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Check prices for these dates

Next weekend
31 Jul - 2 Aug
In two weeks
7 Aug - 9 Aug

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Our top choices for Highland Beach hotels

Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,008 reviews)
"Room was pleasant and clean and breakfast was great!"
United States
Karen
The price is SARĀ 304
SARĀ 335 total
includes taxes & fees
25 Aug - 26 Aug
St Michaels Inn
Bungalow | Living area | 50-inch Smart TV with cable channels

Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort
2.5 star property
Queenstown
The price is SARĀ 3,514
SARĀ 4,005 total
includes taxes & fees
2 Aug - 3 Aug
Queenstown Harbor Golf Resort
Breakfast, lunch, dinner and brunch served

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (395 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is SARĀ 2,254
SARĀ 2,479 total
includes taxes & fees
23 Aug - 24 Aug
Inn at Perry Cabin
Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (484 reviews)
"Wonderful hotel!"
United States
Tracey
The price is SARĀ 935
SARĀ 1,122 total
includes taxes & fees
28 Jul - 29 Jul
The Wildset
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (76 reviews)
"This weekend was an anniversary gift for my daughter and her husband. They had a wonderful time and were highly complimentary of the accommodations, the delicious breakfast and the location."
United States
Erin
The price is SARĀ 794
SARĀ 873 total
includes taxes & fees
27 Jul - 28 Jul
George Brooks House B&B
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, WiFi (free), 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, (941 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is SARĀ 377
SARĀ 418 total
includes taxes & fees
19 Aug - 20 Aug
Quality Inn Grasonville near Kent Island
Terrace/patio

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,006 reviews)
"Me and my husband went for a one year anniversary. Staying at the hilton was wonderful relaxing, everyone was so pleasant and helpful.The restaurants nearby were great. I love the view we'll be coming back again."
United States
Tammy
The price is SARĀ 551
SARĀ 612 total
includes taxes & fees
3 Aug - 4 Aug
Hilton Garden Inn Kent Island Marina
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,006 reviews)
"I have stayed several times over the last few years and the place continues to be very good."
United States
Thomas R.
The price is SARĀ 427
SARĀ 474 total
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 reviews)
"Good hotel for the price"
United States
Brenda
The price is SARĀ 430
SARĀ 478 total
includes taxes & fees
2 Aug - 3 Aug
Best Western Kent Narrows Inn
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (795 reviews)
"Great location"
United States
jeanette
The price is SARĀ 634
SARĀ 704 total
includes taxes & fees
2 Aug - 3 Aug
Hyatt Place Kent Narrows & Marina
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (69 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
The price is SARĀ 677
SARĀ 752 total
includes taxes & fees
27 Jul - 28 Jul
Inn at Huntingfield Creek
Exterior

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (390 reviews)
"Breakfast is excellent, staff very friendly"
United States
Polina
The price is SARĀ 563
SARĀ 619 total
includes taxes & fees
27 Jul - 28 Jul
Knapps Narrows Marina & Inn
Exterior

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (103 reviews)
"Super lovely, very cute even when our weather was pretty rainy."
United States
Jennifer
The price is SARĀ 1,206
SARĀ 1,515 total
includes taxes & fees
26 Aug - 27 Aug
Wylder Tilghman Island
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.8 out of 10, Exceptional, (6 reviews)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
The price is SARĀ 508
SARĀ 564 total
includes taxes & fees
26 Aug - 27 Aug
Haven Point Inn and Gallery
Terrace/patio

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.4 out of 10, Exceptional, (151 reviews)
"Totally charming. We had a lovely time and our dogs loved it."
United States
Wm
The price is SARĀ 845
SARĀ 929 total
includes taxes & fees
9 Aug - 10 Aug
The Tilghman Island Inn
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (168 reviews)
"Wonderful room, bar and food!"
United States
Leigh
The price is SARĀ 547
SARĀ 734 total
includes taxes & fees
10 Aug - 11 Aug
Kent Island Resort
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (471 reviews)
"helpful staff, nice rooms"
United Kingdom
Jamie
The price is SARĀ 847
SARĀ 1,036 total
includes taxes & fees
23 Aug - 24 Aug
The Inn at Chesapeake Bay Beach Club
Outdoor wedding area

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,006 reviews)
"The staff was wonderful, the rooms were nice and clean. Breakfast at The Rod 'N' Reel Restaurant was great."
United States
Jeannette M
The price is SARĀ 651
SARĀ 847 total
includes taxes & fees
13 Aug - 14 Aug
Rod 'N' Reel Resort
Fridge, microwave

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (513 reviews)
"Always clean staff friendly professional used to pretty much live here years ago always worked with me treated me right.Highly recommend šŸ‘Œ šŸ‘"
United States
Stephen
The price is SARĀ 312
SARĀ 355 total
includes taxes & fees
28 Jul - 29 Jul
Village Inn Annapolis MD
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, (952 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
United States
Salvatore
The price is SARĀ 830
SARĀ 946 total
includes taxes & fees
16 Aug - 17 Aug
Annapolis Waterfront Hotel, Autograph Collection
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good
"You will not be disappointed"
JD 1-night trip
Posted 10 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

More cheap stays in Highland Beach

St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
The price is SARĀ 304 per night from Aug 25 to Aug 26
SARĀ 304
SARĀ 335 total
25 Aug - 26 Aug
includes taxes & fees
8.2/10 Very Good! (1,008 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 Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Highland Beach.
What are some of the best vacation rentals in Highland Beach?
Cute, Cozy 2-bedroom house near Annapolis with water access: This vacation home rental near Highland Beach offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. 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 Maryland Quiet Waters Park and Annapolis Landing Marina 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 75Ā°F, while the coldest months are January and February with an average of 40Ā°F. Average annual precipitation for Highland Beach is 52 inches.