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: 86
$150/night

Hideaway with Spectacular Berkshire Views

1 bed
1 bath
2 guests
Average Price:  
$165
9% Cheaper
than normal
AirDNA Score: 77
$250/night

The Brook House at Race Brook Lodge

1 bed
1 bath
5 guests
Average Price:  
$268
7% Cheaper
than normal
AirDNA Score: 66
$130/night

Wow! Best BERKSHIRE SnowHome #2 Private SuperClean

1 bed
1 bath
2 guests
Average Price:  
$176
26% Cheaper
than normal
AirDNA Score: 66
$675/night

Gorgeous Sheffield Home

5 beds
3.5 baths
15 guests
Average Price:  
$683
1% Cheaper
than normal
AirDNA Score: 64
$349/night

Large Log Cabin in the Southern Berkshires near GB

4 beds
3 baths
10 guests
Average Price:  
$468
25% 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
$300/night

Belle Meade

2 beds
2 baths
4 guests
Average Price:  
$387
22% Cheaper
than normal
AirDNA Score: 60
$650/night

Amazing Loft

3 beds
3 baths
6 guests
Average Price:  
$779
17% Cheaper
than normal
AirDNA Score: 59
$130/night

Quiet and peaceful Garage studio Apartment

1 bed
1 bath
2 guests
Average Price:  
$170
24% Cheaper
than normal
AirDNA Score: 53
$325/night

Serene Berkshire Artist''s House

3 beds
2.5 baths
6 guests
Average Price:  
$364
11% Cheaper
than normal
AirDNA Score: 51
$250/night

“Elterwater”—the house on the lake

2 beds
2 baths
4 guests
Average Price:  
$281
11% Cheaper
than normal
AirDNA Score: 51
$525/night

Elegant Berkshire All Season Vacation Home

3 beds
2.5 baths
6 guests
Average Price:  
$570
8% Cheaper
than normal
AirDNA Score: 36
$750/night

Berkshire Home with a View/Close to Skiing

4 beds
3 baths
9 guests
Average Price:  
$775
3% Cheaper
than normal