Poughkeepsie Holiday Rentals

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

Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Poughkeepsie

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, (2)
"House worked perfectly for our needs. Newly renovated home. Parking was plentiful behind the home. "
United States
Wayne S.
The price is HK$1,287
HK$4,556 total
includes taxes & fees
1 Dec - 2 Dec
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
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 HK$2,013
HK$2,594 total
includes taxes & fees
30 Nov - 1 Dec
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (43)
"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 HK$863
HK$1,521 total
includes taxes & fees
18 Nov - 19 Nov
Mid-Century DJ’s Dream
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, (259)
"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
Terrace/patio
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (34)
"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
The Farm at Hyde Park

The Farm at Hyde Park

Staatsburg
9.8 out of 10, Exceptional, (85)
"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
Terrace/patio
Cove - King Bed Escape w/Hot Tub, Unit A

Cove - King Bed Escape w/Hot Tub, Unit A

Ellenville
10.0 out of 10, Exceptional, (2)
"The place was great, really enjoyed our stay! "
United States
Abby
Cove - King Bed Escape w/Hot Tub, Unit A
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 HK$1,154
HK$1,867 total
includes taxes & fees
17 Nov - 18 Nov
Esopus Creek modern Tiny house Retreat!
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 HK$972
HK$1,262 total
includes taxes & fees
16 Nov - 17 Nov
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds
Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2

Newburgh
9.4 out of 10, Exceptional, (27)
"My partner and I stayed at the cabin for a writing retreat/getaway. It served us well and was perfect for our short trip. The host, Julie was very kind and helpful throughout our stay!"
United States
Thani B.
The price is HK$847
HK$1,368 total
includes taxes & fees
16 Nov - 17 Nov
Cabin in the heart of the Hudson Valley, Cabin 2
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
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 HK$3,358
HK$5,372 total
includes taxes & fees
16 Nov - 17 Nov
Large,Cozy,Bright Apartment, Business Themed.
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)
"Everything was super clean and the hosts are very easy to deal with. They came and took care of an issue with wasps for us. The view is phenomenal and having the patio to enjoy it from was great. "
United States
Samantha W.
The price is HK$1,461
HK$2,391 total
includes taxes & fees
18 Nov - 19 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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
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 HK$2,351
HK$3,513 total
includes taxes & fees
27 Nov - 28 Nov
Rustic Cabin in Fishkill!
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 HK$1,399
HK$2,438 total
includes taxes & fees
23 Nov - 24 Nov
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Exterior
The Studio at the Inn at High Falls

The Studio at the Inn at High Falls

High Falls
8.0 out of 10, Very good, (32)
"Lovely!"
United States
Julia H.
The price is HK$874
HK$2,084 total
includes taxes & fees
19 Nov - 20 Nov
The Studio at the Inn at High Falls
Outdoor dining
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

Newburgh
10.0 out of 10, Exceptional, (311)
"Beautiful location- owner was very responsive to any questions we had."
United States
Richard K.
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Fridge, microwave, oven, stovetop
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Monroe
6.8 out of 10, (5)
The price is HK$4,400
HK$8,855 total
includes taxes & fees
16 Nov - 17 Nov
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Exterior
TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE

Pine Bush
10.0 out of 10, Exceptional, (4)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is HK$852
HK$1,580 total
includes taxes & fees
19 Nov - 20 Nov
TRANQUIL MOUNTAIN SOLITUDE
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 Poughkeepsie Hotel Reviews

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

10/10 Excellent
"It’s a beautiful environment, it’s like Christmas all year round"
Judith 1-night trip
Posted 4 hours ago
Hotel Zero Degrees Danbury

Find out more about Poughkeepsie

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

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

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

Frequently asked questions

Are there holiday rentals in Poughkeepsie?

Yes, there are holiday rentals in Poughkeepsie close to Mid-Hudson Civic Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the university campus and scenic riverfront in Poughkeepsie. While you're in the area, you can also enjoy the top-notch restaurants and entertainment venues.

What are some of the best holiday rentals that Poughkeepsie has to offer?

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY: This highly rated holiday home rental in Poughkeepsie offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Poughkeepsie?

Expedia has 24 holiday rentals for your stay in Poughkeepsie.

What can I see and do in Poughkeepsie?

Mid-Hudson Civic Center and McCann Ice Arena are a couple of the family-friendly sights, whereas cultural attractions include Bardavon 1869 Opera House and Locust Grove. Other places in town to visit include Mid-Hudson Bridge and Poughkeepsie Bridge.

What are holiday rentals like in Poughkeepsie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Poughkeepsie. Holiday rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family getaway.