Highland Beach Hotels from S$121

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16 Jul - 17 Jul
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17 Jul - 18 Jul
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18 Jul - 20 Jul
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25 Jul - 27 Jul

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Top 10 trending Highland Beach hotels

St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Great spot to be close to town for a modest price. "
The price is S$155
includes taxes & fees
21 Jul - 22 Jul
St Michaels Inn
The Wildset
1 bedroom, Frette Italian sheets, premium bedding, iron/ironing board

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (335)
"The room was lovely - comfortable beds, it bathroom, nice toiletries. It’s quiet yet right in the center of town so you can walk to all the shops and restaurants. "
The price is S$306
includes taxes & fees
21 Jul - 22 Jul
The Wildset
Inn at Perry Cabin
Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (354)
"Grounds are beautiful. Staff very friendly and attentive "
The price is S$917
includes taxes & fees
24 Jul - 25 Jul
Inn at Perry Cabin
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (128)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is S$367
includes taxes & fees
21 Jul - 22 Jul
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (60)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is S$343
includes taxes & fees
21 Jul - 22 Jul
George Brooks House B&B
Quality Inn
In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (787)
"full breakfast, comfortable bed and nice pillows"
The price is S$140
includes taxes & fees
10 Aug - 11 Aug
Quality Inn
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (959)
"Great spot with beautiful views. "
The price is S$217
includes taxes & fees
28 Jul - 29 Jul
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (870)
"Great place"
The price is S$170
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is S$180
includes taxes & fees
24 Jul - 25 Jul
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (583)
"Great place to stay. "
The price is S$217
includes taxes & fees
4 Aug - 5 Aug
Hyatt Place Kent Narrows & Marina
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is S$221
includes taxes & fees
17 Jul - 18 Jul
Mariners Motel
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
The price is S$343
includes taxes & fees
17 Jul - 18 Jul
Inn at Haven Harbour
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (334)
"Extremely clean, wonderful place "
The price is S$226
includes taxes & fees
21 Jul - 22 Jul
Knapps Narrows Marina & Inn
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (52)
"Excellent stay. Very relaxing and great facilities."
The price is S$291
includes taxes & fees
13 Aug - 14 Aug
Wylder Tilghman Island
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (96)
"What a great surprise! A great Inn "
The price is S$353
includes taxes & fees
22 Jul - 23 Jul
The Tilghman Island Inn
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (104)
"Welcoming and well-staffed property, in a lovely and tranquil setting. Staff was friendly and helpful. Restaurant/bar service and food were outstanding. Great quiet getaway weekend spot. "
The price is S$396
includes taxes & fees
29 Jul - 30 Jul
Kent Island Resort
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (401)
"Staff was very polite and friendly. "
The price is S$339
includes taxes & fees
22 Jul - 23 Jul
The Inn at Chesapeake Bay Beach Club
Rod 'N' Reel Resort
Balcony

Rod 'N' Reel Resort

4.0 star property
8.2 out of 10, Very good, (1000)
"Lovely place"
The price is S$242
includes taxes & fees
17 Jul - 18 Jul
Rod 'N' Reel Resort
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
The price is S$503
includes taxes & fees
4 Aug - 5 Aug
Inn at Horn Point
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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Learn more about Highland Beach

Head to Bay Ridge Beach and Maryland Quiet Waters Park—just two of the sights around Highland Beach.

See all hotels in Highland Beach

Top Highland Beach Hotel Reviews

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"The place was nice"
Carmalita 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis

Frequently asked questions

Where is the best place for a stay in Highland Beach?

Located 3.6 mi (5.8 km) from the heart of Highland Beach, Historic Inns of Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Graduate by Hilton Annapolis and DoubleTree by Hilton Hotel Annapolis. 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, most hotel room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel 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.

What are some accommodation options with pools in Highland Beach?

Hilton Garden Inn Annapolis: 3-star hotel located near Westfield Annapolis Mall. Features free Internet, an outdoor pool and free self-parking. The Westin Annapolis and Courtyard by Marriott Bowie are a couple of other choices that feature an on-site pool. View all hotels with pools in Highland Beach.

What is staying in Highland Beach like?

Visitors to Highland Beach will definitely find plenty to explore and enjoy. There are 1213 hotels and other accommodation options in the surrounding area. Find out more about Highland Beach.

What should I do while I'm visiting Highland Beach?

Places to visit in the wider area include Bay Ridge Beach, Maryland Quiet Waters Park and Annapolis Landing Marina. You'll also find Annapolis Maritime Museum and Ego Alley in the area. Take a look at what more there is to see and do in Expedia's Highland Beach guide.

What's the seasonal weather in Highland Beach?

The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Highland Beach is 1313 mm.