Highland Beach Vacation Rentals

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Browse Select Highland Beach Vacation Homes

Our top choices for Highland Beach vacation homes

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $345
CA $578 total
includes taxes & fees
Aug 21 - Aug 22
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

The price is CA $299
CA $471 total
includes taxes & fees
Aug 21 - Aug 22
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

8.0 out of 10, Very good, (1)
"The property itself was very clean and cozy, and having our own private entry was also very nice. Towels and shower supplies were provided, and the bed was nice and comfortable. The host was also very kind and answered any questions we had. However, every morning we were woken up at around 7:30 am by someone (I assume children) stomping around right over our heads. There were also times we didn't really feel comfortable hanging out to watch TV in the living room area, because we could hear the...
The price is CA $125
CA $174 total
includes taxes & fees
Aug 21 - Aug 22
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is CA $153
CA $434 total
includes taxes & fees
Aug 27 - Aug 28
Relax on Kent Island in 3 Bedroom Home w/Waterview

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is CA $130
CA $405 total
includes taxes & fees
Aug 24 - Aug 25
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (16)
"Excellent"
The price is CA $114
CA $453 total
includes taxes & fees
Aug 24 - Aug 25
Beach Home with King Bed and Beach Passes in a Cute Town

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is CA $291
CA $651 total
includes taxes & fees
Aug 25 - Aug 26
The Cottage

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock

Lower Level Loft - Adorable Studio Apt. Near BWI

9.4 out of 10, Exceptional, (13)
"This property was perfect for a one night stay. It had everything we needed and was super cozy."
The price is CA $87
CA $171 total
includes taxes & fees
Sep 3 - Sep 4
Lower Level Loft - Adorable Studio Apt. Near BWI

Holly Hill Haven - Sleeps 10

10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
The price is CA $250
CA $753 total
includes taxes & fees
Aug 22 - Aug 23
Holly Hill Haven - Sleeps 10

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
The price is CA $279
CA $698 total
includes taxes & fees
Aug 22 - Aug 23
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (3)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is CA $261
CA $700 total
includes taxes & fees
Aug 25 - Aug 26
Charming Pet-Friendly Stay - Near Bay & Beaches.

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (28)
"Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. "
The price is CA $203
CA $652 total
includes taxes & fees
Aug 24 - Aug 25
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
The price is CA $319
CA $579 total
includes taxes & fees
Sep 15 - Sep 16
Bayside Cottage steps from Rock Hall Harbor

Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is CA $268
CA $660 total
includes taxes & fees
Aug 25 - Aug 26
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is CA $207
CA $525 total
includes taxes & fees
Aug 21 - Aug 22
Waterfront Getaway, Dock Your Boat & Play!

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (46)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is CA $276
CA $405 total
includes taxes & fees
Sep 8 - Sep 9
BAYSIDE BUNGALOW

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
The price is CA $222
CA $397 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Home in Beautiful Annapolis

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is CA $1,179
CA $1,918 total
includes taxes & fees
Aug 21 - Aug 22
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

London Towne Bungalow w/Loft - Walk to the Beach!

8.0 out of 10, Very good, (2)
"The water that comes out of the house tastes bad."
The price is CA $193
CA $650 total
includes taxes & fees
Aug 25 - Aug 26
London Towne Bungalow w/Loft - Walk to the Beach!
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