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Jan 27 - Jan 28
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Jan 28 - Jan 29
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Jan 30 - Feb 1
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Feb 6 - Feb 8

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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, (416 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 ￥29,176
￥35,490 total
includes taxes & fees
Jan 28 - Jan 29
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, (557 reviews)
  • cleanliness
    Cozy Upper Marlboro motel with free WiFi and attentive 24-hour service.
"The staff is so amazing here! "
United States
Selina
Executive Inn And Suites
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (130 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 ￥23,001
￥25,301 total
includes taxes & fees
Jan 28 - Jan 29
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 ￥26,243
￥28,867 total
includes taxes & fees
Jan 28 - Jan 29
George Brooks House B&B
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)
  • 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 ￥15,216
￥16,738 total
includes taxes & fees
Jan 28 - Jan 29
St Michaels Inn
Property amenity

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Elegant hotel near U.S. Naval Academy with spa, indoor pool, and fitness center.
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is ￥23,001
￥26,221 total
includes taxes & fees
Jan 28 - Jan 29
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, (900 reviews)
  • cleanliness
    Stroll to shops and dining from this yacht-dotted harbor hotel with a rooftop terrace.
"Great location, nice and clean "
United States
Micah
The price is ￥28,984
￥33,041 total
includes taxes & fees
Feb 15 - Feb 16
Annapolis Waterfront Hotel, Autograph Collection
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, (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 ￥74,269
￥81,696 total
includes taxes & fees
Feb 27 - Feb 28
Inn at Perry Cabin
Lobby

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,009 reviews)
  • cleanliness
    Modern comfort in downtown Annapolis with quick access to the Naval Academy.
"An amazing cozy place to stay during this snow storm!"
United States
zhanna
The price is ￥14,054
￥16,021 total
includes taxes & fees
Feb 10 - Feb 11
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, (1,009 reviews)
  • cleanliness
    Enjoy peaceful elegance minutes from U.S. Naval Academy in heart of Annapolis.
"Room was clean, great location"
United States
Brian
The price is ￥22,854
￥26,053 total
includes taxes & fees
Feb 15 - Feb 16
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, (1,001 reviews)
"Great location and friendly staff. "
United States
Shana
The price is ￥11,678
￥13,313 total
includes taxes & fees
Feb 22 - Feb 23
SpringHill Suites by Marriott Annapolis
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,011 reviews)
  • cleanliness
    Experience Annapolis proximity to top attractions and Navy Academy.
"Great stay "
United States
Jose Miguel
The price is ￥11,729
￥13,371 total
includes taxes & fees
Feb 8 - Feb 9
DoubleTree by Hilton Hotel 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, (1,003 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 ￥15,445
￥17,608 total
includes taxes & fees
Feb 17 - Feb 18
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, (1,906 reviews)
  • cleanliness
    Explore Annapolis history in an iconic hotel steps from the U.S. Naval Academy.
"Great rooms, very clean, loved our stay "
United States
Matthew
Historic Inns of Annapolis
Property amenity

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 center.
"Wonderful stay. "
United States
Angela
The price is ￥12,967
￥14,782 total
includes taxes & fees
Feb 15 - Feb 16
Courtyard by Marriott Annapolis
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, (869 reviews)
  • cleanliness
    Quiet hotel near Chesapeake Bay offers convenient access to local attractions.
"Nice staff and rooms"
United States
Walter
The price is ￥13,101
￥14,542 total
includes taxes & fees
Feb 18 - Feb 19
Quality Inn Grasonville near Kent Island
Indoor pool

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,012 reviews)
  • cleanliness
    Serene retreat near Naval Academy with indoor pool and dining options.
"Nice hotel"
United States
Jane
The price is ￥16,504
￥18,815 total
includes taxes & fees
Feb 24 - Feb 25
Crowne Plaza Annapolis by IHG
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 ￥20,811
￥29,685 total
includes taxes & fees
Feb 7 - Feb 8
Wylder Tilghman Island
Terrace/patio

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (172 reviews)
  • cleanliness
    Stylish hotel with fitness center near Naval Academy and Annapolis attractions.
"Clean rooms"
United States
David
The price is ￥15,591
￥17,774 total
includes taxes & fees
Jan 31 - Feb 1
Fairfield Inn & Suites By Marriott Annapolis
Exterior

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1,011 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 ￥12,207
￥13,915 total
includes taxes & fees
Feb 22 - Feb 23
Microtel Inn & Suites by Wyndham Gambrills
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

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Quiet lodging, great location "
Daniel 6-night trip
Posted 3 days ago
Comfort Inn Conference Center

More cheap stays in Highland Beach

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ￥10,422 per night from Feb 8 to Feb 9
￥10,422
￥11,881 total
Feb 8 - Feb 9
includes taxes & fees
7.6/10 Good! (1,001 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 Crowne Plaza Annapolis by IHG 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?
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!: This vacation home near Highland Beach is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 1221 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 Maryland Quiet Waters Park and Annapolis Maritime Museum 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.

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