Highland Beach Hotels

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Check prices for these dates

Tonight
Jan 22 - Jan 23
Tomorrow
Jan 23 - Jan 24
This weekend
Jan 24 - Jan 26
Next weekend
Jan 31 - Feb 2

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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)
"Enjoyed the stay. It was close to town and a lot of great attractions "
The price is P5,560
P6,116 total
includes taxes & fees
Jan 26 - Jan 27
St Michaels Inn
The Wildset
Frette Italian sheets, premium bedding, iron/ironing board, free WiFi

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (293)
"Loved the overall appearance. Modern but still quaint"
The price is P11,638
P14,088 total
includes taxes & fees
Feb 3 - Feb 4
The Wildset
Inn at Perry Cabin
Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (329)
"The property is beautiful and, the atmosphere is relaxing. I loved the fresh floral Christmas decorations."
The price is P16,664
P20,164 total
includes taxes & fees
Feb 10 - Feb 11
Inn at Perry Cabin
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (125)
"Great stay. We will be returning"
The price is P10,527
P11,579 total
includes taxes & fees
Jan 28 - Jan 29
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (55)
"Very nice property, cozy and clean rooms, excellent service."
The price is P9,357
P10,293 total
includes taxes & fees
Jan 27 - Jan 28
George Brooks House B&B
Quality Inn
In-room safe, iron/ironing board, rollaway beds, free WiFi

Quality Inn

2.5 star property
7.8 out of 10, Good, (728)
"Very clean rooms and polite staff."
The price is P5,173
P5,742 total
includes taxes & fees
Jan 23 - Jan 24
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, (863)
"Excellent front desk team, even under a stressful situation like the room key maker not working. They were super accommodating and gave us a free breakfast ticket for the trouble. "
The price is P6,168
P6,847 total
includes taxes & fees
Jan 27 - Jan 28
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis - Kent Island, an IHG Hotel
Exterior

Holiday Inn Express Annapolis - Kent Island, an IHG Hotel

2.5 star property
9.2 out of 10, Wonderful, (797)
"it need a little bit of cleaning in the bathroom (bath and floor corners) "
The price is P6,086
P6,756 total
includes taxes & fees
Feb 3 - Feb 4
Holiday Inn Express Annapolis - Kent Island, an IHG Hotel
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)
"Easy check in, clean room "
The price is P5,256
P5,835 total
includes taxes & fees
Jan 28 - Jan 29
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, (474)
"We enjoyed our overnight stay! Our room was very clean, spacious and comfy. Even managed to have a beautiful sunset from our balcony before the snowstorm rolled in the next day. "
The price is P7,427
P8,244 total
includes taxes & fees
Feb 3 - Feb 4
Hyatt Place Kent Narrows & Marina
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (49)
"We had a great stay at this nice inn. It is exactly what we are looking for: a quiet place on the eastern shore surrounded by nature. The cottage (one of seven) is spacious and well appointed. The bed is very comfortable. The tranquility of sitting on the back porch looking at the golden sunset beyond the vast field and tree line!! We took many walks across the 70 plus acre property to the shore and just absorbed the peace and sound of the wind blowing over the water. It’s amazing. The living...
The price is P7,144
P7,930 total
includes taxes & fees
Feb 2 - Feb 3
Inn at Huntingfield Creek
Mariners Motel
Outdoor pool

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (88)
"Great location and very well cared for older motel. Updating extremely well done. We enjoyed the complimentary bikes, being so close to the water and the many good restaurants nearby. We will be back!"
The price is P8,407
P9,332 total
includes taxes & fees
Jan 28 - Jan 29
Mariners Motel
Wylder Tilghman Island
Living area

