Find hotels in Highland Beach, MD from CA $132

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Our top choices for Highland Beach hotels

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,079 reviews)
"Always great stay "
United States
Damani
The price is CA $127
CA $144 total
includes taxes & fees
May 26 - May 27
Microtel Inn & Suites by Wyndham Gambrills

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (903 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is CA $136
CA $151 total
includes taxes & fees
May 11 - May 12
Quality Inn Grasonville near Kent Island

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is CA $207
CA $230 total
includes taxes & fees
May 19 - May 20
Haven Point Inn and Gallery

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,004 reviews)
"Not unique but friendly staff Excellent breakfast Clean"
United States
Kevin
The price is CA $157
CA $174 total
includes taxes & fees
May 26 - May 27
Best Western Kent Narrows Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,004 reviews)
"We were very pleased with our overnight here - it was economical and more than sufficient. It was clean, comfortable and it was nice to have breakfast included (try the cinnamon buns!) "
United States
Susan
The price is CA $183
CA $203 total
includes taxes & fees
May 10 - May 11
Holiday Inn Express Annapolis East-Kent Island by IHG

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,007 reviews)
"Great place to stay with lovely views"
United States
David
The price is CA $183
CA $231 total
includes taxes & fees
May 10 - May 11
Rod 'N' Reel Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Very nice room and wonderful stay."
United States
Julie
The price is CA $244
CA $318 total
includes taxes & fees
May 12 - May 13
Kent Island Resort

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,001 reviews)
"We had a lovely stay and would go back again! Pleasant staff and a short ride to everything."
United States
JoAnn
The price is CA $164
CA $181 total
includes taxes & fees
Jun 1 - Jun 2
St Michaels Inn

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,010 reviews)
"Had a very nice stay"
United States
Laura
The price is CA $134
CA $151 total
includes taxes & fees
Jun 7 - Jun 8
Comfort Inn Conference Center

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (441 reviews)
"Best HOTEL EVER!!!"
United States
Ama
The price is CA $313
CA $374 total
includes taxes & fees
May 26 - May 27
The Wildset

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (132 reviews)
"Spotless room! Well kept grounds. Would definitely stay here again."
United States
Bethany
The price is CA $341
CA $375 total
includes taxes & fees
May 27 - May 28
The Tilghman Island Inn

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (485 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is CA $330
CA $376 total
includes taxes & fees
May 10 - May 11
Anchored Inn at Hidden Harbour Marina

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (134 reviews)
"We really enjoyed our stay at The Parsonage. The property and room were kept well. The staff were sweet and attentive. Very good location as far as walking distance to shops, restaurants and the waterfront area. I would certainly return and certainly recommend to anyone visiting St. Michael’s. "
United States
Katie
The price is CA $244
CA $268 total
includes taxes & fees
May 10 - May 11
Parsonage Inn

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,008 reviews)
"Older Hotel but clean and staff was great."
United States
Gregory
The price is CA $116
CA $132 total
includes taxes & fees
May 10 - May 11
Best Western Annapolis

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (241 reviews)
"Rooms were clean staff very welcoming."
United States
Maurice
The price is CA $146
CA $173 total
includes taxes & fees
May 24 - May 25
Candlewood Suites Annapolis by IHG

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is CA $246
CA $273 total
includes taxes & fees
May 10 - May 11
Inn at Huntingfield Creek

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, (1,011 reviews)
"Beds were very comfortable and the shower was nice !"
United States
Jocelyn
The price is CA $146
CA $167 total
includes taxes & fees
Jun 7 - Jun 8
Country Inn & Suites by Radisson, Annapolis, MD

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
"Beautiful area"
United States
Dan
The price is CA $222
CA $247 total
includes taxes & fees
May 31 - Jun 1
Hilton Garden Inn Kent Island Marina

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,003 reviews)
"Very friendly and helpful staff. Room was very comfortable and well laid out. Would definitely stay again! "
United States
Cristi
The price is CA $144
CA $164 total
includes taxes & fees
May 24 - May 25
SpringHill Suites by Marriott Annapolis

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,015 reviews)
"Convenient to downtown"
United States
John
The price is CA $175
CA $199 total
includes taxes & fees
May 10 - May 11
Hilton Garden Inn Annapolis Downtown
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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, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 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 Highland Beach hotel booking with Expedia?
Members always get our best prices. Find our best Highland Beach hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Highland Beach hotel?
Prices for hotels in Highland Beach often vary, but you can find a great deal from CA $132 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 the cheapest rate.

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