Hotels in Sheffield

With a stay at Wilder House Berkshires in Sheffield, you'll be within a 5-minute drive of Lime Kiln Farm Wildlife Sanctuary and Thom Reed UFO Monument Park. This bed & breakfast is 2.2 mi (3.5 km) from Drury Preserve and 2.2 mi (3.6 km) from Magnolia Bluffs Casino. Take in the views from a garden and make use of amenities such as a fireplace in the lobby and a picnic area. A complimentary cooked-to-order breakfast is served on weekends from 8:00 AM to 10:00 AM. Free self parking is available onsite. Make yourself at home in one of the 5 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers. Conveniences include electric kettles and free tea bags/instant coffee.

Nestled in history and nature, The Historic Kellogg House, built in 1739, is the third oldest house in the Berkshires. Recently updated, the farmhouse seamlessly blends rich history with modern comforts, offering an exceptional retreat. Just 7 minutes from Great Barrington's center less than 12 minutes from Butternut and Catamount Ski Areas, and adjacent to the Appalachian Trail and the tranquil Housatonic River. Your home away from home is a charming 1 bedroom duplex apartment, thoughtfully constructed in the 1940’s as a separate wing to The Kellogg Farmhouse. Recently renovated it offers all the amenities required for a comfortable and memorable stay. You can still find local Sheffield marble around the property which was also used to build the Washington Memorial. This modern oasis within a historic setting seamlessly combines the past with the present. Tons of light filters through the large windows that face the gardens that look out into a large field with gardens. There are plenty of areas to enjoy the outdoors and you are a short walk away from the Historic Appalachian Trail. There are two main entrances to the house; if you are facing the property, your entryway is the door to the left with a stone walkway leading you from the parking area straight into the house (please look at the pictures provided). Your unit is located on the first floor of the house. You have an outdoor patio area overlooking beautiful gardens, and a lovely field with a row of 150-year-old willow trees that line the Housatonic River. During winter months, we ask our guests to use the main entrance as an exit, as the stairs in the back can get slippery.Nearby Amenities:- A mere 7 minutes from the center of scenic Great Barrington, offering delightful shops, restaurants, theatre, and opera house.- 10 minutes from Racebrook Falls, Bartholomew's Cobble, Ashley House Museum (oldest house standing in Berkshire County - perfectly preserved) - Less than 15 minutes away from both Butternut Ski Resort and Catamount Ski Resort, ideal for winter sports enthusiasts. - Conveniently located 2 miles from Guido's Supermarket and Big Y for all your grocery needs.- 20 minutes away from the Berkshire Botanical Gardens, Norman Rockwell Museum, Bash Bish Falls, - 30 minutes away from Tanglewood, Shakespeare & Co. , The Mount (home of Edith Wharton)- More to Explore:The Berkshires region, known for its vibrant arts scene, cultural festivals, and breathtaking landscapes, is yours to explore. Don't miss the local events, antique shops, concerts, and art galleries that bring the area to life. Enjoy scenic drives through the Berkshire Mountains and savor the beautiful foliage in the fall.Historical Significance:Deacon Silas Kellogg, born on April 7, 1714, in Westfield, Massachusetts, constructed the Kellogg House in 1739 upon marrying Ruth Root. Silas, a descendant of influential families, became a prominent figure in Sheffield, serving as a gentleman farmer, and deacon, and holding government positions, including County Treasurer. He played a pivotal role in the Stockbridge Convention of 1774, and Massachusetts call for freedom from English rule.Silas Kellogg's legacy intertwines with the Sheffield Resolves, a document preceding the Declaration of Independence. Silas, a signatory to the resolves, exemplified his commitment to fighting British grievances. His sons, Asa and Silas Jr., actively participated in the War of Independence, embodying the family's dedication to freedom.Despite Silas's roles as a patriot, rumors suggest involvement in counterfeiting prevalent in Sheffield during the 1700s. Ruth Kellogg, Silas's wife, met a tragic end at 96, succumbing to burns from a fireplace accident. Buried at Sheffield Plain Cemetery, both Silas and Ruth left a lasting imprint on American history.The Kellogg Farmhouse bears witness to this transformative period. Built in 1739, the homestead preserves the spirit of independence, reflecting the Kellogg family's role in shaping America's narrative of freedom. As custodians of this history, we, as first-generation immigrants, honor the Kellogg legacy, acknowledging its vital contribution to the founding of the United States. Every beam in this historic dwelling resonates with the enduring legacy of those who once called it home, inviting guests to marvel at the layers of history within.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 2:00 PM.About smoking:Smoking allowed: in designated areas.About minBookingAge:Minimum age to rent: 20.About events:No events allowed.

