Search Hotels in Hillsmere, Annapolis

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Tonight
12 Dec - 13 Dec
Tomorrow
13 Dec - 14 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

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Our top choices for Hillsmere hotels

Breakfast, lunch, dinner served; sea views
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
29.3 km from Hillsmere
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is 12.369.364 ₫
14.966.984 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Inn at Perry Cabin
Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi
The Wildset

The Wildset

The Wildset
2.5 star property
29.5 km from Hillsmere
9.8 out of 10, Exceptional, (408)
"Awesome! Love the room and fireplace!"
United States
Brian
The price is 5.239.471 ₫
6.342.656 ₫ total
includes taxes & fees
16 Dec - 17 Dec
The Wildset
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

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 4.845.618 ₫
6.049.158 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The Inn at Chesapeake Bay Beach Club
Exterior
George Brooks House B&B

George Brooks House B&B

George Brooks House B&B
3.0 star property
28.7 km from Hillsmere
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is 4.028.337 ₫
4.431.171 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
George Brooks House B&B
Outdoor banquet area
The Tilghman Island Inn

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
28.4 km from Hillsmere
9.6 out of 10, Exceptional, (120)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is 5.265.800 ₫
5.792.380 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Tilghman Island Inn
Horse riding
The Inn at Tacaro Estate

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
20.3 km from Hillsmere
9.4 out of 10, Exceptional, (11)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
30.4 km from Hillsmere
10.0 out of 10, Exceptional, (58)
"We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!"
United States
Aaron
Inn at Huntingfield Creek
Exterior
86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
2.0 star property
Historic District, 4.5 km from Hillsmere
10.0 out of 10, Exceptional, (3)
"Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels."
Norway
Jo
The price is 9.989.223 ₫
11.387.715 ₫ total
includes taxes & fees
14 Dec - 15 Dec
86 State Circle - Luxury Boutique Hotel
Front of property
Flag House Inn

Flag House Inn

Flag House Inn
3.5 star property
Historic District, 4.5 km from Hillsmere
9.4 out of 10, Exceptional, (83)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is 5.021.204 ₫
5.724.188 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Flag House Inn
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
28.6 km from Hillsmere
9.4 out of 10, Exceptional, (360)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is 3.159.480 ₫
3.475.428 ₫ total
includes taxes & fees
13 Dec - 14 Dec
Knapps Narrows Marina & Inn
Aerial view
Kent Island Resort

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 3.776.251 ₫
5.132.558 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Kent Island Resort
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
4.2 km from Hillsmere
9.4 out of 10, Exceptional, (1002)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is 3.427.728 ₫
3.907.610 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

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, (1000)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is 3.185.809 ₫
3.631.822 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Crowne Plaza Annapolis by IHG
Porch
Parsonage Inn

Parsonage Inn

Parsonage Inn
3.5 star property
29.3 km from Hillsmere
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is 5.265.800 ₫
5.792.380 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Parsonage Inn
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
Hilton Garden Inn Annapolis Downtown

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, (1007)
"Great value for stay with breakfast included "
United States
Aisling
The price is 2.085.257 ₫
2.377.193 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Hilton Garden Inn Annapolis Downtown
Exterior
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
4.5 km from Hillsmere
9.8 out of 10, Exceptional, (31)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
View from property
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
4 km from Hillsmere
8.6 out of 10, Excellent, (1000)
"Spectacular "
United States
Dennis
The price is 4.054.666 ₫
4.622.319 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Westin Annapolis
Basic Single Room | Desk, laptop workspace, blackout curtains, free WiFi
Rips Country Inn

Rips Country Inn

Rips Country Inn
2.5 star property
18.5 km from Hillsmere
6.6 out of 10, (60)
"Good stay"
United States
David
Rips Country Inn
Terrace/patio
Historic Inns of Annapolis

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, (1898)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Terrace/patio
Hyatt Place Kent Narrows & Marina

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, (674)
"Great view, good ambiance all around"
United States
Dianne
The price is 3.056.797 ₫
3.393.045 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hyatt Place Kent Narrows & Marina
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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Where to stay in Hillsmere

Find the best Hillsmere areas for the activities you enjoy most.
Annapolis featuring a city and street scenes 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

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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.