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30 Sept - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
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9 Oct - 11 Oct

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Our top choices for Highland Beach hotels

1. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Michele
NZ$182
includes taxes & fees
4 Oct - 5 Oct
DoubleTree by Hilton Hotel Annapolis

2. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Lisa
NZ$281
includes taxes & fees
1 Oct - 2 Oct
SpringHill Suites by Marriott Annapolis

3. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
Canada
Omer
NZ$212
includes taxes & fees
4 Oct - 5 Oct
Holiday Inn Express & Suites Annapolis by IHG

4. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Cynthia
NZ$223
includes taxes & fees
4 Oct - 5 Oct
Crowne Plaza Annapolis by IHG

5. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Leslie
NZ$193
includes taxes & fees
20 Oct - 21 Oct
Country Inn & Suites by Radisson, Annapolis, MD

6. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
United States
Courtney
NZ$213
includes taxes & fees
28 Oct - 29 Oct
Hampton Inn & Suites Annapolis

7. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
Philip
NZ$183
includes taxes & fees
28 Oct - 29 Oct
Sonesta ES Suites Annapolis

8. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
Annapolis
United States
Nkusu Lauren
NZ$223
includes taxes & fees
7 Oct - 8 Oct
TownePlace Suites by Marriott Annapolis

9. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
Sanaul
NZ$158
includes taxes & fees
4 Oct - 5 Oct
Best Western Annapolis

10. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Jim
NZ$228
includes taxes & fees
6 Oct - 7 Oct
Courtyard by Marriott Annapolis

11. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
United States
Glenn
NZ$205
includes taxes & fees
12 Oct - 13 Oct
Hilton Garden Inn Annapolis

12. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United Kingdom
petra
NZ$246
includes taxes & fees
27 Oct - 28 Oct
Hilton Garden Inn Annapolis Downtown

13. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
Annapolis
United States
Imola
NZ$273
includes taxes & fees
27 Oct - 28 Oct
Fairfield Inn & Suites By Marriott Annapolis

14. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
Annapolis
United States
Darren
NZ$213
includes taxes & fees
26 Oct - 27 Oct
Candlewood Suites Annapolis by IHG

15. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
princess
NZ$297
includes taxes & fees
26 Oct - 27 Oct
Graduate by Hilton Annapolis

16. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Ashley
NZ$274
includes taxes & fees
18 Oct - 19 Oct
Historic Inns of Annapolis

17. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
NZ$217
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG

18. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
Annapolis
United States
Francis
NZ$307
includes taxes & fees
27 Oct - 28 Oct
Residence Inn By Marriott Annapolis

19. Red Roof Inn Annapolis

Red Roof Inn Annapolis
Annapolis
United States
Slobodan
NZ$149
includes taxes & fees
13 Oct - 14 Oct
Red Roof Inn Annapolis

20. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Bobbi
NZ$403
includes taxes & fees
25 Oct - 26 Oct
The Westin Annapolis
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Top Highland Beach Hotel Reviews

Recent Reviews in Highland Beach

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Beautiful inn. Upscale, beds and room space very comfortable, clean, newly decorated. Grounds are lovely with cozy spaces outdoors to comfortably sit at a firepit or walk through the chefs garden its a place to relax, gather with friends, or simply enjoy."
Laura 1-night trip
Posted 20 hours ago
The Inn at Chesapeake Bay Beach Club
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

8/10 Good
"We stayed for 3 nights and we had a good experience."
Omer 4-night trip
Posted 21 hours ago
Holiday Inn Express & Suites Annapolis by IHG
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"convenient"
Judith 3-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Excellent location. Marriott has renovated the bar downstairs; one side is a Mexican restaurant and the other is Italian. Both have great food and service."
Tammy 2-night trip
Posted 1 day ago
Annapolis Waterfront Hotel, Autograph Collection
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"The staff were super friendly."
Jim 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"We stayed in the 2 bedroom and there was plenty of room. Loved that each bedroom had a bathroom. It felt more lime staying in an apartment having your own entrance. Not having to worry about breakfast was a plus, really liked that it was included. The staff was very helpful. We did use the exercise room that was small but good enough for a quick workout to start the day. We would most definitely stay again."
kelly 2-night trip
Posted 3 days ago
Sonesta ES Suites Annapolis
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent
"I stay here when I’m flying home because it’s close enough to the airport, friendly staff, clean rooms, quiet at night and lots of dining choices close by!"
Mark 1-night trip
Posted 4 days ago
Microtel Inn & Suites by Wyndham Gambrills/Odenton
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"The room was clean and well maintained. The lobby was pleasant, and the staff was friendly and attentive. The breakfast was excellent for this price point, with a wide selection of hot and cold items."
William 1-night trip
Posted 9 days ago
Best Western Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 9 days ago
The Westin Annapolis

