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Chesapeake City Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Chesapeake City.
Waterfront Cottage on the C&D Canal!, vacation rental in Chesapeake City
Waterfront Cottage on the C&D Canal!, vacation rental in Chesapeake City
Waterfront Cottage on the C&D Canal!, vacation rental in Chesapeake City

Waterfront Cottage on the C&D Canal!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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CHESAPEAKE CITY DIRECT VIEW OF C&D CANAL WITH WATER TOY PARKING, vacation rental in Chesapeake City
CHESAPEAKE CITY DIRECT VIEW OF C&D CANAL WITH WATER TOY PARKING, vacation rental in Chesapeake City
CHESAPEAKE CITY DIRECT VIEW OF C&D CANAL WITH WATER TOY PARKING, vacation rental in Chesapeake City

CHESAPEAKE CITY DIRECT VIEW OF C&D CANAL WITH WATER TOY PARKING

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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MD 5 Star Event: Perfect stay Chesapeake City Overlook, vacation rental in Chesapeake City
MD 5 Star Event: Perfect stay Chesapeake City Overlook, vacation rental in Chesapeake City
MD 5 Star Event: Perfect stay Chesapeake City Overlook, vacation rental in Chesapeake City

MD 5 Star Event: Perfect stay Chesapeake City Overlook

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Summer Season in Chesapeake City, MD  Old Lock View  * C&D Canal, vacation rental in Chesapeake City
Summer Season in Chesapeake City, MD  Old Lock View  * C&D Canal, vacation rental in Chesapeake City
Summer Season in Chesapeake City, MD  Old Lock View  * C&D Canal, vacation rental in Chesapeake City

Summer Season in Chesapeake City, MD Old Lock View * C&D Canal

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hook Wine & Sinker~sleeps 14 to 16 � includes slip at Inn �water views!!!, vacation rental in Chesapeake City
Hook Wine & Sinker~sleeps 14 to 16 � includes slip at Inn �water views!!!, vacation rental in Chesapeake City
Hook Wine & Sinker~sleeps 14 to 16 � includes slip at Inn �water views!!!, vacation rental in Chesapeake City

Hook Wine & Sinker~sleeps 14 to 16 � includes slip at Inn �water views!!!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Bella Vista Holiday Family Gatherings in Coastal Maryland!, vacation rental in Chesapeake City
Bella Vista Holiday Family Gatherings in Coastal Maryland!, vacation rental in Chesapeake City
Bella Vista Holiday Family Gatherings in Coastal Maryland!, vacation rental in Chesapeake City

Bella Vista Holiday Family Gatherings in Coastal Maryland!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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The following properties within 20 miles of Chesapeake City match all your filters:
Sandy Cove - Second East Family Deluxe, vacation rental in Chesapeake City
Sandy Cove - Second East Family Deluxe, vacation rental in Chesapeake City
Sandy Cove - Second East Family Deluxe, vacation rental in Chesapeake City

Sandy Cove - Second East Family Deluxe

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Sandy Cove - Third East Family Deluxe, vacation rental in Chesapeake City
Sandy Cove - Third East Family Deluxe, vacation rental in Chesapeake City
Sandy Cove - Third East Family Deluxe, vacation rental in Chesapeake City

Sandy Cove - Third East Family Deluxe

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Sandy Cove - First East Family Deluxe, vacation rental in Chesapeake City
Sandy Cove - First East Family Deluxe, vacation rental in Chesapeake City
Sandy Cove - First East Family Deluxe, vacation rental in Chesapeake City

Sandy Cove - First East Family Deluxe

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Sandy Cove - Third Conference Standard Deluxe, vacation rental in Chesapeake City
Sandy Cove - Third Conference Standard Deluxe, vacation rental in Chesapeake City
Sandy Cove - Third Conference Standard Deluxe, vacation rental in Chesapeake City

Sandy Cove - Third Conference Standard Deluxe

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Sandy Cove - First Bay Standard Deluxe Bay View, vacation rental in Chesapeake City
Sandy Cove - First Bay Standard Deluxe Bay View, vacation rental in Chesapeake City
Sandy Cove - First Bay Standard Deluxe Bay View, vacation rental in Chesapeake City

