Find hotels in Highland Beach, MD from ฿2,420

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Our top choices for Highland Beach hotels

Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1002)
"This place is extremely impressive!!! The room was clean, the view was AMAZING, and the staff were friendly. This is our new spot. Even the guy at the gift shop was really helpful and cool. "
United States
Stacy
The price is ฿2,825
฿3,757 total
includes taxes & fees
3 Jan - 4 Jan 2026
Rod 'N' Reel Resort
Front of property
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1001)
Experience serene stays at this peaceful inn with seasonal outdoor pool and garden terrace. Located conveniently near Saint Michaels Village and Classic Motor Museum, guests appreciate the helpful staff, clean rooms, and complimentary breakfast, WiFi, and parking.
"Staff was friendly, courteous, and helpful."
United States
Donna
The price is ฿3,122
฿3,434 total
includes taxes & fees
4 Jan - 5 Jan 2026
St Michaels Inn
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (940)
Discover tranquility on Kent Island with beautiful bay views and a seasonal outdoor pool. This hotel sits right on a bike trail with rentals available on-site. Enjoy complimentary breakfast and explore nearby Chesapeake Bay Environmental Centre after a quiet night's rest.
"It was very comfortable and clean"
United States
Maria
The price is ฿2,455
฿2,725 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
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

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
This Grasonville hotel provides a peaceful environment with a seasonal outdoor pool and complimentary breakfast, WiFi, and parking. Located near Chesapeake Bay Environmental Centre and Queenstown Harbour Golf Links for easy exploration.
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ฿2,612
฿2,899 total
includes taxes & fees
19 Jan - 20 Jan 2026
Quality Inn Grasonville near Kent Island
Exterior
Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1004)
Business travellers appreciate this well-maintained hotel offering complimentary continental breakfast, WiFi, and parking. Located near popular attractions, guests praise the helpful staff and clean rooms. The convenient location provides easy access to Baltimore Washington Intl. Airport.
"Nice place to stay! Clean, friendly staff, close to restaurants,stores, and movies!"
United States
Valda
The price is ฿2,359
฿2,689 total
includes taxes & fees
5 Jan - 6 Jan 2026
Microtel Inn & Suites by Wyndham Gambrills
Exterior
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1001)
"Best Western provided a clean comfortable room for our stay at Annapolis. There was plentiful parking and the staff was courteous and helpful. The breakfast was adequate and centrally located. I would definitely recommends this establishment"
United States
Charles
The price is ฿2,123
฿2,420 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Annapolis
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is ฿3,808
฿5,311 total
includes taxes & fees
28 Dec - 29 Dec
Kent Island Resort
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is ฿3,657
฿5,388 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wylder Tilghman Island
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1005)
Located just 5 minutes from US Naval Academy, this hotel offers convenient access to Annapolis Harbour Centre and Westfield Annapolis Mall. Enjoy the 24-hour fitness centre, restaurant serving 3 meals daily, and garden. Guests particularly praise the helpful staff and prime location.
"Great stay "
United States
Jose Miguel
The price is ฿2,316
฿2,640 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Annapolis
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (680)
Experience a refreshing stay at this waterfront hotel with an indoor pool and helpful staff. Just minutes from Chesapeake Bay Environmental Centre and Paul Reed Smith Guitars, enjoy convenient access to local attractions with free WiFi and parking.
"The staff are the absolute best. Our room was perfect."
United States
Deborah
The price is ฿3,600
฿3,996 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Kent Narrows & Marina
American cuisine
Comfort Inn Conference Center

