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Chestertown Holiday Apartments

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43 rentals in Chestertown.
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Chestertown's Pet-Friendly Little Red Cottage, holiday rental in Chestertown

Chestertown's Pet-Friendly Little Red Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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River Lodge, Casual Riverfront setting, holiday rental in Chestertown

River Lodge, Casual Riverfront setting

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Cozy & Spacious Chestertown Home, holiday rental in Chestertown

Cozy & Spacious Chestertown Home

4 bedrooms
3 bathrooms
Sleeps 8
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Cottage On Kent, holiday rental in Chestertown

Cottage On Kent

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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First time VRBO Offering!, holiday rental in Chestertown

First time VRBO Offering!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Carriage House Hideaway in Middle of Chestertown, holiday rental in Chestertown

Carriage House Hideaway in Middle of Chestertown

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wren Retweet-Country Estate in the Center of Chestertown, holiday rental in Chestertown

Wren Retweet-Country Estate in the Center of Chestertown

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Waterfront Estate - Special Summer Rates, holiday rental in Chestertown

Beautiful Waterfront Estate - Special Summer Rates

11 bedrooms
9 bathrooms
Sleeps 27
Match: Sleeps
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Cottage within walking distance to the Bay!, holiday rental in Chestertown

Cottage within walking distance to the Bay!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Carriage House Hideaway in Middle of Chestertown

0 bedrooms
0 bathrooms
Sleeps 0
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Eastern Shore beach cottage get-away, holiday rental in Chestertown

Eastern Shore beach cottage get-away

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Eastern Shore Get Away, holiday rental in Chestertown

Eastern Shore Get Away

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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240' Private Beachfront *Kent Island Love Point-Reunions/Rehearsal Dinners, holiday rental in Chestertown

240' Private Beachfront *Kent Island Love Point-Reunions/Rehearsal Dinners

5 bedrooms
5 bathrooms
Sleeps 26
Match: Sleeps
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Secluded Waterfront Cottage on 200 acre farm near Queenstown, holiday rental in Chestertown

Secluded Waterfront Cottage on 200 acre farm near Queenstown

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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This house is a 6 bedroom(s), 6 bathrooms, located in Earleville, MD., holiday rental in Chestertown

This house is a 6 bedroom(s), 6 bathrooms, located in Earleville, MD.

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Waterfront with Chesapeake Sunsets, holiday rental in Chestertown

Waterfront with Chesapeake Sunsets

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Retreat Located in Rock Hall - walk to everything!, holiday rental in Chestertown

Beautiful Retreat Located in Rock Hall - walk to everything!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Peaceful getaway convenient to local amenities including beach, boating & food, holiday rental in Chestertown

Peaceful getaway convenient to local amenities including beach, boating & food

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stay in the landmark Lighthouse!, holiday rental in Chestertown

Stay in the landmark Lighthouse!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront House, pier, close to Betterton Chestertown & Rockhall, holiday rental in Chestertown

Waterfront House, pier, close to Betterton Chestertown & Rockhall

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Blissful Retreat In Rock Hall, holiday rental in Chestertown

Blissful Retreat In Rock Hall

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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BEAUTIFUL BAY FRONT VIEW, holiday rental in Chestertown

BEAUTIFUL BAY FRONT VIEW

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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rancher a half block from the bay, holiday rental in Chestertown

rancher a half block from the bay

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Winehouse at Love Point Vineyards and Winery, holiday rental in Chestertown

The Winehouse at Love Point Vineyards and Winery

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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200 steps to the beach!, holiday rental in Chestertown

200 steps to the beach!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Eastern Shore Getaway: Sleeps 10, Large Yard, Close To Beach, holiday rental in Chestertown

Eastern Shore Getaway: Sleeps 10, Large Yard, Close To Beach

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Life is better at the RIVER!--Cozy waterfront cottage, holiday rental in Chestertown

Life is better at the RIVER!--Cozy waterfront cottage

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A European styled retreat on Marylands Eastern Shore with Private pool, holiday rental in Chestertown

A European styled retreat on Marylands Eastern Shore with Private pool

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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5 acre estate with deep water dock and 1,700 feet of coastline, holiday rental in Chestertown

5 acre estate with deep water dock and 1,700 feet of coastline

5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4, holiday rental in Chestertown

Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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In Town Beautiful Studio Cottage with Sauna, Lawton Avenue, holiday rental in Chestertown

In Town Beautiful Studio Cottage with Sauna, Lawton Avenue

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Lodge on Main Street, a Victorian Apartment, walk to everything!, holiday rental in Chestertown

The Lodge on Main Street, a Victorian Apartment, walk to everything!

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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The Shallow Creek Shore Shack, holiday rental in Chestertown

The Shallow Creek Shore Shack

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Serene Waterfront Cottage with dock and gorgeous views., holiday rental in Chestertown

Serene Waterfront Cottage with dock and gorgeous views.

1 bedroom
2 bathrooms
Sleeps 7
Match: Sleeps
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Overton Farm Cottage, holiday rental in Chestertown

Overton Farm Cottage

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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This is truly a Baydream!, holiday rental in Chestertown

This is truly a Baydream!

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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The Cottage at Broken Spoke Winery, holiday rental in Chestertown

The Cottage at Broken Spoke Winery

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bay Cottage, holiday rental in Chestertown

Bay Cottage

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Bayside Retreat, holiday rental in Chestertown

Bayside Retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious Home on the Chesapeake Bay, Fantastic Views, W/ Pool, holiday rental in Chestertown

Luxurious Home on the Chesapeake Bay, Fantastic Views, W/ Pool

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!, holiday rental in Chestertown

3BR 1BA Private Beach / Pool / Boat Launch / Pier / Golf Cart and much more!

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Abay Palace of Kent Narrows in a King Bed, holiday rental in Chestertown

Abay Palace of Kent Narrows in a King Bed

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Big house w/ big backyard! Everything you need in a house & stay is right here., holiday rental in Chestertown

Big house w/ big backyard! Everything you need in a house & stay is right here.

3 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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