Sandy Cove - First Bay Standard Deluxe Bay View

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Sandy Cove - First Bay Standard Deluxe, vacation rental in Chesapeake City
Sandy Cove - First Bay Standard Deluxe, vacation rental in Chesapeake City
Sandy Cove - First Bay Standard Deluxe, vacation rental in Chesapeake City

Sandy Cove - First Bay Standard Deluxe

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Chesapeake Bay House with Dock & Private Beach, vacation rental in Chesapeake City
Chesapeake Bay House with Dock & Private Beach, vacation rental in Chesapeake City
Chesapeake Bay House with Dock & Private Beach, vacation rental in Chesapeake City

Chesapeake Bay House with Dock & Private Beach

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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The Cove On The Waterfront, vacation rental in Chesapeake City
The Cove On The Waterfront, vacation rental in Chesapeake City
The Cove On The Waterfront, vacation rental in Chesapeake City

The Cove On The Waterfront

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sandy Cove - Second Bay Master Suite Bay View, vacation rental in Chesapeake City
Sandy Cove - Second Bay Master Suite Bay View, vacation rental in Chesapeake City
Sandy Cove - Second Bay Master Suite Bay View, vacation rental in Chesapeake City

Sandy Cove - Second Bay Master Suite Bay View

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Country Get Away 1 Bedroom Apartment, vacation rental in Chesapeake City
Country Get Away 1 Bedroom Apartment, vacation rental in Chesapeake City
Country Get Away 1 Bedroom Apartment, vacation rental in Chesapeake City

Country Get Away 1 Bedroom Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Clean and Cozy 2 BR home blocks away from downtown, vacation rental in Chesapeake City
Clean and Cozy 2 BR home blocks away from downtown, vacation rental in Chesapeake City
Clean and Cozy 2 BR home blocks away from downtown, vacation rental in Chesapeake City

Clean and Cozy 2 BR home blocks away from downtown

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning waterfront villa with indoor pool and kids swing set and play area., vacation rental in Chesapeake City
Stunning waterfront villa with indoor pool and kids swing set and play area., vacation rental in Chesapeake City
Stunning waterfront villa with indoor pool and kids swing set and play area., vacation rental in Chesapeake City

Stunning waterfront villa with indoor pool and kids swing set and play area.

Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Endless Water Views in a 5-Star Sanctuary, vacation rental in Chesapeake City
Endless Water Views in a 5-Star Sanctuary, vacation rental in Chesapeake City
Endless Water Views in a 5-Star Sanctuary, vacation rental in Chesapeake City

Endless Water Views in a 5-Star Sanctuary

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Historic Creekside Home - 2br 2.5ba - Downtown North East, vacation rental in Chesapeake City
Historic Creekside Home - 2br 2.5ba - Downtown North East, vacation rental in Chesapeake City
Historic Creekside Home - 2br 2.5ba - Downtown North East, vacation rental in Chesapeake City

Historic Creekside Home - 2br 2.5ba - Downtown North East

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Riverfront Retreat: panoramic water views and breathtaking sunsets. Sleeps 16, vacation rental in Chesapeake City
Riverfront Retreat: panoramic water views and breathtaking sunsets. Sleeps 16, vacation rental in Chesapeake City
Riverfront Retreat: panoramic water views and breathtaking sunsets. Sleeps 16, vacation rental in Chesapeake City

Riverfront Retreat: panoramic water views and breathtaking sunsets. Sleeps 16

Rental Home
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
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Nancy’s Touch, A Waterfront Paradise!, vacation rental in Chesapeake City
Nancy’s Touch, A Waterfront Paradise!, vacation rental in Chesapeake City
Nancy’s Touch, A Waterfront Paradise!, vacation rental in Chesapeake City

Nancy’s Touch, A Waterfront Paradise!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Waterfront Retreat for Weekends and More!, vacation rental in Chesapeake City
Waterfront Retreat for Weekends and More!, vacation rental in Chesapeake City
Waterfront Retreat for Weekends and More!, vacation rental in Chesapeake City

Waterfront Retreat for Weekends and More!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Bonfire by the Creek!!!, vacation rental in Chesapeake City
Bonfire by the Creek!!!, vacation rental in Chesapeake City
Bonfire by the Creek!!!, vacation rental in Chesapeake City

Bonfire by the Creek!!!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Cozy private waterfront retreat, vacation rental in Chesapeake City
Cozy private waterfront retreat, vacation rental in Chesapeake City
Cozy private waterfront retreat, vacation rental in Chesapeake City

