Holiday Rentals in Highland Beach

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Holiday Rentals in Highland Beach

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

9.6 out of 10, Exceptional, (9)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is €371
includes taxes & fees
9 Jul - 10 Jul
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

#2 Egret Cottage Harris Cove

The price is €333
includes taxes & fees
24 Jul - 25 Jul
#2 Egret Cottage Harris Cove

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is €729
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6

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 €372
includes taxes & fees
21 Jul - 22 Jul
Bayside Cottage steps from Rock Hall Harbor

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (41)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is €262
includes taxes & fees
9 Jul - 10 Jul
BAYSIDE BUNGALOW

Room for an Island getaway

2.0 star property
9.0 out of 10, Wonderful, (2)
"Was a nice place for the night we were there. It had everything we needed for the night"
The price is €188
includes taxes & fees
9 Jul - 10 Jul
Room for an Island getaway

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

9.6 out of 10, Exceptional, (28)
"Great place and location. Not far from good food and local hot spots. Would definitely rebook and stay here again. "
The price is €288
includes taxes & fees
13 Jul - 14 Jul
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is €293
includes taxes & fees
14 Jul - 15 Jul
Relax on Kent Island in 3 Bedroom Home w/Waterview

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 €1,219
includes taxes & fees
14 Jul - 15 Jul
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is €1,137
includes taxes & fees
14 Jul - 15 Jul
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (1)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is €450
includes taxes & fees
9 Jul - 10 Jul
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is €714
includes taxes & fees
15 Jul - 16 Jul
Charming Cottage with Hot Tub 1 Block from the Bay

Neptune by the Water

9.8 out of 10, Exceptional, (9)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is €424
includes taxes & fees
9 Jul - 10 Jul
Neptune by the Water

Charming Historic Row House in The Heart of Eastport's Horn Point

2.5 star property
10.0 out of 10, Exceptional, (1)
"Gorgeous little house in the heart of Eastport, walking distance to fabulous restaurants and a short hop over the bridge to dwtn Annapolis. The house was clean, well stocked, comfy beds, and the patio was a lovely little oasis to kick back in with a glass of wine at the end of the day. The host was very responsive and accommodating. Highly recommend! "
The price is €492
includes taxes & fees
21 Jul - 22 Jul
Charming Historic Row House in The Heart of Eastport's Horn Point

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is €567
includes taxes & fees
9 Jul - 10 Jul
Annapolis Retreat - 7 mins from downtown Annapolis!

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

10.0 out of 10, Exceptional, (26)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is €360
includes taxes & fees
9 Jul - 10 Jul
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

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

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is €415
includes taxes & fees
9 Jul - 10 Jul
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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

10.0 out of 10, Exceptional, (14)
"We had everything we needed in this townhome in North Beach. Nicely decorated, clean and the beds were comfortable! Perfect spot for our girl's weekend."
Beach Home with King Bed and Beach Passes in a Cute Town

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is €394
includes taxes & fees
9 Jul - 10 Jul
The Cottage

Historic Row Home 1 Block from Gate 1 at USNA!

The price is €648
includes taxes & fees
14 Jul - 15 Jul
Historic Row Home 1 Block from Gate 1 at USNA!
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

Can I find a holiday rental in Highland Beach?

Yes, there are holiday rentals close to the most popular sights in Highland Beach, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Highland Beach has to offer?

The Cozy Crab- Your Charming Haven in Lovely North Beach!: This holiday home rental outside of Highland Beach offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What’s there to see and do in Highland Beach?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Bay Ridge Beach. In the wider area, you’ll find Maryland Quiet Waters Park and Annapolis Landing Marina.

What’s a holiday rental in Highland Beach like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland Beach. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a family trip.