Holiday Rentals in Dutchess County

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Top Cities in Dutchess County

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Beacon

Beacon

Featured Holiday Rentals in Dutchess County

The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (71)
"Great location to the historic sites and the areas that I wanted to for me personally. Host was great, kind and informative."
The Farm at Hyde Park
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

9.8 out of 10, Exceptional, (18)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is €289
includes taxes & fees
6 Jul - 7 Jul
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
1 bedroom, desk, WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

The price is €216
includes taxes & fees
26 Jun - 27 Jun
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Property grounds

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

10.0 out of 10, Exceptional, (121)
"My family and I stayed at the Lake House for the holiday. We can not say enough about the amenities, the house & the owners. We look forward to returning to this magical place for our next family reunion."
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.0 out of 10, Wonderful, (25)
"Amazing stay to be away from the city and all the noise and light pollution "
The price is €181
includes taxes & fees
26 Jun - 27 Jun
Postcard Cabins Eastern Catskills
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (104)
"We had an excellent stay, and would certainly book this place again!"
The price is €183
includes taxes & fees
27 Jun - 28 Jun
Micosta Leisure Inn
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (111)
"Great place and host!"
The price is €274
includes taxes & fees
7 Jul - 8 Jul
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (34)
"Had a fantastic stay for a quick overnight trip to ski."
The price is €200
includes taxes & fees
1 Jul - 2 Jul
Esopus Creek modern Tiny house Retreat!
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8
Terrace/patio

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8

10.0 out of 10, Exceptional, (3)
"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 8
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Outdoor dining

Romantic retreat with stunning views of Croton River Gorge, a birder haven

10.0 out of 10, Exceptional, (3)
"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Terrace/patio

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is €265
includes taxes & fees
20 Jul - 21 Jul
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (42)
"Perfect place to reconnect with natural world and yourself"
The price is €144
includes taxes & fees
29 Jun - 30 Jun
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
The Studio at the Inn at High Falls
Exterior

The Studio at the Inn at High Falls

8.0 out of 10, Very good, (25)
"This was a very nice place, great value and comfortable. I would definitely return."
The price is €239
includes taxes & fees
27 Jun - 28 Jun
The Studio at the Inn at High Falls
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (294)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is €518
includes taxes & fees
6 Jul - 7 Jul
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
The House In Highland- Secluded Retreat
Outdoor dining

The House In Highland- Secluded Retreat

10.0 out of 10, Exceptional, (5)
The House In Highland- Secluded Retreat
Indoor Pool Paradise | 6BR + Huge Decks
Outdoor dining

Indoor Pool Paradise | 6BR + Huge Decks

Indoor Pool Paradise | 6BR + Huge Decks
A-Frame of Mind
Exterior

A-Frame of Mind

10.0 out of 10, Exceptional, (55)
"Fantastic location, excellent communication with Nick, cozy and well stocked with necessary supplies, very clean and quiet. Much needed vacation."
The price is €335
includes taxes & fees
16 Jul - 17 Jul
A-Frame of Mind
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (23)
"Beautiful property- not too far from Hunter Mt or Woodstock. House has a lot to offer for adults and/or families with kids. Would highly recommend!"
Hamptons on the Hudson in South Saugerties
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Exterior

A Spectacular 50 Mile View of the Hudson Valley in all seasons

9.8 out of 10, Exceptional, (87)
"This was exactly what we needed for a quick getaway after Christmas. Myra & Jerry were fantastic hosts, and the accommodations were cozy. We'd definitely come back. Thanks Myra & Jerry!"
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (240)
"The house was just as advertised. It is cozy and clean, on a gorgeous stream, and close to town. We'll definitely be back!"
Streamside Cottage Half Mile to Town of Woodstock
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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