Holiday Homes in Dutchess County

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Top Cities in Dutchess County

Franklin D. Roosevelt Presidential Library and Museum featuring heritage elements and heritage architecture
Holiday HomesHoliday Homes

Hyde Park

Hyde Park

Featured Holiday Homes in Dutchess County

Our top choices for Dutchess County holiday homes

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, (29)
"Great place for a quiet stay"
The price is AU$519
includes taxes & fees
26 Sept - 27 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Classy Comfort in Upstate New York
Smart TV, offices

Classy Comfort in Upstate New York

10.0 out of 10, Exceptional, (45)
"We loved the area lots to do great restaurants"
Classy Comfort in Upstate New York
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
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)
"Amazing..superClean and so accommodating. Needed a few things for graduation and they made it happened since we are from Wisconsin This was the best Vrbo ever. "
Modern NY Home w/ Views By Hudson Valley Hiking!
Enjoy pool time at our spacious home; minutes from the village of Millbrook!
Outdoor pool

Enjoy pool time at our spacious home; minutes from the village of Millbrook!

9.8 out of 10, Exceptional, (58)
"Very nice home with pleasant semi country view. Outdoor pool looked nice, but too bad it was snowing and raining during stay."
Enjoy pool time at our spacious home; minutes from the village of Millbrook!
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, (17)
"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
Fire Pit + On-Site Pond: Hudson Valley Home!
Interior

Fire Pit + On-Site Pond: Hudson Valley Home!

9.2 out of 10, Wonderful, (15)
"I recommend this property to all you peace and nature lovers! We spent 10 days here and found it to be exceptional - the cabin, the host, and the surroundings."
Fire Pit + On-Site Pond: Hudson Valley Home!
Bluebird Valley Farmhouse
Property grounds

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (66)
"We stayed at the property while attending a family wedding. The house and yard were perfect. The best Vrbo we’ve ever stayed at. Would stay there again!"
Bluebird Valley Farmhouse
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, (21)
"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
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
Pleasant Valley Pines
Microwave, oven, stovetop, dishwasher

Pleasant Valley Pines

Pleasant Valley Pines
Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay
Interior

Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay

10.0 out of 10, Exceptional, (1)
"We had a wonderful family stay. House was big clean and as shown on the site"
Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay
Hickory on Willow Lake
Children's area

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is AU$962
includes taxes & fees
28 Aug - 29 Aug
Hickory on Willow Lake
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
Spacious New Luxurious holiday house in lovely Hudson Valley
Terrace/patio

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (16)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
Spacious New Luxurious holiday house in lovely Hudson Valley
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, (38)
"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
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
Red Cottage - Lakeside Property!
Exterior

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Family Friendly Fun + Easy Walk to Main Street Center
4 bedrooms, iron/ironing board, travel cot, free WiFi

Family Friendly Fun + Easy Walk to Main Street Center

9.6 out of 10, Exceptional, (14)
"Place is very clean and as shown in listing. Great location and walkable to Main Street. Had a great stay."
Family Friendly Fun + Easy Walk to Main Street Center
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 & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Very helpful front desk was lovely! Brittany was supportive re: a rental car issue we had when it was not her problem!! Brittany always smiled and made us feel welcome in our coming and goings!! "
Mary Kay 2-night trip
Posted 2 days ago
Quality Inn & Suites Fishkill South near I-84

Find out more about Dutchess County

Find out more about Dutchess County

Dutchess County Holiday Homes information

Number of reviews
418
Accommodation
153 Holiday Homes
Lowest Price
AU$519
Highest Price
AU$962