Book Hotels in Highland Beach, MD

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Top Highland Beach hotels

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $149 total per night from Dec 21 to Dec 22
$149 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, ...
Very nice hotel. The dog park could have better lighting.

Reviewed on Dec 3, 2025

Opens in a new windowGraduate by Hilton Annapolis
Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2 out of 5
2525 Evergreen Rd. Gambrills MD
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $88 total per night from Dec 29 to Dec 30
$88 total
Dec 29 - Dec 30
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Staff at the 24-hour ...
Super awesome staff. Clean building. Nice breakfast w/ good coffee.

Reviewed on Dec 4, 2025

Opens in a new windowMicrotel Inn & Suites by Wyndham Gambrills
Comfort Inn Conference Center

Comfort Inn Conference Center

2.5 out of 5
4500 Crain Hwy Bowie MD
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $112 total per night from Dec 15 to Dec 16
$112 total
Dec 15 - Dec 16
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
Everything was great,we stay here when we come to town for the football game

Reviewed on Dec 3, 2025

Opens in a new windowComfort Inn Conference Center
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $187 total per night from Dec 16 to Dec 17
$187 total
Dec 16 - Dec 17
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. ...
Excellent

Reviewed on Dec 7, 2025

Opens in a new windowHistoric Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $203 total per night from Dec 16 to Dec 17
$203 total
Dec 16 - Dec 17
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
Fantastic hotel and they upgraded us to a room with a stunning view!

Reviewed on Dec 8, 2025

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road Annapolis MD
Fully refundable
$87 nightly
The price is $99 total per night from Jan 1 to Jan 2
$99 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot ...
Clean room, friendly staff

Reviewed on Dec 1, 2025

Opens in a new windowCountry Inn & Suites by Radisson, Annapolis, MD
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $87 total per night from Dec 28 to Dec 29
$87 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
Front desk treatment was wonderful . Room was nice but old totally rusty lamp in the room and hallways with Raggy wallpaper justified the discounted room price of received but otherwise it was clean and quiet and courteous but I can’t give it excellent but say very nice.

Reviewed on Dec 3, 2025

Opens in a new windowDoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
$97 nightly
The price is $111 total per night from Dec 15 to Dec 16
$111 total
Dec 15 - Dec 16
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
room was clean, overall hotel was peaceful

Reviewed on Dec 8, 2025

Opens in a new windowCrowne Plaza Annapolis by IHG
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $90 total per night from Dec 21 to Dec 22
$90 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and ...
Excelente the staff and everything was very nice

Reviewed on Dec 5, 2025

Opens in a new windowHilton Garden Inn Annapolis Downtown
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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.

Frequently asked questions

What are the top kid-friendly hotels in Highland Beach?
Take some of the trials out of traveling with young ones by staying in a family-friendly Highland Beach hotel. From special amenities to extra services, these properties come with perks that'll make your visit smooth sailing: NEW, waterfront, private house 5BR 4BA will help make your vacation the most memorable one yet. It comes with plenty of nice touches, such as cycling and animal viewing activities. Otherwise, spend your Highland Beach getaway at Waterfront Chesapeake Cottage in Oyster Bay - Dock. Make the most of a nearby beach, a deck and more here.
Where can I find cheap hotels in Highland Beach?
At Travelocity you'll find really nice hotels in Highland Beach at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Highland Beach rather than in Highland Beach. We may find you even better rates, too.
How do I find the best Highland Beach hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Highland Beach then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Highland Beach?
The cheapest hotel in Highland Beach is $87. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Highland Beach?
There are 1,203 hotels in Highland Beach on Travelocity.
What are the best hotels in Highland Beach?
Highland Beach has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Highland Beach for you!
When is the best time to visit Highland Beach?
If you want the joy of a fun-filled trip in peak season, visit Highland Beach during March, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, October and December.
When is the cheapest time to stay in Highland Beach?
Based on historic data is usually the cheapest month to visit Highland Beach. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Highland Beach?
There are multiple hotels in Highland Beach that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Highland Beach. We have plenty of kid-friendly hotels in Highland Beach to choose from on Travelocity!
Why book a hotel in Highland Beach through Travelocity?
Because we have the top hotels in Highland Beach! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Highland Beach on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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