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Highland Beach Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Highland Beach holiday rentals

A building with a gabled roof and a circular vent on the roof.

1. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is NZ$546
includes taxes & fees
13 Oct - 14 Oct
BAYSIDE BUNGALOW
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

2. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is NZ$519
includes taxes & fees
5 Oct - 6 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A bedroom with a bed, a chair, a bedside table with a lamp, a picture on the wall, and a window with curtains.

3. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is NZ$541
includes taxes & fees
5 Oct - 6 Oct
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A wooden dock extending into a calm body of water with boats docked at the end.

4. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is NZ$759
includes taxes & fees
5 Oct - 6 Oct
Cozy 2br home w/ parking in downtown Annapolis
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

5. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is NZ$886
includes taxes & fees
14 Oct - 15 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A lighthouse with a white exterior, a balcony, and a metal roof.

6. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is NZ$524
includes taxes & fees
4 Oct - 5 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A covered outdoor area with a view of the water, a wicker chair, a table with a plant, and a sofa with pillows.

7. Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (78 reviews)
"Our family had a wonderful stay at your beautiful home! The views are to die for! House was very clean with all equipment and kitchen appliances all available! Very happy with our stay! "
United States
Whitney M.
The price is NZ$1,305
includes taxes & fees
1 Oct - 2 Oct
Charming Annapolis WaterVIEW Home
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

8. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.8 out of 10, Exceptional, (13 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is NZ$1,066
includes taxes & fees
4 Oct - 5 Oct
Renovated Bungalow | Walk to Beach | Dog-Friendly
A sunroom with a dining table, chairs, a sofa, and a chessboard.

9. Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (34 reviews)
"Great place to stay, would book it again, "
United States
Kim M.
The price is NZ$688
includes taxes & fees
8 Oct - 9 Oct
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

10. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is NZ$597
includes taxes & fees
4 Oct - 5 Oct
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

11. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (22 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is NZ$373
includes taxes & fees
12 Oct - 13 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

12. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is NZ$1,027
includes taxes & fees
6 Oct - 7 Oct
Sunset Cottage - West River Access and Views!
A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

13. Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.0 out of 10, Wonderful, (20 reviews)
"This was an adorable little place, perfect for my husband and I. With a few minor tweaks and upgrades, this would easily be a five star stay. I would happily stay here again. Thank you!"
United States
Deanna
The price is NZ$203
includes taxes & fees
25 Oct - 26 Oct
Lower Level Loft - Adorable Studio Apt. Near BWI
Three birds perched on a wooden structure by the water.

14. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is NZ$2,449
includes taxes & fees
13 Oct - 14 Oct
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A house with a deck, a fire pit, and blue Adirondack chairs.

15. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is NZ$547
includes taxes & fees
1 Oct - 2 Oct
Lakefront Home Firepit BWI Marleycreek River
A modern kitchen with dark cabinets, a white countertop, and a large window.

16. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
The price is NZ$471
includes taxes & fees
8 Oct - 9 Oct
Cass-N-Reel Luxury Houseboat
A two-story house with a covered patio, a garage, and a well-maintained lawn.

17. Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (55 reviews)
"Great stay in Annapolis. The property is gorgeous. Everything you need for a great weekend in Annapolis. "
United States
Jennifer G.
The price is NZ$961
includes taxes & fees
19 Oct - 20 Oct
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

18. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is NZ$2,449
includes taxes & fees
13 Oct - 14 Oct
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A swimming pool with lounge chairs, a brick patio, and a house in the background.

19. Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21

Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21
Severn
9.6 out of 10, Exceptional, (37 reviews)
"This was a weekend celebrating our son's retirement from the Navy. The weather and accommodations were great. The family loved the big yard, front and back, and the pool. We would gladly rent it again if we could get our whole family together."
United States
Perry S.
The price is NZ$1,570
includes taxes & fees
4 Oct - 5 Oct
Large Home w/ Pool, Gym, 7 Bedrooms, Sleeps 21
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

20. Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (41 reviews)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is NZ$582
includes taxes & fees
1 Oct - 2 Oct
Large 2 bedroom house with private parking in a nice neighborhood
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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Really nice layout. Large TV. Kitchenette included garbage disposal & small dishwasher. Exterior had a pool, basketball court, fire pit & nice grill in shared area. Really convenient - highly recommend!"
Judith 2-night trip
Posted 1 hour ago
Sonesta ES Suites Annapolis

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, 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 NZ$373 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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Highland Beach is located near the beach, and has a fireplace, a balcony 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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

Northern Chesapeake Bay and 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.