Welcome to The Blue Elm - a cozy and historic Berkshire getaway located in Ashley Falls, MA.Set on 3.5 tranquil acres, the cottage ties into an early 19th century barn and is nestled amongst old growth maple trees.Enjoy this peaceful and convenient Berkshire location - only 15 minute drive to Catamount Ski Area, 17 minutes drive to Ski Butternut, Great Barrington and points north, and 5 minutes drive to Canaan, CT and points south.The SpaceA private mudroom entrance steps you down into an open Dining and Living Room, complete with coffee bar and Queen sized sleeper sofa. From there one steps up into the well equipped kitchen with induction cooktop and custom open wood slab shelving, as well as a convenient 1/2 bathroom.Enjoy outdoor meals and relaxation on the large vaulted screened room with access to the back yard.At the end of your day step up into the vaulted King bedroom suite with generous closet space and bespoke lighting. Relax and unwind in the custom walk-in shower with wall-to-wall marble salvaged from a NYC skyscraper!Amenity Highlights include:✔ Off street parking for two vehicles✔ Private Entrance✔ Numerous reclaimed accents, furniture and materials, including:♥♥ Reclaimed church pews from Berkshire and Columbia Counties♥♥ Reclaimed beams from a historic Canadian barn♥♥ Custom wood shelving salvaged from our 1826 farm houseand other mid-19th century homes♥♥ Salvaged Cipollino marble from the Daily News Building in NYC✔ Bespoke reproduction MCM lighting in the Living and Dining Areas✔ Direct access to the Ashley Falls Wood hiking and walking trails✔ Only a minutes drive to Bartholomew's Cobble Reservation, a 329-acreNational Natural Landmark✔ Enjoy wild black berries that grow along our property in the summermonths✔ Only a minutes drive to the historic Ashley House - the birthplace of theSheffield Resolves, a direct precursor to the United States Constitution,AND the former home of Elizabeth 'Mumbet" Freeman, the first slave towin a legal battle for her freedom in the state of Massachusetts!✔ Lovely in-town walks amongst beautiful 18th-19th centuryresidential architecture✔ Festive holiday atmosphere throughout the year, including:♥♥ A beautiful Memorial Day parade and ceremony at the historic AshleyFalls Burial Ground♥♥ A sought-after tree lighting ceremony each December with the tallestilluminated tree in Berkshire County!Guest AccessGuests have access to clearly marked parking spaces in our shared driveway, along with full access to the 3.5 acres surrounding our home.Other things to notePrivate architecture and sketch tours of nearby Great Barrington are available upon request. Please message Nick when booking The Blue Elm for more details.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

