Dutchess County Vacation Rentals & Ski-in/Ski-out Homes

Compare Vacation Rentals & Ski-in/Ski-out Homes in Dutchess County, New York, USA

rural, serene + sophisticated space
House
rural, serene + sophisticated space
From US $365 per night
10.0 (7 Reviews)
2 Bedrooms 5 Guests
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Stylish Pine Plains Home Near Parks and Hiking!
House
Stylish Pine Plains Home Near Parks and Hiking!
From US $153 per night
|
10.0 (7 Reviews)
1 Bedroom 2 Guests
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the suite @ barn & bike - private, bucolic, serene setting
Other
the suite @ barn & bike - private, bucolic, serene setting
From US $193 per night
9.8 (14 Reviews)
1 Bedroom 2 Guests
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the barn at barn & bike
Villa
the barn at barn & bike
From US $372 per night
10.0 (3 Reviews)
2 Bedrooms 5 Guests
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The Baker House Bed & Breakfast
Bed & Breakfast
The Baker House Bed & Breakfast
From US $305 per night
|
10.0 (71 Reviews)
1 Bedroom 2 Guests
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New Quiet Historic Beacon Home with Garden - Quick Walk to Main St & DIA
House
Quiet Historic Beacon Home with Garden - Quick Walk to Main St & DIA
From US $398 per night
10.0 (4 Reviews)
3 Bedrooms 6 Guests
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New Staatsburg Parsonage - A tranquil 4-bedroom house with AC
House
Staatsburg Parsonage - A tranquil 4-bedroom house with AC
From US $430 per night
10.0 (1 Review)
4 Bedrooms 2 Guests
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Fire Pit and On-Site Pond Hudson Valley Home!
House
Fire Pit and On-Site Pond Hudson Valley Home!
From US $446 per night
|
10.0 (2 Reviews)
4 Bedrooms 10 Guests
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Troutbeck
House
Troutbeck
From US $305 per night
10.0 (1 Review)
36 Bedrooms 47 Guests
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New Charming Gothic Victorian restoration in Beacon
House
Charming Gothic Victorian restoration in Beacon
From US $364 per night
New
2 Bedrooms 5 Guests
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the farmhouse suite at barn & bike
Apartment
the farmhouse suite at barn & bike
From US $191 per night
|
9.9 (14 Reviews)
1 Bedroom 2 Guests
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New Charming studio cottage with AC in the heart of Beacon
Cottage
Charming studio cottage with AC in the heart of Beacon
From US $198 per night
New
1 Bedroom 4 Guests
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Dog-Friendly Fishkill Tiny House in Wine Country
Apartment
Dog-Friendly Fishkill Tiny House in Wine Country
From US $328 per night
|
9.5 (2 Reviews)
3 Bedrooms 5 Guests
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2Br Private Victorian Apartment in City location on half acre Sleeps 5
Apartment
2Br Private Victorian Apartment in City location on half acre Sleeps 5
From US $188 per night
|
9.1 (15 Reviews)
2 Bedrooms 5 Guests
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The House In Highland-nSecluded Retreat
House
The House In Highland-nSecluded Retreat
From US $602 per night
10.0 (10 Reviews)
3 Bedrooms 6 Guests
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Pet-Friendly Beacon Area Vacation Rental 6 Acres
House
Pet-Friendly Beacon Area Vacation Rental 6 Acres
From US $794 per night
|
9.0 (4 Reviews)
5 Bedrooms 13 Guests
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Charming Vacation House w/Pool & HotTub
House
Charming Vacation House w/Pool & HotTub
From US $1,055 per night
10.0 (5 Reviews)
4 Bedrooms 8 Guests
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The Red Country Cottage
House
The Red Country Cottage
From US $5,000 per night
|
9.0 (1 Review)
4 Bedrooms 8 Guests
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6 Acre Private Hudson Valley Estate
House
6 Acre Private Hudson Valley Estate
From US $1,721 per night
9.8 (6 Reviews)
4 Bedrooms 8 Guests
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Mid-Century DJs Dream near Rhinebeck
Apartment
Mid-Century DJs Dream near Rhinebeck
From US $195 per night
|
8.9 (44 Reviews)
1 Bedroom 2 Guests
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The Scenic Mansion With Breathtaking View
Villa
The Scenic Mansion With Breathtaking View
From US $1,035 per night
8.8 (18 Reviews)
4 Bedrooms 10 Guests
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Charming Beacon Apt with Fire Pit Near Hiking!
Apartment
Charming Beacon Apt with Fire Pit Near Hiking!
From US $148 per night
|
8.5 (9 Reviews)
1 Bedroom 4 Guests
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Hudson Escape W/Hot Tub + Bridge View
House
Hudson Escape W/Hot Tub + Bridge View
From US $645 per night
New
3 Bedrooms 6 Guests
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Millbrook Country House
Bed & Breakfast
Millbrook Country House
From US $215 per night
8.4 (49 Reviews)
4 Bedrooms 12 Guests
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Jenny's Country Manor
Bed & Breakfast
Jenny's Country Manor
From US $130 per night
8.3 (11 Reviews)
13 Bedrooms 16 Guests
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Lux Apt
Apartment
Lux Apt
From US $283 per night
8.3 (9 Reviews)
1 Bedroom 2 Guests
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WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
Apartment
WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - THE FOX DEN STUDIO
