Highland Beach, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Highland Beach, Maryland on RentalSaver.com!

Highland Beach Rentals

From $308 per night (USD)
VRBO
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This upscale 2 bedroom, 1 bathroom water view cottage is located in a private beach community off of the Chesapeake Bay ...
From $308 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Private Cottage on gated estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapo ...
From $249 per night (USD)
Expedia
From $152 per night (USD)
VRBO
Private Apartment - Minutes to USNA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Entire home You’ll have the apartment to yourself. Great location 100% of recent guests gave the location a 5-star ratin ...
From $152 per night (USD)
VRBO
From $605 per night (USD)
Expedia
Book for CW 2025 Water views from one-level dog-friendly home with screened porch and backyard
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Still Available for Commissioning Week 2025! Escape to a tranquil waterfront retreat with stunning views of the Chesape ...
From $605 per night (USD)
Expedia
From $837 per night (USD)
VRBO
WATERFRONT Historic Home on the Chesapeake Bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
WATERFRONT - Beautiful 4 bedroom, 2 1/2 bathrooms newly renovated charming historic home ON the Chesapeake Bay. New mode ...
From $837 per night (USD)
VRBO
Click For Pricing
Expedia
Annapolis House
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Traditional 4 bedroom house in neighborhood with loft. Lots of room to move around in with gated back yard. Only 3 mi ...
Click For Pricing
Expedia
Click For Pricing
Expedia
Studio, water community, private entrance, paver patio, off street parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Cozy studio, water access community with oversized windows facing large fenced yard with private paver patio, private en ...
Click For Pricing
Expedia
From $563 per night (USD)
Expedia
Water Views - Close to Downtown Annapolis
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city onl ...
From $563 per night (USD)
Expedia
$Annapolis Cozy Beachfront\/Waterfront w\/Chesapeake Bay Bridge view$
From $612 per night (USD)
VRBO
Annapolis Cozy Beachfront\/Waterfront w\/Chesapeake Bay Bridge view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Annapolis Beachfront w/Bay Bridge view - Wake up to a beautiful view of the sunrise over the Chesapeake Bay. Go to sleep ...
From $612 per night (USD)
VRBO
From $1038 per night (USD)
Expedia
Water-view escape with WFH desk & entertainer's deck - dog-friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Cardinal's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1038 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Pet-Friendly Annapolis Home: Walk to Beach!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Experience the perfect blend of comfort and adventure at this 3-bed, 2-bath Annapolis vacation rental! Start your day wi ...
From $410 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Cozy Cottage with Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Perfect for groups of 4 wanting to be near Annapolis and the Chesapeake Bay, but far enough away for peace, quiet, and e ...
From $399 per night (USD)
Expedia
From $1042 per night (USD)
VRBO
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to The Yellow Annapolis Cottage: A Chesapeake Getaway with Stunning Bay Views Welcome to The Yellow Annapolis C ...
From $1042 per night (USD)
VRBO
From $766 per night (USD)
Expedia
Charming Annapolis WaterVIEW Home
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters o ...
From $766 per night (USD)
Expedia
From $828 per night (USD)
VRBO
Private Waterfront Woods | Dock, Kayaks, Views
Bedrooms:
4
Bathrooms:
5
Sleeps:
19
Welcome to The Compass Rose, a serene haven with backyard shoreline surrounded by 4+ acres of pristine woods. Enjoy excl ...
From $828 per night (USD)
VRBO
$Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w\/private dock\/pier\/ private pool and kayaks.$
From $1256 per night (USD)
VRBO
Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w\/private dock\/pier\/ private pool and kayaks.
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
STR259 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1256 per night (USD)
VRBO
From $685 per night (USD)
VRBO
Coastal Cottage - 3 BR -Retreat Near Annapolis | Bay Views | Beach Access
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
STR-000324 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $685 per night (USD)
VRBO
From $1246 per night (USD)
Expedia
RARELY AVAILABLE FOR COMMISSIONING WEEK! Complete WATERFRONT LIVING!