Cozy private waterfront retreat

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Private Waterfront Estate with Pool, Private Beach and Dock, vacation rental in Chesapeake City
Private Waterfront Estate with Pool, Private Beach and Dock, vacation rental in Chesapeake City
Private Waterfront Estate with Pool, Private Beach and Dock, vacation rental in Chesapeake City

Private Waterfront Estate with Pool, Private Beach and Dock

Rental Home
7 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio, vacation rental in Chesapeake City
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio, vacation rental in Chesapeake City
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio, vacation rental in Chesapeake City

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Short Term Water Oriented Furnished Apartment, vacation rental in Chesapeake City
Short Term Water Oriented Furnished Apartment, vacation rental in Chesapeake City
Short Term Water Oriented Furnished Apartment, vacation rental in Chesapeake City

Short Term Water Oriented Furnished Apartment

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Historic & Quaint Room downtown Middletown, DE awaits you!, vacation rental in Chesapeake City
Historic & Quaint Room downtown Middletown, DE awaits you!, vacation rental in Chesapeake City
Historic & Quaint Room downtown Middletown, DE awaits you!, vacation rental in Chesapeake City

Historic & Quaint Room downtown Middletown, DE awaits you!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Private Carriage House Retreat on a 33 Acre Historic Working Estate, vacation rental in Chesapeake City
Private Carriage House Retreat on a 33 Acre Historic Working Estate, vacation rental in Chesapeake City
Private Carriage House Retreat on a 33 Acre Historic Working Estate, vacation rental in Chesapeake City

Private Carriage House Retreat on a 33 Acre Historic Working Estate

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Casino House One B/R Condo, vacation rental in Chesapeake City
Casino House One B/R Condo, vacation rental in Chesapeake City
Casino House One B/R Condo, vacation rental in Chesapeake City

Casino House One B/R Condo

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Sunset River Cottage encapsulates nautical romance., vacation rental in Chesapeake City
Sunset River Cottage encapsulates nautical romance., vacation rental in Chesapeake City
Sunset River Cottage encapsulates nautical romance., vacation rental in Chesapeake City

Sunset River Cottage encapsulates nautical romance.

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy home, close to town & perfect for a family, vacation rental in Chesapeake City
Cozy home, close to town & perfect for a family, vacation rental in Chesapeake City
Cozy home, close to town & perfect for a family, vacation rental in Chesapeake City

Cozy home, close to town & perfect for a family

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Comfy, Cozy & Perfect!!, vacation rental in Chesapeake City
Comfy, Cozy & Perfect!!, vacation rental in Chesapeake City
Comfy, Cozy & Perfect!!, vacation rental in Chesapeake City

Comfy, Cozy & Perfect!!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Quiet & Private with Fire Pit Out Back!, vacation rental in Chesapeake City
Quiet & Private with Fire Pit Out Back!, vacation rental in Chesapeake City
Quiet & Private with Fire Pit Out Back!, vacation rental in Chesapeake City

Quiet & Private with Fire Pit Out Back!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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House  casino, vacation rental in Chesapeake City
House  casino, vacation rental in Chesapeake City
House  casino, vacation rental in Chesapeake City

House casino

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury condo with elevator access & free parking, vacation rental in Chesapeake City
Luxury condo with elevator access & free parking, vacation rental in Chesapeake City
Luxury condo with elevator access & free parking, vacation rental in Chesapeake City

Luxury condo with elevator access & free parking

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Newark Getaway, vacation rental in Chesapeake City
Newark Getaway, vacation rental in Chesapeake City
Newark Getaway, vacation rental in Chesapeake City

Newark Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Relaxing Ranch with 1 king and 2 queens, fast WiFi, vacation rental in Chesapeake City
Relaxing Ranch with 1 king and 2 queens, fast WiFi, vacation rental in Chesapeake City
Relaxing Ranch with 1 king and 2 queens, fast WiFi, vacation rental in Chesapeake City

Relaxing Ranch with 1 king and 2 queens, fast WiFi

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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-Sunset River Shack-Amazing water views  of the upper Chesapeake bay, vacation rental in Chesapeake City
-Sunset River Shack-Amazing water views  of the upper Chesapeake bay, vacation rental in Chesapeake City
-Sunset River Shack-Amazing water views  of the upper Chesapeake bay, vacation rental in Chesapeake City

