Find hotels in Highland Beach, MD from NT$2,592

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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, (408)
"Awesome! Love the room and fireplace!"
United States
Brian
The price is NT$6,205
NT$7,512 total
includes taxes & fees
Dec 18 - Dec 19
The Wildset

Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (553)
"The staff is so amazing here! "
United States
Selina
Executive Inn And Suites

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1000)
"clean and comfy, friendly staff"
United States
Tamara
The price is NT$3,467
NT$3,813 total
includes taxes & fees
Dec 17 - Dec 18
St Michaels Inn

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is NT$6,236
NT$6,860 total
includes taxes & fees
Jan 6 - 2026/1/7
Parsonage Inn

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is NT$4,773
NT$5,250 total
includes taxes & fees
Jan 1 - 2026/1/2
George Brooks House B&B

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is NT$16,284
NT$19,704 total
includes taxes & fees
Dec 14 - Dec 15
Inn at Perry Cabin

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (881)
"Great location, nice and clean "
United States
Micah
The price is NT$5,539
NT$6,315 total
includes taxes & fees
Dec 17 - Dec 18
Annapolis Waterfront Hotel, Autograph Collection

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
"Spectacular "
United States
Dennis
The price is NT$4,802
NT$5,474 total
includes taxes & fees
Dec 18 - Dec 19
The Westin Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1898)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis

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)
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
United States
Paul
The price is NT$2,844
NT$3,242 total
includes taxes & fees
Jan 11 - 2026/1/12
Country Inn & Suites by Radisson, Annapolis, MD

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
"Great value for stay with breakfast included "
United States
Aisling
The price is NT$2,470
NT$2,815 total
includes taxes & fees
Dec 21 - Dec 22
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)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is NT$4,055
NT$4,623 total
includes taxes & fees
Dec 21 - Dec 22
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, (1000)
"Friendly staff and comfortable rooms. We love staying here when we visit the area as a family."
United States
Jennifer
The price is NT$2,889
NT$3,293 total
includes taxes & fees
Dec 18 - Dec 19
SpringHill Suites by Marriott Annapolis

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (360)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is NT$3,742
NT$4,116 total
includes taxes & fees
Dec 12 - Dec 13
Knapps Narrows Marina & Inn

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1001)
"Great place!"
United States
Tawnya
The price is NT$2,378
NT$2,711 total
includes taxes & fees
Dec 28 - Dec 29
DoubleTree by Hilton Hotel Annapolis

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (859)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is NT$2,650
NT$2,942 total
includes taxes & fees
Dec 21 - Dec 22
Quality Inn Grasonville near Kent Island

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1001)
"Wonderful stay. "
United States
Angela
The price is NT$2,619
NT$2,986 total
includes taxes & fees
Jan 11 - 2026/1/12
Courtyard by Marriott Annapolis

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is NT$4,210
NT$6,003 total
includes taxes & fees
Jan 11 - 2026/1/12
Wylder Tilghman Island

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1000)
"Great location, near shopping and dining"
United States
Kenney
The price is NT$2,346
NT$2,674 total
includes taxes & fees
Dec 29 - Dec 30
Microtel Inn & Suites by Wyndham Gambrills

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1009)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is NT$3,025
NT$3,448 total
includes taxes & fees
Dec 21 - Dec 22
Crowne Plaza Annapolis by IHG
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 stays in Highland Beach

Hotels in Highland Beach with star-rating

Find out more about Highland Beach

Top reasons to visit Highland Beach

  • Scenic Beaches: Highland Beach boasts beautiful sandy shores perfect for relaxation and sunbathing.
  • Outdoor Activities: Enjoy thrilling water sports and a scenic boardwalk for walking and biking.
  • Charming Neighborhoods: Explore quaint shopping spots and historic homes that reflect local culture.
  • Family-Friendly Atmosphere: Ideal for vacationing families, offering fun and engaging activities for all ages.
  • Diverse Accommodations: Choose from cozy bed & breakfasts to comfortable hotels catering to various needs.

Find great hotels near Highland Beach

Highland Beach, Maryland offers a diverse selection of accommodations, from cozy bed & breakfasts to comfortable hotels, catering to various traveler needs. Whether you’re seeking a pet-friendly environment, a welcoming space for LGBTQIA guests, or a spot for business travel, you'll find the perfect place to unwind. With a range of options available, Highland Beach ensures a memorable stay for every visitor.

