Hillsmere Hotels, Annapolis

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1217 Cheap Hotels in Hillsmere - Specials, Reviews, & Last Minute Deals

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 NZ$446
includes taxes & fees
23 Dec - 24 Dec
The Wildset
Inn at Perry Cabin
Breakfast, lunch, dinner served; sea 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 NZ$781
includes taxes & fees
9 Jan - 10 Jan 2025
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 NZ$350
includes taxes & fees
6 Jan - 7 Jan 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 NZ$311
includes taxes & fees
2 Jan - 3 Jan 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 NZ$167
includes taxes & fees
23 Dec - 24 Dec
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 NZ$232
includes taxes & fees
29 Dec - 30 Dec
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)
"Great "
The price is NZ$171
includes taxes & fees
1 Jan - 2 Jan 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 NZ$177
includes taxes & fees
29 Dec - 30 Dec
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)
"Clean. "
The price is NZ$232
includes taxes & fees
25 Dec - 26 Dec
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 NZ$306
includes taxes & fees
23 Dec - 24 Dec
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 NZ$282
includes taxes & fees
23 Dec - 24 Dec
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 NZ$330
includes taxes & fees
2 Jan - 3 Jan 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 NZ$350
includes taxes & fees
29 Dec - 30 Dec
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 NZ$394
includes taxes & fees
23 Dec - 24 Dec
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 NZ$455
includes taxes & fees
23 Dec - 24 Dec
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 NZ$230
includes taxes & fees
5 Jan - 6 Jan 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 NZ$748
includes taxes & fees
9 Jan - 10 Jan 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 NZ$151
includes taxes & fees
23 Dec - 24 Dec
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 NZ$418
includes taxes & fees
29 Dec - 30 Dec
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 NZ$361
includes taxes & fees
23 Dec - 24 Dec
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?

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.

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 traveller data.

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 10 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 Historic Mount Moriah AME Church.