Photo by Michelle Rapier

Search Cottages in Castleton-on-Hudson

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
9.0 out of 10, Wonderful, (4)
"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming Cottage in Private Lake Community (Pet-Friendly!)

10.0 out of 10, Exceptional, (31)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (84)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

10.0 out of 10, Exceptional, (11)
"Our family rented this property for a long weekend trip and had a great experience. We enjoyed the beauty of the local area, including some great local restaurants and coffee shops. We were snowed in for one day of our trip and enjoyed the coziness of the property and the full kitchen came in clutch to avoid needing to travel during the storm. "
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

Near Hospitals: Home w/ Yard in Albany!

3.0 star property
Near Hospitals: Home w/ Yard in Albany!

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (15)
"The house was very convenient to anywhere we wanted to go. We even had 5 deer welcome us the first night. House was very comfortable and we loved it."
Cozy cottage with pool, walking distance to lake

Pet-friendly Latham Retreat ~ 7 Mi to Albany!

3.0 star property
Pet-friendly Latham Retreat ~ 7 Mi to Albany!

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is HK$9,129
HK$14,931 total
includes taxes & fees
2 Sept - 3 Sept
Berkshires farm, 30+ guests, 50 acres

Private Hot Tub: Hudson Valley Cabin Retreat!

3.0 star property
Private Hot Tub: Hudson Valley Cabin Retreat!

Albany Home w/ Fenced Yard & Patio - Pets Welcome!

3.0 star property
Albany Home w/ Fenced Yard & Patio - Pets Welcome!

Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!

Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy

3.0 star property
Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy

Charming Albany Retreat ~ 3 Mi to Downtown!

3.0 star property
Charming Albany Retreat ~ 3 Mi to Downtown!

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3.0 star property
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Chic Troy Home Near Downtown, 9 Mi to Albany!

3.0 star property
8.0 out of 10, Very good, (1)
Chic Troy Home Near Downtown, 9 Mi to Albany!

Spacious Cozy Getaway in the Catskills: King bed/ Game Room

9.4 out of 10, Exceptional, (18)
"The house was beautiful and comfy."
Spacious Cozy Getaway in the Catskills: King bed/ Game Room

Sleepy Hollow Lake Home w/ Deck, Pool Access!

3.0 star property
Sleepy Hollow Lake Home w/ Deck, Pool Access!

Cozy Catskills Home w/ Pond on 2 Acres!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely gorgeous property, the owner is awesome and can’t forget Leo the cat. "
Cozy Catskills Home w/ Pond on 2 Acres!

Modern-chic Athens Home - Fish, Ski & Swim!

3.0 star property
Modern-chic Athens Home - Fish, Ski & Swim!
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

Top Castleton-on-Hudson Hotel Reviews

Frequently asked questions

Why book your cottage in Castleton-on-Hudson with Expedia?
We think that a holiday should be hassle-free, so if you're in search of cottages in Castleton-on-Hudson at a competitive rate, Expedia has your back. Keep costs down and opt for a cheap option far away from the city rush, or splurge on a 5-star cottage to spoil your favourite people.
How can I find cheap cottages in Castleton-on-Hudson?
The best way to compare cheap cottages in Castleton-on-Hudson is with Expedia's filter tool. Narrow down your search by star rating, amenities and budget to snag awesome rates in a couple of clicks.
What is there to do in Castleton-on-Hudson near my cottage?
The perfect travel accessory is a well-planned schedule. Brookview Station Winery is a good spot to kick off your adventures in Castleton-on-Hudson.