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Dover Plains Vacation Rentals

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50 rentals in Dover Plains.
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Beautiful Log Home - Great Escape for the Holidays!  Strong WIFI!, vacation rental in Dover Plains
Beautiful Log Home - Great Escape for the Holidays!  Strong WIFI!, vacation rental in Dover Plains
Beautiful Log Home - Great Escape for the Holidays!  Strong WIFI!, vacation rental in Dover Plains

Beautiful Log Home - Great Escape for the Holidays! Strong WIFI!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Charming Country House, vacation rental in Dover Plains
Charming Country House, vacation rental in Dover Plains
Charming Country House, vacation rental in Dover Plains

Charming Country House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful mountaintop getaway for peace and quiet, vacation rental in Dover Plains
Beautiful mountaintop getaway for peace and quiet, vacation rental in Dover Plains
Beautiful mountaintop getaway for peace and quiet, vacation rental in Dover Plains

Beautiful mountaintop getaway for peace and quiet

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Horse Farm, vacation rental in Dover Plains
Beautiful Horse Farm, vacation rental in Dover Plains
Beautiful Horse Farm, vacation rental in Dover Plains

Beautiful Horse Farm

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to The Lake: Your Private Paradise Awaits!, vacation rental in Dover Plains
Welcome to The Lake: Your Private Paradise Awaits!, vacation rental in Dover Plains
Welcome to The Lake: Your Private Paradise Awaits!, vacation rental in Dover Plains

Welcome to The Lake: Your Private Paradise Awaits!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful contemporary house in Kent, CT, built in 2018., vacation rental in Dover Plains
Beautiful contemporary house in Kent, CT, built in 2018., vacation rental in Dover Plains
Beautiful contemporary house in Kent, CT, built in 2018., vacation rental in Dover Plains

Beautiful contemporary house in Kent, CT, built in 2018.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., vacation rental in Dover Plains
Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., vacation rental in Dover Plains
Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., vacation rental in Dover Plains

Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six.

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Beech House - Light, Open, Stunning Views, in the heart of the Hudson Valley, vacation rental in Dover Plains
The Beech House - Light, Open, Stunning Views, in the heart of the Hudson Valley, vacation rental in Dover Plains
The Beech House - Light, Open, Stunning Views, in the heart of the Hudson Valley, vacation rental in Dover Plains

The Beech House - Light, Open, Stunning Views, in the heart of the Hudson Valley

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stylish and modern house in the quaint town of Millbrook., vacation rental in Dover Plains
Stylish and modern house in the quaint town of Millbrook., vacation rental in Dover Plains
Stylish and modern house in the quaint town of Millbrook., vacation rental in Dover Plains

Stylish and modern house in the quaint town of Millbrook.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Warren/Kent Home, vacation rental in Dover Plains
Historic Warren/Kent Home, vacation rental in Dover Plains
Historic Warren/Kent Home, vacation rental in Dover Plains

Historic Warren/Kent Home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres, vacation rental in Dover Plains
House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres, vacation rental in Dover Plains
House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres, vacation rental in Dover Plains

House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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In town, walk to everything, close to Kent, South Kent and Marvelwood schools, vacation rental in Dover Plains
In town, walk to everything, close to Kent, South Kent and Marvelwood schools, vacation rental in Dover Plains
In town, walk to everything, close to Kent, South Kent and Marvelwood schools, vacation rental in Dover Plains

In town, walk to everything, close to Kent, South Kent and Marvelwood schools

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spectacular Short Term Vacation Rental in Kent, vacation rental in Dover Plains
Spectacular Short Term Vacation Rental in Kent, vacation rental in Dover Plains
Spectacular Short Term Vacation Rental in Kent, vacation rental in Dover Plains

Spectacular Short Term Vacation Rental in Kent

Rental Home
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Modern cottage on the Housatonic River, vacation rental in Dover Plains
Modern cottage on the Housatonic River, vacation rental in Dover Plains
Modern cottage on the Housatonic River, vacation rental in Dover Plains

Modern cottage on the Housatonic River

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Cottage and Waterfront Access, vacation rental in Dover Plains
Beautiful Cottage and Waterfront Access, vacation rental in Dover Plains
Beautiful Cottage and Waterfront Access, vacation rental in Dover Plains

Beautiful Cottage and Waterfront Access

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Warren country retreat, vacation rental in Dover Plains
Warren country retreat, vacation rental in Dover Plains
Warren country retreat, vacation rental in Dover Plains

Warren country retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views, vacation rental in Dover Plains
Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views, vacation rental in Dover Plains
Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views, vacation rental in Dover Plains

Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views

Rental Home
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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TREEMENDOUS VIEWS COTTAGE, vacation rental in Dover Plains
TREEMENDOUS VIEWS COTTAGE, vacation rental in Dover Plains
TREEMENDOUS VIEWS COTTAGE, vacation rental in Dover Plains

TREEMENDOUS VIEWS COTTAGE

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sharon Country Estate On 300 Acres With 100 Mile Views, vacation rental in Dover Plains
Sharon Country Estate On 300 Acres With 100 Mile Views, vacation rental in Dover Plains
Sharon Country Estate On 300 Acres With 100 Mile Views, vacation rental in Dover Plains