From US $240 per night
10.0 (178 Reviews)
1 Bedroom 2 Guests
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Quiet Lakefront Retreat only 80 minutes from NYC- with Private Dock
House
Quiet Lakefront Retreat only 80 minutes from NYC- with Private Dock
From US $554 per night
10.0 (125 Reviews)
3 Bedrooms 6 Guests
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Charming Brick House -Hudson Valley
House
Charming Brick House -Hudson Valley
From US $345 per night
10.0 (79 Reviews)
3 Bedrooms 6 Guests
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Bluebird Valley Farmhouse
House
Bluebird Valley Farmhouse
From US $509 per night
10.0 (69 Reviews)
4 Bedrooms 8 Guests
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Pet-Friendly Beacon Area Vacation Rental: 6 Acres
House
Pet-Friendly Beacon Area Vacation Rental: 6 Acres
From US $615 per night
10.0 (20 Reviews)
5 Bedrooms 13 Guests
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Private setting on country farm near Rhinebeck
Bed & Breakfast
Private setting on country farm near Rhinebeck
From US $134 per night
8.2 (31 Reviews)
4 Bedrooms 6 Guests
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Inn at Pine Plains
Bed & Breakfast
Inn at Pine Plains
From US $288 per night
|
9.8 (291 Reviews)
1 Bedroom 2 Guests
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East Fishkill Escape, Close to Red Wing Park!
Apartment
East Fishkill Escape, Close to Red Wing Park!
From US $182 per night
|
8.0 (4 Reviews)
1 Bedroom 4 Guests
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Inn the Woods Bed and Breakfast
Bed & Breakfast
Inn the Woods Bed and Breakfast
From US $187 per night
|
9.8 (127 Reviews)
1 Bedroom 2 Guests
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Beautiful lake view home on Whaley Lake in Holmes, NY.
House
Beautiful lake view home on Whaley Lake in Holmes, NY.
From US $725 per night
10.0 (17 Reviews)
4 Bedrooms 8 Guests
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Debdorkdave Hospitality Services
House
Debdorkdave Hospitality Services
From US $192 per night
7.5 (10 Reviews)
3 Bedrooms 3 Guests
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Journey Inn Bed & Breakfast
Bed & Breakfast
Journey Inn Bed & Breakfast
From US $253 per night
|
9.6 (330 Reviews)
1 Bedroom 2 Guests
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LOCATION LOCATION LOCATION IN THE HEART OF BEACON & RIGHT ON MAIN STREET.
Apartment
LOCATION LOCATION LOCATION IN THE HEART OF BEACON & RIGHT ON MAIN STREET.
From US $408 per night
10.0 (17 Reviews)
1 Bedroom 2 Guests
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Main Street cabin
Apartment
Main Street cabin
From US $248 per night
5.0 (1 Review)
1 Bedroom 4 Guests
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B&B on seven acres with private bed & bath
Bed & Breakfast
B&B on seven acres with private bed & bath
From US $135 per night
4.5 (7 Reviews)
1 Bedroom 2 Guests
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Beacons Great Getaway Near hike, parks, shops and art
House
Beacons Great Getaway Near hike, parks, shops and art
From US $235 per night
2.0 (1 Review)
3 Bedrooms 7 Guests
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Tower Hill - Hilltop Country Retreat with Panoramic Views
House
Tower Hill - Hilltop Country Retreat with Panoramic Views
From US $775 per night
10.0 (15 Reviews)
4 Bedrooms 6 Guests
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Beautiful Lake View House Overlooking Peaceful Whaley Lake
House
Beautiful Lake View House Overlooking Peaceful Whaley Lake
From US $657 per night
10.0 (15 Reviews)
4 Bedrooms 8 Guests
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Hilltop Home on 10 acres w/hot tub, fire-pit + solar
House
Hilltop Home on 10 acres w/hot tub, fire-pit + solar
From US $473 per night
10.0 (15 Reviews)
3 Bedrooms 9 Guests
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Twin Island Lake House Hot Tub
House
Twin Island Lake House Hot Tub
From US $386 per night
10.0 (15 Reviews)
3 Bedrooms 6 Guests
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About Dutchess County Vacation Rentals

Explore over 736 vacation rentals in Dutchess County with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Dutchess County for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Dutchess County. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Dutchess County tailored to your preferences. On average, these rentals offer 1129.77 ft² of space, and are priced at an average of US $512 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Dutchess County at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

Other Places to Stay in Dutchess County, NY


Lower Hudson Valley 2,612 Properties
Poughkeepsie 697 Properties
Staatsburg 74 Properties
Fishkill 51 Properties
Red Hook 43 Properties
Beacon 39 Properties
Rhinebeck 38 Properties
Town of Stanford 33 Properties
Pine Plains 33 Properties
Clinton Corners 32 Properties
Town of East Fishkill 25 Properties
Hopewell Junction 24 Properties

Frequently Asked Questions About Dutchess County?

What are the top vacation rentals in Dutchess County?

How many SunSkiResorts vacation rentals or resorts are available in Dutchess County?

Discover the ideal vacation rental in Dutchess County with SunSki Resorts™. We provide an extensive selection of over 736 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Dutchess County.

There are 736 Dutchess County, NY Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Dutchess County