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Chestertown Vacation Rentals

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31 rentals in Chestertown.
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Water Front Retreat - Sunrise and Sunset Water Views, vacation rental in Chestertown
Water Front Retreat - Sunrise and Sunset Water Views, vacation rental in Chestertown
Water Front Retreat - Sunrise and Sunset Water Views, vacation rental in Chestertown

Water Front Retreat - Sunrise and Sunset Water Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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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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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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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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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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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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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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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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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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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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 8
Match: Sleeps
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Carriage House Hideaway in Middle of Chestertown

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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
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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 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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Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay, vacation rental in Chestertown
Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay, vacation rental in Chestertown
Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay, vacation rental in Chestertown

Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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
7 bedrooms
5 bathrooms
Sleeps 12
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 12
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 27
Match: Sleeps
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Lovely fully restored townhouse in the heart of historic Chestertown, vacation rental in Chestertown
Lovely fully restored townhouse in the heart of historic Chestertown, vacation rental in Chestertown
Lovely fully restored townhouse in the heart of historic Chestertown, vacation rental in Chestertown

Lovely fully restored townhouse in the heart of historic Chestertown

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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
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Private Beach Access w/ Water Sports & Shared Ramp Access, vacation rental in Chestertown
Private Beach Access w/ Water Sports & Shared Ramp Access, vacation rental in Chestertown
Private Beach Access w/ Water Sports & Shared Ramp Access, vacation rental in Chestertown

Private Beach Access w/ Water Sports & Shared Ramp Access

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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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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 12
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
2 bathrooms
Sleeps 8
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
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Historic downtown Chestertown Home. #1 Location., vacation rental in Chestertown
Historic downtown Chestertown Home. #1 Location., vacation rental in Chestertown
Historic downtown Chestertown Home. #1 Location., vacation rental in Chestertown

Historic downtown Chestertown Home. #1 Location.

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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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 16
Match: Sleeps
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Lovely, Recently-Renovated Home in Chestertown, vacation rental in Chestertown
Lovely, Recently-Renovated Home in Chestertown, vacation rental in Chestertown
Lovely, Recently-Renovated Home in Chestertown, vacation rental in Chestertown

Lovely, Recently-Renovated Home in Chestertown

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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NEW! Chestertown Family Hideaway w/ Kayaks + Deck!, vacation rental in Chestertown
NEW! Chestertown Family Hideaway w/ Kayaks + Deck!, vacation rental in Chestertown
NEW! Chestertown Family Hideaway w/ Kayaks + Deck!, vacation rental in Chestertown

NEW! Chestertown Family Hideaway w/ Kayaks + Deck!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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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