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Sheffield Vacation Rentals

Find 42 available offers from 6 partners
Sheffield
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
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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Best Vacation Home Deals in Sheffield

Save up to 58%

House Sheffield
Oct 28 - Nov 4
-58%
$500
$211 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Sheffield + Pond Views
4.7
Excellent (13 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
Vrbo
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Cottage Sheffield
Jun 7 - Jun 14
-32%
$227
$155 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Ashley Falls with Yard & Grill
4.7
Excellent (14 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
Vrbo
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Cottage Sheffield
Oct 28 - Nov 4
-58%
$612
$257 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
Cottage in Sheffield
Sheffield, Berkshire County, Massachusetts, United States
Details
HomeToGo
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Find a vacation rental fitting your expectations among the 42 welcoming options from more than 6 providers in Sheffield. HomeToGo instantly compares all of these properties to help you save up to 56%!

Top-Rated Rentals and Accommodations in Sheffield

Book Vacation Rental Offers with the Highest User Rating

House Sheffield
Mar 16 - Mar 23
$283 per night
House ∙ 4 guests ∙ 2 bedrooms
Whole Vacation Home in Sheffield with Botanical Garden
4.9
Outstanding (166 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
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House Sheffield
Jul 21 - Jul 28
$528 per night
House ∙ 16 guests ∙ 4 bedrooms
Unique House in Sheffield with Yard & Grill
4.9
Outstanding (58 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
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House Sheffield
Sep 7 - Sep 14
-39%
$256
$156 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Sheffield with Yard & Grill
4.9
Outstanding (26 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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Recommended Vacation Rentals in Sheffield

Find your perfect vacation rental in Sheffield: from $92 per night

House Sheffield
Dec 23 - Dec 30
$188 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Sheffield with Grill
Sheffield, Berkshire County, Massachusetts, United States
Details
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House Sheffield
Jun 7 - Jun 14
$224 per night
House ∙ 6 guests ∙ 2 bedrooms
House in Sheffield with Yard & Grill + Gorgeous Views
4.9
Outstanding (42 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Jan 13 - Jan 20
$255 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Sheffield with Grill & Sauna
5.0
Outstanding (22 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
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House Sheffield
Dec 9 - Dec 16
$189 per night
House ∙ 5 guests ∙ 2 bedrooms
Vacation Home in Ashley Falls with Grill & Yard
5.0
Outstanding (5 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
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House Sheffield
Nov 11 - Nov 18
$289 per night
House ∙ 4 guests ∙ 3 bedrooms
House in Sheffield with Yard & Grill + Scenic Views
5.0
Outstanding (4 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
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House Sheffield
Nov 4 - Nov 11
$386 per night
House ∙ 12 guests ∙ 4 bedrooms
Vacation Home in Sheffield with Yard & Grill
5.0
Outstanding (25 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
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House Sheffield
Oct 28 - Nov 4
-64%
$540
$195 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Sheffield with Wood-Burning Fireplace + Pond Views
Sheffield, Berkshire County, Massachusetts, United States
Free cancellation
Details
Evolve
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House Sheffield
Dec 9 - Dec 16
$198 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Sheffield with Yard & Grill
5.0
Outstanding (4 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
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House Sheffield
Oct 20 - Oct 27
$500 per night
House ∙ 8 guests ∙ 4 bedrooms
Lovely Vacation Home in Ashley Falls with Front Garden + Mountain Views
5.0
Outstanding (4 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
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Budget-friendly Vacation Rentals in Sheffield

Find Fantastic yet Inexpensive Offers

House Sheffield
Oct 7 - Oct 14
$599 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Sheffield with Grill & Pool
5.0
Outstanding (7 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Jul 21 - Jul 28
$875 per night
House ∙ 9 guests ∙ 4 bedrooms
Family Friendly Spacious Vacation Home in Sheffield with Yard & Grill + Mountain Views
5.0
Outstanding (80 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Sheffield
Jul 21 - Jul 28
$328 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
Details
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Sheffield accommodation with high-speed internet.

House  Sheffield
Sep 23 - Sep 30
-54%
$900
$411 per night
House ∙ 9 guests ∙ 4 bedrooms
Modern House in Sheffield with Yard, Grill & Jacuzzi + Mountain Views
4.8
Outstanding (16 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Internet
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Cottage  Sheffield
Nov 4 - Nov 11
-58%
$609
$257 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Sheffield with Patio
Sheffield, Berkshire County, Massachusetts, United States
Internet
Details
Expedia
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House  Sheffield
Sep 23 - Sep 30
$686 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Sheffield with Pool
Sheffield, Berkshire County, Massachusetts, United States
Internet
Details
FlipKey
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Sheffield and book a vacation rental with air conditioning.

