A large, historic building with a symmetrical facade, green shutters, and a central entrance with steps leading up to it.

Holiday Rentals in Dutchess County

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Top Cities in Dutchess County

MacEachron Waterfront Park and the Hudson river
Holiday RentalsHoliday Rentals

Beacon

Beacon
A suspension bridge over a river, surrounded by lush green hills.
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Wappingers Falls

Wappingers Falls

Our top choices for Dutchess County holiday rentals

Coffee/tea maker, fridge, oven, stovetop

1. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (5 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is €179
includes taxes & fees
8 Sept - 9 Sept
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Property grounds

2. Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (8 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is €120
includes taxes & fees
10 Aug - 11 Aug
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Property grounds

3. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
The price is €182
includes taxes & fees
10 Aug - 11 Aug
Hoppy Hill Farm House
Property grounds

4. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (56 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is €198
includes taxes & fees
13 Aug - 14 Aug
Mid-Century DJ’s Dream
Exterior

5. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.4 out of 10, Exceptional, (20 reviews)
"great place tostay"
United States
Anonymous traveller
The price is €82
includes taxes & fees
1 Sept - 2 Sept
2 Full Beds | Non-Smoking, Kitchen
1 bedroom, free WiFi

6. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
9.8 out of 10, Exceptional, (20 reviews)
"Schöne Zimmer, Internet war kostenpflichtig, funktionierte aber nicht. Das Personal war jedoch nett."
Germany
Anonymous traveller
The price is €80
includes taxes & fees
1 Sept - 2 Sept
2 Queen Beds | Non-Smoking, Kitchen
Exterior

7. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is €178
includes taxes & fees
10 Aug - 11 Aug
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
1 bedroom, desk, free WiFi, bed sheets

8. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (31 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is €269
includes taxes & fees
1 Sept - 2 Sept
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Smart TV, fireplace

9. Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
The price is €205
includes taxes & fees
17 Aug - 18 Aug
Private, Cozy, Clean apartment in lovely Hyde Park
Property grounds

10. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is €200
includes taxes & fees
10 Aug - 11 Aug
Hudson Valley Farm Getaway- West/Llama Lover Lane
Interior

11. Architect-Designed Dome on Private 7-Acre Retreat

Architect-Designed Dome on Private 7-Acre Retreat
Dover Plains
The price is €416
includes taxes & fees
10 Aug - 11 Aug
Architect-Designed Dome on Private 7-Acre Retreat
Outdoor dining

12. 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, (73 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is €279
includes taxes & fees
10 Aug - 11 Aug
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Living area

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

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Red Hook
10.0 out of 10, Exceptional, (25 reviews)
"It was pet friendly, even for a dog, was comfortable for the entire family and is a great location with easy access to surrounding villages."
United States
Susan T.
The price is €388
includes taxes & fees
23 Aug - 24 Aug
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Coffee/tea maker, fridge, microwave, oven

14. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is €512
includes taxes & fees
17 Aug - 18 Aug
"Country outside the city " 3 bedrooms 2 full bathrooms
Interior

15. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is €543
includes taxes & fees
11 Aug - 12 Aug
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
TV, fireplace, books

16. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (2 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is €658
includes taxes & fees
17 Aug - 18 Aug
NEW: Chic Modern Barn Style Home in Fun Area
Exterior

17. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.6 out of 10, Exceptional, (4 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is €425
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Exterior

18. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is €391
includes taxes & fees
10 Aug - 11 Aug
Rustic Cabin in Fishkill!
Dining

19. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (8 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is €964
includes taxes & fees
10 Aug - 11 Aug
The George is an elegant restored home in the Hudson Valley
Interior

20. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is €739
includes taxes & fees
23 Aug - 24 Aug
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
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

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

8/10 Good
"We have stayed at this hotel before and once again, I was pleased with the location, the friendly staff, and the ample breakfast."
Joseph 2-night trip
Posted 5 hours ago
Holiday Inn Express Poughkeepsie by IHG

Find out more about Dutchess County

Holiday Homes in Dutchess County

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