Search Poughkeepsie Cottage Rentals

Check prices for these dates

Next weekend
Jul 18 - Jul 20
In two weeks
Jul 25 - Jul 27
In one month
Aug 8 - Aug 10
In two months
Sep 5 - Sep 7

Cottages in Poughkeepsie

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Stroll through a serene residential setting surrounded by a lush lawn, a tree, and a picturesque bridge.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (115)
"The greatest spot anyone could imagine. We will be back in the fall for the beautiful colors. "
The price is ￥27,491
￥44,499 total
includes taxes & fees
Jul 14 - Jul 15
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (241)
"Incredible location and comfortable space. Would make this my exclusive place to stay everytime I visit woodstock."
Streamside Cottage Half Mile to Town of Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Set amidst a serene wooded area, this two-story house offers a retreat with a well-manicured lawn and a small deck.

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (66)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Experience serenity in this traditional Tibetan temple, featuring a central statue surrounded by ornate decorations and prayer flags.

Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!

9.8 out of 10, Exceptional, (115)
"The location was exceptional, close to restaurants and shops, quiet neighborhood, comfortable bed and the house was well stocked with everything you’d need."
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Charming Cottage in the Heart of the Shawangunks
Enjoy cooking in this well-lit kitchen with a double sink, toaster oven, and a window overlooking the surrounding trees.

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (12)
"Wonderful stay, exactly as advertised, everything brand new and very cozy."
The price is ￥36,192
￥81,971 total
includes taxes & fees
Jul 20 - Jul 21
Charming Cottage in the Heart of the Shawangunks
Charming Artist's Retreat
Exterior

Charming Artist's Retreat

10.0 out of 10, Exceptional, (138)
"Enjoyed our stay!"
Charming Artist's Retreat
Cedar Cottage with hot tub as seen in New York Times escape section.
Cozy cabin nestled in a dense forest, offering a serene retreat with a central window and small porch area.

Cedar Cottage with hot tub as seen in New York Times escape section.

9.4 out of 10, Exceptional, (84)
"The cottage was very comfortable and the grounds were peaceful and private. The location was perfect. Definitely recommend."
Cedar Cottage with hot tub as seen in New York Times escape section.
Charming Cottage in the Heart of Catskill & Pet Friendly
Enjoy outdoor dining at The New York Restaurant with tables and chairs set amidst lush greenery.

Charming Cottage in the Heart of Catskill & Pet Friendly

10.0 out of 10, Exceptional, (12)
"Really enjoyed my stay! Very thoughtful host. "
Charming Cottage in the Heart of Catskill & Pet Friendly
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Enjoy outdoor dining or relaxation on the upper-floor balcony overlooking a beautifully maintained garden.

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

10.0 out of 10, Exceptional, (166)
"The hosts had thought of everything to make our stay comfortable - lovely bright rooms, well stocked kitchen, plush linens and towels, within walking distance of all restaurants and shops and a beautiful stream and lawn outside! Excellent!"
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Relax in this inviting living room with a bookshelf, sofas, and a coffee table.

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

9.8 out of 10, Exceptional, (133)
"We had a marvelous visit!"
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Hits Adjacent | Pet Friendly | Caraway Cottage
Relax in this stylish living room with a sofa, armchair, and dining area.

Hits Adjacent | Pet Friendly | Caraway Cottage

10.0 out of 10, Exceptional, (8)
"It was super cozy and very comfortable. It really is a lovely cottage. Perfect getaway. "
The price is ￥32,902
￥66,044 total
includes taxes & fees
Jul 20 - Jul 21
Hits Adjacent | Pet Friendly | Caraway Cottage
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Two houses nestled among lush greenery, surrounded by a park with a play structure.

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is ￥26,321
￥45,694 total
includes taxes & fees
Jul 13 - Jul 14
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Relax in a serene outdoor space with a seating area, fire pit, and comfortable chairs.

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (91)
"This is a beautiful home even if you live in the area and just want to spend the weekend at the lake, it’s a perfect getaway. We love that it was dog friendly. The host was wonderful and very accommodating. The house came stocked with everything that you would need for a perfect stay. "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Cozy Cottage with a Pond 2
Winding garden pathway surrounded by lush greenery and a low hedge.

Cozy Cottage with a Pond 2

6.0 out of 10, (12)
"Was perfect place to stay with lots of hiking and waterfalls near by"
The price is ￥14,623
￥21,291 total
includes taxes & fees
Jul 13 - Jul 14
Cozy Cottage with a Pond 2
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Compact kitchen with a stove, microwave, coffee maker, and sink.

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

10.0 out of 10, Exceptional, (37)
"Great place to stay in the winter. Hunter mountain and Woodstock are near by. Will definitely be back."
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Country Cottage with beautiful views and easy access to Catskills activities.
Cozy cabin with a porch, featuring a front door, window, and chimney, surrounded by a grassy lawn and stone pathway.

Country Cottage with beautiful views and easy access to Catskills activities.

10.0 out of 10, Exceptional, (10)
"Cozy little spot for a quick getaway. Very clean, quiet location. Easy check-in. "
The price is ￥14,477
￥26,041 total
includes taxes & fees
Jul 22 - Jul 23
Country Cottage with beautiful views and easy access to Catskills activities.
Be in Nature at this Gorgeous Riverfront Cabin
Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of lush greenery.

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (18)
"Property was as advertised. Clean and nearby places we wanted to visit while, still being out of the way and quiet."
Be in Nature at this Gorgeous Riverfront Cabin
Pet-friendly Cottage at Historic Millbrook Farm Estate
Traditional dresser with ornate carvings and multiple drawers, featuring a mirror above and a decorative candelabra.

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.0 out of 10, Wonderful, (6)
"Stayed in this renovated farmhouse for a very snowy weekend. Nicely redone and furnished with spacious living/dining area. Could have fit 2 more adults or 2-3 kids. Hosts were lovely and introduced us to the goats. Too snowy and icy to get outdoors or explore much but local village has shops and kitchen was stocked with pantry staples and bottled water, milk/creamers for coffee so arrival day grocery run was not needed. Bonus large picture window let us enjoy the abundant snow from the warmth of...
Pet-friendly Cottage at Historic Millbrook Farm Estate
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Situated on a corner of Old Forge Rd. and Mill Hill Rd., this traditional building offers a charming garden setting.

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

10.0 out of 10, Exceptional, (119)
"The property was lovely, and the perfect location. Chelsea was great to work with!"
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Enjoy al fresco dining on the deck surrounded by a serene forest.

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

10.0 out of 10, Exceptional, (80)
"This was just what we were looking for. The host was very quick to respond to any of my questions. We enjoyed the location and all the amenities. The outdoor grill, outdoor firepit and inside fireplace were enjoyed and it was a nice bonus that there was plenty of firewood."
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.