House  Sheffield
Mar 23 - Mar 30
-29%
$199
$141 per night
House ∙ 6 guests ∙ 3 bedrooms
Lovely Vacation Home in Copake Lake with Grill & Pool + Great Views
4.7
Excellent (79 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Air conditioning
Details
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Cottage  Sheffield
May 1 - May 8
$153 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
Cottage in Monterey with Grill & Yard
4.8
Outstanding (60 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Air conditioning
Details
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House  Sheffield
Mar 23 - Mar 30
-43%
$312
$177 per night
House ∙ 6 guests ∙ 3 bedrooms
Wonderful Vacation Home in Copake Lake with Grill & Yard + Lake Views
4.7
Excellent (38 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Air conditioning
Details
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Best vacation rentals with a balcony

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

House  Sheffield
Jul 21 - Jul 28
$234 per night
House ∙ 8 guests ∙ 2 bedrooms
House in Great Barrington with Marble Fireplace
4.8
Outstanding (67 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony
Details
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Apartment  Sheffield
Dec 9 - Dec 16
-57%
$441
$192 per night
Apartment ∙ 7 guests ∙ 3 bedrooms
Apartment in Stockbridge with Grill
4.9
Outstanding (7 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony
Details
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Apartment  Sheffield
Dec 2 - Dec 9
$175 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Rental Apartment in Housatonic with Botanical Garden + Spectacular View
5.0
Outstanding (41 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony
Details
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Popular Rental Amenities in Sheffield

  • Pet-friendly (14)
  • Pool (3)
  • WiFi (44)
  • Fireplace (25)
  • Hot tub (1)
  • Kitchen (37)
  • TV (33)
  • Balcony/patio (1)
  • Air conditioning (37)
  • Parking (5)
  • Yard (27)
  • Washing machine (29)

Choose a filter above to find an accommodation fitting your needs among the 42 properties in Sheffield. HomeToGo's data reveals that "Pets allowed" and "Pool" prove to be the most commonly provided features in Sheffield. Three features that are not often provided are "Fenced," "Smoking," and "Wheelchair accessible."

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

Fri, 22 Sep
68°
44°

40%

6 h

4 mi/h

Sat, 23 Sep
59°
50°

15%

0 h

6 mi/h

Sun, 24 Sep
69°
46°

15%

6 h

4 mi/h

Mon, 25 Sep
71°
50°

5%

11 h

4 mi/h

Tue, 26 Sep
62°
51°

10%

2 h

6 mi/h

Wed, 27 Sep
57°
48°

0%

0 h

8 mi/h

Thu, 28 Sep
51°
50°

15%

0 h

6 mi/h

Accommodations for your vacation in Sheffield

In Sheffield, most of the 42 vacation accommodations are house rental, which represent 82.76% of its available properties. In addition, the average size of house rental in Sheffield is 247 m² with a median price of $516 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 cabin, which are the other most frequent property type in Sheffield. The average size of cabin in Sheffield is 232 m², and the average price is $474 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 available 42 homes
💳 Possible discounts up to 56%
🌙 Nightly prices starting at $92
⭐ Popular amenities Pets allowed, Pool and Internet
🐾 Pet friendly homes 11 homes

Frequently Asked Questions

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

The nightly price of accommodations in Sheffield starts at $92. If you’re interested in a house rental, the average price is $516 per night. A cabin Sheffield will cost $474 per night on average.

How many vacation homes are available to book in Sheffield?

There are 42 vacation homes to choose from for your next trip.

What amenities are most popular for vacation homes in Sheffield?

Usually travelers search for Pool, Pets allowed, and Internet when booking a vacation rental in Sheffield.

How many vacation homes with a pool are there in Sheffield?

Choose from 2 vacation rentals available in Sheffield.

Are pets allowed in vacation rentals in Sheffield?

Absolutely, currently there are 11 vacation rentals in Sheffield that allow pets , with an average nightly cost of $491.

What are the best months to travel to Sheffield?

July and August are usually the warmest months in Sheffield with temperatures around 81 °F. The coldest months in Sheffield are January and February, with 16 °F on average.

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