Sheffield Cottage Rentals

Compare Cottages, Resorts, & Rentals in Sheffield, Massachusetts, USA

Wilder House Berkshires
FromUS $235 per night
|
9.5 (50 Reviews)
5 Bedrooms 11 Guests
Wilder House Berkshires
FromUS $206 per night
9.8 (43 Reviews)
1 Bedroom 2 Guests
Little House in the Woods by Evergreen Home
10.0 (34 Reviews)
2 Bedrooms 6 Guests
Water-View Home in the Berkshires
|
9.0 (3 Reviews)
3 Bedrooms 6 Guests
Race Brook Lodge
FromUS $190 per night
8.4 (31 Reviews)
1 Bedroom 2 Guests
The Blue Elm - A Historic Berkshire Cottage
10.0 (15 Reviews)
1 Bedroom 4 Guests
Copper Kettle Farm by AvantStay
|
New
4 Bedrooms 14 Guests
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts
10.0 (7 Reviews)
1 Bedroom 2 Guests
Whitney by AvantStay
FromUS $217 per night
New
5 Bedrooms 10 Guests
South Berkshire Barn Apartment with Stunning Views
10.0 (4 Reviews)
2 Bedrooms 8 Guests
Cheerful 3-bedroom cottage with woodstove
10.0 (43 Reviews)
3 Bedrooms 6 Guests
Majestic Mountain Side Sheffield/Great Barrington/SKI
10.0 (6 Reviews)
4 Bedrooms 8 Guests
Peaceful and Private Setting
10.0 (6 Reviews)
3 Bedrooms 6 Guests
Escape & Explore! NEW Beautiful Berkshires Farmhouse
10.0 (5 Reviews)
4 Bedrooms 8 Guests
Serene Berkshire Artist's House
9.8 (29 Reviews)
3 Bedrooms 6 Guests
Berkshires Walk to Brewery or Distillery with Peloton!
9.8 (9 Reviews)
3 Bedrooms 5 Guests
Water-View Home in the Berkshires
9.6 (26 Reviews)
3 Bedrooms 6 Guests
The Race Mountain House
FromUS $838 per night
9.6 (7 Reviews)
4 Bedrooms 12 Guests

About Sheffield Vacation Rentals

There are over 47 amazing vacation rentals available in Sheffield. Choose from a variety of options including villas, hotels, and other rental properties. Explore a vast selection of luxury amenities at unbeatable prices, providing you with the ideal spot for your next getaway. Life is Better at the Cottage with Vacation Cottage, where you can discover fantastic stays in Sheffield.

Vacation Cottage offers numerous last-minute deals on villas, hotels, and rentals, both near you and across the globe. Whether you need accommodations for a group or event, such as a hotel or vacation rental (including cabins and private luxury villas), let us assist you. With Vacation Cottage in Sheffield, you can easily compare options from multiple suppliers with just a click to find the perfect price point, amenities, and style of stay for you. Whether you're seeking group discounts, private pools, hot tubs, pet-friendly options, or spacious master suite bedrooms with open-air showers, you can find it all with Vacation Cottage vacation rentals, resorts, and Airbnb-style properties in Sheffield. The average size of places to stay near Sheffield is approximately 1662.44 ft², with prices averaging US $444 per night.

Vacation Cottage helps you discover the perfect holiday rental to create lasting travel memories in Sheffield. Prices listed often feature discounts compared to rack rates. Simply search for your destination and secure your ideal place to stay today.

Find Vacation Cottage Rentals in these Cities and Neighborhoods Sheffield, MA


Frequently Asked Questions About Sheffield?

What are the top cottages, summer homes, and lake houses in Sheffield?

How many rentals, hotels, or resorts are available in Sheffield?

Vacation Cottage consistently updates its selection, offering a blend of new options alongside well-established accommodations in prime locations. Currently, there are over 47 properties listed by Vacation Cottage in the Sheffield area for the year 2026, with this number increasing daily. By aggregating listings from various websites and travel providers, Vacation Cottage ensures a diverse array of choices for the best luxury stays in Sheffield.