Dutchess County Holiday Rentals

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Top Holiday Rentals Destinations in Dutchess County

Apartment, 2 Bedrooms, Balcony, Garden View | Exterior
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
2.0 star property
10.0 out of 10, Exceptional, (4)
"My friends and I rented this property for a long girls weekend to attend an event in the area. We liked the historical aspect of the property and Gary was an excellent host. His banana bread was amazing! We would definitely stay again. "
United States
Sara
The price is AU$416
includes taxes & fees
6 Nov - 7 Nov
2Br Private Victorian Apartment in City Location on Half Acre Sleeps 5
Property grounds
Hudson Valley Farm Getaway- West/Llama Lover Lane
Hudson Valley Farm Getaway- West/Llama Lover Lane
2.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is AU$321
includes taxes & fees
3 Nov - 4 Nov
Hudson Valley Farm Getaway- West/Llama Lover Lane
Fridge, microwave, oven, stovetop
Lux APT Your home away from home.
Lux APT Your home away from home.
10.0 out of 10, Exceptional, (1)
"Very clean and great place to stay. "
United States
Charlene D.
The price is AU$414
includes taxes & fees
3 Nov - 4 Nov
Lux APT Your home away from home.
TV, fireplace
1 Br Private Victorian Apt in convenient City location on half acre sleeps 4
1 Br Private Victorian Apt in convenient City location on half acre sleeps 4
10.0 out of 10, Exceptional, (3)
"The host was gracious and the apartment had everything I could want to feel comfortable. The location was very convenient to the colleges and in a gorgeous neighborhood. I will definitely be coming back again. "
United States
Sarah D.
The price is AU$351
includes taxes & fees
3 Nov - 4 Nov
1 Br Private Victorian Apt in convenient City location on half acre sleeps 4
Outdoor dining
Mid-Century DJ’s Dream
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (41)
"Great place to stay! Close to many attractions by car - most 10-15 minutes. Clean and comfortable. Kevin has lots of great suggestions on places to go and restaurants."
United States
Anonymous traveller
The price is AU$274
includes taxes & fees
3 Nov - 4 Nov
Mid-Century DJ’s Dream
Fridge, microwave, oven, stovetop
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
10.0 out of 10, Exceptional, (44)
"Great location, so clean and comfortable. "
United States
Barbara
The price is AU$375
includes taxes & fees
20 Nov - 21 Nov
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
1 bedroom, desk, free WiFi
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
9.4 out of 10, Exceptional, (9)
"It was a perfect quiet spot surrounded by trees in a beautiful, safe neighborhood. I loved how close it was to a bagel shop and some cool eateries just a few minutes downtown. The whole area is beautiful in general. "
United States
Vivian
The price is AU$375
includes taxes & fees
3 Nov - 4 Nov
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
10.0 out of 10, Exceptional, (1)
"Great host"
United States
Lindsey F.
The price is AU$913
includes taxes & fees
9 Nov - 10 Nov
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Smart TV, books
Family friendly Spacious 4 bedroom 3 bathroom getaway
Family friendly Spacious 4 bedroom 3 bathroom getaway
10.0 out of 10, Exceptional, (4)
"Very easy checkin, great communication from owner. Bring your own travel soap shampoo etc. Store was right down the road for these things so not a big deal. Would rent again in a heartbeat."
United States
Ann H.
The price is AU$624
includes taxes & fees
5 Nov - 6 Nov
Family friendly Spacious 4 bedroom 3 bathroom getaway
3 bedrooms, iron/ironing board, travel cot, WiFi
"Country outside the city " 3 bedrooms 2 full bathrooms
"Country outside the city " 3 bedrooms 2 full bathrooms
2.0 star property
9.6 out of 10, Exceptional, (4)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is AU$978
includes taxes & fees
3 Nov - 4 Nov
"Country outside the city " 3 bedrooms 2 full bathrooms
1 bedroom, WiFi, bed sheets
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (41)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is AU$361
includes taxes & fees
4 Nov - 5 Nov
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Exterior
2Br Private Victorian Apartment in City location on half acre Sleeps 5
2Br Private Victorian Apartment in City location on half acre Sleeps 5
8.0 out of 10, Very good, (2)