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
STR-250 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1246 per night (USD)
Expedia
From $733 per night (USD)
VRBO
DISCOUNTED FOR USNA COMMISSIONING WEEK 2024 and 2025! Short term and weekends.
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Beautiful, remodeled 3 BR home with stunning great room addition, 20' x 20' screened, covered porch with newly added out ...
From $733 per night (USD)
VRBO
From $2907 per night (USD)
VRBO
Nantucket on the Chesapeake Heated Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy comfort and convenience in this beautifully-appointed home! Nantucket on the Chesapeake has an old-world feel yet ...
From $2907 per night (USD)
VRBO
From $597 per night (USD)
VRBO
Chesapeake Bay single family home
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Quaint community of Arundel on the Bay in Annapolis, Maryland. Spacious 4 bedroom, 3.5 bathrooms in 3000 s.f. waterfront ...
From $597 per night (USD)
VRBO
From $553 per night (USD)
Expedia
Charming Cottage with Hot Tub 1 Block from the Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy Annapolis with family & friends all year at this fully stocked and freshly renovated cottage just a block from the ...
From $553 per night (USD)
Expedia
From $1110 per night (USD)
VRBO
Bay Ridge Beauty with Wooded Serenity and Community Water Views
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
STR00711 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $1110 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Available for Commissioning Week 2025! Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks Welcome to the ...
From $759 per night (USD)
Expedia
Click For Pricing
VRBO
Stunning Waterfront Home with Incredible Views
Bedrooms:
6
Bathrooms:
5
Sleeps:
15
Perfect home for a family getaway, Commissioning Week or Boat Show event. Room for all to sleep, gather and play in thi ...
Click For Pricing
VRBO
From $1388 per night (USD)
Expedia
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
Summary: Located only 5 miles from Annapolis, this newly updated, 3-story home with great views of the Chesapeake Bay is ...
From $1388 per night (USD)
Expedia
$Cozy 3-bdrm home in Annapolis. Steps away from the beach\/4.7 miles to downtown.$
From $439 per night (USD)
VRBO
Cozy 3-bdrm home in Annapolis. Steps away from the beach\/4.7 miles to downtown.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3-bedroom bungalow in Annapolis is perfect for your escape. With 2 full beds and 1 full sofa bed in the 3rd room. I ...
From $439 per night (USD)
VRBO
$Commissioning Week by the Bay! 2027\/8 Available!$
From $1010 per night (USD)
Expedia
Commissioning Week by the Bay! 2027\/8 Available!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Available for CW 2027-2028 at $7,700. 5 bedroom, 3.5 bath located 5 miles from Gate 1 in the waterfront community of Aru ...
From $1010 per night (USD)
Expedia
$Entire house on quiet street w\/fenced yard—1 block from river, 3 from bay$
From $424 per night (USD)
VRBO
Entire house on quiet street w\/fenced yard—1 block from river, 3 from bay
Bedrooms:
4
Bathrooms:
2
Sleeps:
6
Arundel-on-the-Bay is a private community on Annapolis Neck peninsula, and this home sits right in the middle. Ideal sp ...
From $424 per night (USD)
VRBO
From $783 per night (USD)
Expedia
Oyster Harbor Waterfront Vacation Home -- Private Dock and Backyard
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Spacious and luxurious vacation home in Oyster Harbor, Annapolis. Features 4 bedrooms (7 beds), 3 full baths. A lively o ...
From $783 per night (USD)
Expedia
From $792 per night (USD)
VRBO
BY THE BAY
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
WATER, WATER everywhere! Our home is centrally located to all the water Bay Ridge has to offer. Our home is located jus ...
From $792 per night (USD)
VRBO
From $160 per night (USD)
Expedia
Private Cottage in quiet Annapolis Bay Front Community
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Quaint cottage in Bay front community 4 miles from Historic Downtown Annapolis! Cozy living space, fully equipped kitch ...
