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Chestertown Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
36 rentals in Chestertown.
Carriage House Hideaway in Middle of Chestertown, vacation rental in Chestertown
Carriage House Hideaway in Middle of Chestertown, vacation rental in Chestertown
Carriage House Hideaway in Middle of Chestertown, vacation rental in Chestertown

Carriage House Hideaway in Middle of Chestertown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Carriage House Hideaway in Middle of Chestertown, vacation rental in Chestertown
Carriage House Hideaway in Middle of Chestertown, vacation rental in Chestertown
Carriage House Hideaway in Middle of Chestertown, vacation rental in Chestertown

Carriage House Hideaway in Middle of Chestertown

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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First Floor Studio Apartment in Historic Chestertown, vacation rental in Chestertown
First Floor Studio Apartment in Historic Chestertown, vacation rental in Chestertown
First Floor Studio Apartment in Historic Chestertown, vacation rental in Chestertown

First Floor Studio Apartment in Historic Chestertown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Breathtaking waterfront home on the Chester River, vacation rental in Chestertown
Breathtaking waterfront home on the Chester River, vacation rental in Chestertown
Breathtaking waterfront home on the Chester River, vacation rental in Chestertown

Breathtaking waterfront home on the Chester River

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Charming  Chestertown Waterfront Cottage, vacation rental in Chestertown
Charming  Chestertown Waterfront Cottage, vacation rental in Chestertown
Charming  Chestertown Waterfront Cottage, vacation rental in Chestertown

Charming Chestertown Waterfront Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Home w/ Private Dock & Hot Tub - Harbor View Haven, vacation rental in Chestertown
Waterfront Home w/ Private Dock & Hot Tub - Harbor View Haven, vacation rental in Chestertown
Waterfront Home w/ Private Dock & Hot Tub - Harbor View Haven, vacation rental in Chestertown

Waterfront Home w/ Private Dock & Hot Tub - Harbor View Haven

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock, vacation rental in Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock, vacation rental in Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock, vacation rental in Chestertown

350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Circa 1900 Home in the Heart of Historic Downtown Chestertown, vacation rental in Chestertown
Circa 1900 Home in the Heart of Historic Downtown Chestertown, vacation rental in Chestertown
Circa 1900 Home in the Heart of Historic Downtown Chestertown, vacation rental in Chestertown

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hidden gem with water and golf course views! Bike ride to downtown!, vacation rental in Chestertown
Hidden gem with water and golf course views! Bike ride to downtown!, vacation rental in Chestertown
Hidden gem with water and golf course views! Bike ride to downtown!, vacation rental in Chestertown

Hidden gem with water and golf course views! Bike ride to downtown!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!, vacation rental in Chestertown
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!, vacation rental in Chestertown
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!, vacation rental in Chestertown

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown, vacation rental in Chestertown
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown, vacation rental in Chestertown
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown, vacation rental in Chestertown

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly restored apartment in the heart of Chestertown, vacation rental in Chestertown
Newly restored apartment in the heart of Chestertown, vacation rental in Chestertown
Newly restored apartment in the heart of Chestertown, vacation rental in Chestertown

Newly restored apartment in the heart of Chestertown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Downtown Garden Oasis with Private Patio, vacation rental in Chestertown
Historic Downtown Garden Oasis with Private Patio, vacation rental in Chestertown
Historic Downtown Garden Oasis with Private Patio, vacation rental in Chestertown

Historic Downtown Garden Oasis with Private Patio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Chestertown's Pet-Friendly Little Red Cottage, vacation rental in Chestertown
Chestertown's Pet-Friendly Little Red Cottage, vacation rental in Chestertown
Chestertown's Pet-Friendly Little Red Cottage, vacation rental in Chestertown

Chestertown's Pet-Friendly Little Red Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Manor House on Beautiful Eastern Shore Estate, vacation rental in Chestertown
Manor House on Beautiful Eastern Shore Estate, vacation rental in Chestertown
Manor House on Beautiful Eastern Shore Estate, vacation rental in Chestertown

Manor House on Beautiful Eastern Shore Estate

Rental Home
6 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Cottage within walking distance to the Bay!, vacation rental in Chestertown
Cottage within walking distance to the Bay!, vacation rental in Chestertown
Cottage within walking distance to the Bay!, vacation rental in Chestertown

Cottage within walking distance to the Bay!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Quaint cottage with amazing sunset views to soak up nature, vacation rental in Chestertown
Quaint cottage with amazing sunset views to soak up nature, vacation rental in Chestertown
Quaint cottage with amazing sunset views to soak up nature, vacation rental in Chestertown

Quaint cottage with amazing sunset views to soak up nature

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, vacation rental in Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, vacation rental in Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, vacation rental in Chestertown

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Contemporary waterfront house with private dock & kayaks!, vacation rental in Chestertown
Contemporary waterfront house with private dock & kayaks!, vacation rental in Chestertown
Contemporary waterfront house with private dock & kayaks!, vacation rental in Chestertown

Contemporary waterfront house with private dock & kayaks!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cottage on Chesapeake Bay with shared pool and dock, vacation rental in Chestertown
Cottage on Chesapeake Bay with shared pool and dock, vacation rental in Chestertown
Cottage on Chesapeake Bay with shared pool and dock, vacation rental in Chestertown

