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Discover 1,313 Hillsmere hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (887)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is ₩181,943
₩201,958 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Annapolis East-Kent Island by IHG
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (983)
"Great spot with beautiful views. "
The price is ₩218,776
₩242,842 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Garden Inn Kent Island Marina
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (608)
"Great place to stay. "
The price is ₩234,721
₩260,540 total
includes taxes & fees
Sep 15 - Sep 16
Hyatt Place Kent Narrows & Marina
The Westin Annapolis
View from property

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1006)
"The Hotel was very clean and convenient to everything that we wanted to do!!!!"
The price is ₩220,832
₩251,749 total
includes taxes & fees
Aug 24 - Aug 25
The Westin Annapolis
Courtyard by Marriott Annapolis
Exterior

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1004)
"Great place and great staff "
The price is ₩145,832
₩166,249 total
includes taxes & fees
Aug 24 - Aug 25
Courtyard by Marriott Annapolis
Hilton Garden Inn Annapolis
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very Good, (1004)
"Property is in a nice location, staff were courteous and nice."
The price is ₩145,444
₩165,807 total
includes taxes & fees
Aug 21 - Aug 22
Hilton Garden Inn Annapolis
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1829)
"Great stay"
The price is ₩141,549
₩208,866 total
includes taxes & fees
Aug 25 - Aug 26
Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, 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, (854)
" Very clean, spacious room, friendly staff"
The price is ₩329,373
₩375,485 total
includes taxes & fees
Aug 24 - Aug 25
Annapolis Waterfront Hotel, Autograph Collection
Hampton Inn & Suites Annapolis
Premium bedding, pillowtop beds, in-room safe, individually furnished

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very Good, (1002)
"Very nice stay. Front desk staff was friendly and the pool is a great bonus."
The price is ₩134,305
₩153,109 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn & Suites Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
1 bedroom, hypo-allergenic bedding, desk, blackout drapes

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1008)
"Great visit "
The price is ₩134,582
₩153,423 total
includes taxes & fees
Aug 24 - Aug 25
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, (411)
"Great location and amenities"
The price is ₩312,498
₩382,206 total
includes taxes & fees
Aug 25 - Aug 26
The Inn at Chesapeake Bay Beach Club
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (59)
"Good service and good options to enjoy the stays. "
The price is ₩237,498
₩322,359 total
includes taxes & fees
Aug 25 - Aug 26
Wylder Tilghman Island
DoubleTree by Hilton Hotel Annapolis
Garden

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1004)
"The Double Tree was a great place to stay! Great location amd the staff are very pleasant and helpful! "
The price is ₩133,457
₩152,140 total
includes taxes & fees
Aug 31 - Sep 1
DoubleTree by Hilton Hotel Annapolis
SpringHill Suites by Marriott Annapolis
Free daily self-serve breakfast

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great place"
The price is ₩140,485
₩160,153 total
includes taxes & fees
Aug 24 - Aug 25
SpringHill Suites by Marriott Annapolis
Crowne Plaza Annapolis by IHG
Indoor pool

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1002)
"Good location"
The price is ₩144,444
₩164,666 total
includes taxes & fees
Aug 28 - Aug 29
Crowne Plaza Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHG
Free daily buffet breakfast

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very Good, (1001)
"Great staff….property a bit “tired” but a very friendly staff working hard to make it comfortable. A decent value for location and price!"
The price is ₩134,721
₩153,582 total
includes taxes & fees
Aug 20 - Aug 21
Holiday Inn Express & Suites Annapolis by IHG
Fairfield Inn & Suites By Marriott Annapolis
Property amenity

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (133)
"complimentry breakfast is good ,friendly staff,clean and quite "
The price is ₩176,388
₩201,082 total
includes taxes & fees
Aug 24 - Aug 25
Fairfield Inn & Suites By Marriott Annapolis
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (109)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is ₩228,365
₩304,285 total
includes taxes & fees
Sep 1 - Sep 2
Kent Island Resort
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (101)
"Beautiful location on the water. The staff are super nice and helpful. The restaurant is very good. We had an excellent house smoked pulled pork sandwich and a shrimp po boy."
The price is ₩284,720
₩313,192 total
includes taxes & fees
Aug 26 - Aug 27
The Tilghman Island Inn
Sonesta ES Suites Annapolis
1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (859)
"Great room for a great price... Very friendly staff, too."
The price is ₩131,944
₩150,416 total
includes taxes & fees
Sep 7 - Sep 8
Sonesta ES 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.

Where to stay in Hillsmere

Find the best Hillsmere areas and neighborhoods for the activities you enjoy most.
Annapolis which includes street scenes and a city as well as a small group of people
Historic District map

Historic District

1 out of top 10 points of interest in this area

Discover a well-preserved historic district with elements of the original town plan, featuring landmarks like the Maryland State House, St. Ann's Church, and Paca House and Gardens. The neighborhood features prestigious educational institutions like St. John's College and the U.S. Naval Academy.

Eastport map

Eastport

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

Murray Hill map

Murray Hill

While visiting Murray Hill, you might make a stop by sights like Ballet Theater of Maryland and Spa Creek.

Cape Saint Claire map

Cape Saint Claire

Boasting three marinas, multiple parks and beaches, Cape St. Claire offers a shopping center and various churches, with easy access to Annapolis and the Chesapeake Bay Bridge via U.S. Route 50.

Admiral Heights map

Admiral Heights

Admiral Heights might not have many top sights, but Navy-Marine Corps Memorial Stadium and Maryland Hall for Creative Arts are two attractions nearby that you can check out.

Top Hillsmere Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Lovely room. Comfortable bed. "
Anne 1-night trip
Posted 4 days ago
Historic Inns of Annapolis

Frequently asked questions

What is Hillsmere like?

Travelers are sure to enjoy a stay in Annapolis's Hillsmere neighborhood. Be sure to check out Maryland Quiet Waters Park and Great Frogs Winery as part of your Hillsmere travel plans.

How many hotels are there in the Hillsmere area?

When you want to kick up your feet after a day of exploring the sights in Annapolis, you can choose from 11 Expedia hotels and other accommodations in Hillsmere.

If I need to cancel my hotel reservation in Hillsmere, will I receive a refund?

Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and be given a refund within 24 hours of your booking. Enter dates in and click on "Search", then use the filter option "fully refundable" to get the best deals in Hillsmere.

Where can I learn more about changing or cancelling my trip to Hillsmere?

To find more details about changing or cancelling your trip to Hillsmere, head over to our customer service page.

What is there to do in this Annapolis neighborhood?

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, be sure to visit other sights like Bay Bridge Market Place Shopping Center or Historic Mount Moriah AME Church.