Vacation Rentals By Owner In Sheffield, MA

$307.18

“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

Sheffield, Massachusetts, United States

One of the very few waterfront homes available for rent. What other houses offer you 150 feet private lakefront where you can awake to birdsong absolute best house in the best little town for the full Berkshire experience. If you want your own totally private oasis, and a whole house to yourself, leaving crowds and hassle behind, come up to this lovely, quiet, lakefront Berkshire house with a Zen-like feel, just a mile from the center of Sheffield. Just sit and listen to the silence. brbrImmaculately behaved, non-shedding, totally house trained small dogs welcome.brAsk about special rates for longer stays.brbrPerfect location for all Berkshire activities, including Tanglewood and Jacob’s Pillow, plus Shakespeare and Company, Norman Rockwell, The Mount, Berkshire Botanical Gardens.brbr Light-filled, year-round lakefront house (150 feet on private lake with own dock). with fireplace and fire pit, all decorated in mid-century retro style and immaculately clean. Think 'Walden,' think 'On Golden Pond.' Two bedrooms with A/C—one queen-sized bed, two twins, two full baths, living room with fireplace and A/C, dining area, kitchen with dishwasher and microwave, den with pull-out couch. brWater softener, plus screened in porch, full laundry room, two car garage, fire pit, comfortable outdoor seating for five plus two—and all on the most blissful private 150 acre lake with wonderful fishing--bass and pike--and just a mile off Route 7, Sheffield, handy to everything and spotlessly clean. Cleaned, bleached and treated with UVC wand sanitizer. Self checkin and checkout. brLake is natural, pure and lovely to look at (but not good for swimming due to natural vegetation). Canoeing, fishing and kayaking are great. Your own dock and 150 feet on the lake. Kayaks and canoe. Ping pong table! Electric bikes available to rent. Dog walkers available!!brbrYou can work from home here. WiFi, 5G, good cell reception, slightly rare in the Berkshires., Smart cable tv. Spectrum service. This is a slice of heaven! Everything you need for that perfect Berkshire getaway—we can give lots of tips for top-notch local restaurants and things to do. Local owners readily available to answer questions and make recommendations.brGreat local hiking on closeby Appalachian trail, great biking (we have 4 good bikes), wildlife observation (meet our otter and nesting bald Eagle), riveting local history (Shays Rebellion, Mum Bett), local swimming recommendations. brbrVery convenient for Berkshire School and Hotchkiss parents.brAlso convenient for nearby Litchfield County, Conn, including Music Mountain events, plus Lime Rock Park racing.brFurther west, Hudson, NY, is fun to explore, along with houses like Olana, built by Frederic Church of the Hudson River School. brYou will never run out of things to do here—or nothing at all—whatever you want.brBliss!!!!

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$867.91

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Cabin

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield, Massachusetts, United States

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.brbrUndermountain 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.brbrHere's a detailed breakdown of the bedrooms:brbrBedroom #1 (Upstairs): This room features two queen beds and showcases rustic log and shiplap walls, providing a cozy and rustic atmosphere.brbrBedroom #2 (Main Floor): Offering a queen bed and adorned with rustic log walls, this bedroom exudes warmth and comfort.brbrBedroom #3 (Finished Lower Floor): With a queen bed and rustic cedar walls, this bedroom offers a unique and natural aesthetic.brbrBedroom #4 (Finished Lower Floor): Perfect for a group, this room boasts two queen beds and natural shiplap walls, providing a comfortable and welcoming environment.brbrThe 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.brbrStep 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.brbrYour stay at Undermountain Lodge promises both comfort and the opportunity to immerse yourself in the beauty of the outdoors.brbrModern Rustic Comfort: The house is fully furnished in a modern rustic log style, offering a cozy and inviting atmosphere.brbrSpacious Dining: The kitchen and dining areas are generously sized, accommodating up to 12 people comfortably.brbrWell-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.brbrComfort and Convenience: Linens, towels, soaps, shampoo, and conditioner are provided. However, feel free to bring your own personal bathroom items.brbrEntertainment: Enjoy TVs in the main living space and bedrooms 2, 3, & 4. Stay connected with free Spectrum Wifi Internet.brbrOutdoor Delight: Unwind by the firepit at the roundabout, furnished with 6 Adirondack chairs, offering a panoramic view.brbrSafety and Information: Detailed instructions on water and fire safety are provided in the house, along with information about local activities, shopping, and dining options.

