Search Cottages in Staatsburg

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Our top choices for Staatsburg cottages

Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (248)
"A beautiful quiet setting! "
The price is HK$1,162
HK$2,524 total
includes taxes & fees
2 Sept - 3 Sept
Streamside Cottage Half Mile to Town of Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior

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

10.0 out of 10, Exceptional, (71)
"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
Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (62)
"It’s adorable exactly What’s on the photos and equipped with everything you need for your stay definitely will be visiting it again. "
Mountain View escape
Leggett Cottage, High Falls, NY.
Outdoor dining

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (77)
"We really enjoyed our stay! The space was very nice & beautiful during the fall!"
Leggett Cottage, High Falls, NY.
Pet-friendly Cottage at Historic Millbrook Farm Estate
Interior

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.4 out of 10, Exceptional, (8)
"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
Cedar Cottage with hot tub as seen in New York Times escape section.
Exterior

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

9.4 out of 10, Exceptional, (84)
"Diana’s property was the perfect spot to reconnect with old friends. We enjoyed the art, food and music of Woodstock and a side trip to Bethel to check out the Woodstock Museum. Diana’s home was a comfortable place to retreat to after our days of exploring. We would love to make it an annual event. "
Cedar Cottage with hot tub as seen in New York Times escape section.
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
TV, DVD player, books, video library

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

9.8 out of 10, Exceptional, (134)
"We had a marvelous visit!"
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Be in Nature at this Gorgeous Riverfront Cabin
Smart TV, books

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

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

9.8 out of 10, Exceptional, (116)
"The location was exceptional, close to restaurants and shops, quiet neighborhood, comfortable bed and the house was well stocked with everything you’d need."
The price is HK$2,574
HK$5,093 total
includes taxes & fees
23 Aug - 24 Aug
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Reset and Relax in Luxury Cottage
Property grounds

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (40)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Children’s area

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (43)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is HK$1,404
HK$2,332 total
includes taxes & fees
14 Sept - 15 Sept
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (81)
"Amazing cabin, thank you for a beautiful stay! We came in for a wedding and this was a great location to where the wedding was held. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Charming Artist's Retreat
Exterior

Charming Artist's Retreat

9.8 out of 10, Exceptional, (140)
"Enjoyed our stay!"
Charming Artist's Retreat
Private Woodstock cottage. Don't forget your dog!
Interior

Private Woodstock cottage. Don't forget your dog!

10.0 out of 10, Exceptional, (9)
"The property was Great! It was close to town, but far enough away for a little peace and quiet. The place itself was very clean, comfortable, and great for a couples weekend retreat."
Private Woodstock cottage. Don't forget your dog!
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Exterior

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
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Exterior

Charming 2-bedroom cottage with large deck in beautiful Accord NY.

10.0 out of 10, Exceptional, (13)
"It was better than the pictures! Very peaceful and a lovely little house. Judy was very responsive with any questions or needs we had. "
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Outdoor dining

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

10.0 out of 10, Exceptional, (80)
"My friend and I really enjoyed the solace of our stay. Highly recommend!"
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Exterior

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
Waterfall, Back Yard, and Fire Pit!
Exterior

Waterfall, Back Yard, and Fire Pit!

Waterfall, Back Yard, and Fire Pit!
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
Exterior

THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need

9.0 out of 10, Wonderful, (8)
"We really enjoyed our stay and will definitely come back. Highly recommended!"
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
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

Top Staatsburg Hotel Reviews

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"Very comfortable room and beds. Staff was friendly. Clean. Cont breakfast was great. Only downside is the noise from the main road in our room in the late evening. Lots of motorcyles going by."
Robert 1-night trip
Posted 11 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

Frequently asked questions

Why book your cottage in Staatsburg with Expedia?
Expedia has some wonderful cottages in Staatsburg, so start packing for an unforgettable holiday on nature's doorstep. If you need to stick to a budget, choose how much you're willing to spend and your preferred property star rating. Or, try out our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect fit whatever your getaway looks like.
How can I find cheap cottages in Staatsburg?
Expedia is here to help you track down cheap cottages in Staatsburg. To lock in your special stay in just a few clicks, use our handy filter tool to refine your search results by amenities, star rating and budget.
What is there to do in Staatsburg near my cottage?
Once you've unpacked your suitcases, venture out and explore the fantastic things Staatsburg has for you to experience. Mills Mansion is a popular attraction to add to your must-do list.