Wylder Tilghman Island

2.0 star property
8.4 out of 10, Very Good, (23)
"It is located approximately 15 min outside St. Michael’s. We had a waterfront bungalow and did not have a minimum 2 or more night stay which we prefer. Restaurant has water views and food was very good. The rooms very clean, beautiful property, quiet and staff very accommodating. Also they had a waterfront fire pit blazing and ready for us to enjoy. There are beautiful views and fresh air and outdoor pit games, too. Will definitely book here again. "
The price is P7,895
P10,907 total
includes taxes & fees
Jan 28 - Jan 29
Wylder Tilghman Island
The Tilghman Island Inn
View from room

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (77)
"Loved our secluded it was and right in the water. Very peaceful. "
The price is P9,737
P10,711 total
includes taxes & fees
Jan 26 - Jan 27
The Tilghman Island Inn
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (90)
"Historic charm and clean."
The price is P9,793
P13,016 total
includes taxes & fees
Feb 18 - Feb 19
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, (373)
"We stayed one night for New Year’s Eve. And everything was awesome. We also had a great dinner in your restaurant"
The price is P11,646
P14,416 total
includes taxes & fees
Jan 29 - Jan 30
The Inn at Chesapeake Bay Beach Club
Rod 'N' Reel Resort
Balcony

Rod 'N' Reel Resort

3.0 star property
8.2 out of 10, Very Good, (1001)
"The check in was awesome. Caleb was so knowledgeable and gave me so much good information. He gave me the room details that was staying in. The bonus details he gave was future places to fish from. He made my 10th anniversary with my significant other a great stay. Also his colleague that was with him was great. "
The price is P5,418
P7,184 total
includes taxes & fees
Feb 3 - Feb 4
Rod 'N' Reel Resort
Inn at Horn Point
Beach nearby

Inn at Horn Point

3.0 star property
9.6 out of 10, Exceptional, (18)
"I booked the trip to celebrate an anniversary weekend away with my husband. The property came up through a Yelp review so I checked it out. I was impressed with the location, the detail to cleanliness, and the commitment to the environment. Once I booked the room, the innkeepers were very helpful in offering things to do and places to eat, as well as offering to help make our anniversary stay more memorable. Once we arrived, Cory took the time to greet us as we came in and share some of the...
The price is P19,521
P22,253 total
includes taxes & fees
Jan 29 - Jan 30
Inn at Horn Point
Village Inn
TV

Village Inn

2.0 star property
6.2 out of 10, (469)
"Clean and cozy"
The price is P4,854
P5,534 total
includes taxes & fees
Jan 26 - Jan 27
Village Inn
Annapolis Waterfront Hotel, Autograph Collection
Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (787)
"Clean and comfortable hotel, friendly staff."
The price is P10,253
P11,688 total
includes taxes & fees
Feb 2 - Feb 3
Annapolis Waterfront Hotel, Autograph Collection
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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Frequently asked questions

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

Located 3.7 mi (6 km) from the heart of Highland Beach, Graduate by Hilton Annapolis is a top choice for your stay based on our traveler data. Two other options for your stay in the area are Crowne Plaza Annapolis, an IHG Hotel 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, you'll find most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it 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.

Where can I learn more about changing or cancelling my trip to Highland Beach?

For additional details about rescheduling or cancelling your trip to Highland Beach, head over to our customer service page.

What are some accommodations 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 parking. The Westin Annapolis and Courtyard by Marriott Bowie are a couple of other choices with an onsite pool. View all hotels with pools in Highland Beach.

What is staying in Highland Beach like?

Visitors to Highland Beach are sure to find plenty to explore and enjoy. There are 1145 hotels and other accommodations in the surrounding area. Find out more about Highland Beach.

What should I see while I'm in Highland Beach?

Places to visit in the wider area include Maryland Quiet Waters Park, Annapolis Maritime Museum, and Spa Creek. You'll also find Ego Alley and Annapolis City Dock in the area. Check out what more to see and do in Expedia's Highland Beach guide.

What's the seasonal weather like in Highland Beach?

The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Highland Beach is 52 inches.