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Chestertown Holiday Rentals

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50 rentals in Chestertown.
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Water Front Retreat - Sunrise and Sunset Water Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Chestertown's Pet-Friendly Little Red Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Contemporary waterfront house with private dock & kayaks!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Social Distance on 350 Acre Waterfront Farm with Dock, Pool, Sport Court WiFi.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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River Lodge, Casual Riverfront setting

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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Country Estate in Historic District

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Chester River Waterfront, Magnificent Views, Dock, Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Manor House on Beautiful Eastern Shore Estate

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 13
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Carriage House Hideaway in Middle of Chestertown

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Beautiful Waterfront Estate - Special Summer Rates

Holiday Rental House
11 bedrooms
9 bathrooms
Sleeps 27
Match: Sleeps
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Cottage within walking distance to the Bay!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Waterfront home with private pier and pool!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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Eastern Shore beach cottage get-away

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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240' Private Beachfront *Kent Island Love Point-Reunions/Rehearsal Dinners

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 26
Match: Sleeps
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Blissful Retreat In Rock Hall

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Secluded Waterfront Cottage on 200 acre farm near Queenstown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Eastern Shore Get Away

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
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Peaceful getaway convenient to local amenities including beach, boating & food

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Life is better at the RIVER!--Cozy waterfront cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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Waterfront with Chesapeake Sunsets

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Brand New Cottage Steps from the Beach!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Beautiful Retreat Located in Rock Hall - walk to everything!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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5 acre estate with deep water dock and 1,700 feet of coastline

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 15
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BEAUTIFUL BAY FRONT VIEW

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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200 steps to the beach!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Stay in the landmark Lighthouse!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Waterfront House, pier, close to Betterton Chestertown & Rockhall

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
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The Winehouse at Love Point Vineyards and Winery

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
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EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 11
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Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Luxurious Home on the Chesapeake Bay, Fantastic Views, W/ Pool

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Overton Farm Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Beautiful, spacious, quiet waterfront house!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Lodge on Main Street, a Victorian Apartment, walk to everything!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 9
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Serene Waterfront Cottage with dock and gorgeous views.

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 7
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Love Point Waterfront

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
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Wye River Cottage and Horse Barn

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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This is truly a Baydream!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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A stunning waterfront property that sleeps 14

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Rambling Victorian Beach House on Maryland's Eastern Shore

Holiday Rental House
8 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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This house is a 6 bedroom(s), 6 bathrooms, located in Earleville, MD.

Holiday Rental House
8 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Creek Cottage - Idyllic, Pet-Friendly Waterfront Farm - Pool, Dock, Grilling!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Abay Palace of Kent Narrows in a King Bed

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Waterfront property on 3/4 acres with private beach, pool, hot tub, and pier.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The Little Blue Cottage by the Bay

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
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Waterfront Views and a Sandy Beach

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Charming 3 bdrm cottage with lovely front porch

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Great deal 4 Bedroom House Near the Ferry Park

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Big house w/ big backyard! Everything you need in a house & stay is right here.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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