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$837.75

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Private Vacation Home

The Race Mountain House

Sheffield, Massachusetts, United States

High on the slopes of Race Mountain, this spacious 4-bedroom villa offers sweeping east-facing views. In the early hours, the house floods with morning light and sunrises are spectacular. The inviting, creative design invokes a true sense of retreat. Swimming Pool is available at the neighboring Race Brook Lodge... and Mountain House guests get a discount at The Stagecoach Tavern restaurant.brbrThe spacebrThe open floor plan centers on a great room, with cathedral ceilings, large fireplace, sunken seating area, and generous windows facing the eastern views. Reclining sofas are just asking to be lounged on in front of a crackling fire. The well-appointed kitchen easily accommodates the hustle and bustle of preparing meals for large gatherings- we’ve had a wonderful time testing that out! The dining table seats 10.brbrFour bright, comfortably furnished bedrooms offer flexible sleeping options. 3 of the rooms can be configured with a king bed or two twins. Crisp bedding and uncluttered spaces allow for a deeply relaxing night of sleep. Three full bathrooms, all have tile floors and thoughtful lighting.brbrSpecial touches are sprinkled throughout the house, from the family-heirloom Steinway baby grand piano to the handmade copper chandelier above the dining table. Perhaps best of all, climb a ladder, Tree House-style, from the airy common area on the second floor to reach the loft. Wall-to-wall cushions invite cuddling, movie watching or the creation of an imaginary kid’s fort. Two decks, one on each level, and a screened porch provide space to entertain in the fresh air or to look out at the stars.brbrGuest accessbrGuests will have private access to the house.brMany of the Race Brook Lodge amenities, including the outdoor swimming pool, are available for house guests to share. Guests also have access to the beautiful surrounding land and hiking trails.brbrOther things to notebrWe do have additional wood available for the fireplace at an extra cost of $20 dollars for 2 full milk crates per delivery.

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Select Dates for Price

Private Vacation Home

Charming Ashley Falls Getaway

Sheffield, Massachusetts, United States

About this spacebrThe home is set back from the road in a quiet rural neighborhood, nestled among stately pines. There is a partially fenced yard & front screened-in porch with comfortable wicker furniture. Conveniently located to ski areas, hiking trails, antique shops, restaurants, brewery, winery, distillery, Towns of Sheffield, Great Barrington, Stockbridge, Lenox (home of Tanglewood), and many other cultural attractions.brThe spacebrRemodeled with new Kitchen and baths, refinished original wood floors with deep rich mahogany tones, bring this unique home back to life.brConvenient first floor bedroom with ample closet space and queen-sized bed. First floor full bath, next to the bedroom, den with roll-top desk for dedicated workspace. Spacious living room, well equipped eat-in kitchen and breakfast bar with plenty of counter space for food prep, complete the first floor.brThe second floor has a separate laundry room with washer/dryer and second bedroom with queen-sized bed and private bath with soaking tub.brGuest accessbrGuest have full access to the property, except for the basement (which is unfinished).brOther things to notebrThe weather closed in on us before we were able to complete some of the exterior improvements, including landscaping which will be completed in the Spring 2023, but there is a fire pit in the backyard for those who wish to toast marshmallows.brWe welcome any suggestions from current guests to improve our property. Simply notify us of any concerns/ suggestions. We will do our best to accommodate.

