An aerial view of a town with a river, a bridge, and autumn-colored trees.

Search Poughkeepsie Cottage Rentals

  • 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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Poughkeepsie cottages

Exterior

1. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (16 reviews)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
The price is ￥15,121
￥31,041 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Property grounds

2. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (296 reviews)
"Wonderful property with an easy check in and checkout process. The property and surrounding areas are beautiful. We would stay here again. "
United States
Anonymous traveler
The price is ￥22,361
￥47,619 total
includes taxes & fees
Sep 7 - Sep 8
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

3. Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston

Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston
Kingston
9.6 out of 10, Exceptional, (10 reviews)
"Perfect place for a short vacation in the Catskills!"
United States
Jennifer C.
The price is ￥41,596
￥80,541 total
includes taxes & fees
Sep 8 - Sep 9
Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston
Exterior

4. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (24 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥24,675
￥74,050 total
includes taxes & fees
Sep 9 - Sep 10
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Terrace/patio

5. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
8.8 out of 10, Excellent, (48 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is ￥28,549
￥49,127 total
includes taxes & fees
Sep 8 - Sep 9
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds

6. 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, (144 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥30,939
￥51,683 total
includes taxes & fees
Sep 8 - Sep 9
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

7. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.4 out of 10, Exceptional, (3 reviews)
"Tracy was an excellent host. The Mondrian Manor was cozy and perfect for two."
United States
Brandi A.
The price is ￥23,439
￥35,665 total
includes taxes & fees
Sep 7 - Sep 8
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Interior

8. Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (14 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is ￥19,533
￥40,778 total
includes taxes & fees
Sep 23 - Sep 24
Charming loft cottage in tranquil Germantown with WiFi, AC
Terrace/patio

9. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (19 reviews)
"The property was just as described, very private and cozy. We enjoyed the large balcony as well as the yard. There were also several nice hiking trails close by. Overall we were very happy with our stay."
United States
Ryan P.
The price is ￥18,142
￥45,919 total
includes taxes & fees
Sep 14 - Sep 15
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

10. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (25 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
The price is ￥28,127
￥55,304 total
includes taxes & fees
Sep 7 - Sep 8
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior

11. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (1 review)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
The price is ￥37,549
￥79,874 total
includes taxes & fees
Sep 7 - Sep 8
Cozy 2-bedroom cottage in enchanting Catskill Mountains
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

Best Western Plus The Inn & Suites At The Falls

Best Western Plus The Inn & Suites At The Falls

10/10 Excellent
"Good service. Breakfast were always fresh and hot. Staff were friendly and helpful. Room was clean and everything in it worked perfectly."
Ricardo 7-night trip
Posted 3 hours ago
Best Western Plus The Inn & Suites At The Falls

Find out more about Poughkeepsie

Poughkeepsie Cottages information

Number of reviews
456
Accommodation
202 Cottages
Lowest Price
￥31,041
Highest Price
￥80,541

Frequently asked questions

Why book your cottage in Poughkeepsie with Expedia?
We think that a vacay should be a breeze, so if you're chasing cottages in Poughkeepsie at a great price, Expedia is here to help. Stick to the budget and stay in an economical option far away from the downtown buzz, or splurge on an upscale cottage to spoil your loved ones.
How can I find cheap cottages in Poughkeepsie?
The best way to track down cheap cottages in Poughkeepsie is with Expedia's filter tool. Refine your search by budget, amenities and star rating to land awesome rates in a few clicks.
What is there to do in Poughkeepsie near my cottage?
Whatever your tastes or interests, Poughkeepsie has loads of things to capture your imagination. Mid-Hudson Bridge, Casperkill Golf Club and Mid-Hudson Children's Museum are on most travelers' lists. Don't miss Richard L. Skimin Memorial Baseball Field, Mid-Hudson Civic Center and Clinton House State Historic Site either. With Expedia's hotel deals in Poughkeepsie, you'll be able to see more wonderful attractions like these with the money you save.