A rural landscape with a house surrounded by autumn-colored trees and rolling hills.

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Callicoon cottages

Property grounds

Charming 120-year-old farmhouse by the creek

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (26 reviews)
"This is really a beautiful place to stay, we definitely will return in summer. "
United States
Paul C.
$308 nightly
The price is $339
Jul 14 - Jul 15
Total with taxes and fees
Charming 120-year-old farmhouse by the creek
Interior

Explore Livingston Manor-Hiking-Relaxing-Firepit-Dining

Explore Livingston Manor-Hiking-Relaxing-Firepit-Dining
Livingston Manor
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay at this little cottage. Nice and clean, very relaxing, warm and inviting. No issues at all, enjoyable few days of peace and quiet… "
United States
Anonymous traveler
$313 nightly
The price is $352
Jul 8 - Jul 9
Total with taxes and fees
Explore Livingston Manor-Hiking-Relaxing-Firepit-Dining
Exterior

Roscoe Cottage Pet Friendly

Roscoe Cottage Pet Friendly
Roscoe
9.8 out of 10, Exceptional, (19 reviews)
"Me and my family had the most amazing time in this home. If you are looking for a peaceful getaway book this place. We enjoyed the campfire (hosts started it for us), boardgames, sledding right in the back. We will book again it was perfect!"
United States
Christina C.
$264 nightly
The price is $297
Jul 10 - Jul 11
Total with taxes and fees
Roscoe Cottage Pet Friendly
Outdoor dining

Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
Monticello
10.0 out of 10, Exceptional, (43 reviews)
"Great little area- very cozy cabin! "
United States
Valeria S.
$396 nightly
The price is $445
Aug 2 - Aug 3
Total with taxes and fees
Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!
Outdoor dining

Lakefront | Sport Courts | HotTub | GameRoom

Lakefront | Sport Courts | HotTub | GameRoom
Highland Lake
10.0 out of 10, Exceptional, (33 reviews)
"This property is absolutely beautiful. The check in process was easy and the host was super helpful and sweet! Highly recommend this place."
United States
Christina V.
$1,209 nightly
The price is $1,358
Jul 14 - Jul 15
Total with taxes and fees
Lakefront | Sport Courts | HotTub | GameRoom
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 Callicoon Hotel Reviews

Windsong Retreat 2

Windsong Retreat 2

10/10 Excellent
"This place was spectacular! Mary is the best hostess and made us feel right at home. Her personality made everyone feel like we had all been friends for years. Her home cooking was delicious. It felt like having a home cooked meal with family you truly enjoy being around. Our room, the “Nature Room,” was amazing. The bed was so comfortable, the room was very clean, and we had our own private bathroom with our own climate control. Since the room was on the back side of the house, we had a beautiful view of the woods that seemed to go on forever. The location was perfect for Bethel Woods. It is less than two miles away, so you really couldn’t get much closer unless you were camping there. I would definitely recommend this place for a concert weekend or just a quiet getaway."
Marissa 1-night trip
Posted less than an hour ago
Windsong Retreat 2

Find out more about Callicoon

Callicoon Cottages information

Number of reviews
128
Accommodation
144 Cottages
Lowest Price
$297
Highest Price
$1,358

Frequently asked questions

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