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Sheffield Vacation Rentals

Find 58 available offers from 6 partners
Sheffield
Anytime
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Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Farmhouse
Bed & Breakfast
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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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Save up to 42%

Best Vacation Home Deals in Sheffield

House Sheffield
Apr 7 - Apr 14
-42%
$457
$264 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Sheffield with Yard + Undisturbed View
5.0
"Excellent" (2 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Apr 8 - Apr 15
-40%
$897
$537 per night
House ∙ 9 guests ∙ 4 bedrooms
Modern House in Sheffield with Yard & Grill + Mountain Views
4.8
"Excellent" (16 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Apr 8 - Apr 15
-22%
$461
$360 per night
House ∙ 5 guests ∙ 3 bedrooms
Vacation Home in Sheffield with Yard & Grill
4.0
"Very good" (2 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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Find a vacation rental fitting your expectations among the 58 welcoming options from more than 6 providers in Sheffield. HomeToGo instantly compares all of these properties to help you save up to 51%!

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Top-Rated Rentals and Accommodations in Sheffield

House Sheffield
Nov 11 - Nov 18
$384 per night
House ∙ 12 guests ∙ 4 bedrooms
Vacation Home in Sheffield with Yard & Grill
5.0
"Excellent" (22 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Apr 15 - Apr 22
-48%
$405
$212 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Sheffield with Botanical Garden + Pond Views
4.7
"Outstanding" (6 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Nov 4 - Nov 11
$197 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Sheffield with Yard & Grill
5.0
"Excellent" (4 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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Recommended Vacation Rentals in Sheffield

Find your perfect vacation rental in Sheffield: from $91 per night

House Sheffield
Jul 29 - Aug 5
$254 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Sheffield with Grill & Sauna
5.0
"Excellent" (19 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Apr 7 - Apr 14
-48%
$498
$258 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Sheffield with Yard + Undisturbed View
5.0
"Excellent" (2 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
May 13 - May 20
$648 per night
House ∙ 16 guests ∙ 4 bedrooms
Unique House in Sheffield with Yard & Grill + Pastoral View
4.9
"Excellent" (58 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Nov 11 - Nov 18
$409 per night
House ∙ 10 guests ∙ 4 bedrooms
Family Friendly Private Vacation Home in Sheffield with Botanical Garden
5.0
"Excellent" (59 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Mar 25 - Apr 1
-50%
$809
$536 per night
House ∙ 9 guests ∙ 4 bedrooms
Modern House in Sheffield with Yard & Grill + Mountain Views
4.8
"Excellent" (16 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Apr 1 - Apr 8
-39%
$596
$399 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Sheffield with Grill & Pool
5.0
"Excellent" (6 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Aug 19 - Aug 26
$188 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Sheffield with Grill
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Mar 16 - Mar 23
$809 per night
House ∙ 14 guests ∙ 5 bedrooms
Vacation Home in Great Barrington with Private Parking
5.0
"Excellent" (45 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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Chalet Sheffield
Apr 8 - Apr 15
$184 per night
Chalet ∙ 6 guests ∙ 2 bedrooms
Chalet in Monterey with Botanical Garden
5.0
"Excellent" (107 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Sheffield

House Sheffield
Apr 1 - Apr 8
$267 per night
House ∙ 4 guests ∙ 2 bedrooms
Whole Vacation Home in Sheffield with Botanical Garden
4.9
"Excellent" (168 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Mar 16 - Mar 23
-18%
$364
$299 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Sheffield with Grill & Yard
5.0
"Excellent" (119 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Dec 16 - Dec 23
-26%
$209
$156 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Sheffield with Yard & Grill
5.0
"Excellent" (13 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Sheffield!

House Pet-friendly Sheffield
Nov 11 - Nov 18
$284 per night
House ∙ 4 guests ∙ 2 bedrooms
Whole Vacation Home in Sheffield with Botanical Garden
4.9
"Excellent" (168 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Pet-friendly
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House Pet-friendly Sheffield
Mar 16 - Mar 23
-18%
$365
$300 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Sheffield with Grill & Yard
5.0
"Excellent" (120 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Pet-friendly
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House Pet-friendly Sheffield
Dec 16 - Dec 23
-26%
$210
$156 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Sheffield with Yard & Grill
5.0
"Excellent" (13 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Pet-friendly
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Apartments With Balconies or Patios

Looking for a home with a balcony? Check out these vacation homes in Sheffield with their own private patios and balconies.

House Balcony/Patio Sheffield
Nov 11 - Nov 18
$386 per night
House ∙ 12 guests ∙ 4 bedrooms
Vacation Home in Sheffield with Yard & Grill
5.0
"Excellent" (22 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony/Patio
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House Balcony/Patio Sheffield
May 6 - May 13
-44%
$401
$223 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Sheffield with Botanical Garden + Pond Views
4.7
"Outstanding" (6 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony/Patio
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House Balcony/Patio Sheffield
Nov 4 - Nov 11
$198 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Sheffield with Yard & Grill
5.0
"Excellent" (4 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony/Patio
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Vacation Homes With Fishing Spots Nearby

Hoping to catch a few fish on your next vacation? Check out these amazing rentals in Sheffield with fishing spots nearby.

