Dutchess County Vacation Rentals

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Top cities in Dutchess County

A large steel bridge spanning a wide river, with a cityscape and hills in the background.
Vacation Rentals

Poughkeepsie

Poughkeepsie

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Dutchess County vacation rentals

A modern kitchen with white cabinets, a central island, and a view to the outside.

1. 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 CA $162
CA $286 total
includes taxes & fees
Dec 1 - Dec 2
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A brick building with a sign reading 'Lobby' in front.

2. 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 CA $111
CA $128 total
includes taxes & fees
Dec 5 - Dec 6
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A white house with a steeply pitched roof and a small tower-like structure.

3. 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)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is CA $456
CA $675 total
includes taxes & fees
Nov 15 - Nov 16
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

4. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (20 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is CA $100
CA $113 total
includes taxes & fees
Dec 11 - Dec 12
1 King Bed | Non-Smoking, Kitchen, Shower
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, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is CA $130
CA $334 total
includes taxes & fees
Dec 6 - Dec 7
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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 CA $171
CA $289 total
includes taxes & fees
Nov 18 - Nov 19
Mid-Century DJ’s Dream
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, (9 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is CA $246
CA $304 total
includes taxes & fees
Nov 15 - Nov 16
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.

8. 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 CA $234
CA $598 total
includes taxes & fees
Nov 16 - Nov 17
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A brick building with a storefront featuring a sign for 'LUXE Optique'.

9. Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (59 reviews)
"Great location, comfortable spot to sleep in after being out all day."
United States
Kelena B.
The price is CA $228
CA $411 total
includes taxes & fees
Dec 1 - Dec 2
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

10. 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, (8 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 $571
CA $1,086 total
includes taxes & fees
Nov 23 - Nov 24
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.

11. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is CA $642
CA $933 total
includes taxes & fees
Dec 10 - Dec 11
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A brick building with a storefront featuring a sign for 'LUXE Optique'.

12. Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (63 reviews)
"It was a convenient location to downtown."
United States
Brendas S.
The price is CA $174
CA $350 total
includes taxes & fees
Dec 10 - Dec 11
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
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 CA $373
CA $469 total
includes taxes & fees
Nov 15 - Nov 16
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

14. 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 $384 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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
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 $358
CA $531 total
includes taxes & fees
Nov 21 - Nov 22
Rustic Cabin in Fishkill!
A large, two-story house with a covered porch and a stone foundation, surrounded by snow-covered trees.

16. 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, (15 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 $1,230
CA $1,768 total
includes taxes & fees
Nov 23 - Nov 24
The George is an elegant restored home in the Hudson Valley
A two-story house with a balcony, surrounded by lush greenery.

17. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"
United States
stephanie a.
The price is CA $250
CA $759 total
includes taxes & fees
Nov 17 - Nov 18
Quiet Solitude with Firepit, Electric Stove & Private Deck
A spacious living area with a sofa, ottoman, and a dining table with chairs. A staircase leads to an upper level.

18. 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)
"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 $264
CA $1,023 total
includes taxes & fees
Dec 15 - Dec 16
NEW: Chic Modern Barn Style Home in Fun Area
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 CA $1,117
CA $1,811 total
includes taxes & fees
Nov 18 - Nov 19
A Country Lodge Straight Out of the Pages of a Great Novel
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

20. "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, (5 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is CA $294
CA $799 total
includes taxes & fees
Nov 17 - Nov 18
"Country outside the city " 3 bedrooms 2 full bathrooms
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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Find vacation rentals that suit your style

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Top Dutchess County Hotel Reviews

A white house with a green door, black trim, and a porch with a lantern.
Twin Gables of Woodstock

Twin Gables of Woodstock

Twin Gables of Woodstock
Woodstock

10/10 Excellent

Cute property!
Canada
Paola
Reviewed July 14, 2026
Twin Gables of Woodstock

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 $99 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.