-Sunset River Shack-Amazing water views of the upper Chesapeake bay

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Chesapeake Romantic Waterfront Home with Private Pool, vacation rental in Chesapeake City
Chesapeake Romantic Waterfront Home with Private Pool, vacation rental in Chesapeake City
Chesapeake Romantic Waterfront Home with Private Pool, vacation rental in Chesapeake City

Chesapeake Romantic Waterfront Home with Private Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Enjoy Birdwatching from the Deck!, vacation rental in Chesapeake City
Enjoy Birdwatching from the Deck!, vacation rental in Chesapeake City
Enjoy Birdwatching from the Deck!, vacation rental in Chesapeake City

Enjoy Birdwatching from the Deck!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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A European styled retreat on Marylands Eastern Shore with Private pool, vacation rental in Chesapeake City
A European styled retreat on Marylands Eastern Shore with Private pool, vacation rental in Chesapeake City
A European styled retreat on Marylands Eastern Shore with Private pool, vacation rental in Chesapeake City

A European styled retreat on Marylands Eastern Shore with Private pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront Property in North East MD, vacation rental in Chesapeake City
Waterfront Property in North East MD, vacation rental in Chesapeake City
Waterfront Property in North East MD, vacation rental in Chesapeake City

Waterfront Property in North East MD

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Uniquely Historic & Quaint Room in the center of downtown Middletown,DE, vacation rental in Chesapeake City
Uniquely Historic & Quaint Room in the center of downtown Middletown,DE, vacation rental in Chesapeake City
Uniquely Historic & Quaint Room in the center of downtown Middletown,DE, vacation rental in Chesapeake City

Uniquely Historic & Quaint Room in the center of downtown Middletown,DE

Condo/Apartment
8 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Beautiful Riverfront Home. With dock, kayaks, paddle board. Magnificent views., vacation rental in Chesapeake City
Beautiful Riverfront Home. With dock, kayaks, paddle board. Magnificent views., vacation rental in Chesapeake City
Beautiful Riverfront Home. With dock, kayaks, paddle board. Magnificent views., vacation rental in Chesapeake City

Beautiful Riverfront Home. With dock, kayaks, paddle board. Magnificent views.

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Waterfront Home w/ a Hot Tub, Beach + Private Dock that Sleeps 20 People, vacation rental in Chesapeake City
Waterfront Home w/ a Hot Tub, Beach + Private Dock that Sleeps 20 People, vacation rental in Chesapeake City
Waterfront Home w/ a Hot Tub, Beach + Private Dock that Sleeps 20 People, vacation rental in Chesapeake City

Waterfront Home w/ a Hot Tub, Beach + Private Dock that Sleeps 20 People

Rental Home
7 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
More info
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Waterfront Home w/ Pool and Hot Tub ~ 8000 sq ft, vacation rental in Chesapeake City
Waterfront Home w/ Pool and Hot Tub ~ 8000 sq ft, vacation rental in Chesapeake City
Waterfront Home w/ Pool and Hot Tub ~ 8000 sq ft, vacation rental in Chesapeake City

Waterfront Home w/ Pool and Hot Tub ~ 8000 sq ft

Rental Home
5 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
More info
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Come enjoy our luxurious 10,000 sq, vacation rental in Chesapeake City
Come enjoy our luxurious 10,000 sq, vacation rental in Chesapeake City
Come enjoy our luxurious 10,000 sq, vacation rental in Chesapeake City

Come enjoy our luxurious 10,000 sq

Rental Home
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
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Amazing 432-Acre Waterfront Estate ~ Dock ~ Kayaks ~ Beaches ~ Fire Pit, vacation rental in Chesapeake City
Amazing 432-Acre Waterfront Estate ~ Dock ~ Kayaks ~ Beaches ~ Fire Pit, vacation rental in Chesapeake City
Amazing 432-Acre Waterfront Estate ~ Dock ~ Kayaks ~ Beaches ~ Fire Pit, vacation rental in Chesapeake City

Amazing 432-Acre Waterfront Estate ~ Dock ~ Kayaks ~ Beaches ~ Fire Pit

Rental Home
11 bedrooms
10 bathrooms
Sleeps 24
Match: Sleeps
More info
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Showing results 1-50 of 50
Frequently Asked Questions about Chesapeake City