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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 ￥44,850
￥65,289 total
includes taxes & fees
Oct 11 - Oct 12
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
A kitchen with white cabinetry, granite countertops, and a window with blinds.

2. 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, (16 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is ￥19,357
￥40,539 total
includes taxes & fees
Oct 13 - Oct 14
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.

3. 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 ￥22,032
￥33,970 total
includes taxes & fees
Oct 5 - Oct 6
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
A house with a view of a bridge and mountains.

4. 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 ￥31,159
￥52,050 total
includes taxes & fees
Oct 6 - Oct 7
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A wooden cabin surrounded by lush greenery and trees.

5. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (301 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 ￥26,769
￥55,184 total
includes taxes & fees
Oct 20 - Oct 21
Streamside Cottage Half Mile to Town of Woodstock
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

6. 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 ￥19,286
￥47,512 total
includes taxes & fees
Oct 5 - Oct 6
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A blue house with a porch, an American flag, and a brick pathway leading to the entrance.

7. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is ￥58,384
￥109,899 total
includes taxes & fees
Oct 22 - Oct 23
Bright Cornwall-on-hudson Vacation Rental!
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 ￥28,327
￥56,049 total
includes taxes & fees
Oct 6 - Oct 7
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 ￥39,343
￥66,958 total
includes taxes & fees
Oct 3 - Oct 4
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, (2 reviews)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
The price is ￥37,816
￥79,591 total
includes taxes & fees
Oct 1 - Oct 2
Cozy 2-bedroom cottage in enchanting Catskill Mountains
An outdoor patio with a stone wall, a wooden fence, and a table with chairs.

11. Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is ￥42,962
￥99,118 total
includes taxes & fees
Oct 4 - Oct 5
Updated Home w/ Patio Half Mile to West Point
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.
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Top Poughkeepsie Hotel Reviews

Red Roof Inn PLUS+ Poughkeepsie

Red Roof Inn PLUS+ Poughkeepsie

10/10 Excellent
"Overall good"
Shafqat 14-night trip
Posted 1 hour ago
Red Roof Inn PLUS+ Poughkeepsie

Find out more about Poughkeepsie

Poughkeepsie Cottages information

Number of reviews
560
Accommodation
202 Cottages
Lowest Price
￥33,970
Highest Price
￥109,899

Frequently asked questions

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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.
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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.