Book Holiday Homes in Callicoon

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Featured Holiday Homes in Callicoon

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

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

Narrowsburg
Located in Narrowsburg, this vacation home is on the waterfront, within a 5-minute drive of Upper Delaware Scenic and Recreational Area and Upper Delaware ...
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse

Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse

Hancock
Located in Hancock, this vacation home is in the mountains, within a 10-minute drive of Hancock Town Hall and Hancock Hounds Dog Park.
Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse
Cozy Swan Lake Apt w/ Grill + Private Yard

Cozy Swan Lake Apt w/ Grill + Private Yard

Swan Lake
With a stay at this vacation home in Swan Lake, you'll be within a 10-minute drive of Bethel Woods Center For The Arts and Bethel Woods.
Cozy Swan Lake Apt w/ Grill + Private Yard
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Luxury Lakeside Paradise

Luxury Lakeside Paradise

Monticello
Located in Monticello, this vacation home is on a lake, within a 15-minute drive of Mongaup River and Monticello Casino and Raceway.
Luxury Lakeside Paradise
9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22

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

Narrowsburg
With a stay at 9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22 in Narrowsburg, you'll be within a 5-minute drive of Upper Delaware ...
9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22
Spacious Home w/ Deck, Grill & Delaware River View

Spacious Home w/ Deck, Grill & Delaware River View

Callicoon
When you a stay at this vacation home in Callicoon, you'll be on a river, just steps from Upper Delaware Scenic and Recreational Area and Upper Delaware ...
Spacious Home w/ Deck, Grill & Delaware River View
Pet-Friendly Hancock Home on the Delaware River!

Pet-Friendly Hancock Home on the Delaware River!

Hancock
Located in Hancock, this vacation home is on the waterfront, a 1-minute drive from East Branch Delaware River and 6 minutes from Peas Eddy Island.
Pet-Friendly Hancock Home on the Delaware River!
House w/ Hot Tub on 10 Acres near Delaware River

House w/ Hot Tub on 10 Acres near Delaware River

Barryville
Located in Barryville, this vacation home is on a river, within a 10-minute drive of Upper Delaware Scenic and Recreational Area and Upper Delaware River.
House w/ Hot Tub on 10 Acres near Delaware River
The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski

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

Roscoe
With a stay at this vacation home in Roscoe, you'll be on a lake, and 20.3 mi (32.7 km) from Bethel Woods Center For The Arts and 5.9 mi (9.5 km) from Catskill ...
The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski
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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.

Callicoon Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Callicoon vacation homes are the perfect way for you to wing it.

Holiday houses in Callicoon let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Callicoon in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Callicoon adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Callicoon with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Callicoon vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Callicoon Holiday Homes essential information

Accommodation
341 Holiday Homes
Lowest Price
AU$205
Highest Price
AU$348
Popular accommodation
Peaceful woodsy retreat with stream and hiking on property / near Bethel Woods, Indoor Pool + 3 Homes + Private Lodge/ Entertainment Clubhouse, Cozy Swan Lake Apt w/ Grill + Private Yard, Luxury Lakeside Paradise, 9-bedroom home with Private Indoor heated Pool - Firepit - 7 acres - sleeps 22, Spacious Home w/ Deck, Grill & Delaware River View, Pet-Friendly Hancock Home on the Delaware River!, House w/ Hot Tub on 10 Acres near Delaware River, The Ipê House: Chic Catskills Cabin, 60min to Belleayre Mountain Ski

Top trending hotels in Callicoon

Villa Roma Resort and Conference Center

Villa Roma Resort and Conference Center

3 out of 5
356 Villa Roma Rd, Callicoon, NY
Fully refundableReserve now, pay when you stay
The price is AU$348 per night from 26 Nov to 27 Nov
AU$348
includes taxes & fees
26 Nov - 27 Nov
With a stay at Villa Roma Resort and Conference Center in Callicoon, you'll be 10.5 mi (16.8 km) from White Sulphur Springs Synagogue and 11.1 mi (17.9 km) from ...
Villa Roma Resort and Conference Center
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive, Monticello, NY
Fully refundableReserve now, pay when you stay
The price is AU$345 per night from 8 Dec to 9 Dec
AU$345
includes taxes & fees
8 Dec - 9 Dec
When you stay at The Kartrite Resort & Indoor Waterpark in Monticello, you'll be near ski lifts, within a 10-minute walk of Resorts World Catskills and Concord ...
The Kartrite Resort & Indoor Waterpark
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
888 Resorts World Drive, Monticello, NY
Fully refundableReserve now, pay when you stay
The price is AU$315 per night from 5 Dec to 6 Dec
AU$315
includes taxes & fees
5 Dec - 6 Dec
Located in Monticello, Resorts World Catskills Casino is a 1-minute drive from Resorts World Catskills and 10 minutes from Holiday Mountain Ski and Fun ...
Resorts World Catskills Casino
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Hampton Inn Monticello

Hampton Inn Monticello

2.5 out of 5
29 Golden Ridge Road, Monticello, NY
Fully refundableReserve now, pay when you stay
The price is AU$205 per night from 15 Dec to 16 Dec
AU$205
includes taxes & fees
15 Dec - 16 Dec
With a stay at Hampton Inn Monticello in Monticello, you'll be within a 10-minute drive of Resorts World Catskills and Monticello Casino and Raceway.
Hampton Inn Monticello
Don't see what you're looking for?
See all available properties in Callicoon
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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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^Subject to availability and chosen travel dates.