Find hotels in Highland Beach, MD from CA $134

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Our top choices for Highland Beach hotels

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (94 reviews)
"Very relaxing stay."
United States
Anne
The price is CA $167
CA $244 total
includes taxes & fees
Apr 30 - May 1
Wylder Tilghman Island

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is CA $210
CA $233 total
includes taxes & fees
Apr 28 - Apr 29
Haven Point Inn and Gallery

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (897 reviews)
"Quiet and comfortable"
United States
charles
The price is CA $145
CA $161 total
includes taxes & fees
May 19 - May 20
Quality Inn Grasonville near Kent Island

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (482 reviews)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is CA $208
CA $237 total
includes taxes & fees
Apr 26 - Apr 27
Anchored Inn at Hidden Harbour Marina

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is CA $148
CA $164 total
includes taxes & fees
May 5 - May 6
Best Western Kent Narrows Inn

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is CA $204
CA $272 total
includes taxes & fees
Apr 29 - Apr 30
Kent Island Resort

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,074 reviews)
"We stayed here while visiting our kids in the area! Very nice staff and clean hotel. Good place to stay for the money! "
United States
Lonnie
The price is CA $130
CA $148 total
includes taxes & fees
May 10 - May 11
Microtel Inn & Suites by Wyndham Gambrills

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,000 reviews)
"Had a very nice stay"
United States
Laura
The price is CA $129
CA $145 total
includes taxes & fees
Apr 28 - Apr 29
Comfort Inn Conference Center

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,002 reviews)
"Great place to stay with lovely views"
United States
David
The price is CA $198
CA $247 total
includes taxes & fees
Apr 29 - Apr 30
Rod 'N' Reel Resort

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 $192
CA $213 total
includes taxes & fees
Apr 27 - Apr 28
Inn at Huntingfield Creek

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (380 reviews)
"Such a marvelous retreat! And the balcony facing the boats and the Bay at sunset is so welcome after exploring St Michael’s (a short 17 mins drive). Extremely friendly staff and good breakfast. Highly recommend to any nature lovers."
United States
Nadia
The price is CA $205
CA $226 total
includes taxes & fees
May 3 - May 4
Knapps Narrows Marina & Inn

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Beautiful area"
United States
Dan
The price is CA $189
CA $210 total
includes taxes & fees
Apr 29 - Apr 30
Hilton Garden Inn Kent Island Marina

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (230 reviews)
"Hotel was clean staff was friendly"
United States
Kim
The price is CA $127
CA $152 total
includes taxes & fees
Apr 29 - Apr 30
Candlewood Suites Annapolis by IHG

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is CA $246
CA $271 total
includes taxes & fees
Apr 28 - Apr 29
Parsonage 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, (993 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is CA $171
CA $190 total
includes taxes & fees
Apr 27 - Apr 28
Holiday Inn Express Annapolis East-Kent Island by IHG

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 reviews)
" Great place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is CA $179
CA $197 total
includes taxes & fees
Apr 27 - Apr 28
St Michaels Inn

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (433 reviews)
"Best HOTEL EVER!!!"
United States
Ama
The price is CA $313
CA $374 total
includes taxes & fees
May 5 - May 6
The Wildset

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,001 reviews)
"Clean room, amenities were great. Breakfast very good and parking safe. "
United States
Adriana M
The price is CA $103
CA $118 total
includes taxes & fees
Apr 26 - Apr 27
Best Western Annapolis

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The price is CA $352
CA $401 total
includes taxes & fees
Apr 26 - Apr 27
The Inn at Tacaro Estate

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"The B&B website and other on-line links claims "...excellent breakfast" and "the best breakfast in Annapolis". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere. "
United States
Linda
The price is CA $248
CA $283 total
includes taxes & fees
Apr 26 - Apr 27
Flag House Inn
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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 $134 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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