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

Dutchess County Holiday Rentals

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Our top choices for Dutchess County holiday rentals

A brick building with a sign reading 'Lobby' in front.

1. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
9.2 out of 10, 19, (19 reviews)
"Nice place to stay"
United States
Anonymous traveller
The price is AU$132
includes taxes & fees
5 Oct - 6 Oct
1 Queen Bed | Non-Smoking, Kitchen
A modern kitchen with white cabinets, a central island, and a view to the outside.

2. 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, 7, (7 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is AU$289
includes taxes & fees
16 Sept - 17 Sept
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A deck with a red umbrella, wooden chairs, and a table with potted plants.

3. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, 58, (58 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is AU$373
includes taxes & fees
20 Sept - 21 Sept
Mid-Century DJ’s Dream
A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

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

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, 2, (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 AU$311
includes taxes & fees
30 Sept - 1 Oct
Private, Cozy, Clean apartment in lovely Hyde Park

5. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.6 out of 10, 24, (24 reviews)
"Worst hotel experience I have ever had. Grounds were unkept. No one was at the front desk when I first arrived. Waited 20 minutes for someone to arrive and had to leave for dinner. Came back to find out that they were overbooked."
United States
Glenn
The price is AU$129
includes taxes & fees
6 Oct - 7 Oct
2 Queen Beds | Non-Smoking, Kitchen
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

6. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, 32, (32 reviews)
"great place for homebase to visit Hudson Valley area and host was very communicative and helpful"
United States
Brian C.
The price is AU$450
includes taxes & fees
29 Sept - 30 Sept
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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, 15, (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 AU$346
includes taxes & fees
7 Oct - 8 Oct
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

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

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, 8, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is AU$328
includes taxes & fees
24 Sept - 25 Sept
Hudson Valley Farm Getaway- West/Llama Lover Lane
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

9. 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, 13, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is AU$390
includes taxes & fees
20 Sept - 21 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

10. 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, 5, (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 AU$642
includes taxes & fees
20 Sept - 21 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

11. 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, 3, (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 AU$894
includes taxes & fees
22 Sept - 23 Sept
NEW: Chic Modern Barn Style Home in Fun Area
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, 4, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is AU$808
includes taxes & fees
16 Sept - 17 Sept
"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, 76, (76 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is AU$475
includes taxes & fees
16 Sept - 17 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, 5, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is AU$621
includes taxes & fees
16 Sept - 17 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, 6, (6 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is AU$673
includes taxes & fees
16 Sept - 17 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, 6, (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 AU$1,142
includes taxes & fees
20 Sept - 21 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 AU$976
includes taxes & fees
17 Sept - 18 Sept
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, 9, (9 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 AU$1,502
includes taxes & fees
20 Sept - 21 Sept
The George is an elegant restored home in the Hudson Valley
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

19. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, 6, (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 AU$993
includes taxes & fees
16 Sept - 17 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

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"Awesome Experience"
Nicole 1-night trip
Posted 2 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

Find out more about Dutchess County

Everything you need to know about Dutchess County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dutchess County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dutchess County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Dutchess County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dutchess County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dutchess County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Dutchess County holiday rentals we have chosen for you start as low as AU$132 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Dutchess County rentals

At Expedia, we put the best Dutchess County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Dutchess County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dutchess County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dutchess County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.