"Amazing apartment in a restored antique home. We loved the stay, but would not stay there again because Gary keeps his dogs outside in a pen 24/7 and we have a moral issue with that. "
United States
Danielle T.
The price is AU$421
includes taxes & fees
3 Nov - 4 Nov
2Br Private Victorian Apartment in City location on half acre Sleeps 5
Exterior
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
9.0 out of 10, Wonderful, (10)
"We had a wonderful time staying at this charming and unique getaway! The accommodations were very comfortable. The property was beautiful and felt secluded without being isolated. The chapel itself is beautiful. The bathroom was overall nicer than we anticipated; just be mindful to put the camping shower out in the sun so the water warms up! Overall, highly recommend this experience. The hosts were also very responsive and kind."
United States
Avery D.
The price is AU$398
includes taxes & fees
3 Nov - 4 Nov
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Exterior
Charming 3-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Charming 3-bedroom apartment on 2nd floor in Millbrook NY, right in the village
10.0 out of 10, Exceptional, (1)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is AU$758
includes taxes & fees
3 Nov - 4 Nov
Charming 3-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Interior
Charming 2-bedroom cabin on 25 acres with loft space and full basement
Charming 2-bedroom cabin on 25 acres with loft space and full basement
The price is AU$560
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom cabin on 25 acres with loft space and full basement
Outdoor dining
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.6 out of 10, Exceptional, (44)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is AU$510
includes taxes & fees
3 Nov - 4 Nov
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Exterior
Rustic Cabin in Fishkill!
Rustic Cabin in Fishkill!
10.0 out of 10, Exceptional, (2)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
United States
Brady K.
The price is AU$644
includes taxes & fees
3 Nov - 4 Nov
Rustic Cabin in Fishkill!
Property grounds
Private Studio Close to Downtown Rhinebeck
Private Studio Close to Downtown Rhinebeck
10.0 out of 10, Exceptional, (25)
"This a an adorable, well designed, spotless space which was perfect for our over night stay in Rhinebeck. Property a quick walk away from the fairgrounds and downtown was also walkable…the host was absolutely amazing with great communication and detailed instructions! "
United States
Kathy
The price is AU$337
includes taxes & fees
3 Nov - 4 Nov
Private Studio Close to Downtown Rhinebeck
Fridge, microwave, oven, stovetop
Cozy Escape -Strong Wi-Fi -Prime Location
Cozy Escape -Strong Wi-Fi -Prime Location
7.0 out of 10, Good, (4)
"Apartment was clean but certain areas seemed to have litter box smell. This apartment is located up some narrow stairs. I didn't feel like the listing accurately explained that. We had one in our group that uses a cane & has a lot of difficulty with stairs so we intentionally search for ADA friendly - no stairs required and so when we had the stairs felt as it wasn't an accurate listing. Also listing shows parking onsite. It is actually street parking - luckily on our second time around the...
United States
Laurie H.
The price is AU$482
includes taxes & fees
4 Nov - 5 Nov
Cozy Escape -Strong Wi-Fi -Prime Location
Dining
Modern Converted Barn with Hot Tub!
Modern Converted Barn with Hot Tub!
9.8 out of 10, Exceptional, (6)
"My family and I had a lovely stay at this property. The home and yard are beautiful, everything was clean and well appointed. We had an issue with the hot tub when we arrived and Ben called to walk us through the process of getting it back on, and sent a technician out to ensure everything was running properly. Check in and out was very easy. Would recommend a stay here! "
United States
Rachel E.
The price is AU$2,081
includes taxes & fees
30 Nov - 1 Dec
Modern Converted Barn with Hot Tub!
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

Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

10/10 Excellent
"Clean, quiet and comfortable stay. "
Karen 1-night trip
Posted 2 days ago
Home2 Suites By Hilton Poughkeepsie

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$202 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.