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Vacation Rentals and House Rentals in Chesapeake Beach, MD
Vacation Rentals
USA
Maryland (MD)
Calvert County
Chesapeake Beach Vacation Rentals
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Bedrooms
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Bathrooms
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Amenities
Air Conditioning (50)
Internet or Wifi (49)
Washer/Dryer (45)
Other outdoor space (44)
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Suitability
Kid friendly (46)
Pet friendly (27)
Elder access (1)
Wheelchair access (0)
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Property type
Vacation Rental House (43)
Condominium/Apartment (8)
Cabin Vacation Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (16)
Boat Available (1)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
Breezy Point Beach
Chesapeake Beach Railway Trail
Bruce Snake Gabrielson's Surf Art Gallery and Museum
The Chesapeake Beach Railway Museum
Bayfront Park
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51 rentals
in Chesapeake Beach.
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
45
Rental Home
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2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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Spacious 4 Bdr Home Chesapeake Beach
16
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
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Waterfront Home On The Chesapeake Bay
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Coastal Pet-Friendly Cottage <1/2 Mi to Beaches
4
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Cozy Getaway - Breezy Point Beach & Marina
2
Rental Home
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Indoor pool and spa in contemporary French home secluded in surrounding woods
8
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Family Beach House: Spacious Deck, Grill & Views
4
Rental Home
View on map
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Cozy Home in Private Beach Community Close to City
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps
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Bahia Breeze - Beachfront Cottage
3
Rental Home
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2 bedrooms
1 bathroom
Sleeps 7
Match:
Sleeps
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Charming Villa
1
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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The following properties within 20 miles of Chesapeake Beach match all your filters:
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
26
Rental Home
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5 bedrooms
6 bathrooms
Sleeps 16
Match:
Sleeps
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The Lazy Crab Beach House - Free beach passes
36
Rental Home
View on map
3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
North Beach Cottage - Walk to Chesapeake Bay
27
Rental Home
View on map
4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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The Blue Crab Beach House - Free beach passes
31
Rental Home
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
BeachWalk Cottage - Charm by the Chesapeake Bay
15
Rental Home
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Sweet Bamboo Beach Cottage
23
Rental Home
View on map
3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Cute Bay Home/Fantastic View and Sandy Beach
10
Rental Home
View on map
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Updated North Beach Cottage: Pet Friendly!
10
Rental Home
View on map
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Blocks to the Boardwalk!
15
Rental Home
View on map
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
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Walk to the Chesapeake Bay! Herrington Harbour is a few blocks away.
12
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
14
Rental Home
View on map
3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Waterfront North Beach Home ~ 2 Mi to Beach!
14
Rental Home
View on map
5 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Guest Quarters at the Inn - 101
10
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Guest Quarters at the Inn - 103
15
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Guest Quarters at the Inn - 102
13
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Guest quarters at the inn - 204
12
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Guest quarters at the inn - 205
10
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Luxury Cottage w/ Bay & Boardwalk Views--steps from the water
1
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 3
Match:
Sleeps
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As seen on
Plant-Filled Oasis Near Beach Town with Passes & Tips
10
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Osprey's Perch
7
Rental Home
View on map
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Cozy Cottage 3 beds 2 baths
15
Rental Home
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Waterfront, Private Beach, Peaceful Family Getaway
12
Rental Home
View on map
3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington
10
Rental Home
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Club Carp North Beach
10
Rental Home
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Bayfront Home w/Hot Tub
5
Rental Home
View on map
2 bedrooms
3 bathrooms
Sleeps 5
Match:
Sleeps
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Beautiful home in walkable beach town near DC & Herrington Harbor Yacht Club!
5
Rental Home
View on map
3 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
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As seen on
Bell Estates-Brand New Bay View, Beautiful Cottage
12
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
15
Rental Home
View on map
3 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
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Bay Views in Heart of North Beach!
Rental Home
View on map
3 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk
13
Rental Home
View on map
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Harbor Breezes at Herrington Harbor
10
Rental Home
View on map
5 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps
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As seen on
Charming Beach House Top Floor - Walk Everywhere!
Condo/Apartment
View on map
3 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
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Just steps away from the Boardwalk & Beaches, Walkable to Entertainment!
2
Rental Home
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Cozy 1st Level Beach House - Walk Everywhere
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
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Experience the Chesapeake Bay lifestyle at the historic and waterfront Bay
2
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
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Bayfront Maryland Retreat w/ Deck, Near Beaches!
5
Rental Home
View on map
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Sweet Gumball Cottage North Beach MD Free Beach Pass!
1
Rental Home
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Unbelievable beach views for 6
1
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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Walk to Bay, Family + Dog Friendly, Fenced Yard, Beach Passes - 3BD/2BA
3
Rental Home
View on map
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
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Waterfront- 5-bedroom house with dock in charming North Beach
Rental Home
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5 bedrooms
6 bathrooms
Sleeps 18
Match:
Sleeps
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1
2
Showing results 1-50 of 51
Frequently Asked Questions about Chesapeake Beach
Do any vacation rentals in Chesapeake Beach have a pool?
Yes, here are some popular vacation rentals in Chesapeake Beach that have a pool:
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Spacious 4 Bdr Home Chesapeake Beach
Waterfront Home On The Chesapeake Bay
See all vacation rentals with a pool in Chesapeake Beach on Tripadvisor
Do any vacation rentals in Chesapeake Beach have internet access?
Yes, here are some popular vacation rentals in Chesapeake Beach that have internet access:
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Spacious 4 Bdr Home Chesapeake Beach
Waterfront Home On The Chesapeake Bay
See all vacation rentals in Chesapeake Beach on Tripadvisor
What are the best pet friendly rentals in Chesapeake Beach?
The best pet friendly rentals in Chesapeake Beach are:
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Waterfront Home On The Chesapeake Bay
Coastal Pet-Friendly Cottage <1/2 Mi to Beaches
See all pet friendly vacation rentals in Chesapeake Beach on Tripadvisor
What are some great rentals in Chesapeake Beach that are kid friendly?
Some of the most popular kid friendly rentals in Chesapeake Beach are:
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Spacious 4 Bdr Home Chesapeake Beach
Waterfront Home On The Chesapeake Bay
See all kid friendly vacation rentals in Chesapeake Beach on Tripadvisor
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