Holiday Rentals in Highland Beach

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Holiday Rentals in Highland Beach

Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
Stephanie S.
The price is €222
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (30)
"Nice and peaceful stay for a quick local getaway. "
Anthony R. M.
The price is €230
includes taxes & fees
21 Oct - 22 Oct
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Lower Level Loft - Adorable Studio Apt. Near BWI
9.4 out of 10, Exceptional, (13)
"This was great for our stay. Nice place to come back to at the end of the day. It’s in a quiet neighborhood and being a lower level there is no traffic noise either. Great communication with the host and the description of the listing is accurate. Enjoy!"
Jack B.
The price is €112
includes taxes & fees
27 Oct - 28 Oct
Lower Level Loft - Adorable Studio Apt. Near BWI
Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (16)
"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!"
Jennifer B.
The price is €331
includes taxes & fees
20 Oct - 21 Oct
Walk to Beach! King Bed & Free Beach Passes
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. "
Joe C.
The price is €360
includes taxes & fees
20 Oct - 21 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Historic Row Home 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (2)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
Tracie B.
Historic Row Home 1 Block from Gate 1 at USNA!
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
10.0 out of 10, Exceptional, (3)
"Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. "
Mark E.
The price is €376
includes taxes & fees
19 Oct - 20 Oct
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
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!"
Dorothy R.
The price is €310
includes taxes & fees
22 Oct - 23 Oct
Bayside Cottage steps from Rock Hall Harbor
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (71)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
Vincent W.
The price is €283
includes taxes & fees
4 Nov - 5 Nov
Cozy 2br home w/ parking in downtown Annapolis
Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (3)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
Ana S.
The price is €328
includes taxes & fees
28 Oct - 29 Oct
Luxury Pool Loft sleeps 4
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (51)
"Very quaint and quiet place to stay. Very relaxing."
Roger
The price is €265
includes taxes & fees
19 Oct - 20 Oct
BAYSIDE BUNGALOW
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (80)
"Clean, safe, joy and owners hospitality perfect"
Ahmet S.
The price is €434
includes taxes & fees
19 Oct - 20 Oct
Waterfront Oasis of Annapolis Star
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
Chris J.
The price is €464
includes taxes & fees
19 Oct - 20 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
New Downtown Annapolis Condo With Free Parking
10.0 out of 10, Exceptional, (31)
"The apartment is exactly what we expected and was a great place to stay! Highly recommend. "
Megan U.
The price is €325
includes taxes & fees
17 Nov - 18 Nov
New Downtown Annapolis Condo With Free Parking
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
10.0 out of 10, Exceptional, (30)
"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. "
Vicki K.
The price is €437
includes taxes & fees
19 Oct - 20 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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...
Zach N.
The price is €111
includes taxes & fees
25 Oct - 26 Oct
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
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! "
Brittnie A.
The price is €127
includes taxes & fees
19 Oct - 20 Oct
Modern New Suite Close to US Capital and BWI Airport
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
10.0 out of 10, Exceptional, (5)
"Great visit! Outstanding experience, beautiful houseboat, great views!"
Nathan M.
Bung-a-flo Tiny Bohemian Designed Floating Home w/ 360 Waterfront Views
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (5)
"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."
Kristina
Charming Pet-Friendly Stay - Near Bay & Beaches.
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!"
Tammy L.
The price is €448
includes taxes & fees
21 Oct - 22 Oct
Cute bungalow blocks to Stadium
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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Find out more about Highland Beach

Everything you need to know about Highland Beach holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highland Beach holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland Beach holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland Beach holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland Beach. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland Beach holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland Beach holiday rentals we have selected for you start as low as €72 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland Beach rentals

At Expedia, we put the best Highland Beach holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Highland Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland Beach holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Highland Beach offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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

Chesapeake Bay and Northern Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Bay Ridge Beach and Maryland Quiet Waters Park.

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.