From $160 per night (USD)
Expedia
From $1303 per night (USD)
VRBO
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Annapolis Bay Ridge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $1303 per night (USD)
VRBO
Click For Pricing
Expedia
Waterfront Beach House with amazing views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The perfect place to experience amazing sunrise/sunset views on the water, beach within walking distance, restaurants, d ...
Click For Pricing
Expedia
From $1040 per night (USD)
VRBO
Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard
Bedrooms:
5
Bathrooms:
8
Sleeps:
16
Base Camp on the Lake Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1040 per night (USD)
VRBO
From $1374 per night (USD)
Expedia
Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
The Morning Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1374 per night (USD)
Expedia
$Lakefront home with private pool, hot tub, outdoor space, central AC, & W\/D$
From $1951 per night (USD)
VRBO
Lakefront home with private pool, hot tub, outdoor space, central AC, & W\/D
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
The Admiral's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1951 per night (USD)
VRBO
From $544 per night (USD)
Expedia
Annapolis Retreat - 7 mins from downtown Annapolis!
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Welcome to this charming five-bedroom, two-bathroom escape nestled in the Hillsmere Shores neighborhood of Annapolis. Ju ...
From $544 per night (USD)
Expedia
From $678 per night (USD)
VRBO
Waterfront Getaway - Dock UR Boat & Walk to Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Luxurious Waterfront Escape in Annapolis ◉ Private Beach Access: Step right onto the shore for a peaceful retreat ◉ Arch ...
From $678 per night (USD)
VRBO
$Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W\/D$
From $697 per night (USD)
Expedia
Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W\/D
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
The Salty Crab Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $697 per night (USD)
Expedia
$Waterfront Estate w\/ Private Beach + Dock$
From $2280 per night (USD)
VRBO
Waterfront Estate w\/ Private Beach + Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Private Nantucket style waterfront estate w/ beach, deep water slips and a 180 waterview. Expansive western sunsets on F ...
From $2280 per night (USD)
VRBO
$Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1\/2 bathrooms.$
Click For Pricing
Expedia
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1\/2 bathrooms.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozy cottage in a serene setting. A week spent in this cottage will decompress, reset, and rejuvenate. 100 year old Cott ...
Click For Pricing
Expedia
$Sunny and spacious water view\/access home in Annapolis.$
From $538 per night (USD)
VRBO
Sunny and spacious water view\/access home in Annapolis.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The property is all set up for boating and fishing with a drive-thru driveway. It is located one block from the boat ram ...
From $538 per night (USD)
VRBO
From $953 per night (USD)
Expedia
Captain's Retreat! Newly Renovated - few steps from the beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay! Steps to the Beach and ...
From $953 per night (USD)
Expedia
From $1561 per night (USD)
VRBO
3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
Bedrooms:
7
Bathrooms:
6
Sleeps:
15
Bella Chateau Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1561 per night (USD)
VRBO
From $1915 per night (USD)
Expedia
Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock
Bedrooms:
6
Bathrooms:
8
Sleeps:
18
Waterside with it All Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1915 per night (USD)
Expedia
$Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W\/D$
From $1179 per night (USD)
VRBO
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W\/D
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
The Ship's Bridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1179 per night (USD)
VRBO
$Spacious home with an outdoor pool, screened porch, washer\/dryer & central AC$
From $1351 per night (USD)
Expedia
Spacious home with an outdoor pool, screened porch, washer\/dryer & central AC
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Thomas Point Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $1351 per night (USD)
Expedia
From $480 per night (USD)
VRBO
Spacious home with bay views, deck, balcony and gas grill
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Oyster Harbor Waterview Home Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $480 per night (USD)
VRBO
From $860 per night (USD)
Expedia
Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This clean, peaceful, 5 BR, 4 BA house features a waterfront view from 2 spacious decks in a quiet community. Perfect fo ...
From $860 per night (USD)
Expedia

Search Your Destination Now!

Highland Beach Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 50 Rentals