Find Vacation Rentals in Sheffield

We have 65 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Sheffield Vacation Rentals

Find the perfect Sheffield vacation rental

House Sheffield
from $891 per night
House ∙ 9 guests ∙ 5 bedrooms

353 m² House

5.0
Outstanding(126 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
House Sheffield
from $431 per night
House ∙ 10 guests ∙ 4 bedrooms

279 m² House

5.0
Outstanding(69 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
House Sheffield
from $275 per night
House ∙ 4 guests ∙ 5 bedrooms

130 m² House

5.0
Outstanding(184 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
House Sheffield
from $543 per night
House ∙ 15 guests ∙ 5 bedrooms

381 m² House

5.0
Outstanding(59 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
House Sheffield
from $252 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(49 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
House Sheffield
from $412 per night
12 guests ∙ 4 bedrooms

House

5.0
Outstanding(33 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
House Sheffield
from $287 per night
House ∙ 6 guests ∙ 3 bedrooms

91 m² House

5.0
Outstanding(43 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
House Sheffield
from $438 per night
House ∙ 5 guests ∙ 3 bedrooms

167 m² House

4.8
Outstanding(10 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
Apartment Sheffield
from $172 per night
4 guests ∙ 2 bedrooms

Apartment

5.0
Outstanding(6 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Details
Show more

Accommodations With Saunas

House  Sheffield
from $957 per night
House ∙ 12 guests ∙ 5 bedrooms

353 m² House

4.4
Very good(10 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Sauna
Details
House  Sheffield
from $754 per night
House ∙ 8 guests ∙ 4 bedrooms

227 m² House

5.0
Outstanding(7 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Sauna
Details
House  Sheffield
from $1,127 per night
6 guests ∙ 3 bedrooms

House

Sheffield, Berkshire County, Massachusetts, United States
Sauna
Details
Show more

Recommended Rentals With Pools

Accommodation  Sheffield
from $801 per night
15 guests ∙ 1 bedroom

Accommodation

4.8
Outstanding(1 rating)
Sheffield, Berkshire County, Massachusetts, United States
Pool
Details
House  Sheffield
from $359 per night
6 guests ∙ 4 bedrooms

House

5.0
Outstanding(8 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Pool
Details
House  Sheffield
from $839 per night
12 guests ∙ 4 bedrooms

House

5.0
Outstanding(1 rating)
Sheffield, Berkshire County, Massachusetts, United States
Pool
Details
Show more

Vacation Homes With Terraces

Bed and breakfast  Sheffield
from $171 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Wilder House Berkshires Room 2

4.9
Outstanding(16 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony/Patio
Details
Bed and breakfast  Sheffield
from $171 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Wilder House Berkshires Room 5

4.9
Outstanding(16 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony/Patio
Details
Bed and breakfast  Sheffield
from $282 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Wilder House Berkshires Room 3

4.9
Outstanding(16 ratings)
Sheffield, Berkshire County, Massachusetts, United States
Balcony/Patio
Details
Show more

Frequently Asked Questions

Is renting a vacation home in Sheffield expensive?

Prices for a stay in Sheffield begin at $171 per night.

Are there any vacation rentals available to book in Sheffield?

Tripping.com offers great selection on vacation rentals with 65 offers currently available in Sheffield.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Sheffield

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Sheffield offers 110 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Sheffield start at an average price of $320 a night with long-term rentals averaging $25 a month. These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 104 of Sheffield’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 17 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 100 vacation home rentals. Traveling with your dog or cat? Choose from 48 pet-friendly rentals in Sheffield that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go! Search properties from 6 vacation rental sites in Sheffield where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 87 HomeAway rentals, 13 TripAdvisor short term rentals and 4 Booking.com vacation rentals.

Popular Day Trips Near Sheffield

image-tag