Spacious 6 BR Private Berkshires Retreat
Vacation Home in Sheffield MA
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Family Friendly Vacation Home

Show more
 
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home near Ski Resorts

Show more
 
27 more hotels nearby!
The Old Inn On The Green 5.4 mi from Sheffield
Inn in New Marlborough MA
8.4
Very Good
From $308
From $308
Info Categories
Dog Friendly Inn

Inn with Swimming Pool

Outdoor Pool  

Inn with Rooms With Fireplace

Show more
 
Blackberry River Inn 8.2 mi from Sheffield
Bed & Breakfast in Norfolk CT
8.6
Very Good
From $198
From $198
Info Categories
Dog Friendly Bed & Breakfast

Bed & Breakfast with Swimming Pool

Outdoor Pool  

Bed & Breakfast with Free Wi-Fi

Show more
 
Thornewood Inn 8.3 mi from Sheffield
Inn in Great Barrington MA
8.1
Very Good
From $280
From $280
Info Categories
Dog Friendly Inn

Inn with Swimming Pool

Outdoor Pool  

Inn near Ski Resorts

Show more
 
Berkshire Vacation Rentals: Mountain View Estate Sleeps 18 8.7 mi from Sheffield
Vacation Home in North Egremont MA
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

Show more
 
Swiss Hütte Inn and Restaurant 8.9 mi from Sheffield
Inn in Hillsdale NY
8.5
Very Good
Info Categories
Dog Friendly Inn

Inn with Swimming Pool

Outdoor Pool  

Inn near Ski Resorts

Show more
 
Sunset 9.3 mi from Sheffield
Vacation Home in Copake Falls NY
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Vacation Home with Free Wi-Fi

Show more
 
Berkshire Vacation Rentals: Private Estate Heated YEARROUND Outdoor Pool 9.3 mi from Sheffield
Vacation Home in North Egremont MA
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

Show more
 
The Red Lion Inn 12.4 mi from Sheffield
Hotel in Stockbridge MA
8.0
Very Good
From $156
From $156
Info Categories
Hotel with Swimming Pool

Outdoor Pool  

Dog Friendly Hotel

Historic Hotel

Show more
 
Country Charmer 12.9 mi from Sheffield
Vacation Home in Lee MA
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

Show more
 
The Inn at Stockbridge 13.9 mi from Sheffield
Bed & Breakfast in Stockbridge MA
10
Excellent
From $330
From $330
Info Categories
Dog Friendly Bed & Breakfast

Bed & Breakfast with Swimming Pool

Luxury Bed & Breakfast

Show more
 
Seven Hills Inn 16.3 mi from Sheffield
Inn in Lenox MA
7.2
Good
From $166
From $166
Info Categories
Dog Friendly Inn

Inn with Swimming Pool

Heated Pool    Outdoor Pool  

Luxury Inn

Show more
 
Wheatleigh 16.5 mi from Sheffield
Hotel in Lenox MA
9.2
Excellent
From $912
From $912
Info Categories
Dog Friendly Hotel

Hotel with Swimming Pool

Heated Pool    Outdoor Pool  

Hotel with Parking

EV charging stations  

Show more
 
Walk to Tnglewd, Stckbrdg Bwl, Wheatleigh, HTd Pool, Hot Tub 16.7 mi from Sheffield
Vacation Home in Lenox MA
8.8
Excellent
From $612
From $612
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Heated Pool    Outdoor Pool  

Luxury Vacation Home

Show more
 
Waterfalls and Trails at The Mills At Green Hole 17.6 mi from Sheffield
Vacation Home in Hillsdale NY
10
Excellent
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Show more
 
Berkshire Travel Lodge 17.9 mi from Sheffield
Motel in Canaan NY
4.7
Rated
From $70
From $70
Info Categories
Dog Friendly Motel

Motel with Swimming Pool

Outdoor Pool  

Motel near Ski Resorts

Show more
 
Clatter Hall 18.8 mi from Sheffield
Vacation Home in Spencertown NY
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home near Ski Resorts

Show more
 
White Pines Campsites - A Cruise Inn Park 18.9 mi from Sheffield
Campground in Winsted CT
Info Categories
Dog Friendly Campground

Campground with Swimming Pool

Campground near Ski Resorts

Show more
 
Berkshire Vacation Rentals: Private Oasis: 16 Acres Pool 20.2 mi from Sheffield
Vacation Home in Chatham NY
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

Show more
 
*Additional taxes or fees may apply. Please check the final price before completing your booking.
Categories:
  •     Pool (29)
  •     Dog Friendly (29)
  •     Outdoor Pool (20)
  •     Heated Pool (5)
  •     Indoor Pool (4)
  •     Parking (19)
  •     Ski (16)
  •     Free Wi-Fi (14)
  •     Accessible (7)
  •     Small (7)
  •     Luxury (7)
  •     Gym (7)
  •     3 Star (7)
  •     4 Star (6)
  •     Business (5)
  •     Honeymoon (5)
  •     Family (5)
  •     Romantic (3)
  •     Spa (2)
  •     Sustainability Journey (2)
  •     Golf (2)
  •     Rooms with Fireplace (2)
  •     5 Star (1)
  •     EV charging stations (1)
  •     Rooms with Jacuzzi / Hot-Tub (1)
  •     Historic (1)
  •     Boutique-Style (1)
  •     Haunted (1)
  •     Tennis (1)
×
Checkin
×
Categories
2
Map
× Home About Press Categories Blog Hotel Awards Travelmyth GPT Contact Terms & Conditions Privacy Policy Cookies Policy FAQ