Find hotels in Highland Beach, MD from Rp1.307.268

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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 Rp3.168.585
Rp3.854.274 total
includes taxes & fees
7 Jan - 8 Jan 2026
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, (1894)
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, (887)
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 Rp3.410.279
Rp3.887.718 total
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 hot tub 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 Rp1.569.204
Rp1.788.894 total
includes taxes & fees
4 Jan - 5 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, (1001)
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 Rp2.330.335
Rp2.656.582 total
includes taxes & fees
30 Dec - 31 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, (1006)
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 Rp1.498.456
Rp1.708.239 total
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, (1002)
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 Rp2.474.849
Rp2.821.328 total
includes taxes & fees
4 Jan - 5 Jan 2026
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 Rp1.695.780
Rp1.933.189 total
includes taxes & fees
1 Jan - 2 Jan 2026
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, (1003)
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 Rp1.261.399
Rp1.437.995 total
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 Rp1.686.224
Rp1.854.880 total
includes taxes & fees
6 Jan - 7 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 Rp1.408.260
Rp1.605.416 total
includes taxes & fees
12 Jan - 13 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 Rp1.779.422
Rp2.028.542 total
includes taxes & fees
25 Jan - 26 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 Rp8.158.482
Rp9.871.764 total
includes taxes & fees
28 Dec - 29 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, (1000)
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 Rp1.274.140
Rp1.452.520 total
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 Rp2.011.800
Rp2.212.980 total
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, (1001)
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 Rp1.360.983
Rp1.551.521 total
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 Rp1.146.726
Rp1.307.268 total
includes taxes & fees
4 Jan - 5 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 Rp1.844.150
Rp2.102.331 total
includes taxes & fees
30 Dec - 31 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, (1001)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is Rp1.327.788
Rp1.513.678 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Annapolis
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Top Highland Beach Hotel Reviews

More cheap stays in Highland Beach

Find out more about Highland Beach

Top reasons to visit Highland Beach

  • Scenic Outdoor Activities: Highland Beach offers stunning views and a range of outdoor pursuits, perfect for nature enthusiasts.
  • Historic Significance: Explore the area's rich African American history and historic houses that add cultural depth to your visit.
  • Family-Friendly Attractions: Enjoy various family-oriented activities and recreational areas that cater to all ages.
  • Charming Accommodations: Experience a variety of lodging options, from quaint bed and breakfasts to modern hotels, ensuring a comfortable stay.
  • Tranquil Beach Escape: Indulge in relaxing beach activities and peaceful strolls along the picturesque boardwalk.

Find great hotels near Highland Beach

Experience a delightful stay in Highland Beach, Maryland, where a range of hotel accommodations await. From charming bed and breakfasts to modern hotels, you’ll find options catering to various preferences, including pet-friendly and LGBTQIA welcoming environments. Whether you’re on business or leisure, discover accessible rooms and exceptional services that ensure a comfortable and enjoyable visit.

  • Best Western Annapolis: Located 9.7km away from Highland Beach, Best Western Annapolis offers a welcoming atmosphere for both business and leisure travellers. This hotel prides itself on being pet-friendly, allowing guests to bring their furry companions along for the stay. With amenities such as a waived fee for service animals and specific pet policies in place, it caters to those who travel with pets. The hotel’s convenient location and comfortable accommodations make it an excellent choice for those seeking a relaxing getaway with their pets.
  • Hampton Inn Baltimore/Glen Burnie: Situated 32.2km from Highland Beach, Hampton Inn Baltimore/Glen Burnie stands out for its inclusive environment, welcoming LGBTQIA travellers alongside business guests. The hotel features a pet-friendly policy that includes amenities like food and water bowls for pets and a variable fee structure. This property is known for its commitment to providing a safe and friendly atmosphere, ensuring all guests feel at home. Its convenient location makes it easy to explore the surrounding area while enjoying comfortable accommodations.
  • Holiday Inn Express Annapolis East-Kent Island by IHG: Just 19.3km from Highland Beach, the Holiday Inn Express Annapolis East-Kent Island is ideal for adventure seekers. With a focus on outdoor activities, this hotel offers access to nearby kayaking, hiking, swimming, and fishing opportunities, making it perfect for guests looking to explore the great outdoors. It also welcomes pets, ensuring that your four-legged friends can join in on the fun. The hotel combines comfort with adventure, promising an unforgettable stay for active travellers.

Where to stay in Highland Beach

Highland Beach offers a delightful blend of outdoor adventures and serene landscapes, perfect for a romantic getaway. Explore the vibrant community with its African American beaches, rich American history, and friendly atmosphere. Nearby, discover family-friendly activities and relaxing spots that enhance your holiday experience. Whether you're seeking a weekend of adventure or a quiet retreat, Highland Beach and its surrounding areas provide a captivating escape for every traveller.

  • Annapolis: As the capital of Maryland, Annapolis is a charming city steeped in history and maritime culture. Located adjacent to Highland Beach, it is renowned for its picturesque waterfront, historic architecture, and vibrant arts scene. Visitors can enjoy educational tours at the United States Naval Academy, indulge in shopping at local boutiques, or simply stroll along the scenic streets lined with colonial-era buildings. The city's outdoor activities are perfect for families, with parks and beaches that provide ample opportunities for relaxation and recreation. The summer months bring a lively atmosphere, making it an ideal time to explore its many attractions.
  • Oyster Harbor: Just 644m from Highland Beach, Oyster Harbor is a delightful neighbourhood that offers a peaceful retreat while still being close to urban attractions. It boasts easy access to recreational areas and is perfect for families looking to enjoy outdoor activities. The local beaches and nearby national state park provide stunning natural landscapes ideal for picnicking, hiking, and water sports. With its welcoming community vibe and a range of educational and shopping facilities, Oyster Harbor is a lovely place to explore and unwind.
  • Arundel on the Bay: Situated 1.3km from Highland Beach, Arundel on the Bay is a quaint neighbourhood known for its stunning views and serene environment. This area is perfect for families and couples seeking outdoor adventures or romantic getaways. Visitors can explore beautiful beaches and tranquil lakes, and enjoy the local historic college university nearby. The community is rich in charm and offers a selection of shopping and educational opportunities, making it an inviting destination for all types of travellers.