Sharon Country Estate On 300 Acres With 100 Mile Views

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Serene, Peaceful Get-Away (Log Cabin by the Lake), vacation rental in Dover Plains
Serene, Peaceful Get-Away (Log Cabin by the Lake), vacation rental in Dover Plains
Serene, Peaceful Get-Away (Log Cabin by the Lake), vacation rental in Dover Plains

Serene, Peaceful Get-Away (Log Cabin by the Lake)

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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THE WATERFALL HOUSE!, vacation rental in Dover Plains
THE WATERFALL HOUSE!, vacation rental in Dover Plains
THE WATERFALL HOUSE!, vacation rental in Dover Plains

THE WATERFALL HOUSE!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC, vacation rental in Dover Plains
Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC, vacation rental in Dover Plains
Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC, vacation rental in Dover Plains

Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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An acclaimed photographers country estate, arts community, near private schools!, vacation rental in Dover Plains
An acclaimed photographers country estate, arts community, near private schools!, vacation rental in Dover Plains
An acclaimed photographers country estate, arts community, near private schools!, vacation rental in Dover Plains

An acclaimed photographers country estate, arts community, near private schools!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Country Studio in private setting, vacation rental in Dover Plains
Country Studio in private setting, vacation rental in Dover Plains
Country Studio in private setting, vacation rental in Dover Plains

Country Studio in private setting

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Private Kent Getaway With Views, Pond & Pool, vacation rental in Dover Plains
Private Kent Getaway With Views, Pond & Pool, vacation rental in Dover Plains
Private Kent Getaway With Views, Pond & Pool, vacation rental in Dover Plains

Private Kent Getaway With Views, Pond & Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Beautiful, All-Season, Rustic Family Getaway, vacation rental in Dover Plains
Beautiful, All-Season, Rustic Family Getaway, vacation rental in Dover Plains
Beautiful, All-Season, Rustic Family Getaway, vacation rental in Dover Plains

Beautiful, All-Season, Rustic Family Getaway

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Modern Barn, NEW Luxurious Home, vacation rental in Dover Plains
Modern Barn, NEW Luxurious Home, vacation rental in Dover Plains
Modern Barn, NEW Luxurious Home, vacation rental in Dover Plains

Modern Barn, NEW Luxurious Home

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Contemporary Custom Built Home On A Country Lane Close To Sharon, vacation rental in Dover Plains
Contemporary Custom Built Home On A Country Lane Close To Sharon, vacation rental in Dover Plains
Contemporary Custom Built Home On A Country Lane Close To Sharon, vacation rental in Dover Plains

Contemporary Custom Built Home On A Country Lane Close To Sharon

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Immaculate 1780 Millbrook Classic, vacation rental in Dover Plains
Immaculate 1780 Millbrook Classic, vacation rental in Dover Plains
Immaculate 1780 Millbrook Classic, vacation rental in Dover Plains

Immaculate 1780 Millbrook Classic

Rental Home
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Apartment in scenic Hudson Valley New York, vacation rental in Dover Plains
Apartment in scenic Hudson Valley New York, vacation rental in Dover Plains
Apartment in scenic Hudson Valley New York, vacation rental in Dover Plains

Apartment in scenic Hudson Valley New York

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Stunning views and privacy!  4BR/2BA - Sleeps 8, vacation rental in Dover Plains
Stunning views and privacy!  4BR/2BA - Sleeps 8, vacation rental in Dover Plains
Stunning views and privacy!  4BR/2BA - Sleeps 8, vacation rental in Dover Plains

Stunning views and privacy! 4BR/2BA - Sleeps 8

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Rustic Country Beach Cottage Candlewood Lake, vacation rental in Dover Plains
Rustic Country Beach Cottage Candlewood Lake, vacation rental in Dover Plains
Rustic Country Beach Cottage Candlewood Lake, vacation rental in Dover Plains

Rustic Country Beach Cottage Candlewood Lake

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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A Charming Cottage with Modern Amenities and Home Office, vacation rental in Dover Plains
A Charming Cottage with Modern Amenities and Home Office, vacation rental in Dover Plains
A Charming Cottage with Modern Amenities and Home Office, vacation rental in Dover Plains

A Charming Cottage with Modern Amenities and Home Office

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Tentrr Signature Site - A Riverwalk, vacation rental in Dover Plains
Tentrr Signature Site - A Riverwalk, vacation rental in Dover Plains
Tentrr Signature Site - A Riverwalk, vacation rental in Dover Plains

Tentrr Signature Site - A Riverwalk

Rental Home
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Tentrr Signature Site - Creekside Solitude, vacation rental in Dover Plains
Tentrr Signature Site - Creekside Solitude, vacation rental in Dover Plains
Tentrr Signature Site - Creekside Solitude, vacation rental in Dover Plains

