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Excellent from check in to check out, highly recommend!"
Eric 1-night trip
Posted 20 hours ago
Crowne Plaza Annapolis by IHG

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Frequently asked questions

What is Hillsmere like?
Travellers are sure to enjoy a stay in Annapolis's Hillsmere neighbourhood. Make sure that you visit Maryland Quiet Waters Park and Great Frogs Winery as part of your Hillsmere travel plans.
How many hotels should I expect to find in the Hillsmere area?
When you want to put your feet up after a day of exploring the sights in Annapolis, you can choose from 12 Expedia hotels and other accommodation options in Hillsmere.
If I need to cancel my hotel reservation in Hillsmere, will I receive a refund?
Yes, most hotel room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. 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 your booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to get the best deals available in Hillsmere.
What is there to do in this Annapolis neighbourhood?
A few attractions you might want to check out while you're in Hillsmere are Maryland Quiet Waters Park and Great Frogs Winery. While you're out sightseeing in Annapolis, make sure that you visit other sights such as Bay Bridge Market Place Shopping Center or Historical Society of Talbot County.