Find hotels in Highland Beach, MD from ฿2,847

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Our top choices for Highland Beach hotels

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (417 reviews)
  • cleanliness
    Unwind in a coastal hotel near Higgins Yacht Yard with complimentary treats.
"Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. "
United States
Fred
The price is ฿6,274
฿7,595 total
includes taxes & fees
11 Feb - 12 Feb
The Wildset

Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (559 reviews)
  • cleanliness
    Cosy Upper Marlboro motel with free WiFi and attentive 24-hour service.
"The staff is so amazing here! "
United States
Selina
Executive Inn And Suites

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Tranquil escape with outdoor pool near town attractions and hiking trails in St. Michaels.
"Good value and close to downtown."
United States
John
The price is ฿3,338
฿3,672 total
includes taxes & fees
10 Feb - 11 Feb
St Michaels Inn

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (131 reviews)
  • cleanliness
    Stroll to historic St. Michaels attractions from this charming B&B with breakfast.
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is ฿4,698
฿5,167 total
includes taxes & fees
11 Feb - 12 Feb
Parsonage Inn

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 ฿5,360
฿5,896 total
includes taxes & fees
10 Feb - 11 Feb
George Brooks House B&B

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (374 reviews)
  • cleanliness
    Enchanting coastal escape with spa, marina, and poolside luxury in St. Michaels.
"Beautiful place to stay."
United States
Ellen
The price is ฿16,173
฿17,791 total
includes taxes & fees
11 Feb - 12 Feb
Inn at Perry Cabin

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Elegant hotel near US Naval Academy with spa, indoor pool, and fitness centre.
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is ฿5,328
฿6,074 total
includes taxes & fees
15 Feb - 16 Feb
The Westin Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (901 reviews)
  • cleanliness
    Stroll to shops and dining from this yacht-dotted harbour hotel with a rooftop terrace.
"Great location, nice and clean "
United States
Micah
The price is ฿6,405
฿7,301 total
includes taxes & fees
22 Feb - 23 Feb
Annapolis Waterfront Hotel, Autograph Collection

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, (1,004 reviews)
  • cleanliness
    Relax in Annapolis with a quiet indoor pool and complimentary hot breakfast.
"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 ฿2,951
฿3,364 total
includes taxes & fees
22 Feb - 23 Feb
Country Inn & Suites by Radisson, Annapolis, MD

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,886 reviews)
  • cleanliness
    Explore Annapolis history in an iconic hotel steps from the US Naval Academy.
"Great rooms, very clean, loved our stay "
United States
Matthew
Historic Inns of Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,006 reviews)
  • cleanliness
    Enjoy peaceful elegance minutes from US Naval Academy in heart of Annapolis.
"Room was clean, great location"
United States
Brian
The price is ฿5,067
฿5,776 total
includes taxes & fees
23 Feb - 24 Feb
Graduate by Hilton Annapolis

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Modern comfort in city centre Annapolis with quick access to the Naval Academy.
"An amazing cozy place to stay during this snow storm!"
United States
zhanna
The price is ฿3,017
฿3,439 total
includes taxes & fees
12 Feb - 13 Feb
Hilton Garden Inn Annapolis Downtown

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,005 reviews)
"Great location and friendly staff. "
United States
Shana
The price is ฿2,921
฿3,330 total
includes taxes & fees
22 Feb - 23 Feb
SpringHill Suites by Marriott Annapolis

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (869 reviews)
  • cleanliness
    Quiet hotel near Chesapeake Bay offers convenient access to local attractions.
"Nice staff and rooms"
United States
Walter
The price is ฿2,653
฿2,945 total
includes taxes & fees
11 Feb - 12 Feb
Quality Inn Grasonville near Kent Island

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Experience Annapolis proximity to top attractions and Navy Academy.
"Great stay "
United States
Jose Miguel
The price is ฿2,611
฿2,977 total
includes taxes & fees
22 Feb - 23 Feb
DoubleTree by Hilton Hotel Annapolis

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 ฿4,007
฿5,795 total
includes taxes & fees
1 Mar - 2 Mar
Wylder Tilghman Island

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121 reviews)
  • cleanliness
    Waterfront escape on Maryland's beautiful Tilghman Island with seasonal pool.
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is ฿5,044
฿5,549 total
includes taxes & fees
12 Feb - 13 Feb
The Tilghman Island Inn

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)
  • cleanliness
    Stylish Gambrills hotel with free breakfast, near Regal Waugh Chapel and Walden Golf Club.
"Great staff & clean rooms. "
United States
Carmelo
The price is ฿2,680
฿3,055 total
includes taxes & fees
1 Mar - 2 Mar
Microtel Inn & Suites by Wyndham Gambrills

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Serene bayfront escape with pool and marina views for water enthusiasts.
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is ฿3,852
฿4,276 total
includes taxes & fees
15 Feb - 16 Feb
Hilton Garden Inn Kent Island Marina

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Relax at this Annapolis hotel with an indoor pool and fitness centre.
"Wonderful stay. "
United States
Angela
The price is ฿3,184
฿3,630 total
includes taxes & fees
16 Feb - 17 Feb
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

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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 Graduate by Hilton Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or 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 1226 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.