Hotels in Hillsmere, Annapolis from CA $108

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Hillsmere hotels and places to stay

The Wildset
Premium Room

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (290)
"Favorite place to stay. The design service and restaurant are impeccable. "
The price is CA $300
CA $362 total
includes taxes & fees
Dec 23 - Dec 24
The Wildset
Inn at Perry Cabin
Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (324)
"Anniversary weekend. We relaxed and enjoyed to town of St Michaels and the beautiful property."
The price is CA $499
CA $604 total
includes taxes & fees
Dec 23 - Dec 24
Inn at Perry Cabin
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (124)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
The price is CA $258
CA $284 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (55)
"Very nice property, cozy and clean rooms, excellent service."
The price is CA $230
CA $253 total
includes taxes & fees
Jan 2 - Jan 3, 2025
George Brooks House B&B
Quality Inn
Suite, 1 Queen Bed, Non Smoking

Quality Inn

2.5 star property
7.8 out of 10, Good, (719)
"It’s a good place to rest 😊"
The price is CA $122
CA $135 total
includes taxes & fees
Dec 23 - Dec 24
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, (854)
"It was beautifully decorated for Christmas! We celebrated both mine and my husband’s birthdays and enjoyed the band playing at the bar across the road from the balcony! "
The price is CA $170
CA $188 total
includes taxes & fees
Dec 26 - Dec 27
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis - Kent Island, an IHG Hotel
Exterior

Holiday Inn Express Annapolis - Kent Island, an IHG Hotel

2.5 star property
9.2 out of 10, Wonderful, (788)
"Friendly staff. Cleanest hotel we've stayed in years. Really good breakfast, too."
The price is CA $125
CA $139 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Holiday Inn Express Annapolis - Kent Island, an IHG Hotel
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very good, (1002)
"Great hotel at the narrows. Indoor pool and sauna is great after sailing up the bay. Waterfront bats are across the street."
The price is CA $129
CA $143 total
includes taxes & fees
Dec 29 - Dec 30
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, (454)
"The hotel staff was good, room confortable and the breakfast was excellent!"
The price is CA $170
CA $188 total
includes taxes & fees
Dec 25 - Dec 26
Hyatt Place Kent Narrows & Marina
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (49)
"We had a great stay at this nice inn. It is exactly what we are looking for: a quiet place on the eastern shore surrounded by nature. The cottage (one of seven) is spacious and well appointed. The bed is very comfortable. The tranquility of sitting on the back porch looking at the golden sunset beyond the vast field and tree line!! We took many walks across the 70 plus acre property to the shore and just absorbed the peace and sound of the wind blowing over the water. It’s amazing. The living...
The price is CA $224
CA $248 total
includes taxes & fees
Dec 23 - Dec 24
Inn at Huntingfield Creek
Mariners Motel
Outdoor pool

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 $206
CA $229 total
includes taxes & fees
Dec 23 - Dec 24
Mariners Motel
Wylder Tilghman Island
Waterfront Suite | Living area

Wylder Tilghman Island

2.0 star property
8.4 out of 10, Very good, (23)
"It is located approximately 15 min outside St. Michael’s. We had a waterfront bungalow and did not have a minimum 2 or more night stay which we prefer. Restaurant has water views and food was very good. The rooms very clean, beautiful property, quiet and staff very accommodating. Also they had a waterfront fire pit blazing and ready for us to enjoy. There are beautiful views and fresh air and outdoor pit games, too. Will definitely book here again. "
The price is CA $194
CA $268 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Wylder Tilghman Island
The Tilghman Island Inn
Garden View Double Queen First Level - Not Dog Friendly | View from room

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (77)
"Loved our secluded it was and right in the water. Very peaceful. "
The price is CA $258
CA $284 total
includes taxes & fees
Dec 29 - Dec 30
The Tilghman Island Inn
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (89)
"Wonderful stay, charming inn. "
The price is CA $240
CA $320 total
includes taxes & fees
Dec 23 - Dec 24
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, (370)
"This was the perfect weekend getaway spot. I booked this stay for my husband’s birthday and the staff was so nice when they learned of the occasion. They even gave him a complimentary piece of pie! (Even if it’s not your birthday, try the apple pie.) We will definitely be back. "
The price is CA $300
CA $370 total
includes taxes & fees
Dec 23 - Dec 24
The Inn at Chesapeake Bay Beach Club
Rod 'N' Reel Resort
Superior Studio Suite | Balcony

Rod 'N' Reel Resort

3.0 star property
8.2 out of 10, Very good, (1000)
"First visit. Overall a nice place. The marina and views were very nice. The shower had mold. Also an extra resort fee was charged but no resort type offerings were open for the winter. Had the bathroom shower been clean and without the resort fee I would have given better ratings. I do however, think we will be back in warmer weather to check it all out. "
The price is CA $141
CA $186 total
includes taxes & fees
Jan 22 - Jan 23, 2025
Rod 'N' Reel Resort
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.6 out of 10, Exceptional, (18)
"I booked the trip to celebrate an anniversary weekend away with my husband. The property came up through a Yelp review so I checked it out. I was impressed with the location, the detail to cleanliness, and the commitment to the environment. Once I booked the room, the innkeepers were very helpful in offering things to do and places to eat, as well as offering to help make our anniversary stay more memorable. Once we arrived, Cory took the time to greet us as we came in and share some of the...
The price is CA $532
CA $607 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Inn at Horn Point
Village Inn
TV

Village Inn

2.0 star property
6.2 out of 10, (468)
"Clean and cozy"
The price is CA $108
CA $123 total
includes taxes & fees
Dec 23 - Dec 24
Village Inn
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Balcony

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (778)
"there is no shower cap, "
The price is CA $298
CA $339 total
includes taxes & fees
Dec 29 - Dec 30
Annapolis Waterfront Hotel, Autograph Collection
Flag House Inn
Chesapeake Suite

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (65)
"Easy check in, nice accommodations."
The price is CA $257
CA $293 total
includes taxes & fees
Dec 23 - Dec 24
Flag House Inn
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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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.

Where is the best place to stay in Hillsmere?

For your stay in Hillsmere, Two Master Suites in this Bayview Charmer! is one of the top choices based on our traveler data.

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.