Cottage on Chesapeake Bay with shared pool and dock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 Beds, 2.5 Baths, Perfect Downtown Location, vacation rental in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location, vacation rental in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location, vacation rental in Chestertown

2 Beds, 2.5 Baths, Perfect Downtown Location

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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River Lodge, Casual Riverfront setting, vacation rental in Chestertown
River Lodge, Casual Riverfront setting, vacation rental in Chestertown
River Lodge, Casual Riverfront setting, vacation rental in Chestertown

River Lodge, Casual Riverfront setting

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Victorian Hideaway: Beautiful Exterior, Modern interior, vacation rental in Chestertown
Victorian Hideaway: Beautiful Exterior, Modern interior, vacation rental in Chestertown
Victorian Hideaway: Beautiful Exterior, Modern interior, vacation rental in Chestertown

Victorian Hideaway: Beautiful Exterior, Modern interior

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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RELAXING HOUSE IN THE HEART OF DOWNTOWN - WALKING DISTANCE TO EVERYTHING, vacation rental in Chestertown
RELAXING HOUSE IN THE HEART OF DOWNTOWN - WALKING DISTANCE TO EVERYTHING, vacation rental in Chestertown
RELAXING HOUSE IN THE HEART OF DOWNTOWN - WALKING DISTANCE TO EVERYTHING, vacation rental in Chestertown

RELAXING HOUSE IN THE HEART OF DOWNTOWN - WALKING DISTANCE TO EVERYTHING

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Lazy River House, vacation rental in Chestertown
The Lazy River House, vacation rental in Chestertown
The Lazy River House, vacation rental in Chestertown

The Lazy River House

Rental Home
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cape Cod Hideaway | Walk to Tolchester Beach & Bike ride to Downtown Rock Hall, vacation rental in Chestertown
Cape Cod Hideaway | Walk to Tolchester Beach & Bike ride to Downtown Rock Hall, vacation rental in Chestertown
Cape Cod Hideaway | Walk to Tolchester Beach & Bike ride to Downtown Rock Hall, vacation rental in Chestertown

Cape Cod Hideaway | Walk to Tolchester Beach & Bike ride to Downtown Rock Hall

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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790 Acre Estate: Waterfront | HOT TUB | 1600 sq foot Deck, vacation rental in Chestertown
790 Acre Estate: Waterfront | HOT TUB | 1600 sq foot Deck, vacation rental in Chestertown
790 Acre Estate: Waterfront | HOT TUB | 1600 sq foot Deck, vacation rental in Chestertown

790 Acre Estate: Waterfront | HOT TUB | 1600 sq foot Deck

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely waterfront retreat on Fairlee Creek!, vacation rental in Chestertown
Lovely waterfront retreat on Fairlee Creek!, vacation rental in Chestertown
Lovely waterfront retreat on Fairlee Creek!, vacation rental in Chestertown

Lovely waterfront retreat on Fairlee Creek!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Private Beach Access, Onsite Kayaks and Shared Boat Ramp, vacation rental in Chestertown
Private Beach Access, Onsite Kayaks and Shared Boat Ramp, vacation rental in Chestertown
Private Beach Access, Onsite Kayaks and Shared Boat Ramp, vacation rental in Chestertown

Private Beach Access, Onsite Kayaks and Shared Boat Ramp

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Historic Stepne Manor on Maryland's Eastern Shore, vacation rental in Chestertown
Historic Stepne Manor on Maryland's Eastern Shore, vacation rental in Chestertown
Historic Stepne Manor on Maryland's Eastern Shore, vacation rental in Chestertown

Historic Stepne Manor on Maryland's Eastern Shore

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Country Estate in Historic District, vacation rental in Chestertown
Country Estate in Historic District, vacation rental in Chestertown
Country Estate in Historic District, vacation rental in Chestertown

Country Estate in Historic District

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Private pier and pool at this waterfront Chestertown home, vacation rental in Chestertown
Private pier and pool at this waterfront Chestertown home, vacation rental in Chestertown
Private pier and pool at this waterfront Chestertown home, vacation rental in Chestertown

Private pier and pool at this waterfront Chestertown home

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Private pier and pool at this waterfront Chestertown home, vacation rental in Chestertown
Private pier and pool at this waterfront Chestertown home, vacation rental in Chestertown
Private pier and pool at this waterfront Chestertown home, vacation rental in Chestertown

Private pier and pool at this waterfront Chestertown home

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Beautiful, spacious waterfront home, an easy walk to historic Chestertown, vacation rental in Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown, vacation rental in Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown, vacation rental in Chestertown

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Rental Home
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Waterfront Estate, vacation rental in Chestertown
Beautiful Waterfront Estate, vacation rental in Chestertown
Beautiful Waterfront Estate, vacation rental in Chestertown

Beautiful Waterfront Estate

Rental Home
11 bedrooms
9 bathrooms
Sleeps 30
Match: Sleeps
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The Spa Estate at windswept, vacation rental in Chestertown
The Spa Estate at windswept, vacation rental in Chestertown
The Spa Estate at windswept, vacation rental in Chestertown

The Spa Estate at windswept

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-36 of 36
Frequently Asked Questions about Chestertown