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Chestertown Holiday Apartments

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32 rentals in Chestertown.
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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown, holiday rental in Chestertown
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown, holiday rental in Chestertown
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown, holiday rental in Chestertown

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Water Front Retreat - Sunrise and Sunset Water Views, holiday rental in Chestertown
Water Front Retreat - Sunrise and Sunset Water Views, holiday rental in Chestertown
Water Front Retreat - Sunrise and Sunset Water Views, holiday rental in Chestertown

Water Front Retreat - Sunrise and Sunset Water Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Contemporary waterfront house with private dock & kayaks!, holiday rental in Chestertown
Contemporary waterfront house with private dock & kayaks!, holiday rental in Chestertown
Contemporary waterfront house with private dock & kayaks!, holiday rental in Chestertown

Contemporary waterfront house with private dock & kayaks!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chestertown's Pet-Friendly Little Red Cottage, holiday rental in Chestertown
Chestertown's Pet-Friendly Little Red Cottage, holiday rental in Chestertown
Chestertown's Pet-Friendly Little Red Cottage, holiday rental in Chestertown

Chestertown's Pet-Friendly Little Red Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, holiday rental in Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, holiday rental in Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, holiday rental in Chestertown

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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River Lodge, Casual Riverfront setting, holiday rental in Chestertown
River Lodge, Casual Riverfront setting, holiday rental in Chestertown
River Lodge, Casual Riverfront setting, holiday rental in Chestertown

River Lodge, Casual Riverfront setting

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock, holiday rental in Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock, holiday rental in Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock, holiday rental in Chestertown

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Country Estate in Historic District, holiday rental in Chestertown
Country Estate in Historic District, holiday rental in Chestertown
Country Estate in Historic District, holiday rental in Chestertown

Country Estate in Historic District

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Circa 1900 Home in the Heart of Historic Downtown Chestertown, holiday rental in Chestertown
Circa 1900 Home in the Heart of Historic Downtown Chestertown, holiday rental in Chestertown
Circa 1900 Home in the Heart of Historic Downtown Chestertown, holiday rental in Chestertown

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming  Chestertown Waterfront Cottage, holiday rental in Chestertown
Charming  Chestertown Waterfront Cottage, holiday rental in Chestertown
Charming  Chestertown Waterfront Cottage, holiday rental in Chestertown

Charming Chestertown Waterfront Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!, holiday rental in Chestertown
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!, holiday rental in Chestertown
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!, holiday rental in Chestertown

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

Holiday Rental House
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, holiday rental in Chestertown
Victorian Hideaway: Beautiful Exterior, Modern interior, holiday rental in Chestertown
Victorian Hideaway: Beautiful Exterior, Modern interior, holiday rental in Chestertown

Victorian Hideaway: Beautiful Exterior, Modern interior

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Manor House on Beautiful Eastern Shore Estate, holiday rental in Chestertown
Manor House on Beautiful Eastern Shore Estate, holiday rental in Chestertown
Manor House on Beautiful Eastern Shore Estate, holiday rental in Chestertown

Manor House on Beautiful Eastern Shore Estate

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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First Floor Studio Apartment in Historic Chestertown, holiday rental in Chestertown
First Floor Studio Apartment in Historic Chestertown, holiday rental in Chestertown
First Floor Studio Apartment in Historic Chestertown, holiday rental in Chestertown

First Floor Studio Apartment in Historic Chestertown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay, holiday rental in Chestertown
Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay, holiday rental in Chestertown
Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay, holiday rental in Chestertown

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private pier and pool at this waterfront Chestertown home, holiday rental in Chestertown
Private pier and pool at this waterfront Chestertown home, holiday rental in Chestertown
Private pier and pool at this waterfront Chestertown home, holiday rental in Chestertown

Private pier and pool at this waterfront Chestertown home

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Private pier and pool at this waterfront Chestertown home, holiday rental in Chestertown
Private pier and pool at this waterfront Chestertown home, holiday rental in Chestertown
Private pier and pool at this waterfront Chestertown home, holiday rental in Chestertown

