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Chestertown Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
28 rentals in Chestertown.
Carriage House Hideaway in Middle of Chestertown, holiday rental in Chestertown
Carriage House Hideaway in Middle of Chestertown, holiday rental in Chestertown
Carriage House Hideaway in Middle of Chestertown, holiday 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, 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 3
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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Harbor View Haven | Waterfront w/ HOT TUB + Dock!, holiday rental in Chestertown
Harbor View Haven | Waterfront w/ HOT TUB + Dock!, holiday rental in Chestertown
Harbor View Haven | Waterfront w/ HOT TUB + Dock!, holiday rental in Chestertown

Harbor View Haven | Waterfront w/ HOT TUB + Dock!

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

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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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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 10
Match: Sleeps
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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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Newly restored apartment in the heart of Chestertown, holiday rental in Chestertown
Newly restored apartment in the heart of Chestertown, holiday rental in Chestertown
Newly restored apartment in the heart of Chestertown, holiday 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, holiday rental in Chestertown
Historic Downtown Garden Oasis with Private Patio, holiday rental in Chestertown
Historic Downtown Garden Oasis with Private Patio, holiday rental in Chestertown

Historic Downtown Garden Oasis with Private Patio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Manor House on Beautiful Eastern Shore Estate, holiday rental in Chestertown
Historic Manor House on Beautiful Eastern Shore Estate, holiday rental in Chestertown
Historic Manor House on Beautiful Eastern Shore Estate, holiday rental in Chestertown

Historic Manor House on Beautiful Eastern Shore Estate

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 13
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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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
3 bedrooms
2 bathrooms
Sleeps 6
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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Cottage upper Chesapeake Eastern Shore on major creek with shared pool and dock., holiday rental in Chestertown
Cottage upper Chesapeake Eastern Shore on major creek with shared pool and dock., holiday rental in Chestertown
Cottage upper Chesapeake Eastern Shore on major creek with shared pool and dock., holiday rental in Chestertown

Cottage upper Chesapeake Eastern Shore on major creek with shared pool and dock.

Holiday Rental House
3 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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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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The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown, holiday rental in Chestertown
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown, holiday rental in Chestertown
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown, holiday rental in Chestertown

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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 10
Match: Sleeps
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Langford Creek Estate | Waterfront w/ HOT TUB + Deck!, holiday rental in Chestertown
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!, holiday rental in Chestertown
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!, holiday rental in Chestertown

Langford Creek Estate | Waterfront w/ HOT TUB + Deck!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Goose Landing on Fairlee Creek, holiday rental in Chestertown
Goose Landing on Fairlee Creek, holiday rental in Chestertown
Goose Landing on Fairlee Creek, holiday rental in Chestertown

Goose Landing on Fairlee Creek

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Stepne Manor on Maryland's Eastern Shore, holiday rental in Chestertown
Historic Stepne Manor on Maryland's Eastern Shore, holiday rental in Chestertown
Historic Stepne Manor on Maryland's Eastern Shore, holiday rental in Chestertown

Historic Stepne Manor on Maryland's Eastern Shore

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 15
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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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 14
Match: Sleeps
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Celebrate Memorial Weekend at a Beautiful Estate with Pool!, holiday rental in Chestertown
Celebrate Memorial Weekend at a Beautiful Estate with Pool!, holiday rental in Chestertown
Celebrate Memorial Weekend at a Beautiful Estate with Pool!, holiday rental in Chestertown

Celebrate Memorial Weekend at a Beautiful Estate with Pool!

Holiday Rental House
11 bedrooms
9 bathrooms
Sleeps 30
Match: Sleeps
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Pet-Friendly Home on Chester River w/ Dock!, holiday rental in Chestertown
Pet-Friendly Home on Chester River w/ Dock!, holiday rental in Chestertown
Pet-Friendly Home on Chester River w/ Dock!, holiday rental in Chestertown

Pet-Friendly Home on Chester River w/ Dock!

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Lovely Home in Chestertown Which Sleeps 7 -  Free EV Charging for guest, holiday rental in Chestertown
Lovely Home in Chestertown Which Sleeps 7 -  Free EV Charging for guest, holiday rental in Chestertown
Lovely Home in Chestertown Which Sleeps 7 -  Free EV Charging for guest, holiday rental in Chestertown

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Eastern Shore Getaway: Walk to Tolchester Marina!, holiday rental in Chestertown
Eastern Shore Getaway: Walk to Tolchester Marina!, holiday rental in Chestertown
Eastern Shore Getaway: Walk to Tolchester Marina!, holiday rental in Chestertown

Eastern Shore Getaway: Walk to Tolchester Marina!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Showing results 1-28 of 28
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