A lake surrounded by hills with autumn foliage, a small island with a historic building, and a cloudy sky.

Vacation Homes in Dutchess County

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Our top choices for Dutchess County vacation homes

1. The Chicken Coop at the Farm at Hyde Park

The Chicken Coop at the Farm at Hyde Park
Staatsburg
9.6 out of 10, Exceptional, (38 reviews)
"Loved this place very clean and very comfy."
United States
Patti G.
The Chicken Coop at the Farm at Hyde Park

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

Enjoy pool time at our spacious home; minutes from the village of Millbrook!
Millbrook
9.8 out of 10, Exceptional, (70 reviews)
"Very comfortable and convenient location with very nice surroundings."
United States
Claude
Enjoy pool time at our spacious home; minutes from the village of Millbrook!

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is AED 960
AED 1,194 total
includes taxes & fees
15 Nov - 16 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

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

Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY
Beacon
9.8 out of 10, Exceptional, (28 reviews)
"Great location for a visit to West Point"
United States
Paul H.
Stunning .5 acre family-friendly home, near everything in the heart of Beacon NY

5. Summit Sanctuary: EV Ready Mountain Views

Summit Sanctuary: EV Ready Mountain Views
Poughkeepsie
9.4 out of 10, Exceptional, (18 reviews)
"Property came as advertised. At the yop.of the hill, wonder views"
United States
Jim M.
Summit Sanctuary: EV Ready Mountain Views

6. Private Retreat on 4+ Acres – Rock Ledge Views, Forest Walks, Creative Space.

Private Retreat on 4+ Acres – Rock Ledge Views, Forest Walks, Creative Space.
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"This lovely peaceful property in a great location. The hosts are friendly and hospitable. The home met all of our needs and was a great retreat from busy life. If you are up for a little challenge, the property has a lot to see. It's steep, but well worth the hike. It was challenging for our little kids, but they did it with help and really enjoyed it!"
United States
Kris D.
Private Retreat on 4+ Acres – Rock Ledge Views, Forest Walks, Creative Space.

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

Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay
Clinton Corners
9.6 out of 10, Exceptional, (5 reviews)
"We had a wonderful family stay. House was big clean and as shown on the site"
United States
Gil B.
Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay

8. The Red Country Cottage

The Red Country Cottage
Amenia
10.0 out of 10, Exceptional, (3 reviews)
"Excellent stay. Very nicely modernized old home. Very cool house! Clean and easy to get to. We enjoyed our stay!"
United States
Jason R.
The Red Country Cottage

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

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
United States
Marianne R.
A Country Lodge Straight Out of the Pages of a Great Novel

10. Cozy Historic Hyde Park Cottage - Near CIA & River

Cozy Historic Hyde Park Cottage - Near CIA & River
Hyde Park
10.0 out of 10, Exceptional, (7 reviews)
"Had a great stay in the cottage. It was very clean and quiet. We had a problem with one of the AC units but it was our error. My advice would be to read all the lovely directions. They are plentiful and helpful. Host was responsive and helpful."
United States
Jen
Cozy Historic Hyde Park Cottage - Near CIA & River

11. Hudson Valley stunning lake side modern barn in an Enchanted Forest

Hudson Valley stunning lake side modern barn in an Enchanted Forest
Clinton Corners
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful home in a lovely serene setting. Highly recommend this home for a relaxing stay in Duchess County."
United States
RHONDA B.
Hudson Valley stunning lake side modern barn in an Enchanted Forest

12. Contemporary Hudson Valley home

Contemporary Hudson Valley home
Staatsburg
9.6 out of 10, Exceptional, (10 reviews)
"Everything was great. Host very responsive."
United States
Lydia W.
Contemporary Hudson Valley home

13. The Church at the Farm at Hyde Park

The Church at the Farm at Hyde Park
Staatsburg
9.8 out of 10, Exceptional, (112 reviews)
"Glen, our host, was so responsive and accommodating, right from the start through our visit. Property is lovely and comfortable with many personal touches. We had a wonderful visit to the Hyde Park area. Property is close to all local activities. Restaurants are great. It’s a great place to visit!"
United States
Catherine B S.
The Church at the Farm at Hyde Park

14. Charming Stone Chalet in Wooded Surroundings with Heated Pool Spring to Fall.

Charming Stone Chalet in Wooded Surroundings with Heated Pool Spring to Fall.
Clinton Corners
9.4 out of 10, Exceptional, (196 reviews)
"House was lovely, great location and very peaceful"
United States
Caroline W.
Charming Stone Chalet in Wooded Surroundings with Heated Pool Spring to Fall.

15. Rhinebeck Chalet: Modern Stylish Retreat

Rhinebeck Chalet: Modern Stylish Retreat
Rhinebeck
10.0 out of 10, Exceptional, (1 review)
"The house is secluded in nature and very quiet. We were there to attend events at the Omega Institute, which is less than ten minutes away. We also visited friends nearby, so the location was excellent for our purposes. We would stay there again."
United States
Paula C.
Rhinebeck Chalet: Modern Stylish Retreat

16. 1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Hopewell Junction
8.6 out of 10, Excellent, (64 reviews)
"Great property. Exceeded expectations."
United States
Scott H.
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

17. Peaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit

Peaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit
Holmes
10.0 out of 10, Exceptional, (78 reviews)
"Another wonderful stay on the lake! Everything was perfect to make it an absolutely unforgettable vacation for myself and my family! Already looking forward to next year."
United States
Lynn M.
Peaceful & Quiet Lakeside Home with Hot Tub, Pool Table, Fire Pit

18. Heated Pool, 6 Acres: Beacon Area Vacation Rental

Heated Pool, 6 Acres: Beacon Area Vacation Rental
Lagrangeville
10.0 out of 10, Exceptional, (27 reviews)
"Excellent host interaction and perfect location for family gathering."
United States
Linda J.
Heated Pool, 6 Acres: Beacon Area Vacation Rental

19. Stylish and spacious centrally located one bedroom apartment

Stylish and spacious centrally located one bedroom apartment
Poughkeepsie
9.6 out of 10, Exceptional, (11 reviews)
"Extremely comfortable, clean & convenient!"
United States
jaclyn
Stylish and spacious centrally located one bedroom apartment

20. Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Wingdale
10.0 out of 10, Exceptional, (132 reviews)
"Very nice property.."
United States
Jeffrey W.
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
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

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