Things to do near Highland Beach

Highland Beach is perfect for outdoor enthusiasts seeking scenic views and romantic getaways. Visitors can enjoy various activities including leisurely strolls along the boardwalk, exploring the recreational areas, and indulging in shopping. Beach activities and a tranquil beach escape are essential experiences to savour during your stay, ensuring a fulfilling and delightful holiday.

Shopping

For a delightful shopping experience, visit the Wild Bird Center, located only 4.8km from Highland Beach, offering unique gifts for nature lovers. If you're up for a drive, the Queenstown Premium Outlets and Saint Michaels Village, both 27.4km away, provide a variety of shopping options and charming atmospheres.

Recreation

At Navy-Marine Corps Memorial Stadium, immerse yourself in a vibrant sports atmosphere while enjoying recreational activities. The Annapolis Golf Club offers a serene outdoor setting for golf enthusiasts. Experience the romance and culture at the Ballet Theater of Maryland, where dance performances captivate and entertain.

Adventure

Chesapeake Beach Water Park offers thrilling water slides and family-friendly attractions 27.4km from Highland Beach, perfect for a splash-filled day. For a taste of adventure, the Annapolis Sailing School, located 4.8km away, provides exhilarating sailing experiences, while Tose Family Tennis Center, 6.4km away, offers exciting tennis matches.

Nightlife

Experience the charming nightlife in Highland Beach by visiting The Colonial Players for a romantic theatre performance, or enjoy some fun at Annapolis Bowl's arcadeAdventureZone. For a family-friendly film experience, head to Regal Waugh Chapel cinema to unwind with your loved ones.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Highland Beach

To save money on your trip to Highland Beach, consider visiting between December and February for lower accommodation rates. Opt for a Monday stay, as it's the cheapest day, while Saturday tends to be the priciest. Use Expedia to refine your search based on budget and location, and sort results by price for the best deals. Look for package options that combine flights, hotels, and activities for additional savings. Don't forget to check for app deals and booking fees that could affect your overall costs.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Highland Beach are December to February, where the prices are slightly lower. This is in comparison to May to June and September, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Highland Beach is Monday. The most expensive day to stay in Highland Beach is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as budget, desired location, and preferred type of accommodation. To find the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save money by combining your hotel reservation in Highland Beach with your flights and activities through an Expedia package.

Find the best attractions near Highland Beach

Highland Beach offers a delightful blend of outdoor activities, stunning scenery, and romantic getaways. Visitors can explore a variety of points of interest, including marinas, urban parks, and historic houses. These attractions cater to those seeking cultural experiences, family-friendly outings, and opportunities to immerse themselves in nature, making it an ideal destination for diverse travellers.

  • U.S. Naval Academy: Explore the rich history and stunning architecture of the U.S. Naval Academy, located a mere 6.4km from Highland Beach. Discover its significance in American naval history while enjoying the beautiful campus scenery.
  • Chesapeake Bay Bridge: Experience the impressive Chesapeake Bay Bridge, 9.7km away, showcasing modern engineering marvels. The bridge offers breathtaking views of the bay and a vibrant city atmosphere, making it a perfect stop for photographs.
  • Sandy Point State Park: Just 11.3km from Highland Beach, Sandy Point State Park invites you to immerse yourself in nature. Enjoy outdoor activities, picturesque landscapes, and adventurous trails, ideal for families and nature enthusiasts alike.

Best time to go to Highland Beach

The best time to visit Highland Beach can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Highland Beach falls in July, when visitor numbers are high and weather is mostly sunny with light rain. The coolest average temperature in Highland Beach falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.4°F (1.9°C)Light RainMostly SunnyAverageSlightly Low
February37.9°F (3.3°C)Light RainMostly SunnyAverageSlightly Low
March44.6°F (7.0°C)Light RainMostly SunnyAverageAverage
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnyHighSlightly High
June73.0°F (22.8°C)Light RainMostly SunnyHighSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyHighAverage
August76.8°F (24.9°C)Light RainMostly SunnyAverageAverage
September70.7°F (21.5°C)Light RainMostly SunnyAverageSlightly High
October60.4°F (15.8°C)Light RainMostly SunnyLowAverage
November48.7°F (9.3°C)Light RainMostly SunnyLowAverage
December41.5°F (5.3°C)Light RainMostly SunnyLowSlightly Low

The nearest major airports for your trip to Highland Beach

Reaching Highland Beach, Maryland, is convenient with three major airports nearby. Washington, DC (DCA-Ronald Reagan Washington National) is situated 49.9km away, with luxurious hotels like The Ritz-Carlton, Pentagon City just 1.6km from the airport. Washington, DC (IAD-Washington Dulles International) is 85.3km distant, offering options such as the Hyatt Regency Dulles, located 1.6km from the airport. Lastly, Baltimore, MD (BWI-Baltimore Washington International Thurgood Marshall) lies 32.2km from Highland Beach, featuring elegant accommodations like The Ivy Hotel, 14.5km away. Each hotel provides easy access to its respective airport, ensuring a smooth travel experience.

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.
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.