Airbnb, Vacation Rentals in Chesapeake Beach, VA

Compare 374 available beachfront holiday vacation home properties, starts from $30

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Find the best vacation rental

ACCOMMODATION TYPES

Save Up To 82%

Airbnb, Vacation rentals and hotel deals in Chesapeake Beach, VA

Waterfront House with Private Dock and Fishing
Waterfront House with Private Dock and Fishing
Waterfront House with Private Dock and Fishing
Waterfront House with Private Dock and Fishing
10 (1 review)
Waterfront House with Private Dock and Fishing
Holiday home · 2 Guests · 1 Bedroom
$240 /night*
View deal
SPECTACULAR CORNER UNIT - Direct Waterfront Condo in Crisfield, Md
SPECTACULAR CORNER UNIT - Direct Waterfront Condo in Crisfield, Md
SPECTACULAR CORNER UNIT - Direct Waterfront Condo in Crisfield, Md
SPECTACULAR CORNER UNIT - Direct Waterfront Condo in Crisfield, Md
9.8 (197 reviews)
SPECTACULAR CORNER UNIT - Direct Waterfront Condo in Crisfield, Md
Condo · 2 Guests · 1 Bedroom
$175 /night*
View deal
Enjoy the Great Wicomico River
Enjoy the Great Wicomico River
Enjoy the Great Wicomico River
Enjoy the Great Wicomico River
9.4 (18 reviews)
Enjoy the Great Wicomico River
Holiday home · 2 Guests · 1 Bedroom
$230 /night*
View deal
Bright Reedville Abode w/ Dock on Whays Creek!
Bright Reedville Abode w/ Dock on Whays Creek!
Bright Reedville Abode w/ Dock on Whays Creek!
Bright Reedville Abode w/ Dock on Whays Creek!
9.6 (13 reviews)
Bright Reedville Abode w/ Dock on Whays Creek!
Cottage · 2 Guests · 1 Bedroom
$183 /night*
View deal
Sunrise Cottage with stunning views of the Chesapeake Bay
Sunrise Cottage with stunning views of the Chesapeake Bay
Sunrise Cottage with stunning views of the Chesapeake Bay
Sunrise Cottage with stunning views of the Chesapeake Bay
9.6 (54 reviews)
Sunrise Cottage with stunning views of the Chesapeake Bay
Holiday home · 2 Guests · 1 Bedroom
$267 /night*
View deal
Waterfront property with long pier. Pet friendly, family friendly
Waterfront property with long pier. Pet friendly, family friendly
Waterfront property with long pier. Pet friendly, family friendly
Waterfront property with long pier. Pet friendly, family friendly
10 (3 reviews)
Waterfront property with long pier. Pet friendly, family friendly
Holiday home · 2 Guests · 1 Bedroom
$299 /night*
View deal
Pet-friendly Weems Retreat w/ Grill & Views!
Pet-friendly Weems Retreat w/ Grill & Views!
Pet-friendly Weems Retreat w/ Grill & Views!
Pet-friendly Weems Retreat w/ Grill & Views!
Pet-friendly Weems Retreat w/ Grill & Views!
Cottage · 2 Guests · 1 Bedroom
$203 /night
View deal
Country Getaway in Kinsale: Sunroom, Pond Access!
Country Getaway in Kinsale: Sunroom, Pond Access!
Country Getaway in Kinsale: Sunroom, Pond Access!
Country Getaway in Kinsale: Sunroom, Pond Access!
Country Getaway in Kinsale: Sunroom, Pond Access!
Holiday home · 2 Guests · 1 Bedroom
$104 /night*
View deal
Swanendele Inn
Swanendele Inn
Swanendele Inn
Swanendele Inn
10 (3 reviews)
Swanendele Inn
Accommodation · 2 Guests · 1 Bedroom
$295 /night
View deal
Magnolia Cottage a beautiful waterfront getaway
Magnolia Cottage a beautiful waterfront getaway
