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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Castleton-on-Hudson

Rose Cottage
Escape to a serene cabin nestled in a wooded area, surrounded by lush greenery and a charming front porch.

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Relax on a deck overlooking a serene body of water surrounded by lush greenery and trees.

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

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!!
Charming Cottage in Private Lake Community (Pet-Friendly!)
Experience rural living at this serene farmstead, surrounded by open fields and a simple, functional architecture.

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!)
Near Hospitals: Home w/ Yard in Albany!
Situated in a serene winter landscape, this two-story house offers a cozy retreat with a driveway and a large tree in the foreground.

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
Relax on the front porch with a comfortable seating area.

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!
House (2 Bedrooms) | Interior

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
Situated on a grassy area, this charming home features a traditional two-story design with a prominent porch and a small attached structure.

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is NZ$3,242
includes taxes & fees
2 Sept - 3 Sept
Berkshires farm, 30+ guests, 50 acres
Private Hot Tub: Hudson Valley Cabin Retreat!
House (3 Bedrooms) | Interior

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!
House (3 Bedrooms) | Interior

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

3.0 star property
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy
House (3 Bedrooms) | Interior

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

3.0 star property
Spacious Home w/ Yard & Patio, 2 Mi to Dtwn Troy
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Relax on the deck with comfortable seating and a decorative rug.

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
Charming Albany Retreat ~ 3 Mi to Downtown!
House (3 Bedrooms) | Interior

Charming Albany Retreat ~ 3 Mi to Downtown!

3.0 star property
Charming Albany Retreat ~ 3 Mi to Downtown!
Expansive Upstate Home w/ Home Theater!
House (5 Bedrooms) | Interior

Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
House (4 Bedrooms) | Interior

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!
House (2 Bedrooms) | Interior

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!
Cozy Catskills Home w/ Pond on 2 Acres!
House (2 Bedrooms) | Interior

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!
Sleepy Hollow Lake Home w/ Deck, Pool Access!
House (3 Bedrooms) | Interior

Sleepy Hollow Lake Home w/ Deck, Pool Access!

3.0 star property
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Spacious Cozy Getaway in the Catskills: King bed/ Game Room
Relax on the deck with a view of the serene natural landscape and enjoy outdoor dining or relaxation in the yard.

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
Modern-chic Athens Home - Fish, Ski & Swim!
House (5 Bedrooms) | Interior

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.
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Top Castleton-on-Hudson Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
Kim 3-night trip
Posted 2 days ago
Vacation Village in the Berkshires

Frequently asked questions

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.