Chesapeake Bay Vacation Rentals - HolidayHomes base64Hash Chesapeake Bay Vacation Rentals - HolidayHomes

Chesapeake Bay Vacation Rentals

Browse 10,366 available vacation homes and compared across 31 trusted partners

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Top-Rated Vacation rentals in Chesapeake Bay

Book the highest-rated Chesapeake Bay vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Elkton
Vacation home with patio & barbeque
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House Bohannon
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
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Cabin Port Republic
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
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House Deale
Family-friendly vacation home with garden, barbeque & patio
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Cabin Churchton
Chesapeake Bay Cottage
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House Northwest
Family-oriented vacation home with patio | Close to the beach | Good for workation
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House Madison
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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House Buckroe Beach
Big, Beautiful & Beachside Bliss - Sleeps 10!
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House Fox Hill - Grandview
Waterfront Escape with Indoor Cedar Pool & Hot Tub-Chesapeake Bay Retreat
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House Northeast Virginia Beach
Beach Escape - 2 minute walk to the Beach!
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House Churchton
Vacation home with terrace & jacuzzi
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House Shady Side
Vacation home with garden, patio & barbeque | Nature view
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House Tracys Landing
Cute Bay Home/Fantastic View and Sandy Beach
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House Calvert Beach-Long Beach
Summer Getaway Beach Combing & Relaxation
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House Shady Side
Bay views with kayaks, bikes, fire pit, crabbing and more
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Top 15 most Recommended Vacation Rentals in Chesapeake Bay

Discover your ideal Chesapeake Bay vacation rental with real-time comparisons of 10,366 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Cabin Churchton
8 guests ∙ 3 bedrooms

Cabin

Churchton, Deale, Maryland, United States
This charming cabin in Churchton accommodates 8 guests and features a cozy fireplace for a perfect getaway.
from $252
per night
(92)
View deal
House Northeast Virginia Beach
9 guests ∙ 4 bedrooms

House

Northeast Virginia Beach, Virginia Beach, Virginia, United States
This house rental in Northeast Virginia Beach accommodates 9 guests and features a family-friendly yard for outdoor enjoyment.
from $554
per night
(23)
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House Mathews
House ∙ 6 guests ∙ 4 bedrooms

260 m² House

Mathews, Westville, Virginia, United States
This house rental in Mathews accommodates 6 guests and features a cozy fireplace for warmth and comfort.
from $201
per night
(39)
View deal
House Pasadena
House ∙ 14 guests ∙ 5 bedrooms

279 m² House

Pasadena, Anne Arundel County, Maryland, United States
Spacious house rental in Pasadena for 14 with a cozy fireplace and a family-friendly atmosphere.
from $491
per night
(99)
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House East Ocean View
House ∙ 10 guests ∙ 4 bedrooms

260 m² House

East Ocean View, Norfolk, Virginia, United States
This house rental in East Ocean View accommodates 10 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $223
per night
(80)
View deal
House Annapolis
9 guests ∙ 5 bedrooms

House

Annapolis, Anne Arundel County, Maryland, United States
Spacious house rental in Annapolis accommodating 9 guests, featuring a cozy fireplace for warm gatherings.
from $248
per night
(4)
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House Bay View
House ∙ 12 guests ∙ 4 bedrooms

297 m² House

Bay View, Norfolk, Virginia, United States
This spacious house rental in Bay View accommodates 12 guests and features a balcony for relaxing views.
from $402
per night
(15)
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House Lusby
House ∙ 11 guests ∙ 4 bedrooms

185 m² House

Lusby, Solomons Island, Maryland, United States
Spacious house rental in Lusby accommodates 11 guests and features a family-friendly kitchen for all your culinary needs.
from $426
per night
(2)
View deal
Cabin Deal Island
Cabin ∙ 9 guests ∙ 3 bedrooms

201 m² Cabin

Deal Island, Somerset County, Maryland, United States
This family-friendly cabin in Deal Island accommodates 9 guests and offers stunning sea views for a memorable getaway.
from $213
per night
(5)
View deal

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