Magnolia Cottage a beautiful waterfront getaway
Magnolia Cottage a beautiful waterfront getaway
9.8 (19 reviews)
Magnolia Cottage a beautiful waterfront getaway
Holiday home · 2 Guests · 1 Bedroom
$395 /night*
View deal
Urbanna Cottage w/ Private Yard & Water Views
Urbanna Cottage w/ Private Yard & Water Views
Urbanna Cottage w/ Private Yard & Water Views
Urbanna Cottage w/ Private Yard & Water Views
Urbanna Cottage w/ Private Yard & Water Views
Cottage · 2 Guests · 1 Bedroom
$221 /night
View deal
Peaceful cottage in the quaint Town of Irvington!
Peaceful cottage in the quaint Town of Irvington!
Peaceful cottage in the quaint Town of Irvington!
Peaceful cottage in the quaint Town of Irvington!
10 (1 review)
Peaceful cottage in the quaint Town of Irvington!
Holiday home · 2 Guests · 1 Bedroom
$283 /night*
View deal
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
9.8 (8 reviews)
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Cottage · 2 Guests · 1 Bedroom
$275 /night*
View deal
Heathsville Home w/ Sunroom < 10 Mi to Beach!
Heathsville Home w/ Sunroom < 10 Mi to Beach!
Heathsville Home w/ Sunroom < 10 Mi to Beach!
Heathsville Home w/ Sunroom < 10 Mi to Beach!
Heathsville Home w/ Sunroom < 10 Mi to Beach!
Cottage · 2 Guests · 1 Bedroom
$169 /night
View deal
Best Western Kilmarnock Hotel
Best Western Kilmarnock Hotel
Best Western Kilmarnock Hotel
Best Western Kilmarnock Hotel
8.0 (521 reviews)
Best Western Kilmarnock Hotel
Hotel · 2 Guests · 1 Bedroom
$122 /night
View deal
Scenic Waterfront Getaway w/ Dock, Launch Kayaks, Relax around Firepit!
Scenic Waterfront Getaway w/ Dock, Launch Kayaks, Relax around Firepit!
Scenic Waterfront Getaway w/ Dock, Launch Kayaks, Relax around Firepit!
Scenic Waterfront Getaway w/ Dock, Launch Kayaks, Relax around Firepit!
10 (1 review)
Scenic Waterfront Getaway w/ Dock, Launch Kayaks, Relax around Firepit!
Holiday home · 2 Guests · 1 Bedroom
$187 /night*
View deal
Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and private beach
Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and private beach
Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and private beach
Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and private beach
9.4 (73 reviews)
Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and private beach
Holiday home · 2 Guests · 1 Bedroom
$330 /night*
View deal
Back INN Time B&B
Back INN Time B&B
Back INN Time B&B
Back INN Time B&B
Back INN Time B&B
B & B · 2 Guests · 1 Bedroom
$145 /night
View deal
Welcome to the best view in Crisfield! top floor condo!
Welcome to the best view in Crisfield! top floor condo!
Welcome to the best view in Crisfield! top floor condo!
Welcome to the best view in Crisfield! top floor condo!
9.8 (26 reviews)
Welcome to the best view in Crisfield! top floor condo!
Condo · 2 Guests · 1 Bedroom
$223 /night*
View deal
Relax at the Mystic Seahorse Cottage on Gwynn's Island!
Relax at the Mystic Seahorse Cottage on Gwynn's Island!
Relax at the Mystic Seahorse Cottage on Gwynn's Island!
Relax at the Mystic Seahorse Cottage on Gwynn's Island!
10 (56 reviews)
Relax at the Mystic Seahorse Cottage on Gwynn's Island!
Cottage · 2 Guests · 1 Bedroom
$140 /night*
View deal
Search all

