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Find a Bed and Breakfast in Highland Beach from CA $220

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Highland Beach bed & breakfast

A room with a dark blue wall, a fireplace with lit candles, a leather armchair, and a bookshelf with decorative items.

1. Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (100 reviews)
"Charming and picturesque house steps from all of the best things about Annapolis."
United States
Thomas
The price is CA $308
CA $351 total
includes taxes & fees
Nov 11 - Nov 12
Flag House Inn
Land view from property

2. Laurel Grove Inn on the South

Laurel Grove Inn on the South
3.5 star property
Annapolis
9.4 out of 10, Exceptional, (536 reviews)
"I stayed here with my daughter the night before a lacrosse tournament at the Naval Academy. Beautiful property, excellent host. I will definitely stay here again! Thank you!"
United States
Michael
The price is CA $254
CA $290 total
includes taxes & fees
Nov 12 - Nov 13
Laurel Grove Inn on the South
A boat deck with a white bench and a view of a calm lake and distant trees.

3. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
The price is CA $198
CA $220 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Huntingfield Creek
A residential street with parked cars, a sidewalk, and a tree.

4. Charming Living room in beautiful Annapolis with AC discount long stay

Charming Living room in beautiful Annapolis with AC discount long stay
Historic District
2.0 out of 10, (1 review)
"Place was a bedroom inside the owners townhouse. It is a shared living area. It was messy with stuff thrown around everywhere. It was dirty and musty. Strong unbearable odor. The bedroom for rent was in disarray, stuff on the bed and floors. Owner said previous occupants had left their luggage but there were things all over. Laptop and computer table on the bed, bed in disarray, clothes on the floor. Very dirty space, not suitable for rental. Owner said I didn't have to stay if I...
United States
Lee
The price is CA $240
CA $446 total
includes taxes & fees
Nov 16 - Nov 17
Charming Living room in beautiful Annapolis with AC discount long stay
A hot tub in a grassy area with a building in the background.

5. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (20 reviews)
"The owners are very friendly and accommodating. Relaxing getaway"
United States
kristine
The price is CA $420
CA $479 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Tacaro Estate
A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

6. Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (139 reviews)
"The staff were great. The breakfast was delicious and the location is perfect for walking into town."
United States
Susan
The price is CA $325
CA $357 total
includes taxes & fees
Nov 13 - Nov 14
Parsonage Inn
A two-story house with a swimming pool, outdoor seating, and a covered patio area.

7. George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (78 reviews)
"This weekend was an anniversary gift for my daughter and her husband. They had a wonderful time and were highly complimentary of the accommodations, the delicious breakfast and the location."
United States
Erin
The price is CA $253
CA $278 total
includes taxes & fees
Nov 12 - Nov 13
George Brooks House B&B
An outdoor patio with seating, a table, and a blue umbrella.

8. Carib Comfort B and B

Carib Comfort B and B
3.0 star property
Upper Marlboro
The price is CA $277
CA $313 total
includes taxes & fees
Nov 13 - Nov 14
Carib Comfort B and B
A staircase with a white and gold design, a living room with a grey sofa, and a decorative console table.

9. Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families

Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
Glenn Dale
6.4 out of 10, (6 reviews)
"Easy to find, easy to get in, spacious "
United States
Anonymous traveller
The price is CA $583
CA $1,495 total
includes taxes & fees
Nov 11 - Nov 12
Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families
A spacious living room with a high arched window, a white sofa, a glass coffee table, and a large plant.

10. Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway

Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
Glenn Dale
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful big house. Two of the light fixtures didn't work but it didn't really affect our experience."
United States
Natalia L.
The price is CA $520
CA $1,331 total
includes taxes & fees
Nov 11 - Nov 12
Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway
A house with a porch, a red umbrella, and a garden with pink flowers.

11. Inn at Horn Point

Inn at Horn Point
3.0 star property
Eastport
9.2 out of 10, Wonderful, (25 reviews)
"Very comfortable"
United Kingdom
JOHN
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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Top Highland Beach Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"The hot tub was broken. But the staff was helpful, the rooms were big and clean"
Brian 1-night trip
Posted 13 hours ago
Crowne Plaza Annapolis by IHG

Find out more about Highland Beach

Highland Beach B&B information

Number of reviews
799
Accommodation
14 B&B
Lowest Price
CA $220
Highest Price
CA $1,495

Frequently asked questions

Searching for B&Bs in Highland Beach?
If you're looking for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your trip. When you want to explore some attractions in town, Northern Chesapeake Bay and Chesapeake Bay are worth a stop.
Why would you choose a B&B over a traditional hotel room?
With attentive service, opportunities to mingle with other guests, and top-rated breakfasts, B&Bs all have a one-of-a-kind environment.
What are the best B&Bs in Highland Beach?
Below are some well-liked B&Bs in the surrounding area: Flag House Inn: 5 rooms. 3.5 mi (5.7 km) from the heart of Highland Beach. Enjoy the unique décor and fireplace in the lobby. George Brooks House B&B: 6 rooms. 15.8 mi (25.4 km) from the downtown core. Enjoy the library and fireplace in the lobby. Laurel Grove Inn on the South: 5 rooms. Situated 6.7 mi (10.8 km) from the heart of Highland Beach. Enjoy the deli and arcade game room. Inn at Huntingfield Creek: 12 rooms. 17.9 mi (28.7 km) from the heart of downtown. Enjoy the local cuisine breakfast and jetted tubs. Parsonage Inn: 8 rooms. Located 16.2 mi (26.1 km) from the core of Highland Beach. Enjoy the free full breakfast and unique décor.
What's the best time of year to book my B&B in Highland Beach?
When you're dreaming of a escape to Highland Beach, year-round temperatures and rainfall may be important factors to consider. 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.
What is there to do in Highland Beach?
Spend some time exploring Northern Chesapeake Bay and Chesapeake Bay if you're hoping to see some of the area's natural features. Bay Ridge Beach and Maryland Quiet Waters Park are also some sites to visit if you want to see more of the area.
How can I get to and around Highland Beach?
Planning your excursions in and around Highland Beach is easier with these transportation options. Fly into Fort Meade, MD (FME-Tipton), which is located 19.2 mi (30.9 km) away from the city center. Otherwise, you can search for flights to Baltimore Washington Intl. Airport (BWI), which is 20.4 mi (32.8 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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