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Check prices for these dates

Tonight
15 Feb - 16 Feb
Tomorrow
16 Feb - 17 Feb
Next weekend
20 Feb - 22 Feb
In two weeks
27 Feb - 1 Mar

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Our top choices for Highland Beach hotels

Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (417 reviews)
"Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. "
United States
Fred
The price is AU$310
includes taxes & fees
16 Feb - 17 Feb
The Wildset
King Jacuzzi Room

Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (559 reviews)
"The staff is so amazing here! "
United States
Selina
Executive Inn And Suites
Reception

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 reviews)
"Good value and close to downtown."
United States
John
St Michaels Inn
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (131 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is AU$232
includes taxes & fees
16 Feb - 17 Feb
Parsonage Inn
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (67 reviews)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is AU$264
includes taxes & fees
16 Feb - 17 Feb
George Brooks House B&B
Premium bedding, down duvets, in-room safe, desk

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (374 reviews)
"Beautiful place to stay."
United States
Ellen
The price is AU$798
includes taxes & fees
18 Feb - 19 Feb
Inn at Perry Cabin
Property amenity

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,003 reviews)
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is AU$289
includes taxes & fees
22 Feb - 23 Feb
The Westin Annapolis
Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (901 reviews)
"Great location, nice and clean "
United States
Micah
The price is AU$327
includes taxes & fees
22 Feb - 23 Feb
Annapolis Waterfront Hotel, Autograph Collection
Lobby

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,007 reviews)
"Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. "
United States
Amanda
The price is AU$141
includes taxes & fees
8 Mar - 9 Mar
Country Inn & Suites by Radisson, Annapolis, MD
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,877 reviews)
"Great rooms, very clean, loved our stay "
United States
Matthew
Historic Inns of Annapolis
Lobby

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,003 reviews)
"Room was clean, great location"
United States
Brian
The price is AU$259
includes taxes & fees
22 Feb - 23 Feb
Graduate by Hilton Annapolis
Free daily self-service breakfast

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,002 reviews)
"Great location and friendly staff. "
United States
Shana
The price is AU$136
includes taxes & fees
8 Mar - 9 Mar
SpringHill Suites by Marriott Annapolis
Lobby

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"An amazing cozy place to stay during this snow storm!"
United States
zhanna
The price is AU$160
includes taxes & fees
16 Feb - 17 Feb
Hilton Garden Inn Annapolis Downtown
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,001 reviews)
"The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. "
United States
Kathy
The price is AU$133
includes taxes & fees
22 Feb - 23 Feb
DoubleTree by Hilton Hotel Annapolis
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (872 reviews)
"Nice staff and rooms"
United States
Walter
The price is AU$132
includes taxes & fees
22 Feb - 23 Feb
Quality Inn Grasonville near Kent Island
Exterior

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (92 reviews)
"We were"
United States
Guevara
The price is AU$260
includes taxes & fees
1 Mar - 2 Mar
Wylder Tilghman Island
Outdoor banquet area

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121 reviews)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is AU$249
includes taxes & fees
16 Feb - 17 Feb
The Tilghman Island Inn
Indoor pool

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,002 reviews)
"Nice hotel"
United States
Jane
The price is AU$169
includes taxes & fees
3 Mar - 4 Mar
Crowne Plaza Annapolis by IHG
Exterior

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1,012 reviews)
"Great staff & clean rooms. "
United States
Carmelo
The price is AU$137
includes taxes & fees
1 Mar - 2 Mar
Microtel Inn & Suites by Wyndham Gambrills
Property amenity

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,001 reviews)
"Wonderful stay. "
United States
Angela
The price is AU$161
includes taxes & fees
15 Mar - 16 Mar
Courtyard by Marriott 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.
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Top Highland Beach Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"We had a wonderful stay and really enjoyed it. The courtesy of the stuff was outstanding!"
sandra 1-night trip
Posted 3 days ago
Historic Inns of Annapolis

More cheap accommodation in Highland Beach

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is AU$127 per night from 16 Feb to 17 Feb
AU$127
16 Feb - 17 Feb
includes taxes & fees
7.6/10 Good! (1,003 reviews)

Frequently asked questions

Where is the best place for a stay in Highland Beach?
Located 3.6 mi (5.8 km) from the heart of Highland Beach, Historic Inns of Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are DoubleTree by Hilton Hotel Annapolis and Sonesta ES Suites Annapolis. See all available top hotels, or vacation rentals in Highland Beach.
What are some of the best holiday rentals that Highland Beach has to offer?
The Blue Crab Beach House - Free beach passes: This holiday home rental outside of Highland Beach is located near the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a private garden and a selection of games. See all vacation rentals in Highland Beach.
If I need to cancel my hotel reservation in Highland Beach, will I receive a refund?
Yes, most hotel room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Highland Beach.
What is staying in Highland Beach like?
Visitors to Highland Beach will definitely find plenty to explore and enjoy. There are 1227 hotels and other accommodation options in the surrounding area. Find out more about Highland Beach.
What should I do while I'm visiting Highland Beach?
The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. You'll also find Bay Ridge Beach and Maryland Quiet Waters Park in the area. Take a look at what more there is to see and do in Expedia's Highland Beach guide.
What's the seasonal weather in Highland Beach?
The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Highland Beach is 1313 mm.

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