Find hotels in Highland Beach, MD from ￥11,880

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jan 17 - Jan 18
Tomorrow
Jan 18 - Jan 19
Next weekend
Jan 23 - Jan 25
In two weeks
Jan 30 - Feb 1

Filter by

Guest rating
Guest rating
Star rating

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, (414 reviews)
"The room was very clean. The staff was very pleasant and extremely helpful when we needed something @3:30am."
United States
Harry
The price is ￥29,885
￥36,352 total
includes taxes & fees
Jan 20 - Jan 21
The Wildset
King Jacuzzi Room | Desk, iron/ironing board, free WiFi, wheelchair access

Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (556 reviews)
"The staff is so amazing here! "
United States
Selina
Executive Inn And Suites
Front of property

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
The price is ￥14,633
￥16,097 total
includes taxes & fees
Jan 28 - Jan 29
St Michaels Inn
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (130 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is ￥23,560
￥25,916 total
includes taxes & fees
Jan 20 - Jan 21
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, (66 reviews)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is ￥26,880
￥29,568 total
includes taxes & fees
Jan 20 - Jan 21
George Brooks House B&B
Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (373 reviews)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is ￥81,115
￥89,227 total
includes taxes & fees
Jan 22 - Jan 23
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 ￥23,560
￥26,859 total
includes taxes & fees
Jan 20 - Jan 21
The Westin Annapolis
Premium bedding, down comforters, pillowtop 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, (898 reviews)
"Great location, nice and clean "
United States
Micah
The price is ￥29,434
￥33,555 total
includes taxes & fees
Jan 25 - Jan 26
Annapolis Waterfront Hotel, Autograph Collection
Lobby

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,000 reviews)
"It was delightful, rooms very clean, staff very helpful."
United States
james h
The price is ￥14,175
￥16,159 total
includes taxes & fees
Feb 8 - Feb 9
Hilton Garden Inn Annapolis Downtown
View from property

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,001 reviews)
"Pleasant staff. Good location to walk to restaurants, shops. "
United States
Beth
The price is ￥23,209
￥26,459 total
includes taxes & fees
Jan 25 - Jan 26
Graduate by Hilton Annapolis
Free daily self-serve breakfast

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,003 reviews)
"Breakfast was well prepared, clean, safe room. "
United States
Shana
The price is ￥14,650
￥16,700 total
includes taxes & fees
Jan 22 - Jan 23
SpringHill Suites by Marriott Annapolis
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, (1,002 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 ￥14,463
￥16,488 total
includes taxes & fees
Feb 8 - Feb 9
Country Inn & Suites by Radisson, Annapolis, MD
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (867 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is ￥13,689
￥15,194 total
includes taxes & fees
Jan 19 - Jan 20
Quality Inn Grasonville near Kent Island
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,892 reviews)
" Great place to stay!"
United States
Lewis
Historic Inns of Annapolis
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)
"Great stay "
United States
Jose Miguel
The price is ￥11,834
￥13,490 total
includes taxes & fees
Feb 8 - Feb 9
DoubleTree by Hilton Hotel Annapolis
Exterior

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (91 reviews)
"Very relaxing stay."
United States
Anne
The price is ￥17,135
￥25,805 total
includes taxes & fees
Jan 18 - Jan 19
Wylder Tilghman Island
Property amenity

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,003 reviews)
"We keep coming back to the hotel with every visit to Annapolis. "
United States
Catherine
The price is ￥13,282
￥15,142 total
includes taxes & fees
Feb 1 - Feb 2
Courtyard by Marriott Annapolis
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 ￥31,624
￥34,786 total
includes taxes & fees
Feb 2 - Feb 3
The Tilghman Island Inn
Exterior

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1,001 reviews)
"Very clean and wonderful staff."
United States
Christy
The price is ￥12,397
￥14,133 total
includes taxes & fees
Jan 25 - Jan 26
Microtel Inn & Suites by Wyndham Gambrills
Indoor pool

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,001 reviews)
"The room was great and the staff was super nice. "
United States
Stacy C
The price is ￥16,811
￥19,165 total
includes taxes & fees
Feb 15 - Feb 16
Crowne Plaza Annapolis by IHG
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Beach Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"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. "
Amanda 4-night trip
Posted 4 days ago
Country Inn & Suites by Radisson, Annapolis, MD

More cheap stays in Highland Beach

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ￥10,421 per night from Feb 8 to Feb 9
￥10,421
￥11,880 total
Feb 8 - Feb 9
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 5.6 mi (9 km) from the heart of Highland Beach, DoubleTree by Hilton Hotel Annapolis is a top choice for your stay based on our traveler data. Two other options for your stay in the area are Graduate by Hilton Annapolis and Historic Inns of Annapolis. See all available top hotels, or vacation rentals in Highland Beach.
What are some of the best vacation rentals in Highland Beach?
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This vacation home near Highland Beach is located on the beach and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a 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, you'll find most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it 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.
Where can I learn more about changing or cancelling my trip to Highland Beach?
For additional details about rescheduling or cancelling your trip to Highland Beach, head over to our customer service page.
What is staying in Highland Beach like?
Visitors to Highland Beach are sure to find plenty to explore and enjoy. There are 1218 hotels and other accommodations in the surrounding area. Find out more about Highland Beach.
What should I see while I'm in 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. Check out what more to see and do in Expedia's Highland Beach guide.
What's the seasonal weather like in Highland Beach?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Highland Beach is 52 inches.

Explore a world of travel with Expedia