Dutchess County Vacation Rentals

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Top Cities in Dutchess County

Poughkeepsie featuring autumn leaves and a river or creek
Vacation HomesVacation Homes

Poughkeepsie

Poughkeepsie

Featured Vacation Homes in Dutchess County

The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (76)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (27)
"Perfect for small family stay over for a wedding ! "
The price is CA $356
CA $456 total
includes taxes & fees
Aug 31 - Sep 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV, fireplace

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.0 out of 10, Wonderful, (37)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Modern NY Home w/ Views By Hudson Valley Hiking!
TV, fireplace, books, video library

Modern NY Home w/ Views By Hudson Valley Hiking!

9.8 out of 10, Exceptional, (25)
"Lovely home and great proximity to Taconic Parkway for all points north and south. Owner very accomodating"
Modern NY Home w/ Views By Hudson Valley Hiking!
Stylish Pine Plains Home Near Parks & Hiking!
Fridge, microwave, stovetop, dishwasher

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (16)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!
The Chicken Coop
Outdoor dining

The Chicken Coop

9.2 out of 10, Wonderful, (7)
"Very cool place everything u need is just a short drive away "
The Chicken Coop
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Outdoor dining

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

10.0 out of 10, Exceptional, (4)
"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."
The price is CA $447
CA $840 total
includes taxes & fees
Aug 24 - Aug 25
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Exterior

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

10.0 out of 10, Exceptional, (16)
"We loved our stay at this local and charming Red Hook property, complete with a piano for our son to play!"
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
YOIN: Whispers of Tranquility, a Zen Retreat
Dining

YOIN: Whispers of Tranquility, a Zen Retreat

YOIN: Whispers of Tranquility, a Zen Retreat
Stunning Light-Filled Contemporary Home on 7 Acres
Interior

Stunning Light-Filled Contemporary Home on 7 Acres

10.0 out of 10, Exceptional, (25)
"5-stars. Fantastic property, great communication with host. Perfect stay. Thank you!"
Stunning Light-Filled Contemporary Home on 7 Acres
Indulge in an Elegant Upstate Getaway
Smart TV, offices

Indulge in an Elegant Upstate Getaway

10.0 out of 10, Exceptional, (45)
"We loved the area lots to do great restaurants"
Indulge in an Elegant Upstate Getaway
The Queen City Cottage
Exterior

The Queen City Cottage

7.4 out of 10, Good, (16)
"We had a great stay! Good location and the house was very clean. Would definitely stay here again!"
The Queen City Cottage
Majestic RiverView Estate - Breathtaking Views
Interior

Majestic RiverView Estate - Breathtaking Views

9.8 out of 10, Exceptional, (8)
"The house is very spacious with all necessary utensils. The view is fantastic."
Majestic RiverView Estate - Breathtaking Views
Red Cottage - Lakeside Property!
Exterior

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
The Calf Pen
Interior

The Calf Pen

10.0 out of 10, Exceptional, (34)
"We really enjoyed our stay! So close to Rhinebeck and the house was wonderfully appointed and clean! Can't wait to stay again!"
The Calf Pen
Bluebird Valley Farmhouse
Property grounds

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (66)
"Wonderful welcoming home and host! Views and relaxing lake Will return!!"
Bluebird Valley Farmhouse
Modern Converted Barn with Hot Tub!
Interior

Modern Converted Barn with Hot Tub!

10.0 out of 10, Exceptional, (4)
"The house has a big open floor plan with extra large windows letting light and views in. The bedrooms are comfortable and the kitchen is well equipped. Big playroom was heaven for our toddler. Highly recommend.this property."
The price is CA $1,239
CA $1,808 total
includes taxes & fees
Sep 7 - Sep 8
Modern Converted Barn with Hot Tub!
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Smart TV, fireplace

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

10.0 out of 10, Exceptional, (20)
"Despite the weather we had a great time. The house is very comfortable, well a pointed, nicely updated and was spotless when we arrived. Location is good too!"
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
A Country Lodge Straight Out of the Pages of a Great Novel
4 bedrooms, iron/ironing board, WiFi, bed sheets

A Country Lodge Straight Out of the Pages of a Great Novel

10.0 out of 10, Exceptional, (12)
"We loved the house and it really added to our upstate experience!!"
A Country Lodge Straight Out of the Pages of a Great Novel
The Wheelhaus— Restored Home in Hamlet of Amenia
Exterior

The Wheelhaus— Restored Home in Hamlet of Amenia

10.0 out of 10, Exceptional, (4)
"Kurt was an excellent host and the house was as clean as they get. Plenty to do in the area including events at Lime Rock Park and you are within walking distance to an amazing restaurant with mini golf and a drive in theater on location (Four Brothers). Great yard and very open layout inside. We’ll definitely be back!"
The Wheelhaus— Restored Home in Hamlet of Amenia
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dutchess County Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent
"Kind staff, nice rooms (too small for our toddler to move around), nice breakfast: eggs, sausage, juices, waffle, etc. nice mix of hot and cold stuff. Will definitely come back!"
Rajkumar 1-night trip
Posted 1 day ago
Quality Inn Hyde Park Poughkeepsie North