Nestled in history and nature, The Historic Kellogg House, built in 1739, is the third oldest house in the Berkshires. Recently updated, the farmhouse seamlessly blends rich history with modern comforts, offering an exceptional retreat. Just 7 minutes from Great Barrington's center and less than 15 minutes from Butternut and Catamount Ski Areas, and adjacent to the Appalachian Trail and the tranquil Housatonic River. Your home away from home is a charming 2 bedroom duplex apartment, thoughtfully constructed in the 1940’s as a separate wing to The Kellogg Farmhouse. Recently renovated it offers all the amenities required for a comfortable and memorable stay. You can still find local Sheffield marble around the property which was also used to build the Washington Memorial. This modern oasis within a historic setting seamlessly combines the past with the present.The property looks out into a large field with gardens and plenty of areas to enjoy the outdoors and you are a short walk away from the Historic Appalachian Trail. There are two main entrances to the house; if you are facing the property, then your entryway is the door to the left with a stone walkway leading you from the parking area straight into the house (please look at the pictures provided). Your unit is located on the second floor of the house. You have a deck overlooking a field which in a row of 150-year-old willow trees that line the Housatonic River. During winter months we ask our guests to use the main entrance as an exit, as the stairs from the balcony can get slippery.Nearby Amenities:- A mere 7 minutes from the center of scenic Great Barrington, offering delightful shops, restaurants, theatre, and opera house.- 10 minutes from Racebrook Falls, Bartholomew's Cobble, Ashley House Museum (oldest house standing in Berkshire County - perfectly preserved) - Less than 15 minutes away from both Butternut Ski Resort and Catamount Ski Resort, ideal for winter sports enthusiasts. - Conveniently located 2 miles from Guido's Supermarket and Big Y for all your grocery needs.- 20 minutes away from the Berkshire Botanical Gardens, Norman Rockwell Museum, Bash Bish Falls, - 30 minutes away from Tanglewood, Shakespeare & Co. , The Mount (home of Edith Wharton)- More to Explore:The Berkshires region, known for its vibrant arts scene, cultural festivals, and breathtaking landscapes, is yours to explore. Don't miss the local events, antique shops, concerts, and art galleries that bring the area to life. Enjoy scenic drives through the Berkshire Mountains and savor the beautiful foliage in the fall.Historical Significance:Deacon Silas Kellogg, born on April 7, 1714, in Westfield, Massachusetts, constructed the Kellogg House in 1739 upon marrying Ruth Root. Silas, a descendant of influential families, became a prominent figure in Sheffield, serving as a gentleman farmer, and deacon, and holding government positions, including County Treasurer. He played a pivotal role in the Stockbridge Convention of 1774, and Massachusetts call for freedom from English rule.Silas Kellogg's legacy intertwines with the Sheffield Resolves, a document preceding the Declaration of Independence. Silas, a signatory to the resolves, exemplified his commitment to fighting British grievances. His sons, Asa and Silas Jr., actively participated in the War of Independence, embodying the family's dedication to freedom.Despite Silas's roles as a patriot, rumors suggest involvement in counterfeiting prevalent in Sheffield during the 1700s. Ruth Kellogg, Silas's wife, met a tragic end at 96, succumbing to burns from a fireplace accident. Buried at Sheffield Plain Cemetery, both Silas and Ruth left a lasting imprint on American history.The Kellogg Farmhouse bears witness to this transformative period. Built in 1739, the homestead preserves the spirit of independence, reflecting the Kellogg family's role in shaping America's narrative of freedom. As custodians of this history, we, as first-generation immigrants, honor the Kellogg legacy, acknowledging its vital contribution to the founding of the United States. Every beam in this historic dwelling resonates with the enduring legacy of those who once called it home, inviting guests to marvel at the layers of history within.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 2:00 PM.About smoking:Smoking allowed: in designated areas.About minBookingAge:Minimum age to rent: 20.About events:No events allowed.

This private Luxurious Guest house will Amaze you, with full kitchen, living area and large bedroom with Luxurious Queen bed and plenty of storage only 10 miles to Ski Resorts.Sheffield, Mass. is only 5 miles to Great Barrington with wonderful shops, restaurants and grocery stores. You will have a FULL SIZE kitchen in this wonderful guest house. The first level has a kitchen, living area with recliners and TV, large bath and laundry.Upstairs is a large bedroom with queen bed. The kitchen is fully stocked with anything and everything you could possibly need. We have a Keurig and K-cups but you might want to bring your favorite flavors. We also provide ALL kinds of spices, pam, tin foil and zip locks. If you stay awhile and run out of these items, please replace. The firepit out back is great for spring or fall nights.You have a private entrance away from the main home. The space is very large and comfortable and very private.Way better than any hotel, with all the special comforts of home. Also, includes a brand new Black Samsung washer and dryer for your convenience.This is a 2 person guest home.House rules:1. no smoking pot or cigarettes inside the home2. NO PETS3. no parties or events4. Trash goes in a black garbage bag in front of the washer and dryer on check out.About pets:No pets allowed.About children:Adults only.About smoking:Smoking is not permitted.About events:No events allowed.

