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Dover Plains Holiday Rentals

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50 rentals in Dover Plains.
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Beautiful mountaintop getaway for peace and quiet, holiday rental in Dover Plains

Beautiful mountaintop getaway for peace and quiet

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to The Lake: Your Private Paradise Awaits!, holiday rental in Dover Plains

Welcome to The Lake: Your Private Paradise Awaits!

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Newly Renovated 18th Century Cottage On 4 Acres, holiday rental in Dover Plains

Newly Renovated 18th Century Cottage On 4 Acres

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., holiday rental in Dover Plains

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront Escape with Gorgeous Views a Short Trip from New York City!, holiday rental in Dover Plains

Lakefront Escape with Gorgeous Views a Short Trip from New York City!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Short Term Vacation Rental in Kent, holiday rental in Dover Plains

Spectacular Short Term Vacation Rental in Kent

3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Stylish and modern house in the quaint town of Millbrook., holiday rental in Dover Plains

Stylish and modern house in the quaint town of Millbrook.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Annex/Former Artist Studo, holiday rental in Dover Plains

Private Annex/Former Artist Studo

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Pet & Kid Friendly, Solar, 13 Acres, Salt Water Pool, River Views, holiday rental in Dover Plains

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

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres, holiday rental in Dover Plains

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

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Direct Water Front Home, holiday rental in Dover Plains

Direct Water Front Home

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

Historic Warren/Kent Home

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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TREEMENDOUS VIEWS COTTAGE, holiday rental in Dover Plains

TREEMENDOUS VIEWS COTTAGE

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mountainview - Vacation Rental in Sharon, CT, holiday rental in Dover Plains

Mountainview - Vacation Rental in Sharon, CT

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Warren country retreat, holiday rental in Dover Plains

Warren country retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New England Winter Wonderland - 2 Hrs from NYC, holiday rental in Dover Plains

New England Winter Wonderland - 2 Hrs from NYC

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Modern cottage on the Housatonic River, holiday rental in Dover Plains

Modern cottage on the Housatonic River

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront House on Lake Waramaug!, holiday rental in Dover Plains

Waterfront House on Lake Waramaug!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Secluded country cabin upstate New York, near  metro north train, holiday rental in Dover Plains

Secluded country cabin upstate New York, near metro north train

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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The Hilltop - Stunning, holiday rental in Dover Plains

The Hilltop - Stunning

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Kent Getaway With Views, Pond & Pool, holiday rental in Dover Plains

Private Kent Getaway With Views, Pond & Pool

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU, holiday rental in Dover Plains

SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Immaculate 1780 Millbrook Classic, holiday rental in Dover Plains

Immaculate 1780 Millbrook Classic

5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Serene, Peaceful Get-Away (Log Cabin by the Lake), holiday rental in Dover Plains

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rustic Country Beach Cottage Candlewood Lake, holiday rental in Dover Plains

Rustic Country Beach Cottage Candlewood Lake

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Mabels Hollow Farm, En suite bedroom farm stay,, holiday rental in Dover Plains

Mabels Hollow Farm, En suite bedroom farm stay,

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Prana Residence - Spa, holiday rental in Dover Plains

Prana Residence - Spa

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Harley's Hideaway, A Relaxing Escape, holiday rental in Dover Plains

Harley's Hideaway, A Relaxing Escape

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hudson Valley - Picardy Farm: Entire Estate, holiday rental in Dover Plains

Hudson Valley - Picardy Farm: Entire Estate

10 bedrooms
8 bathrooms
Sleeps 20
Match: Sleeps
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Millbrook Country Dream! Tennis/Swim/Play, holiday rental in Dover Plains

Millbrook Country Dream! Tennis/Swim/Play

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Lake House Rental On Your Own Private Lake, holiday rental in Dover Plains

Lake House Rental On Your Own Private Lake

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Exclusive Rental in Beautiful Amenia!, holiday rental in Dover Plains

Exclusive Rental in Beautiful Amenia!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dainty New Preston Cottage w/ Dock & Lake Views!, holiday rental in Dover Plains

Dainty New Preston Cottage w/ Dock & Lake Views!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Dutchess County Guest House on Working Horse Farm!, holiday rental in Dover Plains

Dutchess County Guest House on Working Horse Farm!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The FarmHouse, holiday rental in Dover Plains

The FarmHouse

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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1790 Classic Colonial Center Hall home, holiday rental in Dover Plains

1790 Classic Colonial Center Hall home

5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Kent Victorian Room 1, holiday rental in Dover Plains

Kent Victorian Room 1

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kent Victorian Room 4, holiday rental in Dover Plains

Kent Victorian Room 4

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kent Victorian Room 5, holiday rental in Dover Plains

Kent Victorian Room 5

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Kent Victorian Room 3, holiday rental in Dover Plains

Kent Victorian Room 3

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kent Victorian Room 2, holiday rental in Dover Plains

Kent Victorian Room 2

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tentrr Signature Site - A Riverwalk, holiday rental in Dover Plains

Tentrr Signature Site - A Riverwalk

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Driftways Farm, holiday rental in Dover Plains

Tentrr Signature Site - Driftways Farm

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Creekside Solitude, holiday rental in Dover Plains

Tentrr Signature Site - Creekside Solitude

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Private Peaceful Farm Venture, holiday rental in Dover Plains

Tentrr Signature Site - Private Peaceful Farm Venture

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Hudson Valley Hilltop 1, holiday rental in Dover Plains

Tentrr Signature Site - Hudson Valley Hilltop 1

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Secluded Home w/Fire Pit: Sip, Ski & Explore!, holiday rental in Dover Plains

NEW! Secluded Home w/Fire Pit: Sip, Ski & Explore!

6 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Family Getaway w/ Fireplace in Sherman on 4 Acres!, holiday rental in Dover Plains

Family Getaway w/ Fireplace in Sherman on 4 Acres!

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Tentrr Signature Site - Maybrook Farm - The Ridge, holiday rental in Dover Plains

Tentrr Signature Site - Maybrook Farm - The Ridge

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Tentrr Signature Site - Hudson Valley Hilltop 2, holiday rental in Dover Plains

Tentrr Signature Site - Hudson Valley Hilltop 2

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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