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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Poughkeepsie cottages

A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

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, (18 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 ￥21,351
￥36,766 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A wooden cabin surrounded by lush greenery and trees.

2. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (299 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
The price is ￥22,648
￥49,649 total
includes taxes & fees
Sep 27 - Sep 28
Streamside Cottage Half Mile to Town of Woodstock
A kitchen with white cabinetry, granite countertops, and a window with blinds.

3. 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 ￥19,151
￥40,239 total
includes taxes & fees
Sep 30 - Oct 1
Charming loft cottage in tranquil Germantown with WiFi, AC
A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

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

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Bloomingburg
9.6 out of 10, Exceptional, (5 reviews)
"The place was as described, quaint, clean, no issues with communication or check in"
United States
Stephen H.
The price is ￥22,043
￥33,987 total
includes taxes & fees
Oct 7 - Oct 8
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A house with a view of a bridge and mountains.

5. 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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥31,337
￥52,347 total
includes taxes & fees
Sep 28 - Sep 29
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A two-story house with a wooden exterior, a front porch, and a staircase leading to the entrance.

6. 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, (25 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is ￥29,473
￥81,039 total
includes taxes & fees
Sep 28 - Sep 29
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

7. 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, (21 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 ￥19,657
￥48,066 total
includes taxes & fees
Sep 29 - Sep 30
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

8. 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, (26 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 ￥28,341
￥56,077 total
includes taxes & fees
Sep 28 - Sep 29
Charming Cottage in the Heart of Catskill & Pet Friendly
A wooden deck with a railing overlooking a body of water and trees.

9. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is ￥39,568
￥67,341 total
includes taxes & fees
Sep 26 - Sep 27
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A single-story house with a dark exterior, a chimney, and a small window.

10. 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 ￥38,032
￥80,046 total
includes taxes & fees
Sep 25 - Sep 26
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"The property is a bit dated and its a bit odd to have to drive to the Inn to check in but it was mostly OK. Very rustic at the lodge and no staff onsite"
Dean 1-night trip
Posted 19 hours ago
Overlook Lodge at Bear Mountain

Find out more about Poughkeepsie

Poughkeepsie Cottages information

Number of reviews
554
Accommodation
202 Cottages
Lowest Price
￥33,987
Highest Price
￥81,039

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.