Historic New Lebanon Hideaway on 33 Private Acres! 16.2 km from Castleton-on-Hudson
Vacation Home in Canaan NY
8.0
Very Good
Info Categories
Vacation Home near Ski Resorts

4-Star Vacation Home

Show more
 
Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak 18.4 km from Castleton-on-Hudson
Vacation Home in Hancock MA
10
Excellent
Info Categories
Vacation Home near Ski Resorts

4-Star Vacation Home

Vacation Home with Parking

Show more
 
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury 19.7 km from Castleton-on-Hudson
Aparthotel in Hancock MA
8.8
Excellent
Info Categories
Aparthotel near Ski Resorts

4-Star Aparthotel

Aparthotel with Swimming Pool

Heated Pool    Indoor Pool  

Show more
 
Disney Magic at Jiminy Mountain 19.9 km from Castleton-on-Hudson
Hotel in Hancock MA
7.2
Good
Info Categories
Hotel near Ski Resorts

4-Star Hotel

Hotel with Swimming Pool

Heated Pool    Outdoor Pool  

Show more
 
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk 19.9 km from Castleton-on-Hudson
Vacation Home in Hancock MA
7.5
Good
Info Categories
Vacation Home near Ski Resorts

4-Star Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Outdoor Pool  

Show more
 
Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 19.9 km from Castleton-on-Hudson
Vacation Home in Hancock MA
9.2
Excellent
Info Categories
Vacation Home near Ski Resorts

4-Star Vacation Home

Vacation Home with Swimming Pool

Indoor Pool    Outdoor Pool  

Indoor Pool    Outdoor Pool  

Show more
 
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor 19.9 km from Castleton-on-Hudson
Apartment in Hancock MA
10
Excellent
Info Categories
Apartment near Ski Resorts

4-Star Apartment

Apartment with Swimming Pool

Outdoor Pool  

Outdoor Pool  

Show more
 
Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort 20.1 km from Castleton-on-Hudson
Vacation Home in Hancock MA
8.8
Excellent
Info Categories
Vacation Home near Ski Resorts

4-Star Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Outdoor Pool  

Show more
 
Chester by AvantStay Amazing Views Secluded Home A True City Escape 21.4 km from Castleton-on-Hudson
Vacation Home in Austerlitz NY
Info Categories
Vacation Home near Ski Resorts
4-Star Vacation Home
Vacation Home with Parking
Show more
 
Shaker Mill Inn 21.5 km from Castleton-on-Hudson
Bed & Breakfast in West Stockbridge MA
9.5
Excellent
From $163
From $163
Info Categories
Bed & Breakfast near Ski Resorts
4-Star Bed & Breakfast
Boutique-style Bed & Breakfast
Show more
 
The Springs Motel 22.4 km from Castleton-on-Hudson
Hotel in New Ashford MA
7.8
Good
Info Categories
Hotel near Ski Resorts

4-Star Hotel

Family Friendly Hotel

Show more
 
Berkshire Vacation Rentals: Chic Pittsfield Home With A View 22.4 km from Castleton-on-Hudson
Vacation Home in Pittsfield MA
9.0
Excellent
Info Categories
Vacation Home near Ski Resorts

4-Star Vacation Home

Dog Friendly Vacation Home

Show more
 
Holiday Inn & Suites Pittsfield-Berkshires by IHG 22.7 km from Castleton-on-Hudson
Hotel in Pittsfield MA
7.8
Good
From $99
From $99
Info Categories
4-Star Hotel

Hotel near Ski Resorts

Hotel near Golf Courses

Show more
 
The Guest House at Field Farm 23.0 km from Castleton-on-Hudson
Bed & Breakfast in Williamstown MA
9.4
Excellent
From $334
From $334
Info Categories
Bed & Breakfast near Ski Resorts

4-Star Bed & Breakfast

Bed & Breakfast with Parking

EV charging stations  

Show more
 
Spacious Historic Home in the Berkshires! 23.0 km from Castleton-on-Hudson
Vacation Home in Pittsfield MA
Info Categories
Vacation Home near Ski Resorts

4-Star Vacation Home

Dog Friendly Vacation Home

Show more
 
Berkshire Mountain Lodge 23.2 km from Castleton-on-Hudson
Lodge in Pittsfield MA
8.4
Very Good
From $187
From $187
Info Categories
Lodge near Ski Resorts

4-Star Lodge

Lodge with Swimming Pool

Heated Pool    Indoor Pool  

Heated Pool    Indoor Pool  

Show more
 
Berkshires Untold 23.5 km from Castleton-on-Hudson
Hotel in Lenox MA
8.5
Very Good
From $136
From $136
Info Categories
Hotel near Ski Resorts

4-Star Hotel

Family Friendly Hotel

Show more
 
Berkshire Vacation Rentals: Loft Style Cabin In West Stockbridge Book Now 23.7 km from Castleton-on-Hudson
Vacation Home in West Stockbridge MA
Info Categories
Vacation Home near Ski Resorts

4-Star Vacation Home

Dog Friendly Vacation Home

Show more
 
Brook Farm Inn 24.1 km from Castleton-on-Hudson
Bed & Breakfast in Lenox MA
9.2
Excellent
From $217
From $217
Info Categories
Bed & Breakfast near Ski Resorts

4-Star Bed & Breakfast

Accessible Bed & Breakfast

Show more
 
Restored 1881 Farm House 24.1 km from Castleton-on-Hudson
Vacation Home in Lenox MA
9.5
Excellent
Info Categories
Vacation Home near Ski Resorts

4-Star Vacation Home

Dog Friendly Vacation Home

Show more
 
*Additional taxes or fees may apply. Please check the final price before completing your booking.
Categories:
  •     Ski (27)
  •     4 Star (27)
  •     Pool (11)
  •     Dog Friendly (10)
  •     Parking (10)
  •     Outdoor Pool (8)
  •     Adult Only (7)
  •     Small (7)
  •     Accessible (6)
  •     Honeymoon (6)
  •     Heated Pool (6)
  •     Free Wi-Fi (6)
  •     Indoor Pool (4)
  •     Luxury (4)
  •     Family (3)
  •     Romantic (3)
  •     Tennis (3)
  •     Gym (2)
  •     Golf (2)
  •     EV charging stations (2)
  •     Health & Safety (1)
  •     Historic (1)
  •     Sustainability Journey (1)
  •     Business (1)
  •     Boutique-Style (1)
  •     Spa (1)
×
Checkin
×
Categories
2
Map
× Home About Press Categories Blog Hotel Awards Travelmyth GPT Contact Terms & Conditions Privacy Policy Cookies Policy FAQ