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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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, (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 ￥12,476
￥27,438 total
includes taxes & fees
Sep 16 - Sep 17
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, (298 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 ￥21,982
￥47,500 total
includes taxes & fees
Sep 27 - Sep 28
Streamside Cottage Half Mile to Town of Woodstock
Interior

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 ￥18,587
￥39,054 total
includes taxes & fees
Sep 23 - Sep 24
Charming loft cottage in tranquil Germantown with WiFi, AC
Terrace/patio

4. 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 ￥28,065
￥46,573 total
includes taxes & fees
Sep 15 - Sep 16
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds

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, (144 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥30,415
￥50,807 total
includes taxes & fees
Sep 14 - Sep 15
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

6. 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 ￥21,505
￥33,158 total
includes taxes & fees
Sep 14 - Sep 15
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Terrace/patio

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, (20 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 ￥17,972
￥45,788 total
includes taxes & fees
Sep 14 - Sep 15
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

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 ￥27,650
￥54,710 total
includes taxes & fees
Sep 14 - Sep 15
Charming Cottage in the Heart of Catskill & Pet Friendly
Room

9. Private Pool House - Pool · Jacuzzi · Fireplace

Private Pool House - Pool · Jacuzzi · Fireplace
Pine Bush
The price is ￥46,083
￥73,807 total
includes taxes & fees
Sep 22 - Sep 23
Private Pool House - Pool · Jacuzzi · Fireplace
Exterior

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 ￥36,912
￥78,187 total
includes taxes & fees
Sep 14 - Sep 15
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.
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Top Poughkeepsie Hotel Reviews

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"It was really an amazing experience, the room was amazing. Loved the fireplace. Loved the bkfst. Would definitely stay again"
Carl 1-night trip
Posted 3 hours ago
Beekman Arms and Delamater Inn

Find out more about Poughkeepsie

Poughkeepsie Cottages information

Number of reviews
428
Accommodation
202 Cottages
Lowest Price
￥27,438
Highest Price
￥78,187

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.