The Best Airbnb Deals in
Sheffield, Massachusetts

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Sheffield, Massachusetts. Enter your travel dates to find the best deals!

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AirDNA Score: 77
$250/night

The Brook House at Race Brook Lodge

1 bed
1 bath
5 guests
Average Price:  
$269
7% Cheaper
than normal
AirDNA Score: 77
$173/night

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

2 beds
1 bath
4 guests
Average Price:  
$236
27% Cheaper
than normal
AirDNA Score: 74
$299/night

House Among Trees - A Perfect Getaway

3 beds
2 baths
6 guests
Average Price:  
$344
13% Cheaper
than normal
AirDNA Score: 73
$275/night

20 min to Butternut; Little House in the Woods

2 beds
2 baths
6 guests
Average Price:  
$307
10% Cheaper
than normal
AirDNA Score: 66
$675/night

Gorgeous Sheffield Home

5 beds
3.5 baths
15 guests
Average Price:  
$774
13% Cheaper
than normal
AirDNA Score: 64
$299/night

Large Cabin in Berkshires near GB & superb hiking

4 beds
3 baths
10 guests
Average Price:  
$451
34% Cheaper
than normal
AirDNA Score: 63
$425/night

Race Mountain House

4 beds
3 baths
15 guests
Average Price:  
$621
32% Cheaper
than normal
AirDNA Score: 63
$250/night

Lovely 3-Bedroom Berkshire Retreat

3 beds
2.5 baths
6 guests
Average Price:  
$149
68% More
than normal
AirDNA Score: 62
$375/night

Belle Meade

2 beds
2 baths
4 guests
Average Price:  
$404
7% Cheaper
than normal
AirDNA Score: 60
$650/night

Amazing Loft

3 beds
3 baths
6 guests
Average Price:  
$737
12% Cheaper
than normal
AirDNA Score: 53
$325/night

Serene Berkshire Artist''s House

3 beds
2.5 baths
6 guests
Average Price:  
$396
18% Cheaper
than normal
AirDNA Score: 53
$400/night

Gordon Place

3 beds
3 baths
9 guests
Average Price:  
$429
7% Cheaper
than normal
AirDNA Score: 51
$250/night

“Elterwater”—the house on the lake

2 beds
2 baths
4 guests
Average Price:  
$284
12% Cheaper
than normal
AirDNA Score: 51
$525/night

Elegant Berkshire All Season Home

3 beds
2.5 baths
6 guests
Average Price:  
$596
12% Cheaper
than normal
AirDNA Score: 36
$650/night

88 Acres of Charm - Berkshire Home w/ Tennis Court

4 beds
3 baths
8 guests
Average Price:  
$766
15% Cheaper
than normal