Vacation Rentals in Dutchess County

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Top Vacation Rentals in Dutchess County

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
9.6 out of 10, Exceptional, (45)
"Plenty of seating & comfortable beds were a plus! The theatre room was really fun for grandkids!"
United States
Lisa B.
The price is ￥39,736
￥51,200 total
includes taxes & fees
Nov 30 - Dec 1
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Exterior
The Farm at Hyde Park

The Farm at Hyde Park

Staatsburg
9.8 out of 10, Exceptional, (84)
"We enjoyed our stay...lots to do in the area. Glen was very friendly and accommodating. "
United States
Robert W.
The Farm at Hyde Park
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥46,410
￥70,219 total
includes taxes & fees
Nov 10 - Nov 11
Rustic Cabin in Fishkill!
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Poughkeepsie
10.0 out of 10, Exceptional, (1)
"Great host"
United States
Lindsey F.
The price is ￥25,406
￥90,491 total
includes taxes & fees
Nov 11 - Nov 12
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (130)
"It's a beautiful little place with a wonderful owner. Rooms are clean and a good price"
United States
Gail
The price is ￥18,102
￥20,274 total
includes taxes & fees
Nov 21 - Nov 22
Micosta Leisure Inn
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (126)
"I cannot say enough on this location. Peaceful, and the view was extraordinary. Highly recommend this to anyone that wants a getaway."
United States
Daniel R.
The price is ￥28,843
￥47,209 total
includes taxes & fees
Nov 10 - Nov 11
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Terrace/patio
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (33)
"The entire process and stay were flawless. We had a rush booking and every request we had was accommodated. I give the highest recommendation and will hopefully being staying here again."
United States
Gordon V.
Hamptons on the Hudson in South Saugerties
Exterior
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
The price is ￥16,876
￥22,338 total
includes taxes & fees
Nov 10 - Nov 11
Sioux Tipi on Chloe's Lake
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

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

Saugerties
8.2 out of 10, Very Good, (46)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
The price is ￥19,178
￥24,916 total
includes taxes & fees
Nov 12 - Nov 13
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons

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

Saugerties
9.8 out of 10, Exceptional, (95)
"Had my mother in law and sister in law in town and booked them this adorable place with an amazing view close to town. "
United States
Emily K.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Children's area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock
9.0 out of 10, Wonderful, (45)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
United States
Paul H.
The price is ￥27,616
￥47,597 total
includes taxes & fees
Nov 16 - Nov 17
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Dining
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Brookfield
9.4 out of 10, Exceptional, (3)
"The host was very kind and welcoming. The home was spacious and the perfect setting for our celebration weekend. Everyone had their own space and we had multiple spaces for group activities. We enjoyed our time and appreciate the hospitality. "
United States
Valerie V.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Outdoor dining
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield
9.4 out of 10, Exceptional, (31)
"Only thing that was a challenge was carrying the kayaks down the hill and across the street. Living room was a bit hot due to no air conditioner. Host was extremely nice and accomodating and the place was well kept. "
United States
Jennifer W.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (60)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
The price is ￥22,783
￥36,342 total
includes taxes & fees
Nov 12 - Nov 13
Esopus Creek modern Tiny house Retreat!
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
8.8 out of 10, Excellent, (3)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥31,068
￥45,671 total
includes taxes & fees
Nov 10 - Nov 11
Pet Friendly Riverfront Home in Great Barrington
Fridge, microwave, oven, stovetop
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville
10.0 out of 10, Exceptional, (123)
"As roomy as promised, and one of the quietest places I've ever been. May return for our annual gathering next year."
United States
Tony G.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
United States
Julie L.
Sexiest Lil Cabin in Saugerties, NY
Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is ￥66,277
￥106,017 total
includes taxes & fees
Nov 10 - Nov 11
Large,Cozy,Bright Apartment, Business Themed.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel Hamlet
10.0 out of 10, Exceptional, (93)
"We loved our stay. It was great for a family Thanksgiving"
United States
Edmund F.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Property grounds
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock
10.0 out of 10, Exceptional, (258)
"Very cozy cottage with everything you need, close to town, and a beautiful stream right in the backyard that we loved listening to."
United States
Kevin M.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dutchess County Hotel Reviews

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent
"Fantastic property"
Nathan 1-night trip
Posted 21 hours ago
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Find out more about Dutchess County

Vacation Apartments in Dutchess County

Search for Vacation rentals in Dutchess County on Expedia! You can easily find your home rentals, villas, Vacation apartments in Dutchess County using one of the methods below:

  • View our selection of featured Vacation rentals in Dutchess County
  • Use the map to find apartments and other Vacation homes in the Dutchess County neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Dutchess County while they last

Look no further and take a look at our great range of rental properties in Dutchess County!