  • Country Inn & Suites by Radisson, Annapolis, MD: This welcoming 3-star hotel is the perfect getaway for pet lovers and those seeking a business-friendly environment. Located 9.7km from Highland Beach, the Country Inn & Suites by Radisson offers a blend of comfort and convenience with amenities tailored for both leisure and business travelers. Guests appreciate the LGBTQIA-friendly atmosphere and the pet-friendly policy, which includes a designated dog exercise area. The hotel features cozy accommodations, complimentary breakfast, and a business center, ensuring a pleasant stay for all types of visitors.
  • Historic Inns of Annapolis: Just 6.4km from Highland Beach, the Historic Inns of Annapolis is a charming 3.5-star property that embodies the spirit of family-friendly vacations. It stands out with its rich history and welcoming atmosphere, making it a delightful option for travelers with children and pets. The hotel offers free cribs and a variety of children’s amenities, ensuring a comfortable stay for families. The LGBTQIA-friendly environment further enhances its appeal, while guests enjoy the beautiful surroundings and inviting common areas, perfect for relaxation after a day of exploring.
  • Comfort Inn Conference Center: Situated 16.4km from Highland Beach, the Comfort Inn Conference Center caters to both business and family travelers. This hotel is well-equipped with meeting facilities, making it an ideal choice for corporate events. Families will appreciate the amenities designed for children, such as the pool area with safety features. The hotel's convenient location and comfortable accommodations provide a solid base for exploring the region, while its commitment to guest satisfaction ensures a pleasant experience for all.

Where to stay in Highland Beach

Highland Beach offers a perfect getaway for those seeking a relaxing beach vacation or a romantic retreat. With its family-friendly atmosphere, visitors can enjoy sun-soaked days on the sandy shores or explore the charming neighborhoods nearby. The Maryland Eastern Shore provides a picturesque backdrop, ideal for weekend escapes. Immerse yourself in the local culture, unwind at oceanfront accommodations, and experience the warmth of friendly locals in this tranquil village by the sea.

  • Annapolis: The capital of Maryland, Annapolis is a vibrant city rich in history and culture. Nestled along the Chesapeake Bay, it offers a delightful mix of educational attractions, shopping centers, and scenic waterfront views. Visitors flock to Annapolis for family-friendly activities, city-themed excursions, and business events. Key highlights include the United States Naval Academy, where you can take guided tours, and the picturesque downtown area filled with charming boutiques and restaurants. The peak tourist season runs from June to August, so plan accordingly to experience its lively summer atmosphere.
  • Oyster Harbor: Located just 644m from Highland Beach, Oyster Harbor is a serene neighborhood that is perfect for outdoor enthusiasts and families alike. With its beautiful natural scenery, this area offers recreational activities such as hiking, fishing, and picnicking. Visitors can explore nearby beaches and the stunning national state park, which provides ample opportunities for adventure. The community's welcoming atmosphere and proximity to local shopping centers make it an ideal spot for a relaxing getaway while still enjoying various amenities.
  • Arundel on the Bay: Just 1.3km from Highland Beach, Arundel on the Bay is a charming neighborhood that captures the essence of coastal living. Known for its outdoor experiences and family-friendly environment, this area is great for those seeking a mix of relaxation and exploration. Local attractions include scenic beaches, a lovely lake, and historic sites such as the nearby college university. Visitors can enjoy various shopping options and educational venues, making it a well-rounded destination for both leisure and business travelers.

Things to do near Highland Beach

Highland Beach is the perfect destination for outdoor and romantic beach vacations. Visitors can enjoy a scenic boardwalk, a recreational area, and charming shopping spots. Water sports are a key attraction, offering thrilling activities for adventure seekers. Whether you're relaxing on the beach or exploring the local area, Highland Beach has something for everyone.

Shopping

In Highland Beach, you can visit the Wild Bird Center, just 4.8km away, for unique gifts. The Annapolis Harbor Center, located 8.0km from you, offers a great shopping atmosphere. If you're up for a drive, check out Westfield Annapolis Mall, 9.7km away, featuring a wide selection of stores and entertainment.

