Highland Beach Holiday Rentals

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Holiday Rentals in Highland Beach

Charming Home Away From Home

2.0 star property
9.4 out of 10, Exceptional, (6)
"My family and I stayed here over the weekend while visiting Gambrills and really enjoyed our stay. The hosts were very responsive and accommodating. It was exactly the type of space we needed. The apartment was clean and nicely furnished. Very comfortable! We would definitely stay again."
The price is NZ$535
includes taxes & fees
31 July - 1 Aug
Charming Home Away From Home

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is NZ$547
includes taxes & fees
23 July - 24 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Lower Level Loft - Adorable Studio Apt. Near BWI

9.4 out of 10, Exceptional, (12)
"This property was perfect for a one night stay. It had everything we needed and was super cozy."
The price is NZ$210
includes taxes & fees
31 July - 1 Aug
Lower Level Loft - Adorable Studio Apt. Near BWI

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. "
The price is NZ$1,353
includes taxes & fees
24 July - 25 July
Gorgeous Creek Side Ranch-Style Estate With Dock

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 NZ$796
includes taxes & fees
18 July - 19 July
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

❤️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 NZ$610
includes taxes & fees
3 Aug - 4 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

The Cottage

10.0 out of 10, Exceptional, (6)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is NZ$759
includes taxes & fees
28 July - 29 July
The Cottage

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!"
Bayside Cottage steps from Rock Hall Harbor

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 NZ$710
includes taxes & fees
17 July - 18 July
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Dean Street's Lower Deck House!

The price is NZ$755
includes taxes & fees
3 Aug - 4 Aug
Dean Street's Lower Deck House!

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 NZ$211
includes taxes & fees
30 July - 31 July
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

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 NZ$853
includes taxes & fees
21 July - 22 July
Charming Pet-Friendly Stay - Near Bay & Beaches.

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
The price is NZ$479
includes taxes & fees
21 July - 22 July
Cozy Home in Beautiful Annapolis

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 NZ$506
includes taxes & fees
17 July - 18 July
BAYSIDE BUNGALOW

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

10.0 out of 10, Exceptional, (15)
"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."
The price is NZ$713
includes taxes & fees
21 July - 22 July
Beach Home with King Bed and Beach Passes in a Cute Town

3 BR Pet Friendly Beverly Beach Cottage

9.8 out of 10, Exceptional, (7)
" Retreating from a construction project in our home, we landed in Grandma's Cottage. What a delightful semi-vactation. Lovely cottage, kind and friendly commuity srrouned by water and nature parks."
The price is NZ$773
includes taxes & fees
17 July - 18 July
3 BR Pet Friendly Beverly Beach Cottage

Modern New Suite Close to US Capital and BWI Airport

10.0 out of 10, Exceptional, (1)
"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! "
The price is NZ$586
includes taxes & fees
22 July - 23 July
Modern New Suite Close to US Capital and BWI Airport

Waterfront Camper with Dock

10.0 out of 10, Exceptional, (1)
"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 NZ$574
includes taxes & fees
17 July - 18 July
Waterfront Camper with Dock

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
The price is NZ$953
includes taxes & fees
30 July - 31 July
Cute bungalow blocks to Stadium

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 NZ$2,219
includes taxes & fees
29 July - 30 July
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Highland Beach is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.