Find hotels in Highland Beach, MD from CA $135

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Our top choices for Highland Beach hotels

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)
"Staff was nice and room was clean "
United States
Lauren
The price is CA $145
CA $161 total
includes taxes & fees
Apr 27 - Apr 28
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
Apr 22 - Apr 23
Haven Point Inn and Gallery

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 $168
CA $245 total
includes taxes & fees
Apr 28 - Apr 29
Wylder Tilghman Island

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,071 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 $126
CA $144 total
includes taxes & fees
May 4 - May 5
Microtel Inn & Suites by Wyndham Gambrills

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 $207
CA $237 total
includes taxes & fees
Apr 23 - Apr 24
Anchored Inn at Hidden Harbour Marina

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 $190
CA $256 total
includes taxes & fees
Apr 27 - Apr 28
Kent Island Resort

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,003 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is CA $135
CA $150 total
includes taxes & fees
Apr 28 - Apr 29
Best Western Kent Narrows Inn

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,009 reviews)
"Had a very nice stay"
United States
Laura
The price is CA $122
CA $138 total
includes taxes & fees
Apr 28 - Apr 29
Comfort Inn Conference Center

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,001 reviews)
" Great place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is CA $173
CA $191 total
includes taxes & fees
Apr 28 - Apr 29
St Michaels Inn

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 $231
CA $255 total
includes taxes & fees
Apr 22 - Apr 23
Parsonage Inn

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 $191
CA $212 total
includes taxes & fees
Apr 27 - Apr 28
Inn at Huntingfield Creek

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,009 reviews)
"Great place to stay with lovely views"
United States
David
The price is CA $197
CA $246 total
includes taxes & fees
Apr 28 - Apr 29
Rod 'N' Reel Resort

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 $138
CA $164 total
includes taxes & fees
Apr 27 - Apr 28
Candlewood Suites Annapolis by IHG

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"Beautiful area"
United States
Dan
The price is CA $178
CA $197 total
includes taxes & fees
Apr 28 - Apr 29
Hilton Garden Inn Kent Island Marina

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 $249
CA $283 total
includes taxes & fees
Apr 26 - Apr 27
Flag House 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, (991 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is CA $170
CA $189 total
includes taxes & fees
Apr 27 - Apr 28
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,003 reviews)
"Great hospitality and breakfast was good…"
United States
Martha
The price is CA $111
CA $126 total
includes taxes & fees
Apr 26 - Apr 27
Best Western Annapolis

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (432 reviews)
"Best HOTEL EVER!!!"
United States
Ama
The price is CA $312
CA $374 total
includes taxes & fees
May 5 - May 6
The Wildset

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 $351
CA $401 total
includes taxes & fees
Apr 27 - Apr 28
The Inn at Tacaro Estate

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (127 reviews)
"A wonderful property with a fantastic location. Super friendly staff. Couldn't ask for a more pleasant stay anywhere. You should book right now."
United States
Timothy
The price is CA $321
CA $353 total
includes taxes & fees
Apr 28 - Apr 29
The Tilghman Island 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 $135 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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