Recreation

Navy-Marine Corps Memorial Stadium offers an energetic atmosphere, perfect for sports enthusiasts looking to enjoy various athletic events. Visit Annapolis Golf Club for a relaxing day on the greens, surrounded by nature. Ballet Theater of Maryland provides a cultural retreat with captivating performances in a romantic setting.

Adventure

Experience the thrill of sailing at Annapolis Sailing School, located 4.8km from Highland Beach, where you can enjoy the wind and waves. For family fun, visit Chesapeake Beach Water Park, 27.4km away, featuring exciting slides and pools. Don't miss hiking the scenic B&A Trail, 14.8km off, perfect for outdoor enthusiasts.

Nightlife

Experience the vibrant nightlife in Highland Beach with a visit to The Colonial Players for a romantic theater performance, or unleash your adventurous spirit at Annapolis Bowl and Crofton Bowl, both family-friendly arcade zones that promise fun and excitement for all ages.

*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 when accommodation prices are lower, and aim for a Monday stay to avoid high Saturday rates. Use Expedia's search tool to filter by budget and sort by price, ensuring you find the best hotel deals, including eco-friendly options. Look for package deals that combine flights, hotels, and activities for additional savings. Lastly, keep an eye out for last-minute deals and flexible booking options to maximize your budget while enjoying free local attractions.

  • 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: Expedia's search tool lets you customize your travel preferences by budget, location, and additional criteria. You can easily organize your results from the lowest to the highest prices, ensuring you find the most affordable hotel options first. Additionally, you have the ability to refine your search by hotel type; for instance, checking the Eco-certified filter will display hotels that are both sustainable and environmentally friendly for your booking.
  • Consider bundling your trip: You can save money by combining your hotel stay in Highland Beach with your flights and activities through an Expedia package deal.

Find the best attractions near Highland Beach

Highland Beach offers a perfect blend of outdoor activities and romantic beach getaways. Visitors can explore local attractions such as marinas, urban parks, and historic homes, providing a rich cultural experience suitable for families. With its picturesque surroundings and variety of points of interest, Highland Beach is an ideal destination for those seeking both relaxation and adventure.

  • U.S. Naval Academy: Located 6.4km from Highland Beach, the U.S. Naval Academy is a historic institution that showcases stunning architecture and rich naval tradition. Visitors can explore the beautiful campus and learn about the Academy's role in training future naval leaders.
  • Chesapeake Bay Bridge: Situated 9.7km away, the Chesapeake Bay Bridge is a modern marvel that connects the Eastern and Western shores of Maryland. With breathtaking views of the bay, it offers a unique blend of engineering and scenic beauty, making it a must-see landmark.
  • Sandy Point State Park: Just 11.3km from Highland Beach, Sandy Point State Park is an outdoor paradise featuring sandy beaches, hiking trails, and opportunities for water sports. It's perfect for adventure seekers and those looking to relax in nature.

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

Traveling to Highland Beach, Maryland, is convenient with access to three major airports. Washington, DC (DCA-Ronald Reagan Washington National) is 49.9km away, featuring nearby hotels like Salamander Washington DC and Riggs Washington DC, both offering easy airport access. Washington, DC (IAD-Washington Dulles Intl.) is 85.3km distant, with options such as the Hyatt Regency Dulles and Hilton Washington Dulles Airport, providing quick transportation to the airport. The closest option is Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), just 32.2km away, with luxury hotels like Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, which offer various transportation services to the airport.

Frequently asked questions

Where is the best place for a stay in Highland Beach?
Located 5.6 mi (9 km) from the heart of Highland Beach, DoubleTree by Hilton Hotel Annapolis is a top choice for your stay based on our traveler data. Two other options for your stay in the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. 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, you'll find most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it 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.
Where can I learn more about changing or cancelling my trip to Highland Beach?
For additional details about rescheduling or cancelling your trip to Highland Beach, head over to our customer service page.
What is staying in Highland Beach like?
Visitors to Highland Beach are sure to find plenty to explore and enjoy. There are 1203 hotels and other accommodations in the surrounding area. Find out more about Highland Beach.
What should I see while I'm in Highland Beach?
The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. You'll also find Bay Ridge Beach and Maryland Quiet Waters Park in the area. Check out what more to see and do in Expedia's Highland Beach guide.
What's the seasonal weather like in Highland Beach?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Highland Beach is 52 inches.

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