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Aug 8 - Aug 9
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Aug 8 - Aug 10
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Discover 1,302 Hillsmere hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

The Wildset
Premium Room | 1 bedroom, Frette Italian sheets, premium bedding, iron/ironing board

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (354)
"This is where we stay everytime we come to St. Michaels - Top Knotch!"
The price is NT$5,866
NT$7,108 total
includes taxes & fees
Aug 18 - Aug 19
The Wildset
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (129)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is NT$6,816
NT$7,498 total
includes taxes & fees
Aug 12 - Aug 13
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is NT$6,965
NT$7,661 total
includes taxes & fees
Aug 12 - Aug 13
George Brooks House B&B
Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (803)
"Conveniently located with overall great value."
The price is NT$2,909
NT$3,229 total
includes taxes & fees
Aug 10 - Aug 11
Quality Inn
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (980)
"Friendly staff, nice environment"
The price is NT$4,605
NT$5,112 total
includes taxes & fees
Aug 17 - Aug 18
Hilton Garden Inn Kent Island Marina
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, (878)
"Great stay beautiful view"
The price is NT$4,018
NT$4,460 total
includes taxes & fees
Aug 17 - Aug 18
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very Good, (1004)
"All around a good place to rest"
The price is NT$3,238
NT$3,594 total
includes taxes & fees
Aug 17 - Aug 18
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (603)
"Great place to stay. "
The price is NT$4,764
NT$5,288 total
includes taxes & fees
Aug 21 - Aug 22
Hyatt Place Kent Narrows & Marina
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is NT$4,621
NT$5,129 total
includes taxes & fees
Aug 10 - Aug 11
Mariners Motel
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
10.0 out of 10, Exceptional, (2)
"We recently had the pleasure of staying at the Inn at Haven Harbour, specifically at their south location, and can't say enough good things about our experience! From the moment we arrived, we were captivated by the immaculate property and stunning surroundings. The views of the water were breathtaking, and having access to a private beach made our stay feel even more special. The amenities were top-notch, with a pool available for those who prefer a swim to the beach. The staff were incredibly...
The price is NT$6,233
NT$7,514 total
includes taxes & fees
Aug 12 - Aug 13
Inn at Haven Harbour
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (338)
"Our room overlooked the channel at Knapp's Narrows. The staff is friendly and helpful. We will definitely stay here again."
The price is NT$6,548
NT$7,203 total
includes taxes & fees
Aug 28 - Aug 29
Knapps Narrows Marina & Inn
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 NT$5,090
NT$6,908 total
includes taxes & fees
Aug 18 - Aug 19
Wylder Tilghman Island
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 NT$6,102
NT$6,712 total
includes taxes & fees
Aug 24 - Aug 25
The Tilghman Island Inn
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (107)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is NT$5,063
NT$6,715 total
includes taxes & fees
Sep 1 - Sep 2
Kent Island Resort
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, (406)
"Staff was very polite and friendly. "
The price is NT$6,102
NT$7,530 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club
Rod 'N' Reel Resort
Superior Studio Suite | Balcony

Rod 'N' Reel Resort

4.0 star property
8.2 out of 10, Very Good, (1002)
"Great place to stay."
The price is NT$3,991
NT$5,026 total
includes taxes & fees
Aug 10 - Aug 11
Rod 'N' Reel Resort
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
The price is NT$10,233
NT$11,665 total
includes taxes & fees
Aug 10 - Aug 11
Inn at Horn Point
Village Inn
TV

Village Inn

2.0 star property
6.2 out of 10, (490)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is NT$2,656
NT$3,028 total
includes taxes & fees
Aug 11 - Aug 12
Village Inn
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, (852)
"Front desk staff was very friendly and helpful."
The price is NT$7,059
NT$8,047 total
includes taxes & fees
Aug 17 - Aug 18
Annapolis Waterfront Hotel, Autograph Collection
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 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.

Arundel on the Bay map

Arundel on the Bay

Former post village turned residential area, Arundel-on-the-Bay boasts a private beach, pier, boat ramp, and boat launch for community use, with the picturesque Thomas Point Lighthouse just a short boat ride away.

Top Hillsmere Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"You all have some of the best staff ever. I liked the property so much that I’m planning my next trip to stay again already. My grandkids love the idea that we can just go downstairs to get breakfast and make your own waffles. Last but not least, the hot tub and swimming pool is on point."
Jamesie 4-night trip
Posted 17 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

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 10 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.