Discover a selection of 500 vacation rentals in Sheffield, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $188 per night, and houses and country houses are popular options for a stay in Sheffield. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Sheffield
Destination guide

The historic area of Sheffield awaits your stay

Enjoy the history and other features of Sheffield. This city is well-known for its casino gaming and local tours. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

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

Transportation to and around Sheffield

The nearest airport is in Albany Intl. Airport (ALB), located 49.6 mi (79.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away.

What are the top vacation rentals in or near Sheffield?

Whether you're looking for an intimate escape for you and your boo or a sprawling house to fit the family, you'll find some top vacation rentals in and around Sheffield. Here are a couple to start you off:

  • "Close To Skiing Beautiful +family Friendly" is popular with guests. Around 2 miles from Sheffield, it has 4 bedrooms and lots of useful amenities, including housekeeping services and lowered locks.
  • "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi" also promises an awesome stay, offering 4 bedrooms, golf, free WiFi and more. It's around 17 miles from Sheffield.

For even more great options, use the search bar at the top of the page to find the perfect Sheffield vacation rental for you.

Can I find log cabins to rent in or near Sheffield?

You certainly can! From basic retreats to high-end escapes, Vrbo has an extensive range of log cabins to rent in or around Sheffield. If you're into adventure, check out these options:

  • "Cozy Log Cabin Adjacent To Beartown Forest": This is the ideal base to enjoy some of the awesome outdoor activities this area has to offer, including snowmobiling and cycling.
  • "Water Front Log Cabin Next To Tanglewood": Spend your vacation taking advantage of all the creature comforts at this escape. When it's time to get active, kayaking and sailing are some fun things to do.

What are the top-rated vacation rentals for weekend getaways in or near Sheffield?

If you've been busier than a squirrel in a nut factory, you deserve to escape for a couple of glorious days. Clock off early on Friday and head for one of these weekend getaways in or near Sheffield:

  • Make yourself at home at "Elterwater - - Your Lakefront Oasis". Around 2 miles to the north of Sheffield, this delightful retreat has all you need for a relaxing stay, including a water view and a hair dryer.
  • Alternatively, cram a few clothes into your suitcase and zip off to "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences". This top-rated getaway is around 30 miles northeast of Sheffield and has internet services and a hair dryer.

Can I find studio apartments for rent in and around Sheffield?

Studio apartments are a simple yet stylish choice, perfectly suited for traveling couples or solo adventurers. Spend your days getting to know your surroundings and your nights chilling out in your cozy hideaway. These properties in or near Sheffield will tick all the boxes:

  • After a fun-filled day of outdoor exploration, relax in total comfort at "Cabin - A - Frame In Sherwood Forest". Off-street parking options and a nearby laundromat are among the useful amenities you'll find here.
  • "One Bedroom Plus Loft" is another superb stay, providing all you could want for a dream Sheffield adventure. Convenient amenities here include a barbecue grill and coffee and tea making facilities.

Can I find short term rentals in or near Sheffield?

Whether you're chasing a comfy cottage or a house big enough to fit the family, you'll find the ideal place on Vrbo. Enjoy some downtime at one of these top picks in or near Sheffield:

  • If you can only spare a few nights, "The Playhouse: 7, 000 Square Feet Of Berkshires Modern Luxury And History" has you covered. It's not too far from the center of Sheffield, so you'll be within easy reach of all the top attractions.
  • "Bargain Rates After Late Cancellation" is also well located. Settle in here and discover why many guests rate this property highly.

What are the best romantic weekend getaways in or near Sheffield?

Nothing says "I love you" like a romantic weekend escape. If you'd like to spend a couple of nights away with your partner, we've got some romantic getaways in and around Sheffield that will get your heart racing:

  • Located around 2 miles from Sheffield, "Close To Skiing Beautiful +family Friendly" is a perfect place for adoring couples. A fireplace and skiing facilities are among the many amenities you'll find here.
  • Otherwise, spend your mini break canoodling and sipping Champagne at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", around 17 miles from Sheffield. A nearby marina and a balcony will help ramp up the romance.

What are the best large group vacation rentals in or near Sheffield?

Share your stay and have even more fun. Whether you're planning an action-packed getaway with pals or an overdue family reunion, you'll have your pick of large group vacation rentals in and around Sheffield:

  • A nice range of amenities including a fireplace and a garden make "The Playhouse: 7, 000 Square Feet Of Berkshires Modern Luxury And History" a group favorite. This generous property has 6 bedrooms and sleeps up to 20 guests. From the center of Sheffield, it's around 16 miles away to the north.
  • "General Williams Estate House Lenox" is another terrific option. It's around 15 miles to the north of Sheffield, has 6 bedrooms and welcomes up to 16 guests. A swimming pool and a garden are among the things that'll help make your visit even more comfortable.

What are the best houses for rent with a pool in or near Sheffield?

A pool is often a nonnegotiable when choosing where to stay on vacation, especially if you've got kids in tow. Check out these houses with a pool in or near Sheffield and fill your days with splashing good fun:

  • Round up your gang and enjoy a memorable break at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". There's plenty to love about this escape apart from its pool, such as outdoor furniture and a stereo.
  • Spend leisurely days swimming or finding some peaceful moments by the water at "General Williams Estate House Lenox". This vacation home is also a firm favorite and features a living room, a separate dining area and more.

Curious what the weather is like in Sheffield? It has a humid continental climate, with average temperatures in summer ranging from 55 ºF to 80 ºF. If you're searching for more inspiration on where to stay in this amazing destination, use the search bar at the top of the page and adjust the filters to check out our entire range of Sheffield vacation rentals.

What are the best large family vacation rentals in or near Sheffield?

The first mission of any great family trip is searching for the right place to stay. Whether you're organizing a quick break with the kids or a multi-generational getaway with relatives, we've got large family vacation rentals in and around Sheffield that'll fit everyone. Here are a couple of popular options worth considering:

  • Make your catch-up one to remember at "88 Acres Of Beauty In The Berkshires". This pad has 4 bedrooms, can fit up to 9 guests and features a range of amenities, including a TV and a balcony. It's around 2 miles west of Sheffield.
  • "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi", around 17 miles to the east of central Sheffield, was made for family getaways. As many as 10 of your relatives or friends can fit into this comfortable vacation rental which offers 4 bedrooms, cable/satellite TV services, a DVD player and more.

If you're looking for family-friendly attractions in the area, Tannery Falls is a fun outing for all ages.

Can I find family cabin rentals in or near Sheffield?

Nothing's more important than family, which is why we'll help you find a place where you can truly connect. Rent one of these family cabin rentals in or near Sheffield and make wonderful new memories with your loved ones:

  • "Cabin - A - Frame In Sherwood Forest" - This sought-after retreat offers a fridge and a DVD player and is located about 20 miles northeast of central Sheffield.
  • "Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating" - Another great option, this cabin comes with a barbecue grill, childrens activities and more. You'll find it around 19 miles to the northeast of Sheffield.

For more options, use the search bar at the top of the page and adjust the filters to find the Sheffield vacation rental that's perfect for your needs.