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

A calm lake with trees and a clear sky.
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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

A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

1. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is €259
includes taxes & fees
29 Sept - 30 Sept
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A brick building with a sign reading 'Lobby' in front.

2. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is €82
includes taxes & fees
6 Oct - 7 Oct
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.8 out of 10, Exceptional, (7 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

4. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (18 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is €72
includes taxes & fees
13 Oct - 14 Oct
1 King Bed | Non-Smoking, Kitchen, Shower
A deck with a red umbrella, wooden chairs, and a table with potted plants.

5. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (59 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is €233
includes taxes & fees
27 Sept - 28 Sept
Mid-Century DJ’s Dream
A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

6. 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.
Private, Cozy, Clean apartment in lovely Hyde Park
A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

7. THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Red Hook
9.2 out of 10, Wonderful, (15 reviews)
"Very sweet little spot that took care of all our needs. Very grateful to have found it and enjoyed our stay."
United States
Jason D.
The price is €215
includes taxes & fees
7 Oct - 8 Oct
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

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

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is €252
includes taxes & fees
24 Sept - 25 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

9. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 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 €670
includes taxes & fees
5 Oct - 6 Oct
Chic Barn Style * Fireplace * Near Stissing House
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

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.
Hudson Valley Farm Getaway- West/Llama Lover Lane
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

11. 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, (5 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 €366
includes taxes & fees
24 Sept - 25 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

12. "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 €513
includes taxes & fees
30 Sept - 1 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
An outdoor patio area with a covered seating area, a pool, and potted plants.

13. 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, (78 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is €303
includes taxes & fees
27 Sept - 28 Sept
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

14. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
The price is €380
includes taxes & fees
28 Sept - 29 Sept
Rustic Cabin in Fishkill!
A white house with a steeply pitched roof and a small tower-like structure.

15. 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
9.8 out of 10, Exceptional, (6 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is €435
includes taxes & fees
24 Sept - 25 Sept
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

16. 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 €741
includes taxes & fees
28 Sept - 29 Sept
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A covered outdoor deck with a grill, a chair, and a view of a lake and forest.

17. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is €598
includes taxes & fees
5 Oct - 6 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

18. 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, (10 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 George is an elegant restored home in the Hudson Valley
A brick building with a sign reading 'Lobby' in front.

19. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.2 out of 10, Wonderful, (21 reviews)
"great place tostay"
United States
Anonymous traveller
The price is €90
includes taxes & fees
6 Oct - 7 Oct
2 Full Beds | Non-Smoking, Kitchen
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

20. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is €612
includes taxes & fees
24 Sept - 25 Sept
Chestnut on Willow Lake
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

10/10 Excellent
"Very nice staff and very helpful. Clean and spacious rooms."
Ruby 1-night trip
Posted 2 days ago
Holiday Inn Express Poughkeepsie by IHG

Find out more about Dutchess County

Holiday Homes in Dutchess County

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