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

Dutchess County Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 $163
CA $395 total
includes taxes & fees
Oct 6 - Oct 7
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

2. 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 $136
CA $154 total
includes taxes & fees
Oct 5 - Oct 6
1 King Bed | Non-Smoking, Kitchen, Shower
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, Exceptional, (60 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is CA $265
CA $410 total
includes taxes & fees
Nov 3 - Nov 4
Mid-Century DJ’s Dream
A brick building with a sign reading 'Lobby' in front.

4. 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 $136
CA $157 total
includes taxes & fees
Oct 5 - Oct 6
2 Full Beds | Non-Smoking, Kitchen
A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.4 out of 10, Exceptional, (10 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is CA $160
CA $297 total
includes taxes & fees
Oct 19 - Oct 20
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
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.
The price is CA $180
CA $277 total
includes taxes & fees
Oct 12 - Oct 13
Private, Cozy, Clean apartment in lovely Hyde Park
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 CA $241
CA $401 total
includes taxes & fees
Oct 5 - Oct 6
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-East/Alpaca Lane-Apt 1

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Hyde Park
8.6 out of 10, Excellent, (4 reviews)
"Great spot if you’re looking for a quiet rural area ! Seeing the llamas made the stay more fun. We weren’t there when the store was open so it was a bit disappointing we couldn’t see more of what the farm offers. We’d definitely go again."
United States
Meg H.
The price is CA $246
CA $321 total
includes taxes & fees
Oct 6 - Oct 7
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

9. 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 $186
CA $322 total
includes taxes & fees
Oct 7 - Oct 8
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
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 $229
CA $622 total
includes taxes & fees
Oct 5 - Oct 6
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)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is CA $456
CA $703 total
includes taxes & fees
Oct 12 - Oct 13
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

12. 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 CA $325
CA $1,050 total
includes taxes & fees
Oct 28 - Oct 29
Chic Barn Style * Fireplace * Near Stissing House
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 CA $372
CA $493 total
includes taxes & fees
Oct 8 - Oct 9
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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 $641
CA $995 total
includes taxes & fees
Oct 5 - Oct 6
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

15. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is CA $392
CA $599 total
includes taxes & fees
Nov 1 - Nov 2
Rustic Cabin in Fishkill!
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 CA $570
CA $1,198 total
includes taxes & fees
Oct 11 - Oct 12
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
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 CA $285
CA $828 total
includes taxes & fees
Oct 13 - Oct 14
"Country outside the city " 3 bedrooms 2 full bathrooms
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 price is CA $1,026
CA $1,602 total
includes taxes & fees
Oct 5 - Oct 6
The George is an elegant restored home in the Hudson Valley
A brick building with a sign reading 'Lobby' in front.

19. 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 CA $124
CA $144 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A modern kitchen with white cabinets, a large island, and a skylight.

20. 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)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is CA $1,133
CA $1,918 total
includes taxes & fees
Oct 16 - Oct 17
A Country Lodge Straight Out of the Pages of a Great Novel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dutchess County Hotel Reviews

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"Large spacious very clean room . Comfortable bed. Staff was very accommodating. Breakfast was above your average continental breakfast with many choices. Located in a center of town with plenty of places in walking distance."
Joseph 3-night trip
Posted 19 hours ago
Beekman Arms and Delamater Inn

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 $144 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.