Search Vacation Homes in Highland Beach

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Dec 26 - Dec 28
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Jan 16 - Jan 18
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Feb 13 - Feb 15

Our top choices for Highland Beach vacation homes

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

Vacation Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
$248 nightly
The price is $263
Dec 21 - Dec 22
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Beach nearby
Walk to Beach! King Bed & Free Beach Passes

Vacation Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (17)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
$273 nightly
The price is $301
Dec 16 - Dec 17
Total with taxes and fees
Walk to Beach! King Bed & Free Beach Passes
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$219 nightly
The price is $233
Dec 16 - Dec 17
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Vacation Home in North Beach

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
$364 nightly
The price is $402
Dec 16 - Dec 17
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Fridge, microwave, oven, stovetop
Modern New Suite Close to US Capital and BWI Airport

Vacation Home in Pasadena

Modern New Suite Close to US Capital and BWI Airport
7.0 out of 10, Good, (2)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
United States
Brittnie A.
$139 nightly
The price is $158
Jan 6 - Jan 7, 2026
Total with taxes and fees
Modern New Suite Close to US Capital and BWI Airport
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
$473 nightly
The price is $503
Dec 16 - Dec 17
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
Smart TV, fireplace
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Vacation Home in Glen Burnie

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
8.0 out of 10, Very Good, (2)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
$110 nightly
The price is $125
Dec 16 - Dec 17
Total with taxes and fees
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Outdoor pool
Secluded Tiny Pool House -Private Pool -Self Check in

Vacation Home in Glen Burnie

Secluded Tiny Pool House -Private Pool -Self Check in
8.8 out of 10, Excellent, (9)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
United States
Robert F.
$129 nightly
The price is $147
Dec 16 - Dec 17
Total with taxes and fees
Secluded Tiny Pool House -Private Pool -Self Check in
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
$493 nightly
The price is $562
Dec 16 - Dec 17
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Vacation Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (7)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
$459 nightly
The price is $519
Dec 16 - Dec 17
Total with taxes and fees
Cute bungalow blocks to Stadium
Exterior
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Vacation Home in Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (4)
"Would stay here again "
United States
Thomas D.
$371 nightly
The price is $423
Dec 16 - Dec 17
Total with taxes and fees
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Vacation Home in Rock Hall

Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
$257 nightly
The price is $272
Dec 18 - Dec 19
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Vacation Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$390 nightly
The price is $413
Dec 16 - Dec 17
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Vacation Home in Glen Burnie

The Hideaway Spot- Waterfront w/ Dock on Long Cove
8.6 out of 10, Excellent, (8)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
$305 nightly
The price is $348
Dec 16 - Dec 17
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$262 nightly
The price is $278
Jan 1 - Jan 2, 2026
Total with taxes and fees
BAYSIDE BUNGALOW
TV, books, offices
Holly Hill Haven - Sleeps 10

Vacation Home in Edgewater

Holly Hill Haven - Sleeps 10
10.0 out of 10, Exceptional, (3)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
$476 nightly
The price is $507
Jan 13 - Jan 14, 2026
Total with taxes and fees
Holly Hill Haven - Sleeps 10
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Vacation Home in Arnold

Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
$285 nightly
The price is $324
Dec 16 - Dec 17
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Vacation Home in Homewood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
$402 nightly
The price is $458
Dec 16 - Dec 17
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Interior
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!

Vacation Home in Historic District

Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$622 nightly
The price is $709
Dec 16 - Dec 17
Total with taxes and fees
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Vacation Home in Arundel on the Bay

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$484 nightly
The price is $552
Dec 19 - Dec 20
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community 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

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 Vacation Homes information

Number of reviews
286
Accommodation
636 Vacation Homes
Lowest Price
$125
Highest Price
$709

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