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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Poughkeepsie cottages

Property grounds

1. 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 ￥69,083
￥116,687 total
includes taxes & fees
Aug 19 - Aug 20
Kapitan’s cottage a Rustic Private Catskill Getaway Near Kingston
Exterior

2. 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, (15 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 ￥22,059
￥38,792 total
includes taxes & fees
Aug 9 - Aug 10
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Property grounds

3. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (291 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 ￥25,344
￥53,580 total
includes taxes & fees
Aug 23 - Aug 24
Streamside Cottage Half Mile to Town of Woodstock
Interior

4. 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, (12 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is ￥22,811
￥41,054 total
includes taxes & fees
Aug 11 - Aug 12
Charming loft cottage in tranquil Germantown with WiFi, AC
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, (141 reviews)
"We had a great stay!!"
United States
Jasmine
The price is ￥31,149
￥51,291 total
includes taxes & fees
Aug 10 - Aug 11
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 ￥23,598
￥35,907 total
includes taxes & fees
Aug 9 - Aug 10
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior

7. Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Terrace/patio

8. 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 ￥28,318
￥49,160 total
includes taxes & fees
Sep 2 - Sep 3
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Exterior

9. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
The price is ￥37,804
￥79,566 total
includes taxes & fees
Aug 16 - Aug 17
Cozy 2-bedroom cottage in enchanting Catskill Mountains
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, (24 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 ￥31,464
￥60,260 total
includes taxes & fees
Aug 23 - Aug 24
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior

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

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.6 out of 10, Exceptional, (19 reviews)
"Host was super welcoming - the pace was gorgeous and had everything we could possibly need! Fabulous stay overall"
United States
Athena P.
The price is ￥23,016
￥47,114 total
includes taxes & fees
Sep 2 - Sep 3
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

8/10 Good
"The room was clean and well furnished and the front desk staff were friendly and very helpful. Even though we were technically in a room where dogs were allowed, the room did not smell like dogs and there was not a trace that anyone had slept in it that had a dog, which is a plus. Love dogs, but not the smell of other's dogs. Additionally, the Inn's restaurant was amazing - rustic, with nooks and dark benches and tables - just like going back into time to the 1700s, but way cleaner. The food was excellent as well, and the wait staff was very attentive. Only negative about the entire Inn experience was the breakfast, which was surprising. The online reviews for breakfast were excellent, so hopes were high, but it was not the greatest experience for us. First, breakfast was in a completely separate building that was about a block away across the street. We trudged through the rain to try and find it but had no luck so had to trudge back and ask the front desk (which was also in a separate building) staff. When we finally found it, the breakfast consisted of some danishes and muffins along with some sad looking hard boiled eggs and toast. No bacon or even a waffle maker. At the same time, a fitness group was pumping weights right outside of the glass doors to the beat of some very upbeat music. And while this was interesting, it was not the best atmosphere for a quiet breakfast. We left and went to a nearby diner where I had freshly cooked scrambled eggs, bacon and toast."
NAERAN 1-night trip
Posted 8 hours ago
Beekman Arms and Delamater Inn

Find out more about Poughkeepsie

Poughkeepsie Cottages information

Number of reviews
562
Accommodation
170 Cottages
Lowest Price
￥35,907
Highest Price
￥116,687

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.