Holiday Homes in Dutchess County

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Featured Holiday Homes in Dutchess County

NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

9.6 out of 10, Exceptional, (50)
"Our family enjoyed our time at the property- it was a great place for us all to gather. The property managers were incredibly helpful and responsive to the few things that needed attention during our stay. The pool area is the shining star of this home. You can expect the house/ furnishings to be in mostly good shape and as photographed-. The layout of the bedrooms/ shared bathrooms did surprise us a bit despite careful review of photos and listing video tour. Overall great stay!"
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

Spacious New 5-bedroom holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (6)
"The home was even more stunning in person and from the moment we pulled onto the block we were welcomed by its beautiful surroundings. The home was very comfortable, plenty of space and each of us were very impressed by the thoughtful layout and features. We were in town for a very special event commemorating our brothers amazing achievements and had everything we needed for a very pleasant and memorable stay. The screened in porch was an added bonus and of course, we all gravitated around the...
The price is AU$1,149
includes taxes & fees
30 Dec - 31 Dec
Spacious New 5-bedroom holiday house in lovely Hudson Valley

The Farm at Hyde Park

9.8 out of 10, Exceptional, (63)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park

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

9.0 out of 10, Wonderful, (32)
"We enjoyed our stay however, the listing states all the beds are king sized and only 2 are. The other 2 are queen. Also (note for host) we forgot a pair of sunglasses and would like to have them mailed back if they are found, could you contact me if possible."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

The Queen City Cottage

7.4 out of 10, Good, (16)
"My wife and I, along with my two daughters and grandchildren stayed at the Queen City Cottage for 4 nights. We needed to add an extra day at the last minute and Marissa was very responsive and accommodating. The house was clean upon our arrival and entry was a breeze. It's a bedroom, 1.5 bath, with extra bathroom in basement in laundry room. Location wa great! Restaurants and shopping minutes away. Outdoor space was tranquil with table and chairs under covered back porch. Wifi was fine, TV had...
The Queen City Cottage

FREE EV charger and NEMA plug! Breathtaking scenery.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house with more features than we expected, clean and accommodating "
FREE EV charger and NEMA plug! Breathtaking scenery.

Beautiful home on acres with deck, fenced area & fireplace

10.0 out of 10, Exceptional, (2)
Beautiful home on acres with deck, fenced area & fireplace

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

10.0 out of 10, Exceptional, (14)
"The house is best for a small family that can be active and not worry about hurting the interior. The property is pretty especially the open fields across the street where an evening walk is lovely. House was well stocked and comfortable ."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

Indulge in an Elegant Upstate Getaway

10.0 out of 10, Exceptional, (45)
"Lovely prio"
Indulge in an Elegant Upstate Getaway

Hopewell Haven w/ heated pool and hot tub

9.4 out of 10, Exceptional, (10)
"This house has a lot of unique touches with furniture that clearly someone put a lot of thought and love into. The main room is much bigger than the listing pics let on. Ample space for a comfortable gathering. Highly recommended this home."
Hopewell Haven w/ heated pool and hot tub

Once in a Lifetime Hudson River Views - 6 bedrooms, sleeps 12

10.0 out of 10, Exceptional, (15)
"Exactly as advertised. Very easy to get to by car and train. The house has many spaces for group activities as well as quiet reading/napping areas. The grounds are well maintained and the view is stunning. We had everything we needed for a family getaway. The kitchen is perfect for group cooking. Check in and check out were super easy and our host responded immediately to our questions. We look forward to our next visit."
Once in a Lifetime Hudson River Views - 6 bedrooms, sleeps 12

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (59)
"If ever in the area again, we will definitely stay at Bluebird Farmhouse. It is so charming with wonderful artwork throughout this warm and comfortable home. A beautiful setting with a very well equipped home providing everything you need. We were in town for a wedding and thoroughly enjoyed our stay at this special farmhouse!!"
Bluebird Valley Farmhouse

Modern Getaway Retreat House on 2 Acres

6.0 out of 10, (1)
"The property was very clean and the beds were very comfortable. The kitchen was updated and was nicely equipped with new appliances and updates. It would have been helpful if the owner had furnished practical dish ware. The “china” that was provided did not include cereal bowls which we would have appreciated as we opted to have breakfast at the house. We also were unsure whether the china was dishwasher or microwave safe so we were very limited in what dishes were usable. A trip to Target with...
Modern Getaway Retreat House on 2 Acres

Stunning Light-Filled Contemporary Home on 7 Acres

10.0 out of 10, Exceptional, (24)
"This home is stunning and filled with charm! Rachel was such an accommodating and communicative host. In addition, the house’s spacious layout with a number of bedrooms and bathrooms, there is a the outdoor space to roam around and enjoy. I live in Brooklyn and the relatively short drive here was absolutely worth it. There’s nothing like a trip upstate in the fall. And Rachel’s home was the perfect place for a great exhale. I’d definitely stay here again."
Stunning Light-Filled Contemporary Home on 7 Acres

Private retreat on 12 acres w hot tub/pool & BBQ

10.0 out of 10, Exceptional, (1)
"Great place to relax and catch up with long time friends."
Private retreat on 12 acres w hot tub/pool & BBQ

Stylish Pine Plains Home Near Parks & Hiking!

9.2 out of 10, Wonderful, (13)
"We had a lovely stay in Pine Plains. Everything with the unit was as described. The only thing I’ll mention is that if you’re traveling in the summer, the AC is only in the living room and is very loud. "
Stylish Pine Plains Home Near Parks & Hiking!

Lakefront Designer House in Pine Plains, NY.

10.0 out of 10, Exceptional, (1)
Lakefront Designer House in Pine Plains, NY.

The George is an elegant restored home in the Hudson Valley

9.4 out of 10, Exceptional, (3)
"Wonderful property."
The price is AU$1,474
includes taxes & fees
4 Dec - 5 Dec
The George is an elegant restored home in the Hudson Valley

Pet-Friendly Beacon Area Vacation Rental: 6 Acres

10.0 out of 10, Exceptional, (10)
"Property worked very well for us. Pool was great. (Couple of notes: The stay listed above is slightly incorrect. We arrived on Wed Jun 26 and left on Sun June 30). We requested additional chairs for the pool area from the owner but they were never delivered."
Pet-Friendly Beacon Area Vacation Rental: 6 Acres

ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail

9.6 out of 10, Exceptional, (24)
"Nice place to stay for anyone who wants to explore nyc surroundings parks and trails and nature!"
ValleyView-Ultimate 3BR Getaway w/Inground Pool by Fahnestock/Appalachian Trail
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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Beautiful view of the beach with palm trees

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