Summer and Fall in Sheffield with Monthly Special Pricing Available 5.8 km from Canaan
Vacation Home in Sheffield MA
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Outdoor Pool  

Dog Friendly Vacation Home

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The Old Inn On The Green 8.2 km from Canaan
Inn in New Marlborough MA
8.4
Very Good
From $308
From $308
Info Categories
Inn near Ski Resorts

Inn with Swimming Pool

Outdoor Pool  

Inn with Rooms With Fireplace

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Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool! 11.9 km from Canaan
Luxury Tent in Great Barrington MA
8.8
Excellent
Info Categories
Luxury Tent near Ski Resorts

Luxury Tent with Swimming Pool

Outdoor Pool  

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Travelodge by Wyndham Great Barrington Berkshires 13.6 km from Canaan
Motel in Great Barrington MA
6.9
Rated
From $69
From $69
Info Categories
Motel near Ski Resorts

Motel with Swimming Pool

Outdoor Pool  

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Swiss Hütte Inn and Restaurant 13.9 km from Canaan
Inn in Hillsdale NY
8.5
Very Good
Info Categories
Inn near Ski Resorts

Inn with Swimming Pool

Outdoor Pool  

Dog Friendly Inn

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Thornewood Inn 14.3 km from Canaan
Inn in Great Barrington MA
8.1
Very Good
From $280
From $280
Info Categories
Inn near Ski Resorts

Inn with Swimming Pool

Outdoor Pool  

Dog Friendly Inn

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Cornwall Inn and Lodge 16.2 km from Canaan
Inn in Cornwall Bridge CT
Info Categories
Inn near Ski Resorts

Inn with Swimming Pool

Outdoor Pool  

Dog Friendly Inn

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Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires an IHG Hotel 17.8 km from Canaan
Hotel in South Lee MA
8.4
Very Good
From $124
From $124
Info Categories
Hotel near Ski Resorts

Hotel with Swimming Pool

Heated Pool    Indoor Pool    Outdoor Pool  

Hotel for Honeymoon

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Experience Leisure - Resort Condos in the Berkshire Hills 17.8 km from Canaan
Apartments in South Lee MA
Info Categories
Apartment near Ski Resorts

Apartment with Swimming Pool

Indoor Pool    Outdoor Pool  

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The Red Lion Inn 18.3 km from Canaan
Hotel in Stockbridge MA
8.0
Very Good
From $156
From $156
Info Categories
Hotel near Ski Resorts

Hotel with Swimming Pool

Outdoor Pool  

Historic Hotel

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Stockbridge Country Inn 18.4 km from Canaan
Bed & Breakfast in Stockbridge MA
9.4
Excellent
From $336
From $336
Info Categories
Bed & Breakfast near Ski Resorts

Bed & Breakfast with Swimming Pool

Outdoor Pool  

Bed & Breakfast for Adults Only

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Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Parking

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Conroy's B&B 19.5 km from Canaan
Bed & Breakfast in Stockbridge MA
8.7
Very Good
From $57
From $57
Info Categories
Bed & Breakfast near Ski Resorts

Bed & Breakfast with Swimming Pool

Outdoor Pool  

Bed & Breakfast with Free Wi-Fi

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Devonfield Inn 19.7 km from Canaan
Bed & Breakfast in Lee MA
9.2
Excellent
From $311
From $311
Info Categories
Bed & Breakfast near Ski Resorts

Bed & Breakfast with Swimming Pool

Heated Pool    Outdoor Pool  

Bed & Breakfast with Rooms With Fireplace

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American Inn Lee 20.8 km from Canaan
Hotel in Lee MA
7.7
Good
Info Categories
Hotel near Ski Resorts

Hotel with Swimming Pool

Outdoor Pool  

Hotel with Free Wi-Fi

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The Ponds at Foxhollow by Capital Vacations 21.2 km from Canaan
Resort in Lenox MA
8.2
Very Good
From $169
From $169
Info Categories
Resort near Ski Resorts

Resort with Swimming Pool

Indoor Pool    Outdoor Pool  

Luxury Resort

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Country Lake House Nestled Between Vineyards 21.5 km from Canaan
Vacation Home in Warren CT
9.3
Excellent
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Outdoor Pool  

Dog Friendly Vacation Home

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Seven Hills Inn 22.0 km from Canaan
Inn in Lenox MA
7.2
Good
From $166
From $166
Info Categories
Inn near Ski Resorts

Inn with Swimming Pool

Heated Pool    Outdoor Pool  

Luxury Inn

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Wheatleigh 22.4 km from Canaan
Hotel in Lenox MA
9.2
Excellent
From $912
From $912
Info Categories
Hotel near Ski Resorts

Hotel with Swimming Pool

Heated Pool    Outdoor Pool  

Dog Friendly Hotel

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Walk to Tnglewd, Stckbrdg Bwl, Wheatleigh, HTd Pool, Hot Tub 22.6 km from Canaan
Vacation Home in Lenox MA
8.8
Excellent
From $612
From $612
Info Categories
Vacation Home near Ski Resorts

Vacation Home with Swimming Pool

Heated Pool    Outdoor Pool  

Luxury Vacation Home

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*Additional taxes or fees may apply. Please check the final price before completing your booking.
Categories:
  •     Ski (26)
  •     Outdoor Pool (26)
  •     Pool (26)
  •     Heated Pool (9)
  •     Indoor Pool (4)
  •     Parking (13)
  •     Dog Friendly (12)
  •     Luxury (10)
  •     Small (9)
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  •     Free Wi-Fi (7)
  •     Tennis (6)
  •     Accessible (5)
  •     Honeymoon (5)
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  •     Rooms with Fireplace (4)
  •     Romantic (3)
  •     3 Star (3)
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  •     5 Star (1)
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  •     Sustainability Journey (1)
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