Book Hotels in Highland Beach, MD

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

Top Highland Beach hotels

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$94 nightly
The price is $107 total per night from Oct 20 to Oct 21
$107 total
Oct 20 - Oct 21
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. ...
"Nice clean property. I love the free shuttle that will take you anywhere within 5 miles. I like that the area around the hotel has improved."

Reviewed on Oct 6, 2026

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
$110 nightly
The price is $125 total per night from Oct 11 to Oct 12
$125 total
Oct 11 - Oct 12
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. ...
"Everything was very nice and clean . Would recommend it to everyone."

Reviewed on Oct 6, 2026

Opens in a new windowCrowne Plaza Annapolis by IHG
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
$91 nightly
The price is $104 total per night from Oct 28 to Oct 29
$104 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
"It is an excellent value for the cost!"

Reviewed on Oct 4, 2026

Opens in a new windowSonesta ES Suites Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $146 total per night from Oct 21 to Oct 22
$146 total
Oct 21 - Oct 22
Total with taxes and fees
A marina, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Make the most of the 24-hour gym and seasonal outdoor pool, and relax ...
"Great experience"

Reviewed on Oct 6, 2026

Opens in a new windowRod 'N' Reel Resort
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
$114 nightly
The price is $130 total per night from Nov 1 to Nov 2
$130 total
Nov 1 - Nov 2
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 ...
"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."

Reviewed on Oct 5, 2026

Opens in a new windowHilton Garden Inn Annapolis Downtown
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $167 total per night from Oct 26 to Oct 27
$167 total
Oct 26 - Oct 27
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, ...
Opens in a new windowGraduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$125 nightly
The price is $142 total per night from Nov 1 to Nov 2
$142 total
Nov 1 - Nov 2
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. ...
Opens in a new windowHistoric Inns of Annapolis
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $109 total per night from Oct 7 to Oct 8
$109 total
Oct 7 - Oct 8
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of ...
Opens in a new windowSt Michaels Inn
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
$109 nightly
The price is $123 total per night from Oct 7 to Oct 8
$123 total
Oct 7 - Oct 8
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 ...
Opens in a new windowComfort Inn Conference Center
Don't see what you're looking for?
See all available properties in Highland Beach
View all properties
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 $104. 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 1,231 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.

Recent Highland Beach hotel reviews by fellow wanderers

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

4 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Everything was very nice and clean . Would recommend it to everyone."
A verified traveler stayed at Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG

Explore More Ways to Travel with Travelocity