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

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 covered outdoor area with a wooden deck and a view of a grassy landscape with trees and a distant white building.

1. Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"The accommodations were wonderful and comfortable."
United States
Chuck S.
The price is CA $152
CA $282 total
includes taxes & fees
Sep 13 - Sep 14
Hoppy Hill Farm House
A brick building with a sign reading 'Lobby' in front.

2. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Nice place to stay"
United States
Anonymous traveller
The price is CA $113
CA $131 total
includes taxes & fees
Oct 5 - Oct 6
1 Queen Bed | 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
9.8 out of 10, Exceptional, (7 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is CA $154
CA $286 total
includes taxes & fees
Sep 16 - Sep 17
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, (58 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is CA $221
CA $357 total
includes taxes & fees
Sep 16 - Sep 17
Mid-Century DJ’s Dream
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

5. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (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 CA $215
CA $457 total
includes taxes & fees
Sep 29 - Sep 30
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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 $195
CA $295 total
includes taxes & fees
Sep 15 - Sep 16
Private, Cozy, Clean apartment in lovely Hyde Park

7. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.6 out of 10, Excellent, (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 CA $113
CA $128 total
includes taxes & fees
Oct 1 - Oct 2
2 Queen Beds | Non-Smoking, Kitchen
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, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is CA $250
CA $326 total
includes taxes & fees
Sep 13 - Sep 14
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.

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 $200
CA $337 total
includes taxes & fees
Oct 7 - Oct 8
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.

10. 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 $233
CA $388 total
includes taxes & fees
Sep 10 - Sep 11
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.

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 CA $293
CA $693 total
includes taxes & fees
Sep 14 - Sep 15
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.

12. 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, Exceptional, (3 reviews)
"The house is very well appointed. The kitchen is fully equipped and the grill is great. The appliances are all "smart" and we even had to Google how to start the stove, but instructions are posted in most cases."
United States
Mark C.
The price is CA $258
CA $912 total
includes taxes & fees
Sep 15 - Sep 16
NEW: Chic Modern Barn Style Home in Fun Area
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, (74 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is CA $360
CA $477 total
includes taxes & fees
Sep 10 - Sep 11
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A white house with a steeply pitched roof and a small tower-like structure.

14. 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)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is CA $441
CA $683 total
includes taxes & fees
Sep 10 - Sep 11
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

15. "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 $273
CA $795 total
includes taxes & fees
Sep 15 - Sep 16
"Country outside the city " 3 bedrooms 2 full bathrooms
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

16. 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 $417
CA $634 total
includes taxes & fees
Sep 10 - Sep 11
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.

17. 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 $551
CA $1,159 total
includes taxes & fees
Sep 13 - Sep 14
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.

18. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is CA $620
CA $945 total
includes taxes & fees
Sep 10 - Sep 11
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

19. 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, (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 CA $992
CA $1,550 total
includes taxes & fees
Sep 10 - Sep 11
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.

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 CA $682
CA $981 total
includes taxes & fees
Sep 10 - Sep 11
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
"I love coming here! It is the best experience ever!"
Nicole 2-night trip
Posted 4 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

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 $131 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.