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Compare 407 Vacation Homes in Callicoon with updated reviews, rates, and availability.

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (73)
"Celebrated my husbands 50th birthday and the property was perfect!"
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

In the cloud ~your cozy lake house

9.6 out of 10, Exceptional, (86)
"Great spot."
The price is AED 691
AED 1,293 total
includes taxes & fees
1 May - 2 May
In the cloud ~your cozy lake house

Sun Drenched Lakefront Cove

9.0 out of 10, Wonderful, (18)
"We had a great time! Plenty of room and very clean."
Sun Drenched Lakefront Cove

Private Indoor Pool - Hot Tub - 2 Fishing Ponds - 33 Acres

9.6 out of 10, Exceptional, (28)
"The house was stocked with all the essentials, the owner was very responsive and the overall experience was fantastic. Would recommend for a large group - more than enough space! "
Private Indoor Pool - Hot Tub - 2 Fishing Ponds - 33 Acres

Breathtaking 44+ Acre Country Estate

10.0 out of 10, Exceptional, (30)
"Jennifer was such a very easy and communicative host. House is very well stocked, nice fluffy towels, plenty of space and clean. We had a wonderful trip to Elk. This is our second year visiting this home and we hope to be back again. "
Breathtaking 44+ Acre Country Estate

Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

10.0 out of 10, Exceptional, (118)
"Wonderful setting, house had everything we needed. Dogs had a great time in the woods."
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods

Masthope Mountain Hideaway walking distance to the lake and 8 min to ski lodge

10.0 out of 10, Exceptional, (7)
"The property was comfortable, clean, and very warm. We felt at home."
Masthope Mountain Hideaway walking distance to the lake and 8 min to ski lodge

Spacious 5 BDRM Masthope Chalet with Private Movie Theater & AWESOME Game Room

10.0 out of 10, Exceptional, (1)
"I can’t say enough positive things about this home! The way each room was perfectly suited for a specific purpose: the basement was all for kids and fun zone, the living room has the MOST comfy giant couch ever - perfect for watching TV together as a family, the kitchen is spacious for cooking and serving meals, and the bar had disco lights which added a pop of color and fun to our evenings, finally the deck was comfy and the fire pit was perfect for late night s’mores! We had a large group of...
Spacious 5 BDRM Masthope Chalet with Private Movie Theater & AWESOME Game Room

Charming 3-bedroom house with HUGE yard in Livingston Manor

Charming 3-bedroom house with HUGE yard in Livingston Manor

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

8.0 out of 10, Very Good, (20)
"Nothing negative to say really. Booked this house for 20 guests and it fit us all comfortably. Everything was clean and loved the way this house was layed out. Lots of room and many things to do even inside the house. Huge backyard. Host was very kind. Not many things like paper towel, toilet paper, garbage bags for 4 days with 20 guests as well as no washer and dryer as it’s listed."
The price is AED 533
AED 2,547 total
includes taxes & fees
5 May - 6 May
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

Massive Roscoe Retreat: Great for Large Groups!

10.0 out of 10, Exceptional, (5)
"This property is really nice. Morgan the caretaker was super helpful. "
Massive Roscoe Retreat: Great for Large Groups!

Amazing All-Season Private Lakefront Retreat!

10.0 out of 10, Exceptional, (52)
"Had a wonderful time. The house was fantastic and the lake was enjoyable. Would definitely come back."
Amazing All-Season Private Lakefront Retreat!

Amber Acres Lodge; Spacious Log Cabin with Mountain Views and Lake Access

10.0 out of 10, Exceptional, (18)
"Perfect escape in the mountains near Woodstock!"
Amber Acres Lodge; Spacious Log Cabin with Mountain Views and Lake Access

Private Heated Pool• Hot Tub• Game Room• Fire Pit• 6 Bdrms

2.0 star property
10.0 out of 10, Exceptional, (3)
"Our stay was perfect! This house was absolutely beautiful and spacious. Perfect for large groups. It had everything we needed and then some. Highly recommend staying here!"
The price is AED 2,083
AED 4,354 total
includes taxes & fees
7 May - 8 May
Private Heated Pool• Hot Tub• Game Room• Fire Pit• 6 Bdrms

Scenic Home on the Delaware River, Pet-Friendly!

9.8 out of 10, Exceptional, (6)
"Perfect stay for a trip to the ares for a family wedding."
Scenic Home on the Delaware River, Pet-Friendly!

5 minutes from original Woodstock site.

9.8 out of 10, Exceptional, (48)
"Amazing stay! Clean home and very cozy "
The price is AED 360
AED 797 total
includes taxes & fees
19 May - 20 May
5 minutes from original Woodstock site.

1920’s charm. In-town retreat. Great for fly fishermen!! Pet Friendly

9.8 out of 10, Exceptional, (23)
"Very charming house - well-located, nicely updated and decorated. We used the home as a base for a weekend visiting family near Livingston Manor and it had everything we needed."
1920’s charm. In-town retreat. Great for fly fishermen!! Pet Friendly

The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski

The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski

9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22

8.6 out of 10, Excellent, (4)
"Amazing stay at an amazing property. Great hosts. My families enjoyed it a lot."
9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22

Charming Catskills Lakefront Cottage

8.8 out of 10, Excellent, (10)
"The house was perfectly spacious and the outside area by the lake was amazing. Easy drive to the nearby small towns. Full of character and the house was well prepared."
Charming Catskills Lakefront Cottage
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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Other property types in Callicoon

Postcard Cabins Western Catskills

2.0 star property
9.8 out of 10, Exceptional, (6)
"My Fiancé And Had Great Stay Here Very Peaceful & Clean. We Enjoyed Our Stay Here, It Was Great To Get Away From The City For A While"
The price is AED 496
AED 687 total
includes taxes & fees
15 May - 16 May
Postcard Cabins Western Catskills

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (151)
"Property was clean and just the right size for our group of 2 people and 2 dogs. Had a great time disconnecting from our everyday and walking the property. Hosts were responsive and helpful. "
The price is AED 455
AED 1,218 total
includes taxes & fees
14 May - 15 May
Handcrafted Riverfront Cabin on 10 acres

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (73)
"Celebrated my husbands 50th birthday and the property was perfect!"
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
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.