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

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. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is AU$129
includes taxes & fees
23 Nov - 24 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

2. 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 AU$374
includes taxes & fees
3 Nov - 4 Nov
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

3. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is AU$127
includes taxes & fees
21 Nov - 22 Nov
1 King Bed | Non-Smoking, Kitchen, Shower
A modern kitchen with white cabinets, a central island, and a view to the outside.

4. 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, (13 reviews)
"We thoroughly enjoyed our stay. We would definitely come back! A fantastic location. And very good communication with the host, Alexander."
United States
elizabeth
The price is AU$300
includes taxes & fees
2 Nov - 3 Nov
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

5. 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 AU$334
includes taxes & fees
30 Nov - 1 Dec
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A deck with a red umbrella, wooden chairs, and a table with potted plants.

6. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (61 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is AU$347
includes taxes & fees
4 Nov - 5 Nov
Mid-Century DJ’s Dream
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

7. 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 AU$377
includes taxes & fees
1 Nov - 2 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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, Exceptional, (9 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is AU$307
includes taxes & fees
3 Nov - 4 Nov
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.

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

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.8 out of 10, Exceptional, (6 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$608
includes taxes & fees
2 Nov - 3 Nov
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A white house with a steeply pitched roof and a small tower-like structure.

10. 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, (9 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$700
includes taxes & fees
13 Nov - 14 Nov
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

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

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (13 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$1,734
includes taxes & fees
3 Nov - 4 Nov
The George is an elegant restored home in the Hudson Valley
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

12. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
The price is AU$518
includes taxes & fees
14 Nov - 15 Nov
Rustic Cabin in Fishkill!
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, (81 reviews)
"The property was as advertised and met our needs for our trip."
United States
Sara
The price is AU$483
includes taxes & fees
3 Nov - 4 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

14. 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 AU$1,032
includes taxes & fees
11 Nov - 12 Nov
Chic Barn Style * Fireplace * Near Stissing House
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

15. 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, (7 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$1,056
includes taxes & fees
1 Dec - 2 Dec
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

16. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AU$962
includes taxes & fees
1 Nov - 2 Nov
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

17. "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 AU$808
includes taxes & fees
5 Nov - 6 Nov
"Country outside the city " 3 bedrooms 2 full bathrooms
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

18. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is AU$560
includes taxes & fees
14 Nov - 15 Nov
Red Cottage - Lakeside Property!
A modern kitchen with white cabinets, a large island, and a skylight.

19. 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.
The price is AU$1,927
includes taxes & fees
3 Nov - 4 Nov
A Country Lodge Straight Out of the Pages of a Great Novel
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)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
United States
Quintina R.
The price is AU$751
includes taxes & fees
14 Nov - 15 Nov
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

Spark by Hilton Fishkill

Spark by Hilton Fishkill

10/10 Excellent
"Great stay"
Shala 3-night trip
Posted 11 hours ago
Spark by Hilton Fishkill

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$129 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.