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Perfectly curated homes for groups of 12 or more

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16 Properties

Kaaterskill Mountain House

5
Beautiful 5 Bedroom Home on 287 Acres with Hiking Trails, Fire Pit & Panoramic Views
Starting at $400 / night
Hunter
House
12
5
3.5
Catamount Mountain: 17.5 miNew

Taghkanic House

5
Scandinavian-Inspired Escape w/ Breathtaking Catskill Mountain Views
Starting at $683 / night
Hudson Valley
House
10
5
3.5
Catamount Mountain: 9.0 miNew

Graybarn at Copake Lake

Restored Barn with Award Winning Design Infinity Edge Pool + Hot Tub Near to Copake Lake
Starting at $800 / night
Berkshires / Hudson / Hudson Valley
House
10
5
4
New

Lotus Lodge

Chic Cabin w/ Heated Pool & Hot Tub Overlooking Stunning Views + Sauna, Gym and Fun Amenities
Starting at $800 / night
Narrowsburg / Southern Catskills
House
16
5
6

Fernbrook

Stylish & Modern Getaway w/ Private Home Gym near Great Barrington
Starting at $1,000 / night
Berkshires / Great Barrington
House
10
5
4.5
Butternut Mountain: 9.4 mi

Crossbridge – Full Property (House + Apartment)

5
Charming Rustic Farm House in the Berkshires
Starting at $750 / night
Berkshires / Great Barrington
House
11
6
7
Catamount Mountain: 17.5 mi

Doodletown Lodge & Cabin

5
100 Acre Estate with 2 Dwellings, Pool, Swimmable Pond, Pickleball, Tennis, Entertainment Barn and more!
Starting at $1,500 / night
Berkshires / Hudson / Hudson Valley / Pine Plains / Rhinebeck
House
21
9
7.5
Catamount Mountain: 17.5 mi

Doodletown Lodge

5
Impressive Home with Large Pool, Tennis, Pickleball, Hiking and more!
Starting at $1,000 / night
Berkshires / Pine Plains / Rhinebeck
House
12
5
4.5
30 nights minimumBelleayre Moutnain: 20.1 mi

Abbey Road Farmhouse

Grand Pool Retreat (Sleeps 14!)
Starting at $233 / night
Woodstock
House
14
7
5.5

The Library Retreat

4.9
Three Building Estate: Farmhouse, Guesthouse & Loft with Heated Pool & Views (Sleeps 12!)
Starting at $800 / night
Hudson Valley / Rhinebeck
House
12
7
5.5

Sunflower Farmhouse

5
Beautifully Renovated Farmhouse with Firepit (Sleeps 12!)
Starting at $300 / night
Hudson
House
12
6
4
Catamount Mountain: 9.6 mi

Olive Pit

4.9
Contemporary, Secluded Home with Private Pool (Sleeps 12!)
Starting at $527 / night
Hudson / Hudson Valley
House
12
5
3

Clementine Creekhouse

5
Treetop Views in Callicoon
Starting at $447 / night
Callicoon / Southern Catskills
Cabin
14
6
3.5

The Gables

5
Redesigned and Renovated May 2025! Spacious, Family & Pet-Friendly Home in Callicoon (Sleeps 17!)
Starting at $700 / night
Callicoon / Southern Catskills
House
17
8
2.5

The Homestead

5
Grand Lakefront Estate with Stunning Views by Bethel (Sleeps 28!)
Starting at $1,500 / night
Callicoon / Southern Catskills
House
28
14
10

The Homestead (House only)

5
Grand Lakefront Estate with Stunning Views by Bethel (Sleeps 22!)
Starting at $1,000 / night
Callicoon / Southern Catskills
House
22
11
8.5