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

Dutchess County Vacation Rentals

Browse 1,117 available vacation homes and compared across 13 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

House Pine Plains
House with grill, garden & terrace
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House Salt Point
Family-friendly beautiful house with BBQ & patio | Pet-friendly
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House Wingdale
House with garden, barbecue & patio | Nature view | Suitable for remote work
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House Fishkill
Vacation home with garden & patio
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House Hyde Park
House with BBQ & garden
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Farmhouse Rhinebeck
Spacious Country Farmhouse on 8 Lush Acres, Five Minutes to Rhinebeck Village
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Cabin Holmes
Lakefront Escape with Gorgeous Views a Short Trip from New York City!
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House Millbrook
Family-friendly house with garden, patio & private pool | Mountain view | Dogs allowed
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House Rhinebeck
House with terrace, yard & private pool | Nature view
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Apartment Pleasant Valley
Apartment with BBQ, garden & patio | Mountain view | Suitable for remote work
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House Rhinebeck
Vacation home with patio & yard | Lake view | Suitable for remote work
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Farmhouse Red Hook
Farm with BBQ, pool & sauna
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House Pine Plains
Stylish Pine Plains Home Near Parks & Hiking!
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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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Cabin Poughkeepsie
Cottage with barbeque, terrace & yard | Nature view
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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 1,117 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Hillside Lake
House ∙ 8 guests ∙ 4 bedrooms

232 m² House

Hillside Lake, East Fishkill, Dutchess County
Spacious house rental in Hillside Lake accommodating 10 guests with a family-friendly kitchen and ample parking available.
from $363
per night
(17)
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House Hopewell Junction
House ∙ 8 guests ∙ 3 bedrooms

172 m² House

Hopewell Junction, East Fishkill, Dutchess County
This house rental in Hopewell Junction accommodates 8 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $359
per night
(101)
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House Beacon
House ∙ 2 guests ∙ 1 bedroom

65 m² House

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 $531
per night
(55)
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House Millerton
House ∙ 6 guests ∙ 3 bedrooms

186 m² House

Millerton, North East, Dutchess County
This house rental in Millerton accommodates 6 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $521
per night
(24)
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House Stanfordville
House ∙ 7 guests ∙ 4 bedrooms

353 m² House

Stanfordville, Stanford, Dutchess County
This house rental in Stanfordville accommodates 7 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $276
per night
(5)
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House Pleasant Valley
House ∙ 6 guests ∙ 3 bedrooms

223 m² House

Pleasant Valley, Dutchess County, New York, United States
This house rental in Pleasant Valley accommodates 6 guests and features a private pool for a relaxing getaway.
from $713
per night
(1)
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House Millerton
8 guests ∙ 4 bedrooms

House

Millerton, North East, Dutchess County
This house rental in Millerton accommodates 8 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $487
per night
(91)
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House Rhinebeck
House ∙ 14 guests ∙ 6 bedrooms

325 m² House

Rhinebeck, Dutchess County, New York, United States
This house rental in Rhinebeck accommodates 14 guests and features a private pool for a relaxing stay.
from $1,048
per night
(88)
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House Pawling
House ∙ 6 guests ∙ 3 bedrooms

232 m² House

Pawling, Dutchess County, New York, United States
This house rental in Pawling accommodates 6 guests and features a private pool for a relaxing getaway.
from $322
per night
(3)
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