Private pier and pool at this waterfront Chestertown home

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Cottage within walking distance to the Bay!, holiday rental in Chestertown
Cottage within walking distance to the Bay!, holiday rental in Chestertown
Cottage within walking distance to the Bay!, holiday rental in Chestertown

Cottage within walking distance to the Bay!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Waterfront Estate, holiday rental in Chestertown
Beautiful Waterfront Estate, holiday rental in Chestertown
Beautiful Waterfront Estate, holiday rental in Chestertown

Beautiful Waterfront Estate

Holiday Rental House
11 bedrooms
9 bathrooms
Sleeps 27
Match: Sleeps
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Lovely fully restored townhouse in the heart of historic Chestertown, holiday rental in Chestertown
Lovely fully restored townhouse in the heart of historic Chestertown, holiday rental in Chestertown
Lovely fully restored townhouse in the heart of historic Chestertown, holiday rental in Chestertown

Lovely fully restored townhouse in the heart of historic Chestertown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Beach Access, Onsite Kayaks and Shared Boat Ramp, holiday rental in Chestertown
Private Beach Access, Onsite Kayaks and Shared Boat Ramp, holiday rental in Chestertown
Private Beach Access, Onsite Kayaks and Shared Boat Ramp, holiday rental in Chestertown

Private Beach Access, Onsite Kayaks and Shared Boat Ramp

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Private Beach Access w/ Water Sports & Shared Ramp Access, holiday rental in Chestertown
Private Beach Access w/ Water Sports & Shared Ramp Access, holiday rental in Chestertown
Private Beach Access w/ Water Sports & Shared Ramp Access, holiday rental in Chestertown

Private Beach Access w/ Water Sports & Shared Ramp Access

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Hidden gem with water and golf course views! Bike ride to downtown!, holiday rental in Chestertown
Hidden gem with water and golf course views! Bike ride to downtown!, holiday rental in Chestertown
Hidden gem with water and golf course views! Bike ride to downtown!, holiday rental in Chestertown

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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The Lazy River House, holiday rental in Chestertown
The Lazy River House, holiday rental in Chestertown
The Lazy River House, holiday rental in Chestertown

The Lazy River House

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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790 Acre Estate: Waterfront | HOT TUB | 1600 sq foot Deck, holiday rental in Chestertown
790 Acre Estate: Waterfront | HOT TUB | 1600 sq foot Deck, holiday rental in Chestertown
790 Acre Estate: Waterfront | HOT TUB | 1600 sq foot Deck, holiday rental in Chestertown

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quaint cottage with amazing sunset views to soak up nature, holiday rental in Chestertown
Quaint cottage with amazing sunset views to soak up nature, holiday rental in Chestertown
Quaint cottage with amazing sunset views to soak up nature, holiday rental in Chestertown

Quaint cottage with amazing sunset views to soak up nature

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Historic downtown Chestertown Home. #1 Location., holiday rental in Chestertown
Historic downtown Chestertown Home. #1 Location., holiday rental in Chestertown
Historic downtown Chestertown Home. #1 Location., holiday rental in Chestertown

Historic downtown Chestertown Home. #1 Location.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful, spacious waterfront home, an easy walk to historic Chestertown, holiday rental in Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown, holiday rental in Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown, holiday rental in Chestertown

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

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Lovely, Recently-Renovated Home in Chestertown, holiday rental in Chestertown
Lovely, Recently-Renovated Home in Chestertown, holiday rental in Chestertown
Lovely, Recently-Renovated Home in Chestertown, holiday rental in Chestertown

Lovely, Recently-Renovated Home in Chestertown

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

NEW! Chestertown Family Hideaway w/ Kayaks + Deck!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Breathtaking waterfront home on the Chester River, holiday rental in Chestertown
Breathtaking waterfront home on the Chester River, holiday rental in Chestertown
Breathtaking waterfront home on the Chester River, holiday rental in Chestertown

Breathtaking waterfront home on the Chester River

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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