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Dutchess County summer vacation rentals

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Top-rated vacation rentals in Dutchess County

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

SUPERHOST
  1. Entire cottage
  2. Pleasant Valley
Entire cozy rustic cottage in family farm

Come relax and unwind in this rustic yet modern farm cottage that's surrounded by tranquility and nature in Pleasant Valley near everything the Hudson Valley has to offer from farms and wineries to small towns and great restaurants. Spacious cottage, covered porch, outdoor heated salt-water pool for your exclusive use, paver patio and a huge deck right outside the loft bedroom for coffee, reading or a drink. Private parking, nature all around and a short drive to the city on the Taconic.

$115 per night
SUPERHOST
  1. Entire rental unit
  2. Pleasant Valley
Get-away gem in Dutchess County near everything

Enjoy country living a short drive from anywhere in this unique, modern and private gem. You'll enjoy everything the HudsonValley has to offer from your base a short distance from the Taconic. Close to Millbrook, Taconic parks, trails, lakes, antique shops, restaurants, etc. This family farm is set back from the road, wooded, beautiful and private 4 acres . The studio is on the ground floor of a family home and comes with everything you'll need for a short or a long term stay.

$100 per night
SUPERHOST
  1. Private room
  2. Pleasant Valley
Cedarhurst 2

Our home was built in 1872 and is used to welcoming guests. In the early 1900's it was a bed&breakfast called Cedarhurst Farm. We are situated at the center of Dutchess County, about one and a half hour north of New York City. This puts you within easy reach of many places of interest in all directions. Beautiful rural towns like Rhinebeck, Hudson, New Paltz at the foothills of the mountainous Catskill area and the artist community of Beacon, to name a few.

$55 per night

Vacation rentals for every style

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Dutchess County vacation rentals

SUPERHOST
  1. Private room
  2. Pleasant Valley
Cedarhurst 1
$65 per night
SUPERHOST
  1. Entire cabin
  2. Rhinebeck
Sunset Bungalow-Mt views on 130acre forest & falls
$166 per night
SUPERHOST
  1. Tiny home
  2. Millbrook
Leonardo Lane Cottage
$200 per night
SUPERHOST
  1. Entire guest suite
  2. Staatsburg
Country Meets Mid-Century Vinyl
$101 per night
SUPERHOST
  1. Entire loft
  2. Millbrook
Leonardo Lane The Bennett Cabin
$150 per night
  1. Entire cottage
  2. Pawling
Country Cottage Getaway with Yoga Shed & Sauna
$138 per night
SUPERHOST
  1. Entire rental unit
  2. Millbrook
Red Tail Ridge
$112 per night
  1. Private room
  2. Hyde Park
Tranquil room in the woods
$97 per night
  1. Private room
  2. Highland
Casa del Arte welcomes you!
$74 per night
SUPERHOST
  1. Entire cottage
  2. Rhinebeck
Fabulous Lemon Cottage in Rhinebeck, NY
$255 per night
SUPERHOST
  1. Entire guest suite
  2. Dover Plains
Hoppy Hill
$101 per night
SUPERHOST
  1. Private room
  2. Poughkeepsie
Home Away From Home!
$64 per night