House Fishing Sheffield
Nov 11 - Nov 18
$265 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Great Barrington with Botanical Garden
4.9
"Excellent" (85 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Fishing
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Cottage Fishing Sheffield
Apr 15 - Apr 22
-34%
$925
$611 per night
Cottage ∙ 8 guests ∙ 3 bedrooms
Cottage in Copake Lake with Grill & Yard + Spectacular Views
5.0
"Excellent" (79 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Fishing
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Apartment Fishing Sheffield
Sep 23 - Sep 30
$175 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Housatonic with Botanical Garden + Spectacular View
5.0
"Excellent" (43 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Fishing
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Popular Rental Amenities in Sheffield

  • Kitchen (48)
  • Internet (47)
  • TV (44)
  • Dishwasher (41)
  • Washer (40)
  • Microwave (40)
  • Fireplace (37)
  • No smoking (37)
  • Grill (34)
  • Air conditioning (33)
  • Yard (29)
  • No pets (24)

Choose a filter above to find an accommodation fitting your needs among the 58 properties in Sheffield. HomeToGo's data reveals that "Kitchen" and "Internet" prove to be the most commonly provided features in Sheffield. Three features that are not often provided are "Balcony/Patio," "Sauna," and "Fenced."

The Weather in Sheffield

max.
Min.
32°
16°
17 days 17
max.
Min.
34°
16°
18 days 18
max.
Min.
41°
23°
16 days 16
max.
Min.
55°
34°
15 days 15
max.
Min.
68°
46°
14 days 14
max.
Min.
75°
54°
14 days 14
max.
Min.
81°
59°
14 days 14
max.
Min.
77°
55°
12 days 12
max.
Min.
72°
48°
11 days 11
max.
Min.
59°
39°
16 days 16
max.
Min.
46°
28°
14 days 14
max.
Min.
37°
25°
20 days 20
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 16° low. The rainiest month is December while the driest month is September.

7-Day Weather Forecast in Sheffield

Sun, 26 Mar
50°
37°

15%

5 h

9 mi/h

Mon, 27 Mar
50°
33°

15%

3 h

4 mi/h

Tue, 28 Mar
44°
30°

15%

1 h

6 mi/h

Wed, 29 Mar
48°
33°

10%

5 h

5 mi/h

Thu, 30 Mar
37°
26°

15%

7 h

10 mi/h

Fri, 31 Mar
35°
32°

15%

0 h

4 mi/h

Sat, 1 Apr
48°
32°

15%

0 h

11 mi/h

Accommodations for your vacation in Sheffield

In Sheffield, nearly all of the 58 vacation accommodations are house rental, which represent 92.31% of its available properties. In addition, the average size of house rental in Sheffield is 259 m² with a median price of $610 per night. Moreover, house rental 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 bed & breakfast, which are the other most frequent property type in Sheffield. The average size of bed & breakfast in Sheffield is 77 m², and the average price is $256 a night.
What are the best places to discover the arts and culture of Sheffield?

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.

Where are the unique attractions in Sheffield?

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.

Information about vacation rentals in Sheffield

🏡 Vacation rentals 58 properties
💳 Possible discounts up to 51%
🌙 Nightly prices starting at $91
⭐ Popular amenities Kitchen, Internet and TV
🐾 Pet friendly accommodations 19 properties
🏊 Vacation rentals with pools 7 properties

Frequently Asked Questions

What is the average price per night for a vacation rental in Sheffield?

The nightly price of accommodations in Sheffield starts at $91. If you would like to stay in a house rental, the average price is $610 per night. A bed & breakfast Sheffield will cost $256 per night on average.

How many vacation homes are available for booking in Sheffield?

There are 58 rentals available for booking for your vacation.

What amenities are most popular for vacation homes in Sheffield?

The most popular amenities for vacation home rentals in Sheffield include accommodations with: Kitchen, Internet, and TV.

How many vacation homes with pools are in Sheffield?

There are 7 vacation rentals across 6 providers in Sheffield.

Are dogs allowed in vacation rentals in Sheffield?

Yes, there are 19 vacation homes in Sheffield that allow dogs , with an average nightly price of $630.

When is it better to travel to Sheffield?

When choosing a vacation rental in Sheffield, keep in mind that rainy season is typically in December or February, with September often being the driest.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals in Sheffield TripAdvisor Vacation Rentals in Sheffield Vrbo Vacation Rentals in Sheffield VacationRentals.com Vacation Rentals in Sheffield HouseTrip Vacation Rentals in Sheffield FlipKey Vacation Rentals in Sheffield Homestay.com Vacation Rentals in Sheffield Only-apartments Vacation Rentals in Sheffield Interhome Vacation Rentals in Sheffield Novasol Vacation Rentals in Sheffield HomeEscape Vacation Rentals in Sheffield

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