Undermountain Lodge offers an escape to a serene cabin, nestled between pristine natural spring lakes with panoramic mountain views, it comfortably accommodates up to 12 guests. Beyond the 6th guest, there's a $135 per person fee. Couples enjoy special discounts, inquire for details. Whether with family or friends, find solace in this tranquil retreat from everyday life. Book now for an unforgettable escape.Undermountain Lodge boasts four inviting bedrooms, comfortably accommodating up to 12 guests. Spread across three levels, it offers two bathrooms, a spacious living room, a charming dining room, and a well-appointed kitchen. The property also features an expansive deck and a covered porch, surrounded by abundant outdoor space.Here's a detailed breakdown of the bedrooms:Bedroom #1 (Upstairs): This room features two queen beds and showcases rustic log and shiplap walls, providing a cozy and rustic atmosphere.Bedroom #2 (Main Floor): Offering a queen bed and adorned with rustic log walls, this bedroom exudes warmth and comfort.Bedroom #3 (Finished Lower Floor): With a queen bed and rustic cedar walls, this bedroom offers a unique and natural aesthetic.Bedroom #4 (Finished Lower Floor): Perfect for a group, this room boasts two queen beds and natural shiplap walls, providing a comfortable and welcoming environment.The main floor includes a bathroom with a shower, a spacious living room, a dining room, and a well-equipped kitchen. For added relaxation, there's an upstairs bathroom with a tub.Step outside to discover a covered porch furnished with comfortable seating, complete with love seats and chairs. Two picnic tables offer a scenic spot to enjoy meals while taking in views of the picturesque valley. Additionally, there's a firepit located in a charming roundabout area, nestled between two ponds, perfect for cozy evenings under the stars.Your stay at Undermountain Lodge promises both comfort and the opportunity to immerse yourself in the beauty of the outdoors.Modern Rustic Comfort: The house is fully furnished in a modern rustic log style, offering a cozy and inviting atmosphere.Spacious Dining: The kitchen and dining areas are generously sized, accommodating up to 12 people comfortably.Well-Equipped Kitchen: The kitchen is equipped with a sink, copper counter space, refrigerator, electric oven and cooktop, dishwasher, a Keurig coffee maker, and a large classic stovetop espresso machine. We provide all necessary dishware, cookware, cooking utensils, eating utensils, and select pantry items for your convenience.Comfort and Convenience: Linens, towels, soaps, shampoo, and conditioner are provided. However, feel free to bring your own personal bathroom items.Entertainment: Enjoy TVs in the main living space and bedrooms 2, 3, & 4. Stay connected with free Spectrum Wifi Internet.Outdoor Delight: Unwind by the firepit at the roundabout, furnished with 6 Adirondack chairs, offering a panoramic view.Safety and Information: Detailed instructions on water and fire safety are provided in the house, along with information about local activities, shopping, and dining options.About pets:Pets allowed: less than 50 lbs per pet (limit one pet total).There is a fee of $300 for pets..About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

With a stay at this cottage in Sheffield, you'll be within a 15-minute walk of Housatonic River and Thom Reed UFO Monument Park. This cottage is 2.3 mi (3.7 km) from Magnolia Bluffs Casino and 3.5 mi (5.6 km) from Lime Kiln Farm Wildlife Sanctuary. Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills. Make yourself comfortable in this cottage, which features a fireplace. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Conveniences include a microwave and a washer/dryer.

When you stay at East Rock Inn in Great Barrington, you'll be near ski lifts, within a 5-minute drive of Ski Butternut and Housatonic River Walk. This motel is 4.1 mi (6.6 km) from W.E.B. Du Bois Boyhood Homesite and 7.6 mi (12.2 km) from Naumkeag Museum. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and ski storage. Featured amenities include express check-in and express check-out. Free self parking is available onsite. Stay in one of 18 guestrooms featuring Smart televisions. Your pillowtop bed comes with premium bedding. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Private bathrooms have designer toiletries and hair dryers.

Located in Great Barrington, The Old Inn On The Green is a 5-minute drive from Dry Hill and 7 minutes from Questing. This inn is 3.8 mi (6.1 km) from Umpachene Falls Park and 4.8 mi (7.8 km) from Les Trois Emme Winery. Take advantage of recreation opportunities such as a seasonal outdoor pool or take in the view from a terrace and a garden. Stop by The Old Inn Fine Dining for lunch, dinner, or brunch, where this restaurant specializes in American cuisine, or grab snacks at the coffee shop/cafe. Mingle with other guests at the complimentary reception, held on select days. Wrap up your day with a drink at the bar/lounge. A complimentary continental breakfast is served daily. Free self parking is available onsite. Make yourself at home in one of the 11 individually decorated guestrooms. Rooms have private balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms have complimentary toiletries and hair dryers.