More cheap accommodation in Highland Beach

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
NZ$158
4 Oct - 5 Oct
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Best Western Annapolis
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
NZ$173
20 Oct - 21 Oct
includes taxes & fees
St Michaels Inn
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD
NZ$191
12 Oct - 13 Oct
includes taxes & fees
9.2/10 Wonderful! (1,160 reviews)
Microtel Inn & Suites by Wyndham Gambrills/Odenton
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
NZ$211
6 Oct - 7 Oct
includes taxes & fees
Best Western Kent Narrows Inn
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
NZ$212
4 Oct - 5 Oct
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Comfort Inn Conference Center

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD
NZ$217
13 Oct - 14 Oct
includes taxes & fees
Comfort Inn Conference Center

Find out more about Highland Beach

Top reasons to visit Highland Beach

  • Stunning Beaches: Highland Beach boasts beautiful sandy shores and breathtaking water views, perfect for relaxation and family outings.
  • Outdoor Adventures: Enjoy activities like evening strolls along the boardwalk and exploring local parks and marinas.
  • Cultural Experiences: Discover historic houses and local attractions that highlight the area’s rich history and charm.
  • Diverse Accommodation: From welcoming bed and breakfasts to cosy waterfront cottages, there’s something for every traveller.
  • Friendly Atmosphere: The local community provides a warm environment, making it easy to explore and enjoy the scenic beauty.

Find great hotels near Highland Beach

Discover the charm of Highland Beach, Maryland, where a variety of accommodation options await you. From welcoming bed and breakfasts to pet-friendly hotels, there's something for every traveller. Whether you're seeking a cosy waterfront cottage or a spacious vacation rental, Highland Beach offers a unique blend of comfort and hospitality tailored for everyone, including LGBTQIA travellers. Enjoy a relaxing getaway while immersing yourself in the stunning coastal scenery and vibrant local culture.

  • Sonesta ES Suites Annapolis: Located 8.0km from Highland Beach, Sonesta ES Suites Annapolis is a welcoming 3-star hotel that offers a home-like atmosphere for travellers. With a guest rating of 8.8, this property caters to both leisure and business guests, including those travelling with pets. Guests can enjoy spacious suites equipped with full kitchens, making it an ideal choice for longer stays. The hotel features a pet-friendly policy, ensuring your furry companions are accommodated, and offers amenities like service animal waivers and designated pet areas for their comfort.
  • Country Inn & Suites by Radisson, Annapolis, MD: Situated 9.7km from Highland Beach, this 3-star hotel boasts a guest rating of 9.0 and is particularly suited for those seeking a blend of comfort and practicality. Country Inn & Suites provides a warm, homely environment with complimentary breakfast and well-appointed rooms. The pet-friendly policy allows for a hassle-free stay with pets, featuring a dog exercise area and specific amenities for pet care, making it a great choice for families and business travellers alike.
  • Comfort Inn Conference Center: Just 22.5km from Highland Beach, Comfort Inn Conference Center is a budget-friendly option with a commendable guest rating of 9.2. This property is ideal for families, offering amenities tailored for children, such as a pool with safety features. Pets are welcome here as well, ensuring a comfortable stay for all family members. With its convenient location and family-oriented features, this hotel is perfect for those looking to explore the area while enjoying a relaxed atmosphere.

Where to stay in Highland Beach

Highland Beach, Maryland, offers a delightful getaway for those seeking sandy shores and stunning water views. This charming village is perfect for a relaxing summer resort experience, where families can unwind and couples can enjoy romantic strolls along the beach. Nearby cities and neighbourhoods provide a friendly atmosphere, making it easy to explore local attractions while soaking in the scenic beauty. Discover the best beaches and create unforgettable memories in this picturesque coastal destination.

  • Annapolis: As the state capital of Maryland, Annapolis is a vibrant city that offers a unique blend of history and modern convenience. Situated close to Highland Beach, it attracts travellers year-round, with peak visits in May and during the summer months. Visitors can enjoy a variety of family-friendly outdoor activities, shopping centres, and local attractions such as the picturesque Chesapeake Bay and the historic Academy. Annapolis is also known for its charming waterfront, making it an ideal spot for a leisurely stroll or a family outing.
  • Hillsmere Shores: Located a mere 3.2km from Highland Beach, Hillsmere Shores is a quaint village that thrives on its scenic beauty and outdoor experiences. This charming community sees a consistent flow of visitors, with the highest numbers in late spring and summer. Families flock here for its lovely parks and proximity to the beach, while the national state park nearby offers wonderful hiking and nature exploration opportunities. The local amenities include shopping centres that cater to all needs, making it a convenient stop for visitors.
  • Eastport: Just 4.8km from Highland Beach, Eastport is a neighbourhood brimming with character and charm. Known for its outdoor recreational opportunities and family-friendly atmosphere, this area attracts visitors throughout the year, peaking in the spring and summer months. Eastport features delightful shopping areas and is close to golf courses for those looking to tee off. Its proximity to the bay and beaches makes it perfect for water activities, while local academies and cultural landmarks provide enriching experiences for all ages.

