Sheffield Vacation Rentals

Compare 247 available properties from 17 providers
Sheffield

Find a vacation rental fitting your expectations among the 247 welcoming options from more than 17 providers in Sheffield. HomeToGo instantly compares all of these properties to help you save up to 10%!

Recommended Vacation Rentals in Sheffield

Rent a vacation accommodation in Sheffield: from $72 per night

House ∙ 6 guests ∙ 3 bedrooms
Sheffield, Berkshire County, Massachusetts, United States
from $186
VRBO
4.9
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Apartment ∙ 2 guests ∙ 1 bedroom
New Marlborough, Berkshire County, Massachusetts, United States
from $94
VRBO
4.4
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House ∙ 9 guests ∙ 3 bedrooms
Sheffield, Berkshire County, Massachusetts, United States
from $456
VRBO
5.0
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House ∙ 9 guests ∙ 3 bedrooms
Sheffield, Berkshire County, Massachusetts, United States
from $230
VRBO
5.0
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House ∙ 8 guests ∙ 3 bedrooms
South Egremont, Berkshire County, Massachusetts, United States
from $168
VRBO
4.8
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House ∙ 12 guests ∙ 6 bedrooms
Sheffield, Berkshire County, Massachusetts, United States
from $749
VRBO
5.0
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House ∙ 5 guests ∙ 3 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $237
VRBO
4.7
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House ∙ 4 guests ∙ 3 bedrooms
South Egremont, Berkshire County, Massachusetts, United States
from $261
VRBO
4.9
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House ∙ 2 guests ∙ 1 bedroom
New Marlborough, Berkshire County, Massachusetts, United States
from $110
VRBO
4.0
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 4 guests ∙ 3 bedrooms
Sheffield, Berkshire County, Massachusetts, United States
from $230
VRBO
5.0
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Fishing
House ∙ 6 guests ∙ 3 bedrooms
Sheffield, Berkshire County, Massachusetts, United States
from $183
VRBO
4.8
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Fishing
House ∙ 7 guests ∙ 3 bedrooms
Sheffield, Berkshire County, Massachusetts, United States
from $183
VRBO
5.0
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Vacation Rentals With Fireplaces

Fireplace
House ∙ 8 guests ∙ 3 bedrooms
Sheffield, Berkshire County, Massachusetts, United States
from $218
VRBO
5.0
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Fireplace
House ∙ 8 guests ∙ 3 bedrooms
Sheffield, Berkshire County, Massachusetts, United States
from $235
VRBO
5.0
View deal
Fireplace
House ∙ 4 guests ∙ 2 bedrooms
South Egremont, Berkshire County, Massachusetts, United States
from $193
VRBO
5.0
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Dog-Friendly Vacation Rentals

Pet-friendly
House ∙ 7 guests ∙ 4 bedrooms
Egremont, Berkshire County, Massachusetts, United States
from $319
VRBO
5.0
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Pet-friendly
House ∙ 4 guests ∙ 2 bedrooms
Salisbury, Litchfield County, Connecticut, United States
from $256
VRBO
4.4
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Pet-friendly
House ∙ 6 guests ∙ 3 bedrooms
Taconic, Salisbury, Connecticut, United States
from $125
VRBO
4.9
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Popular Rental Amenities in Sheffield

  • No smoking (218)
  • Internet (216)
  • Kitchen (212)
  • Parking (203)
  • TV (202)
  • Microwave (184)
  • Grill (183)
  • Washer (176)
  • AC (166)
  • Dishwasher (157)
  • Yard (149)
  • Fishing (142)
Choose a filter above to find an accommodation fitting your needs among the 247 properties in Sheffield. HomeToGo's data reveals that "internet" and "TVs" prove to be the most commonly provided features in Sheffield. Three features that are not often provided are "saunas," "Jacuzzis," and "pools."

Price and Availability Index in Sheffield

Vacation Rental Price Information in Sheffield

We rendered price information data on the above graph to give you more insights on prices in Sheffield. Prices rise in July and reach an average of $325 a night (7/20 - 7/27), making it the most expensive time to book a rental in the next 12 months. Opt for a getaway in February (2/2 - 2/9) for optimal savings when heading to Sheffield.

Rental Availability Information in Sheffield

The availability graph shows the percentage of available rentals in Sheffield. In December (12/22 - 12/29), only 67 are available. On the other hand, the week with the most available offers is in March (3/30 - 4/6).

The Weather in Sheffield

32°
16°
34°
16°
41°
23°
55°
34°
68°
46°
75°
54°
81°
59°
77°
55°
72°
48°
59°
39°
46°
28°
37°
25°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

The above is a climate diagram for Sheffield. The highest average temperatures are in the month of July. No heat wave is expected in January, where minimum average temperatures usally hit a 15° low. The rainiest month is July while the driest month is September.

Accommodations in Sheffield

In Sheffield, two-thirds of the 247 vacation accommodations are house rentals, which represent 72.35% of its available properties. In addition, the average size of house rentals in Sheffield is 2,220 ft² with a median price of $507 per night. Moreover, house rentals are perfect for large groups, as most can welcome 8 guests. If you would prefer to compare a different accommodation type, you may want to check out hotel rooms, which are the other most frequent property type in Sheffield. The average size of hotel rooms in Sheffield is 320 ft², and the average price is $188 a night.

Sheffield vacation rentals are all about the great outdoors

Your vacation rental offers you all the delights of the sophisticated small town of Sheffield, Massachusetts, which is in equal parts laid back and intensely cultural. With a clutch of superb museums and a charming farmer's market every Saturday morning, the town is also known for its antiques.

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Art & Culture

Antiques and artworks

The town of Sheffield is well known for its antiques. From the 18th and 19th century antiques at Susan Silver Antiques to the American furniture at Samuel Herrup Antiques, the town is a cave of wonders. Toulouse Lautrec lithographs jostle rocking chairs.

Local Attractions

Go wild in Massachussetts

Why not come and hole up in Sheffield during the winter for snowshoeing trips? This remarkable town borders some of the most attractive state parks in America. Beartown State Forest for instance is a dream destination for cross country skiers in the wintertime. During summer, the local lakes are the perfect place for tranquil fishing and boating trips, while the Appalachian Trail unfolds for 90 glorious miles through the wilderness.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Sheffield VRBO Vacation Rentals in Sheffield HomeAway Vacation Rentals in Sheffield TripAdvisor Vacation Rentals in Sheffield VacationRentals.com Vacation Rentals in Sheffield HouseTrip Vacation Rentals in Sheffield FlipKey Vacation Rentals in Sheffield 9flats.com Vacation Rentals in Sheffield VaycayHero Vacation Rentals in Sheffield PerfectPlaces.com Vacation Rentals in Sheffield Homestay.com Vacation Rentals in Sheffield Only-apartments Vacation Rentals in Sheffield Interhome Vacation Rentals in Sheffield Bedycasa Vacation Rentals in Sheffield Novasol Vacation Rentals in Sheffield HomeEscape Vacation Rentals in Sheffield

Vacation Destinations Near Sheffield