Destination guide

Explore the treasure trove of the Berkshires

The word charming doesn't begin to do justice to the oldest town in the Berkshires, where rolling farmlands and historic buildings will make you feel is if you've stepped into the perfect New England postcard. Settled in 1725, the town is still dotted with quaint buildings of centuries past, mixed in among brick sidewalks, period lighting, and one of the largest concentrations of antique stores for miles around. The only thing that rivals the small town charm is the breathtaking nature that envelops Sheffield on every side, making the town a perfect home base for a host of outdoor activities.

Things to do

Pack your camera for that postcard-worthy shot

From historic buildings to panoramic vistas, your Instagram feed will thank you for choosing a Sheffield vacation rental. Home to the picturesque Old Covered Bridge, you'll also find the 18th-century Colonel John Ashley House, now a museum featuring period architecture and furnishings. The babbling brooks and flowing rivers of the surrounding Housatonic River valley are peppered with scenic waterfalls. Mount Everett State Reservation offers jaw-dropping panoramic views of Massachusetts, New York, and Connecticut from its peak. Get your adrenaline rush by careening down the slopes of Catamount Ski Area or Butternut Basin.


Antiquing on the Appalachian Trail

If the thought of digging through glittering antique shops for rare finds is your idea of paradise, you've come to the right place. The impressive number of shops, combined with the regular farmers' markets, cements Sheffield's historic small town vibe. For those not into antiquing, there are outdoor activities galore, including swimming, boating, fishing, and biking, just to name a few (and don't forget the skis in the winter). A Sheffield vacation rental also puts you on the path of the Appalachian Trail, so pack your sturdiest boots to get a taste of one of the country's most epic hikes.


Bundle up, baby, it's cold out there

With snowfalls that more than double the national annual average, you'll want a cozy sweater for curling up by the fire at your Sheffield vacation rental. The beautiful blankets of white covering the town make braving the below-freezing temperatures from November to April worth it. Summers are pleasant, with highs typically in the 70s and 80s from June to September. The fall is a leaf peeper's dream, with fiery foliage that people drive from miles around to see. While the exact time varies from year to year, the colors typically peak in October.

Natural features

Among feathers, falls, and forests

When it's not covered in white, the stunning landscape of the Berkshires is green as far as the eye can see. A number of cascades, including Ashley Falls, can be found sprinkled throughout the creeks and rivers of the Housatonic River valley. You'll pass through a large number of working farms on your way to Mount Everett, the high point in the area's verdant landscape of old growth and dwarf forests. For wildlife encounters, head to Bartholomew's Cobble, the town's 329-acre nature sanctuary that's home to more than 700 plant species and 250 species of birds.

How to get there

How to get to and around Sheffield

The nearest airport is in Hudson, NY (HCC-Columbia County), located 22.4 mi (36.1 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is 23.1 mi (37.2 km) away.

Where to stay around Sheffield?

Our 2019 property listings offer a large selection of 575 vacation rentals near Sheffield. From 374 Houses to 74 Cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Sheffield for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Sheffield?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Sheffield:

  • Lenox: 381 vacation rentals
  • Litchfield: 163 vacation rentals
  • Copake Lake: 30 vacation rentals
  • Lee: 633 vacation rentals
  • Lakeville: 24 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Sheffield?

HomeAway offers a large selection of vacation rentals near lovely places in Sheffield. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Ashley House: 627 vacation rentals
  • Magnolia Bluffs Casino: 692 vacation rentals
  • Tanglewood Music Center: 659 vacation rentals
  • Ski Butternut: 595 vacation rentals
  • Mohawk Mountain Ski Area: 270 vacation rentals

But there are many other points of interest around Sheffield listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Sheffield?

Yes, of course. HomeAway has 374 Houses in Sheffield. Our other popular types of vacation rentals in Sheffield include:

  • Cabins: 74 rentals available
  • Cottages: 74 rentals available
  • Bungalows: 74 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Country houses and more.

Can I find a vacation rental with pool in Sheffield?

Yes, you can select your preferred vacation rental with pool among our 87 vacation rentals with pool available in Sheffield. Please use our search bar to access the selection of vacation rentals available.