We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Holiday Rentals
Restaurants
Things to do
Skip to main content
Discover
Trips
Review
More
AUD
Sign in
Inbox
See all
Sign in
to get trip updates and message other travellers.
Sheffield
Sheffield Tourism
Sheffield Accommodation
Sheffield Bed and Breakfast
Sheffield Holiday Rentals
Sheffield Flights
Sheffield Restaurants
Sheffield Attractions
Sheffield Travel Forum
Sheffield Photos
Sheffield Map
Sheffield Guide
Hotels
All Sheffield Hotels
Sheffield Hotel Deals
By Hotel Class
Near Airports
Near Colleges
5-stars Hotels in Sheffield
4-stars Hotels in Sheffield
3-stars Hotels in Sheffield
Hotels near (BDL) Bradley Intl Airport
Hotels near (ALB) Albany Intl Airport
Hotels near Bard College at Simon's Rock
Things to Do
Restaurants
Flights
Holiday Rentals
Places of Interest
Colleges & Universities
Holiday Rentals near Ski Butternut
Holiday Rentals near Monument Mountain
Holiday Rentals near Housatonic River Walk
Holiday Rentals near O'Hara's Landing
Holiday Rentals near Bard College at Simon's Rock
Travel Stories
Cruises
Rental Cars
Tours
Add a Place
Travel Forum
Airlines
Travellers' Choice
Help Centre
Travel Stories
Sheffield, MA Holiday Rentals, Apartments and Villas
Holiday Rentals
USA
Massachusetts (MA)
Berkshires
Sheffield, MA Holiday Rentals, Apartments and Villas
Search
List your property
Owner log in
Sheffield
Holiday Apartments
Destination
Check In
Check Out
Guests
2 Guests
Map
Tripadvisor Sort
Revenue impacts this sort order.
Learn more
Bedrooms
Any
Bathrooms
Any
Amenities
Internet or Wifi (25)
Washer/Dryer (25)
Grill (22)
Air Conditioning (21)
Show all
Suitability
Kid friendly (23)
Pet friendly (16)
Smoking allowed (4)
Wheelchair access (0)
Show more
Property type
Holiday Rental House (25)
Condominium/Apartment (0)
Cabin Holiday Rental (0)
Private Room (0)
Show more
Distinctive Features
Waterfront (5)
Boat Available (3)
Private Chef (0)
Private Beach (0)
Show all
Distance from
5 km
Berkshire Mountain Distillers
Bartholomew's Cobble Reservation
Race Brook Falls
Big Elm Brewing Sheffield
Colonel John Ashley House
Show all
25 rentals
in Sheffield.
Family Friendly in Sheffield, private yet close to everything!
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
“Elterwater”—Your own lakefront oasis, a true Berkshire getaway.
131 reviews
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Gorgeous Sheffield Home in Heart of Berkshires
Holiday Rental House
View on map
5 bedrooms
4 bathrooms
Sleeps 15
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room
4 reviews
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Antique Farmhouse Totally Restored
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 16
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Whitney by AvantStay | Private Berkshires Estate
Holiday Rental House
View on map
5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
August thru Labor Day is still available. Hurry. Berkshires 1 BR. 2 Person Max.
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Make your getaway to the Berkshires! Convenient to skiing, races, music & dance!
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Winter in the Berkshires- warm and loved 3 bedroom home
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Little House in the Woods
6 reviews
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Charming Ashley Falls Getaway
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Beautiful Mountainside House with nearby Lake and Hiking Trails
10 reviews
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
COME STAY AT THE SHEFFIELD CHALET!
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
4 reviews
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterfront Sheffield Escape w/ Spacious Yard!
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Private Berkshire County Retreat
3 reviews
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Cheerful 3-bedroom cottage with woodstove
4 reviews
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
River Orchard Meadow
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Serene Berkshire Artist's House
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Maplewood: Historic home with pool and hot tub
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
88 acres of Beauty in the Berkshires - Family Friendly w/ Tennis Court
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Historic (updated)1812 Federal brick house well situated in Berkshires with pool
1 review
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Private Berkshire County Retreat
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
9 reviews
Holiday Rental House
View on map
7 bedrooms
6 bathrooms
Sleeps 30
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
1
Showing results 1-25 of 25
Frequently Asked Questions about Sheffield
Do any holiday rentals in Sheffield have a pool?
Yes, here are some popular holiday rentals in Sheffield that have a pool:
Private Berkshire County Retreat
Family Friendly in Sheffield, private yet close to everything!
“Elterwater”—Your own lakefront oasis, a true Berkshire getaway.
See all holiday rentals with a pool in Sheffield on Tripadvisor
Do any holiday rentals in Sheffield have internet access?
Yes, here are some popular holiday rentals in Sheffield that have internet access:
Family Friendly in Sheffield, private yet close to everything!
“Elterwater”—Your own lakefront oasis, a true Berkshire getaway.
Gorgeous Sheffield Home in Heart of Berkshires
See all holiday rentals in Sheffield on Tripadvisor
What are the best pet friendly rentals in Sheffield?
The best pet friendly rentals in Sheffield are:
Family Friendly in Sheffield, private yet close to everything!
“Elterwater”—Your own lakefront oasis, a true Berkshire getaway.
Antique Farmhouse Totally Restored
See all pet friendly holiday rentals in Sheffield on Tripadvisor
What are some great rentals in Sheffield that are kid friendly?
Some of the most popular kid friendly rentals in Sheffield are:
Family Friendly in Sheffield, private yet close to everything!
“Elterwater”—Your own lakefront oasis, a true Berkshire getaway.
Gorgeous Sheffield Home in Heart of Berkshires
See all kid friendly holiday rentals in Sheffield on Tripadvisor