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Dec 26 - Dec 28
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Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Highland Beach cottages

Exterior detail
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
2.0 star property
North Beach
9.6 out of 10, Exceptional, (4)
"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"
United States
Jana S.
$260 nightly
The price is $276
Jan 1 - Jan 2, 2026
Total with taxes and fees
Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.
Property grounds
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$802 nightly
The price is $885
Dec 18 - Dec 19
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Marina
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (16)
"We had a very lovely stay . This is an excellent location . "
United States
Kimberly B.
$447 nightly
The price is $510
Dec 16 - Dec 17
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Dec 16 - Dec 17
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Room was clean The staff was excellent.we were greeted each morning with a smile when we came down for coffee. Great service from Sarah in the evening "
Teresa 2-night trip
Posted 9 hours ago
Hilton Garden Inn Kent Island Marina

Find out more about Highland Beach

Highland Beach Cottages information

Number of reviews
19
Accommodation
91 Cottages
Lowest Price
$276
Highest Price
$885

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