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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, (410)
Located in St. Michaels, this welcoming hotel offers free breakfast, WiFi, and parking. Enjoy drinks at the bar or grab a bite at the café. Nearby attractions include Higgins Yacht Yard and Muskrat Park, with attentive staff to enhance your stay.

"Well decorated inn w spacious and clean rooms, walking distance to shops, great restaurant with bar & breakfast included. Would absolutely come back. "
United States
Jenn
The price is NZ$393
includes taxes & fees
28 Dec - 29 Dec
The Wildset

Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (554)
Experience comfortable accommodation near Lake Presidential Golf Club. This motel offers complimentary parking and WiFi, plus clean rooms praised by past guests. Darnall's Chance House Museum is just minutes away, with helpful staff ready to assist around the clock.

"The staff is so amazing here! "
United States
Selina
Executive Inn And Suites

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1907)
Immerse in Maryland's maritime heritage at this historic hotel with a 24-hour fitness centre and garden terrace. Just a short walk from the US Naval Academy and colonial attractions, this hotel offers comfortable beds and exceptional service.

" Great place to stay!"
United States
Lewis
Historic Inns of Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (886)
Located steps from Ego Alley and Susan Campbell Park, this hotel offers Caribbean cuisine at Pussers Grille and panoramic harbour views. Enjoy luxury yacht sightings, a 24-hour fitness centre, and quick access to the US Naval Academy.

"Great location, nice and clean "
United States
Micah
The price is NZ$396
includes taxes & fees
1 Jan - 2 Jan 2026
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, (1001)
Just 10 minutes from the US Naval Academy, this serene hotel offers free parking and WiFi. Unwind in the indoor pool and spa pool after exploring nearby Westfield Annapolis Mall and local restaurants. Guests consistently praise the peaceful atmosphere and attentive staff.

"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is NZ$191
includes taxes & fees
5 Jan - 6 Jan 2026
Country Inn & Suites by Radisson, Annapolis, MD

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
Discover peaceful luxury in Annapolis with a full-service spa offering massages and facials. After enjoying Captain's Daughter restaurant, take a refreshing dip in the indoor pool or maintain your workout routine at the 24-hour fitness centre.

"Beautiful and perfect location"
United States
Lauren
The price is NZ$271
includes taxes & fees
25 Dec - 26 Dec
The Westin Annapolis

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1004)
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 NZ$174
includes taxes & fees
8 Jan - 9 Jan 2026
Hilton Garden Inn Annapolis Downtown

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1001)
Just a 5-minute drive from US Naval Academy, this hotel offers a calm atmosphere with comfortable beds and helpful staff. Enjoy Trophy Room for dinner, a bar/lounge, and complimentary bike rentals to explore nearby attractions and dining options.

"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is NZ$283
includes taxes & fees
30 Dec - 31 Dec
Graduate by Hilton Annapolis

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1003)
"Great location and friendly staff. "
United States
Shana
The price is NZ$197
includes taxes & fees
30 Dec - 31 Dec
SpringHill Suites by Marriott Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
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 NZ$146
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Annapolis

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1000)
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 NZ$176
includes taxes & fees
4 Jan - 5 Jan 2026
St Michaels Inn

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 NZ$164
includes taxes & fees
11 Jan - 12 Jan 2026
Courtyard by Marriott Annapolis

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1006)
Dive into comfort at this Annapolis hotel with a serene indoor pool, on-site restaurant, and bar. Just 10 minutes from the Naval Academy and steps from Westfield Mall, guests love the peaceful atmosphere, attentive staff, and clean rooms.

"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is NZ$213
includes taxes & fees
12 Jan - 13 Jan 2026
Crowne Plaza Annapolis by IHG

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (372)
Set on the waterfront, this charming inn offers a relaxing retreat with a full-service spa and outdoor pool. Play golf, dine at Stars restaurant, or enjoy drinks at 2 bars. Close to Perry Cabin Park with helpful staff to enhance your stay.

"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is NZ$1,081
includes taxes & fees
30 Dec - 31 Dec
Inn at Perry Cabin

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1006)
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 NZ$148
includes taxes & fees
12 Jan - 13 Jan 2026
Microtel Inn & Suites by Wyndham Gambrills

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 NZ$226
includes taxes & fees
27 Dec - 28 Dec
Knapps Narrows Marina & Inn

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very good, (1005)
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 NZ$158
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1000)
"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 NZ$130
includes taxes & fees
10 Jan - 11 Jan 2026
Best Western 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 NZ$215
includes taxes & fees
29 Dec - 30 Dec
Fairfield Inn & Suites By Marriott Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is NZ$156
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn 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

More cheap accommodation in Highland Beach

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 DoubleTree by Hilton Hotel Annapolis and Annapolis Waterfront Hotel, Autograph Collection. See all available top hotels, or vacation rentals in Highland Beach.
What are some of the best holiday rentals that Highland Beach has to offer?
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Highland Beach offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all 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 1200 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.

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