Dutchess County Vacation Rentals - HolidayHomes base64Hash Dutchess County Vacation Rentals - HolidayHomes

Dutchess County Vacation Rentals

Browse 1,157 available vacation homes and compared across 11 trusted partners

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Top-Rated Vacation rentals in Dutchess County

Book the highest-rated Dutchess County vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Cabin Holmes

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

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House Pine Plains

House with grill, garden & terrace

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House Wingdale

House with garden, barbecue & patio | Nature view | Suitable for remote work

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House Staatsburg

Family-oriented house with BBQ, yard & patio | Nature view | Good for workation | Dogs allowed

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House Staatsburg

House with patio & jacuzzi | Nature view

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House Millerton

House with yard, patio & barbeque

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Farmhouse Rhinebeck

Spacious Country Farmhouse on 8 Lush Acres, Five Minutes to Rhinebeck Village

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House Millbrook

Family-friendly house with garden, patio & private pool | Mountain view | Perfect for remote work | Dogs allowed

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House Salt Point

Vacation home with terrace, hot tub & yard | Mountain view

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House Beacon

Child-friendly wonderful vacation home with barbeque, private pool & yard | Mountain view | Perfect for remote work

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House Lagrangeville

Vacation home with BBQ, patio & private pool | Perfect for remote work

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House Red Hook

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

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House Clinton Corners

Hudson Valley stunning lake side modern barn in an Enchanted Forest

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Cabin Holmes

Family-friendly nice cabin with garden, terrace & hot tub | Lake view | Good for workation

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House Staatsburg

Child-friendly big house with barbeque, garden & jacuzzi | Suitable for remote work

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Top 15 most Recommended Vacation Rentals in Dutchess County

Discover your ideal Dutchess County vacation rental with real-time comparisons of 1,157 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Salt Point
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly beautiful house with BBQ & patio | Pet-friendly

Salt Point, Pleasant Valley, Dutchess County
Charming house rental in Salt Point accommodates 6 guests and features a fully equipped kitchen for family-friendly gatherings.
from $495
per night
(80)
View deal
House La Grange
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped beautiful vacation home with yard, private pool & terrace | Perfect for remote work

La Grange, Dutchess County, New York, United States
This house rental in Pleasant Valley accommodates 10 guests and features a inviting fireplace for cozy gatherings.
from $619
per night
(5)
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Apartment Milan
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday apartment with terrace, barbecue & yard | Nature view

Milan, Dutchess County, New York, United States
Cozy apartment rental in Milan for 2 featuring a modern kitchen and convenient parking.
from $246
per night
(207)
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House Holmes
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly house with yard, terrace & grill | Lake view

Holmes, Pawling, Dutchess County
This house rental in Holmes accommodates 6 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $487
per night
(151)
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House Beacon
House ∙ 2 guests ∙ 1 bedroom

Family-friendly wonderful house with hot tub, BBQ & garden | City view

Beacon, Dutchess County, New York, United States
Cozy house rental in Beacon for 2 featuring a charming fireplace and a lovely yard for relaxation.
from $532
per night
(56)
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Apartment Staatsburg
Apartment ∙ 3 guests ∙ 1 bedroom

Apartment with yard, barbeque & private pool | Mountain view

Staatsburg, Hyde Park, Dutchess County
This cozy apartment rental in Staatsburg accommodates 3 guests and features a private pool for a relaxing stay.
from $242
per night
(33)
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Cabin Stanfordville
Cabin ∙ 2 guests ∙ 1 bedroom

Cabin with barbeque, terrace & yard | Lake view

Stanfordville, Stanford, Dutchess County
Cozy cabin in Stanfordville for 2 featuring a charming fireplace and surrounded by nature's beauty.
from $262
per night
(105)
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House Dover Plains
House ∙ 10 guests ∙ 3 bedrooms

House with private pool, yard & jacuzzi | Good for workation

Dover Plains, Dover, Dutchess County
Spacious house rental in Dover Plains for 10 guests featuring a private pool and a family-friendly environment.
from $576
per night
(8)
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Cabin Clinton
Cabin ∙ 8 guests ∙ 3 bedrooms

Fully equipped cottage with barbecue & pool

Clinton, Dutchess County, New York, United States
This cozy cabin in Clinton accommodates 8 guests and features a welcoming fireplace for relaxing evenings.
from $498
per night
(1)
View deal

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