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

Dutchess County Vacation Rentals

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Top Cities in Dutchess County

A calm lake with trees and a clear sky.
Vacation RentalsVacation Rentals

Beacon

Beacon

Our top choices for Dutchess County vacation 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 CA $176
CA $411 total
includes taxes & fees
Nov 3 - Nov 4
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A brick building with a sign reading 'Lobby' in front.

2. 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 CA $123
CA $143 total
includes taxes & fees
Nov 2 - Nov 3
2 Full Beds | Non-Smoking, Kitchen
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
9.6 out of 10, Exceptional, (11 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is CA $160
CA $296 total
includes taxes & fees
Oct 19 - Oct 20
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A deck with a red umbrella, wooden chairs, and a table with potted plants.

4. 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 CA $225
CA $370 total
includes taxes & fees
Oct 18 - Oct 19
Mid-Century DJ’s Dream
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

5. 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 CA $112
CA $127 total
includes taxes & fees
Oct 22 - Oct 23
1 King Bed | Non-Smoking, Kitchen, Shower
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, (3 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 CA $179
CA $275 total
includes taxes & fees
Oct 19 - Oct 20
Private, Cozy, Clean apartment in lovely Hyde Park
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

7. 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 CA $245
CA $318 total
includes taxes & fees
Oct 18 - Oct 19
Hudson Valley Farm Getaway- West/Llama Lover Lane
A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

8. 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 CA $206
CA $348 total
includes taxes & fees
Oct 31 - Nov 1
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.

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, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is CA $240
CA $403 total
includes taxes & fees
Oct 18 - Oct 19
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, 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 CA $228
CA $619 total
includes taxes & fees
Oct 18 - Oct 19
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.

11. 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, (8 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 CA $454
CA $706 total
includes taxes & fees
Oct 18 - Oct 19
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
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 CA $356
CA $551 total
includes taxes & fees
Nov 6 - Nov 7
Rustic Cabin in Fishkill!
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

13. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
The price is CA $557
CA $1,405 total
includes taxes & fees
Oct 21 - Oct 22
Chic Barn Style * Fireplace * Near Stissing House
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

14. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is CA $639
CA $991 total
includes taxes & fees
Oct 26 - Oct 27
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
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 CA $568
CA $1,193 total
includes taxes & fees
Oct 26 - Oct 27
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
An outdoor patio area with a covered seating area, a pool, and potted plants.

16. 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, (80 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is CA $390
CA $517 total
includes taxes & fees
Oct 28 - Oct 29
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

17. 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, (12 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 CA $1,022
CA $1,596 total
includes taxes & fees
Oct 18 - Oct 19
The George is an elegant restored home in the Hudson Valley
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

18. "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 CA $284
CA $827 total
includes taxes & fees
Oct 21 - Oct 22
"Country outside the city " 3 bedrooms 2 full bathrooms
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

19. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is CA $390
CA $602 total
includes taxes & fees
Nov 13 - Nov 14
Red Cottage - Lakeside Property!
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 CA $546
CA $805 total
includes taxes & fees
Nov 11 - Nov 12
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

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

8/10 Good
"Basic lobby but employees seem nice. No idea if they served breakfast as we were in the far end of the courtyard. Oddest hotel I’ve ever been in! You have to walk down a long corridor to the elevators, opposite end of lobby with no signs….definitely seemed off.? A Lot of parking."
Elaine 2-night trip
Posted 2 hours ago
Courtyard by Marriott Poughkeepsie

Find out more about Dutchess County

Everything you need to know about Dutchess County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dutchess County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Dutchess County vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dutchess County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dutchess County vacation rentals we have selected for you start as low as CA $130 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 vacation 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 vacation.

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.