Tentrr Signature Site - Creekside Solitude

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Millbrook Country Dream! Tennis/Swim/Play, vacation rental in Dover Plains
Millbrook Country Dream! Tennis/Swim/Play, vacation rental in Dover Plains
Millbrook Country Dream! Tennis/Swim/Play, vacation rental in Dover Plains

Millbrook Country Dream! Tennis/Swim/Play

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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Lake House Rental On Your Own Private Lake, vacation rental in Dover Plains
Lake House Rental On Your Own Private Lake, vacation rental in Dover Plains
Lake House Rental On Your Own Private Lake, vacation rental in Dover Plains

Lake House Rental On Your Own Private Lake

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Exclusive Rental in Beautiful Amenia!, vacation rental in Dover Plains
Exclusive Rental in Beautiful Amenia!, vacation rental in Dover Plains
Exclusive Rental in Beautiful Amenia!, vacation rental in Dover Plains

Exclusive Rental in Beautiful Amenia!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Tentrr Signature Site - A Riverwalk, vacation rental in Dover Plains
Tentrr Signature Site - A Riverwalk, vacation rental in Dover Plains
Tentrr Signature Site - A Riverwalk, vacation rental in Dover Plains

Tentrr Signature Site - A Riverwalk

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Tentrr Signature Site - Creekside Solitude, vacation rental in Dover Plains
Tentrr Signature Site - Creekside Solitude, vacation rental in Dover Plains
Tentrr Signature Site - Creekside Solitude, vacation rental in Dover Plains

Tentrr Signature Site - Creekside Solitude

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Tentrr Signature Site - Private Peaceful Farm Venture, vacation rental in Dover Plains
Tentrr Signature Site - Private Peaceful Farm Venture, vacation rental in Dover Plains
Tentrr Signature Site - Private Peaceful Farm Venture, vacation rental in Dover Plains

Tentrr Signature Site - Private Peaceful Farm Venture

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Luxury home with extraordinary amenities nestled in an idyllic rural setting, vacation rental in Dover Plains
Luxury home with extraordinary amenities nestled in an idyllic rural setting, vacation rental in Dover Plains
Luxury home with extraordinary amenities nestled in an idyllic rural setting, vacation rental in Dover Plains

Luxury home with extraordinary amenities nestled in an idyllic rural setting

Rental Home
5 bedrooms
8 bathrooms
Sleeps 10
Match: Sleeps
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1870s secluded Farmhouse on 10 acres 75 minutes to NYC or Metro North, vacation rental in Dover Plains
1870s secluded Farmhouse on 10 acres 75 minutes to NYC or Metro North, vacation rental in Dover Plains
1870s secluded Farmhouse on 10 acres 75 minutes to NYC or Metro North, vacation rental in Dover Plains

1870s secluded Farmhouse on 10 acres 75 minutes to NYC or Metro North

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Check Out Cute Summer Cottage on Lake Warmaug, vacation rental in Dover Plains
Check Out Cute Summer Cottage on Lake Warmaug, vacation rental in Dover Plains
Check Out Cute Summer Cottage on Lake Warmaug, vacation rental in Dover Plains

Check Out Cute Summer Cottage on Lake Warmaug

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Red Door Country Retreat, vacation rental in Dover Plains
Red Door Country Retreat, vacation rental in Dover Plains
Red Door Country Retreat, vacation rental in Dover Plains

Red Door Country Retreat

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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FARM HOUSE ON 30 ACRES PRIVATE BED AND BATH USE OF 1ST FLOOR, vacation rental in Dover Plains
FARM HOUSE ON 30 ACRES PRIVATE BED AND BATH USE OF 1ST FLOOR, vacation rental in Dover Plains
FARM HOUSE ON 30 ACRES PRIVATE BED AND BATH USE OF 1ST FLOOR, vacation rental in Dover Plains

FARM HOUSE ON 30 ACRES PRIVATE BED AND BATH USE OF 1ST FLOOR

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Country Living at its best in this Sharon Estate with indoor pool*, vacation rental in Dover Plains
Country Living at its best in this Sharon Estate with indoor pool*, vacation rental in Dover Plains
Country Living at its best in this Sharon Estate with indoor pool*, vacation rental in Dover Plains

Country Living at its best in this Sharon Estate with indoor pool*

Rental Home
3 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
More info
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Stay on an Alpaca Farm, vacation rental in Dover Plains
Stay on an Alpaca Farm, vacation rental in Dover Plains
Stay on an Alpaca Farm, vacation rental in Dover Plains

Stay on an Alpaca Farm

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Maybrook Farm - The Ridge, vacation rental in Dover Plains
Tentrr Signature Site - Maybrook Farm - The Ridge, vacation rental in Dover Plains
Tentrr Signature Site - Maybrook Farm - The Ridge, vacation rental in Dover Plains

Tentrr Signature Site - Maybrook Farm - The Ridge

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Tranquil, Private, Luxury Retreat, vacation rental in Dover Plains
Tranquil, Private, Luxury Retreat, vacation rental in Dover Plains
Tranquil, Private, Luxury Retreat, vacation rental in Dover Plains

Tranquil, Private, Luxury Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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