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1002)
Just steps from Prince George's Stadium, this tranquil retreat offers free breakfast, WiFi and parking. Guests love the quiet atmosphere and convenient location near shopping and dining options. The 24-hour fitness centre and American cuisine at Chessies Chesapeake Grill complete your relaxing stay.
"The staff was amazing , very friendly. Rooms were very clean."
United States
Victoria
The price is ฿3,072
฿3,472 total
includes taxes & fees
29 Dec - 30 Dec
Comfort Inn Conference Center
Front of property
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (471)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is ฿4,162
฿4,745 total
includes taxes & fees
29 Dec - 30 Dec
Anchored Inn at Hidden Harbour Marina
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.2 out of 10, Very good, (1001)
Wake up to a delicious buffet breakfast at this Annapolis hotel, just 5 minutes from the US Naval Academy. Enjoy complimentary WiFi and parking, plus a 24-hour fitness centre. Located within easy walking distance to restaurants and shops.
"Clean room and friendly staff! "
United States
Silvia
The price is ฿2,483
฿2,830 total
includes taxes & fees
10 Jan - 11 Jan 2026
Holiday Inn Express & Suites Annapolis by IHG
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
Situated just a short drive from the US Naval Academy, this hotel offers American cuisine at The Bistro. Guests praise the peaceful atmosphere, helpful staff, and clean rooms. Free WiFi and parking enhance your stay near Annapolis Harbour Centre.
"We keep coming back to the hotel with every visit to Annapolis. "
United States
Catherine
The price is ฿2,607
฿2,972 total
includes taxes & fees
19 Jan - 20 Jan 2026
Courtyard by Marriott Annapolis
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1003)
Experience Art Deco style at this city centre Annapolis hotel, just minutes from the US Naval Academy. Enjoy regional cuisine at Kitchen on West St, unwind at the bar/lounge, or maintain your routine in the 24-hour fitness centre.
"Great value for stay with breakfast included "
United States
Aisling
The price is ฿2,774
฿3,162 total
includes taxes & fees
11 Jan - 12 Jan 2026
Hilton Garden Inn Annapolis Downtown
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1002)
Ideally located near restaurants and walking trails, this Grasonville getaway offers superior rooms with spectacular sunset views over the water. Enjoy the indoor pool, hot tub, and sauna after exploring nearby Chesapeake Bay Environmental Centre.
"Nice place "
United States
Tucker T
The price is ฿2,589
฿2,874 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Kent Narrows Inn
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (363)
Discover serenity on the water at this Tilghman hotel with marina access, seasonal outdoor pool, and complimentary kayaking adventures. Comfortable rooms include refrigerators and microwaves, while free breakfast, WiFi and parking enhance your Chesapeake Bay getaway.
"nice clean room staff very nice would stay again "
United States
mario
The price is ฿3,724
฿4,097 total
includes taxes & fees
29 Dec - 30 Dec
Knapps Narrows Marina & Inn
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1000)
Overlooking the bay in Grasonville, this hotel offers an indoor pool and fitness centre for active travellers. Explore nearby Chesapeake Bay Environmental Centre, then unwind with drinks at the bar. Rooms include microwaves and refrigerators for added convenience.
"Clean and friendly staff"
United States
Lisa
The price is ฿3,537
฿3,926 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hilton Garden Inn Kent Island Marina
Property amenity
Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (167)
Located near Navy-Marine Corps Memorial Stadium, this hotel offers free breakfast and WiFi. Guests can enjoy drinks at the bar and a workout in the 24-hour fitness centre. Annapolis Civil Rights Plaque and other attractions are just minutes away.
"Beautiful and very modern, breakfast was great"
United States
Dominic
The price is ฿3,414
฿3,892 total
includes taxes & fees
1 Jan - 2 Jan 2026
Fairfield Inn & Suites By Marriott Annapolis
Premium bedding, pillow-top beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very good, (1004)
Located within a 10-minute drive of US Naval Academy, this hotel offers a seasonal outdoor pool and fitness centre. Guests praise the helpful staff and free breakfast. Annapolis Harbour Centre Shopping Centre is nearby for all your needs.
"Perfect "
United States
Coleen
The price is ฿2,519
฿2,872 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites 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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Room was perfect"
Moshe 1-night trip
Posted 2 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 ฿2,123 per night from 4 Jan to 5 Jan
฿2,123
฿2,420 total
4 Jan - 5 Jan 2026
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 traveller 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.
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 1207 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 Maryland Quiet Waters Park and Annapolis Landing Marina 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.