Things to do in Highland Beach

Shopping

Highland Beach offers charming local shops for unique souvenirs, but if you're up for a drive, consider visiting the Westfield Annapolis Mall, about 19.3km away, for a wider selection of gifts and popular brands. You might also explore nearby markets for local crafts and treats.

Recreation

Highland Beach offers a tranquil escape with its charming wellness retreats, where you can indulge in rejuvenating spa treatments and yoga sessions by the sea. Explore the scenic shoreline for relaxing walks and immerse yourself in the natural beauty of this quaint coastal community.

Adventure

Explore the scenic shores of Highland Beach by kayaking or paddleboarding on the calm waters of the Chesapeake Bay, offering a chance to enjoy nature up close. For a different thrill, hike along nearby trails that provide stunning views and a sense of adventure amidst the natural beauty.

Nightlife

In Highland Beach, the local nightlife features cozy beach bars and intimate live music venues. Enjoy laid-back evenings with ocean views, where you can sip cocktails and listen to local musicians while soaking in the vibrant atmosphere of this charming coastal community.

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

Find the best attractions near Highland Beach

Highland Beach offers a delightful escape for those seeking outdoor adventures, stunning scenery, and cultural experiences. Visitors can explore urban parks, marinas, and historic houses, making it a perfect destination for family outings and beachside relaxation. Whether you're keen on soaking up the sun or delving into local history, there's plenty to keep you entertained in and around Highland Beach.

  • Chesapeake Bay Bridge: Experience the thrill of crossing this impressive modern bridge, which spans the stunning Chesapeake Bay. With its sweeping views of the water and city vibes, it's an iconic sight that connects you to the beauty of Maryland.
  • Maryland State House: Immerse yourself in history at the Maryland State House, the oldest state capitol still in continuous legislative use. Admire its beautiful architecture and learn about the rich culture and heritage of Maryland through its exhibits and guided tours.
  • Sandy Point State Park: Enjoy the great outdoors at Sandy Point State Park, where adventure awaits. With picturesque scenery, hiking trails, and opportunities for swimming and picnicking, it's an ideal spot to soak up nature's beauty and unwind.

Best time to go to Highland Beach

The best time to visit Highland Beach is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Flying into Highland Beach, Maryland, offers several airport options. Philadelphia International Airport (PHL) is situated 149.7km away, with luxury accommodations like the W Philadelphia and The Ritz-Carlton, both around 6 to 11.3km from the airport. Ronald Reagan Washington National Airport (DCA) is closer at 49.9km, featuring excellent hotels such as the InterContinental Washington D.C. - The Wharf and Pendry Washington DC - The Wharf, both within 3.2km. Washington Dulles International Airport (IAD) is located 85.3km away, with options like the Hyatt Regency Dulles International Airport and The Westin Washington Dulles Airport, both just 1.6km from the airport, ensuring convenient access to your Highland Beach destination.

Frequently asked questions

What is the best area to stay in Highland Beach?
The best area to stay in Highland Beach is directly along the beachfront, where most of the premier accommodation options are situated.This small, exclusive community is primarily residential, offering a peaceful and private setting. Properties here typically boast direct access to the beach, providing stunning views of the Chesapeake Bay. The main street, Bayfront Drive, runs parallel to the water, connecting the various homes and a few select luxury rentals.Couples seeking a tranquil and romantic getaway will find Highland Beach ideal. The focus here is on relaxation, enjoying the natural beauty of the bay, and spending unhurried time together. Long walks on the beach, watching the sunrise over the water, and dining in private settings are key activities.For families, the beachfront properties offer a wonderful escape. Children can enjoy playing directly on the sand and in the gentle bay waters, while parents appreciate the calm environment and the convenience of having the beach just steps from their accommodation.
When is the best time to go to Highland Beach?
The best time to visit Highland Beach is during the summer months, from June to August, when the weather is ideal for enjoying the beach and outdoor activities.During this period, you'll find warm temperatures superb for swimming in the Atlantic Ocean and relaxing on the sand. The town truly comes alive with a pleasant buzz, as many locals and visitors enjoy the coastal setting. It's a great time for couples looking for a romantic seaside escape, with opportunities for sunset strolls along the shore and dining with ocean views.Families will also find summer an excellent time to visit. The calm waters are suitable for children, and there are often community events and ice cream parlours open, adding to the holiday feel. Most of the local shops and eateries are fully operational, offering convenience and a wide range of options.While summer is peak season, the shoulder months of May and September also offer pleasant weather with fewer crowds, which can be appealing if you prefer a quieter experience.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to 'My Trips' and selecting your reservation. To find flexible deals, filter your search by 'Fully refundable property' for hotels in Highland Beach.
How can I save on a hotel booking in Highland Beach with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Highland Beach hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Highland Beach?
Prices for hotels in Highland Beach often vary, but you can find a great deal from NZ$158 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by 'Price: low to high' for our cheapest rates.

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