Book Hotels in Highland Beach, MD

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Aug 7 - Aug 9
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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
$130 nightly
The price is $149 total per night from Aug 23 to Aug 24
$149 total
Aug 23 - Aug 24
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, ...
"When we arrived at the hotel, we had a very friendly staff member check us in and iafter that unfortunately the front staff were very unfriendly. The rooms are very nice and clean, but the Atrium room is very dark so if you can get a room facing outside. They do not offer room service."

Reviewed on Aug 5, 2026

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
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $150 total per night from Aug 19 to Aug 20
$150 total
Aug 19 - Aug 20
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. ...
"Nice very well location"

Reviewed on Aug 6, 2026

Opens in a new windowHistoric Inns of Annapolis
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
$91 nightly
The price is $104 total per night from Aug 30 to Aug 31
$104 total
Aug 30 - Aug 31
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 ...
"The air conditioning wasn't working...it completely died the 3rd night. The first 2 nights at least the loud fan was working enough to keep the air circulating. They did offer for us to change rooms on the 3rd night but we had had enough and just wanted to leave. We are in our 70s and my husband ..."

Reviewed on Aug 5, 2026

Opens in a new windowCountry Inn & Suites by Radisson, Annapolis, MD
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
$120 nightly
The price is $137 total per night from Aug 16 to Aug 17
$137 total
Aug 16 - Aug 17
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. ...
"This was an amazing stay! My room got serviced daily while I was out exploring and they kept everything nice and clean! The breakfast add on was so worth it so if you have the option to definitely add it! I had an amazing time and can’t wait to stay again!"

Reviewed on Aug 3, 2026

Opens in a new windowCrowne Plaza Annapolis by IHG
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
$227 nightly
The price is $252 total per night from Aug 20 to Aug 21
$252 total
Aug 20 - Aug 21
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 ...
"A big thing for me with hotels is cleanliness. Our room was nice, clean with no carpet which I prefer and well maintained. The bathroom had a shower with no tub which is also what I prefer. It feels cleaner. We got a king room which is on the smaller side but perfect for a couple. The area is nice ..."

Reviewed on Aug 6, 2026

Opens in a new windowRod 'N' Reel Resort
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
$92 nightly
The price is $101 total per night from Aug 30 to Aug 31
$101 total
Aug 30 - Aug 31
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 ...
"nice people."

Reviewed on Aug 6, 2026

Opens in a new windowSt Michaels Inn
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
$98 nightly
The price is $111 total per night from Aug 30 to Aug 31
$111 total
Aug 30 - Aug 31
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. ...
Opens in a new windowDoubleTree by Hilton Hotel 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
$207 nightly
The price is $236 total per night from Aug 16 to Aug 17
$236 total
Aug 16 - Aug 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 ...
Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
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
$107 nightly
The price is $122 total per night from Aug 16 to Aug 17
$122 total
Aug 16 - Aug 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 business center, free WiFi in public areas, and ...
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 $101. 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 1,214 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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"A big thing for me with hotels is cleanliness. Our room was nice, clean with no carpet which I prefer and well maintained. The bathroom had a shower with no tub which is also what I prefer. It feels cleaner. We got a king room which is on the smaller side but perfect for a couple. The area is nice too with some small shops, nice boardwalk just for walking or sitting, a good amount of restaurants and some fun water activities which can be accessed right from the hotel."
A verified traveler stayed at Rod 'N' Reel Resort
Rod 'N' Reel Resort

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