Holiday Homes in Poughkeepsie

  • 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

Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Poughkeepsie holiday homes

Outdoor dining

Holiday Home in Fishkill

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
9.4 out of 10, Exceptional, (60 reviews)
"Quiet, clean and comfortable! Great stay!"
United States
Joseph G.
The price is NZ$464
includes taxes & fees
2 Mar - 3 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Exterior detail

Holiday Home in New Paltz

Cozy private suite in the heart of beautiful Gardiner.
10.0 out of 10, Exceptional, (7 reviews)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is NZ$400
includes taxes & fees
2 Mar - 3 Mar
Cozy private suite in the heart of beautiful Gardiner.
Private kitchen

Holiday Home in new paltz

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
9.4 out of 10, Exceptional, (6 reviews)
"Very clean Good communication with host Close to town & hiking Recommend! "
United States
Jennifer E.
The price is NZ$1,156
includes taxes & fees
2 Mar - 3 Mar
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Smart TV

Holiday Home in Poughkeepsie

King Bed | Private Parking | Strong WiFi
The price is NZ$522
includes taxes & fees
16 Mar - 17 Mar
King Bed | Private Parking | Strong WiFi
Interior

Holiday Home in Poughkeepsie

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
10.0 out of 10, Exceptional, (2 reviews)
"Great host"
United States
Lindsey F.
The price is NZ$1,078
includes taxes & fees
12 Mar - 13 Mar
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Outdoor spa tub

Holiday Home in New Paltz

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
9.4 out of 10, Exceptional, (26 reviews)
"We stayed for wedding preparation. The space is clean and great layout for multiple guests. I am extremely satisfied with my reservation!"
United States
Jean G.
The price is NZ$808
includes taxes & fees
25 Mar - 26 Mar
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Smart TV

Holiday Home in Poughkeepsie

Cozy Escape -Strong Wi-Fi -Prime Location
6.8 out of 10, (5 reviews)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
United States
Andrea C.
The price is NZ$532
includes taxes & fees
15 Mar - 16 Mar
Cozy Escape -Strong Wi-Fi -Prime Location
Property grounds

Holiday Home in Hyde Park

Beautiful home with Hudson River views & adjacent rushing waterfall in Hyde Park
The price is NZ$449
includes taxes & fees
3 Mar - 4 Mar
Beautiful home with Hudson River views & adjacent rushing waterfall in Hyde Park
Terrace/patio

Holiday Home in New Paltz

Vineyard Retreat: 3BR Home-Live Music, Wine+Hiking
6.8 out of 10, (6 reviews)
"10 minutes to town, great view off the deck, peaceful."
United States
irv h.
The price is NZ$753
includes taxes & fees
17 Mar - 18 Mar
Vineyard Retreat: 3BR Home-Live Music, Wine+Hiking
Exterior

Holiday Home in Fishkill

Chestnut on Willow Lake
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 NZ$1,173
includes taxes & fees
9 Mar - 10 Mar
Chestnut on Willow Lake
Property grounds

Holiday Home in Fishkill

Red Cottage - Lakeside Property!
The price is NZ$1,212
includes taxes & fees
9 Mar - 10 Mar
Red Cottage - Lakeside Property!
Exterior

Holiday Home in Fishkill

Hickory on Willow Lake
9.6 out of 10, Exceptional, (5 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is NZ$1,279
includes taxes & fees
9 Mar - 10 Mar
Hickory on Willow Lake
TV, fireplace

Holiday Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (13 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is NZ$572
includes taxes & fees
4 Mar - 5 Mar
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Interior

Holiday Home in Kingston

Esopus Creek modern Tiny house Retreat!
9.8 out of 10, Exceptional, (69 reviews)
"We came for our daughter’s wedding in town . The place was conveniently located near the wedding siteIt was small and just perfect for 3 members of my family -Woke up to birds chirping Would surely plan for a second stay "
United States
Pratistha L.
The price is NZ$396
includes taxes & fees
2 Mar - 3 Mar
Esopus Creek modern Tiny house Retreat!
Smart TV, video games, offices

Holiday Home in Saugerties

Peaceful Cabin w/ Fire Pit & Creek Access
9.6 out of 10, Exceptional, (15 reviews)
"House was very clean, host was welcoming "
United States
David C.
The price is NZ$454
includes taxes & fees
3 Mar - 4 Mar
Peaceful Cabin w/ Fire Pit & Creek Access
Fridge, microwave, oven, stovetop

Holiday Home in New Fairfield

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
10.0 out of 10, Exceptional, (18 reviews)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
The price is NZ$825
includes taxes & fees
5 Mar - 6 Mar
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
1 bedroom, free WiFi, bed sheets

Holiday Home in High Falls

The Studio at the Inn at High Falls
8.0 out of 10, Very good, (34 reviews)
"Just wasn't our cup of tea. Quiet location, close to attractions, and easy to find. "
United States
William K.
The price is NZ$444
includes taxes & fees
2 Mar - 3 Mar
The Studio at the Inn at High Falls
Interior

Holiday Home in Kerhonkson

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
10.0 out of 10, Exceptional, (33 reviews)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
The price is NZ$263
includes taxes & fees
5 Mar - 6 Mar
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Fridge, microwave, oven, stovetop

Holiday Home in Lake Peekskill

Contemporary Cozy Cottage
10.0 out of 10, Exceptional, (31 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is NZ$690
includes taxes & fees
2 Mar - 3 Mar
Contemporary Cozy Cottage
Terrace/patio

Holiday Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$560
includes taxes & fees
3 Mar - 4 Mar
House on the Babbling Brook- Quiet 2BR + King Bed!
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

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Poughkeepsie Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Excellent stay! "
Paulina 2-night trip
Posted 3 days ago
Overlook Lodge at Bear Mountain

Find out more about Poughkeepsie

Poughkeepsie Holiday Homes information

Number of reviews
277
Accommodation
962 Holiday Homes
Lowest Price
NZ$263
Highest Price
NZ$1,279