Vacation Destinations Near Chesapeake Beach, VA

Airbnb, Holiday Beachfront House with Air Conditioning in Chesapeake Beach, VA

Back INN Time B&B
Back INN Time B&B
Back INN Time B&B
Back INN Time B&B
Air Conditioning
Back INN Time B&B
B & B · 2 Guests · 1 Bedroom
$145 /night
View deal
Rustic Quaint Cabin In the woods--Pets welcomed
Rustic Quaint Cabin In the woods--Pets welcomed
Rustic Quaint Cabin In the woods--Pets welcomed
Rustic Quaint Cabin In the woods--Pets welcomed
Air Conditioning
Rustic Quaint Cabin In the woods--Pets welcomed
Holiday home · 2 Guests · 1 Bedroom
$117 /night
View deal
Rodo Beach Cottage
Rodo Beach Cottage
Rodo Beach Cottage
Rodo Beach Cottage
Air Conditioning
Rodo Beach Cottage
Holiday home · 2 Guests · 1 Bedroom
$500 /night
View deal
Search all
How Does The Amenity Info Looks Like at Chesapeake Beach, VA?
Best Amenities in Chesapeake Beach, VA
+
Above shows the popular amenities in Chesapeake Beach and the number of the rental properties associated with each amenity. In Chesapeake Beach, 183 rentals offer Air Conditioning, 176 rentals offer No Smoking, 173 rentals offer TV. So, if you need Air Conditioning during your vacation, use the Air Conditioning filter to compare these properties. Two amenities that are not typical are Hot Tub, Pool.
Which Price Range Is Considered As A Good Deal in Chesapeake Beach, VA Area?
Vacation House & Cottage Rental Price Information in Chesapeake Beach, VA
+
The graph shows the percentages of vacation homes in each price bucket. Chesapeake Beach has the largest percentage (19.23%) of homes in $150 - $200 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
What Are The Popular Property Types in Chesapeake Beach, VA?
Rental Accommodation Info in Chesapeake Beach, VA
+
Before visiting Chesapeake Beach, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: House, Cottage, Estate, Condo, Apartment, Studio, Cabin, Farmhouse, Guest House, Lodge, Yacht, Chateau / Country House. House is the most-liked rental type, with the largest percentage of 71.66%. The biggest home in this area available for rent is around 10500 square feet.The least popular accommodation in Chesapeake Beach is Chateau / Country House rentals
How Many Accommodations Are Not Pets Friendly in Chesapeake Beach, VA?
Pets Allowed vs Not Allowed in Chesapeake Beach, VA
+
53.48% of vacation homes in Chesapeake Beach are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.

Airbnb, Holiday Beachfront House with Full Kitchen, and Other Rental Options in Chesapeake Beach, VA

PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline
PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline
PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline
PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline
Full Kitchen
9.8 (108 reviews)
PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline
Holiday home · 2 Guests · 1 Bedroom
$400 /night*
View deal
Magnolia Cottage a beautiful waterfront getaway
Magnolia Cottage a beautiful waterfront getaway
Magnolia Cottage a beautiful waterfront getaway
Magnolia Cottage a beautiful waterfront getaway
Full Kitchen
9.8 (19 reviews)
Magnolia Cottage a beautiful waterfront getaway
Holiday home · 2 Guests · 1 Bedroom
$395 /night*
View deal
Beachfront Urbanna Home w/ Gas Grill & Deck!
Beachfront Urbanna Home w/ Gas Grill & Deck!
Beachfront Urbanna Home w/ Gas Grill & Deck!
Beachfront Urbanna Home w/ Gas Grill & Deck!
Full Kitchen
Beachfront Urbanna Home w/ Gas Grill & Deck!
Cottage · 2 Guests · 1 Bedroom
$596 /night
View deal
Search all

Airbnb, Vacation Cottage with Fireplace, and Other Rental Options in Chesapeake Beach, VA

Welcoming Cottage w/ Outdoor Pool & Water Views!
Welcoming Cottage w/ Outdoor Pool & Water Views!
Welcoming Cottage w/ Outdoor Pool & Water Views!
Welcoming Cottage w/ Outdoor Pool & Water Views!
Fireplace
Welcoming Cottage w/ Outdoor Pool & Water Views!
Cottage · 2 Guests · 1 Bedroom
$304 /night
View deal
Idyllic Waterfront Home w/ Game Room, Shared Dock
Idyllic Waterfront Home w/ Game Room, Shared Dock
Idyllic Waterfront Home w/ Game Room, Shared Dock
Idyllic Waterfront Home w/ Game Room, Shared Dock
Fireplace
Idyllic Waterfront Home w/ Game Room, Shared Dock
Cottage · 2 Guests · 1 Bedroom
$358 /night
View deal
Waterfront Scotland Beach Retreat W/private Beach!
Waterfront Scotland Beach Retreat W/private Beach!
Waterfront Scotland Beach Retreat W/private Beach!
Waterfront Scotland Beach Retreat W/private Beach!
Fireplace
Waterfront Scotland Beach Retreat W/private Beach!
Cottage · 2 Guests · 1 Bedroom
$930 /night
View deal
Search all
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers