Dutchess County Holiday Rentals

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Our top choices for Dutchess County holiday rentals

Exterior

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
10.0 out of 10, Exceptional, (2 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is HK$2,507
HK$3,838 total
includes taxes & fees
1 Jun - 2 Jun
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (4 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 HK$3,878
HK$5,504 total
includes taxes & fees
2 Jun - 3 Jun
Chestnut on Willow Lake
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
Fishkill
9.2 out of 10, Wonderful, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is HK$1,939
HK$2,532 total
includes taxes & fees
31 May - 1 Jun
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior

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
Beacon
10.0 out of 10, Exceptional, (50 reviews)
"We loved our stay. The room was so comfortable and had everything we needed. We loved being abl to walk to so many great restaurants and bars. "
United States
Amanda W.
The price is HK$979
HK$2,056 total
includes taxes & fees
1 Jun - 2 Jun
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is HK$862
HK$1,622 total
includes taxes & fees
28 May - 29 May
Hoppy Hill Farm House
Exterior

Charming Cabin in Fishkill!

Charming Cabin in Fishkill!
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"What a sweet little spot in a gorgeous area - clean, simple, and beautiful. Thanks for a great stay! "
United States
Julia T.
The price is HK$2,543
HK$3,586 total
includes taxes & fees
16 Jun - 17 Jun
Charming Cabin in Fishkill!
Exterior

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
10.0 out of 10, Exceptional, (17 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is HK$783
HK$906 total
includes taxes & fees
2 Jun - 3 Jun
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fridge, oven, stovetop, coffee/tea maker

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, (5 reviews)
The price is HK$818
HK$1,546 total
includes taxes & fees
4 Jun - 5 Jun
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Lobby

1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
10.0 out of 10, Exceptional, (16 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is HK$705
HK$798 total
includes taxes & fees
3 Jun - 4 Jun
1 King Bed | Non-Smoking, Kitchen, Shower
Smart TV, fireplace

Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
The price is HK$1,015
HK$1,547 total
includes taxes & fees
2 Jun - 3 Jun
Private, Cozy, Clean apartment in lovely Hyde Park
Fridge, microwave, oven, stovetop

"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 HK$1,586
HK$4,489 total
includes taxes & fees
9 Jun - 10 Jun
"Country outside the city " 3 bedrooms 2 full bathrooms
Exterior detail

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, (47 reviews)
"Great place to stay. Cozy, warm, and clean! The host was also a good communicator and everything went smoothly."
United States
Samantha Esmé W.
The price is HK$901
HK$1,885 total
includes taxes & fees
31 May - 1 Jun
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Property grounds

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
9.8 out of 10, Exceptional, (30 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is HK$980
HK$2,234 total
includes taxes & fees
8 Jun - 9 Jun
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Fridge, microwave, oven, stovetop

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, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is HK$6,973
HK$11,539 total
includes taxes & fees
4 Jun - 5 Jun
A Country Lodge Straight Out of the Pages of a Great Novel
Dining

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, (7 reviews)
"This our 3rd stay at the property and once again we thoroughly enjoyed the house and the grounds. We had an opportunity to enjoy horseback riding on site and would definitely recommend that to any visitors. The hosts were very kind and hospitable. "
United States
Eric L.
The price is HK$5,642
HK$8,590 total
includes taxes & fees
28 May - 29 May
The George is an elegant restored home in the Hudson Valley
Interior

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, (4 reviews)
"Great host"
United States
Lindsey F.
The price is HK$1,398
HK$4,015 total
includes taxes & fees
28 May - 29 May
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Property grounds

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is HK$4,094
HK$5,605 total
includes taxes & fees
2 Jun - 3 Jun
Red Cottage - Lakeside Property!
Exterior

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (11 reviews)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is HK$1,100
HK$1,909 total
includes taxes & fees
1 Jun - 2 Jun
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Property grounds

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (52 reviews)
"Great host and excellent accommodations! "
United States
Elaine L.
The price is HK$1,293
HK$2,083 total
includes taxes & fees
15 Jun - 16 Jun
Mid-Century DJ’s Dream
Property grounds

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Hyde Park
8.0 out of 10, Very good, (3 reviews)
"Great experience, Attentive and responsive host. Recommend"
United States
Tony S.
The price is HK$1,421
HK$1,834 total
includes taxes & fees
1 Jun - 2 Jun
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
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

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Large room and large bathroom. Did not like placement of bathroom light switch. Hard to find in the dark so had to leave the light on. Suggest adding a night light. Electric plug near tv fridge and coffee maker nweds to be upgraded to four outlets. Put a night stand on the window side of the bed not just between beds. Add a second suitcase stand. The door had barricade that was beyond any I had ever seen in an upscale area. Probably it is just standard hardware. Anyhow, it VERY secure! Parking was plentiful. Right next to Comfort Inn & Suites so a bit confusing to find."
Susan 1-night trip
Posted less than an hour ago
Quality Inn & Suites Fishkill South near I-84