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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

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

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
5 bedrooms, desk, iron/ironing board, free WiFi

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

9.0 out of 10, Wonderful, (74)
"This beautiful getaway was just what we needed. Fresh air, nature, and a gorgeous home. Already planning our next trip back..."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
In the cloud ~your cozy lake house
Interior

In the cloud ~your cozy lake house

9.6 out of 10, Exceptional, (87)
"Great spot."
The price is AED 691
AED 1,293 total
includes taxes & fees
13 May - 14 May
In the cloud ~your cozy lake house
Sun Drenched Lakefront Cove
Fridge, microwave, oven, stovetop

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
Indoor pool, a heated pool

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
Fridge, microwave, oven, stovetop

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
Property grounds

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

10.0 out of 10, Exceptional, (121)
"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
Fridge, microwave, oven, stovetop

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
Pool

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

10.0 out of 10, Exceptional, (2)
"This house was perfect for the 9 of us. Spacious and plenty of room for all. House was spotless and the owner provided everything you can possible need and was very easy to communicate with. We enjoyed all the games in the basement and the movie room. It really was the perfect house for our family get together and would highly recommend. We will definitely come back."
Spacious 5 BDRM Masthope Chalet with Private Movie Theater & AWESOME Game Room
Charming 3-bedroom house with HUGE yard in Livingston Manor
Exterior

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
Outdoor spa tub

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

8.0 out of 10, Very Good, (21)
"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 2,553
AED 5,139 total
includes taxes & fees
13 May - 14 May
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski
Massive Roscoe Retreat: Great for Large Groups!
Outdoor dining

Massive Roscoe Retreat: Great for Large Groups!

10.0 out of 10, Exceptional, (6)
"This property is really nice. Morgan the caretaker was super helpful. "
Massive Roscoe Retreat: Great for Large Groups!
Amazing All-Season Private Lakefront Retreat!
Fridge, microwave, oven, stovetop

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
Smart TV, fireplace, video games, books

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
Aerial view

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 2,445
AED 4,819 total
includes taxes & fees
5 Jun - 6 Jun
Private Heated Pool• Hot Tub• Game Room• Fire Pit• 6 Bdrms
Scenic Home on the Delaware River, Pet-Friendly!
Terrace/patio

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.
Fridge, microwave, oven, stovetop

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 801 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
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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
Indoor pool, a heated pool

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
Sun loungers

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
Exterior

Postcard Cabins Western Catskills

2.0 star property
9.8 out of 10, Exceptional, (8)
"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 551
AED 747 total
includes taxes & fees
13 May - 14 May
Postcard Cabins Western Catskills
Secluded modern log cabin with picturesque private water fall on 12 acres!
Fridge, microwave, oven, stovetop

Secluded modern log cabin with picturesque private water fall on 12 acres!

10.0 out of 10, Exceptional, (121)
"Wonderful setting, cozy tastefully decorated interior, well stocked and very clean. We enjoyed every minute we were there. Our host was terrific!!!"
Secluded modern log cabin with picturesque private water fall on 12 acres!
Handcrafted Riverfront Cabin on 10 acres
Exterior

Handcrafted Riverfront Cabin on 10 acres

10.0 out of 10, Exceptional, (151)
"Beautiful experience girlfriend very happy and excited about the adventure thank you so much."
The price is AED 393
AED 1,142 total
includes taxes & fees
22 May - 23 May
Handcrafted Riverfront Cabin on 10 acres
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.