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$1005.3

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Private Vacation Home

Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly

Sheffield, Massachusetts, United States

Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. brThe rarest of New England homes, with historic bones and bright contemporary additions, August Moon sits on 88 acres of private and peaceful land in the heart of the Berkshires with mountain views from various parts of the property. Just steps away from beautiful hiking trails, it features a perfect blend of new and old, urbane and rustic, and with an eternal quality that is felt throughout the home and the vast property. Enjoy western views of Mount Race and Mount Everett from the grounds, or explore the walking trail through the woods. The trailhead to Racebrook Falls can be accessed by walking down the dirt road where the house is located.brbrWith 3100 sq. ft of wood floors and cozy decor, this spacious house was renovated with two additions: sunroom with master bedroom above, and a gourmet kitchen. The original portion of the house includes a den with fireplace and 42 plasma tv with satellite surround sound home theater system. Built-in bookshelves have loads of great reading and an eclectic DVD library that should have something for everyone. The Parlor is a wood-paneled room with a wood-burning stove, opening up to a small deck with Adirondack chairs for lounging. This is a great room for entertaining with a stereo, turntable, and vinyl record collection. Connecting to the parlor is the traditional dining room which has a table that can seat 10 and a candle fireplace.brbrA bright sunroom opens up to a back patio with teak outdoor furniture, an umbrella, and vast flower gardens that bloom in every season.brbrIn the Master Suite, wake up to beautiful mountain views particularly spectacular during fall foliage season, and go to bed relaxed after taking a soak in the private master bath jacuzzi. Bath and shower products and candles along with luxurious bath robes complete the experience. Vaulted ceilings, cherry hardwood floors, and walk-around deck make this room a relaxing retreat. All bedrooms feature down comforters, high thread count sheets and fans. All bathrooms feature hair dryers, robes, plush towels, Shampoo, Conditioner and Shower Gel. brbrBedrooms: In addition to the spacious master, there are three guestrooms with great architectural details like original wood beams and hardwood floors. The upstairs landing with skylights and gas stove features a day bed perfect for reading in the afternoon. brKitchen: The gourmet kitchen features top-notch equipment like a WOLF eight-burner stove and is fully stocked with cookware, utensils, barware, dishware and other essential cooking tools. A secondary kitchen with another refrigerator makes entertaining for larger groups easy. brbrFlower gardens are in abundance and you will be enticed to the hammock to unwind and soak in the incredible mountain views. After playing a round of tennis on the clay court, enjoy a glass of iced-tea on the outdoor porch furniture at the tennis house bar. Or retreat to the shaded seated area behind the cutting garden or shady hideaway under the canopy of the weeping Katsura tree.brbrOther amenities include: walking trails, tennis court, two fireplaces, wood-burning stove, gas stove, air conditioning in the tv room, master suite, sunroom, and kitchen. WI-FI, cable HDTV, DVD, VCR, stereo, CDs, Jacuzzi tub, microwave, dishwasher, linens, washer/dryer. The three-story garage features a ping-pong and pool table game room on the 2nd story. In the garage, find bikes and helmets for kids and adults, and loads of outdoor games like bocce, croquet, corn hole, badminton, and more. A kids' outdoor playhouse and secret playroom in the twin bedroom are great places for the little ones to play.brbrSmoking is **strictly not permitted.** Large Parties are prohibited. br*** No Longer accepting Wedding Inquiries. brbrKeywords: skiing, snow, fall foliage, tanglewood, berkshires, mountains, hiking, tennis, peace, privacy, country roads, escape, country living.

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$489.02

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Private Vacation Home

PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music

Sheffield, Massachusetts, United States

I JUST purchased my dream house! I have been searching for a lake house in the Berkshires for years & when this came on the market I just had to say YES! It is a cozy newly renovated home situated on a 2 acre private peninsula surrounded on 3 sides by Mill Pond. Come swim, kayak, canoe, fish on the pond & hang out on the dock and the deck! 3 bedrooms & 2 full baths- can sleep up to 9. Enjoy music, theater, dance, hiking, museums, skiing, dining, relaxing in the Berkshires!brDeck, fire pit, 3 kayaks, 1 canoe, 2 bikes, 2 yoga mats. family and pet friendly. Fenced in wooded yard.

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Private Vacation Home

River Orchard Meadow

Sheffield, Massachusetts, United States

Tasteful, comfortable & tidy family Berkshire home located on the Housatonic River minutes from all the Berkshire offerings. River Orchard Meadow is a quiet riverfront property in the charming town of Sheffield offering a serene vista from orchard, fields to water providing a rural, yet upscale getaway for a family. brbrThis well-decorated property has 3 bedrooms plus an additional fully furnished & finished basement queen-bedroom for an additional charge. The home has 3 sitting areas - living room, entertainment room and a reading room. This sophisticated home is furnished with all the necessities and comforts to make your stay effortless and memorable.brbrRiver Orchard Meadow is a lovely setting with a flourishing vegetable and berry garden, new orchard (apples, cherries, peaches and pears) and a stunning fire pit to have evening gatherings. Our deck is outfitted with a charcoal grill and picnic table for 10, 2 large umbrellas, 2 large cushy club chairs and ottomans, and large outdoor fan. brbrWe supply 2 recreational bicycles, 2 kayaks and yoga mats. There is an easy access 90-min gentle kayak route from the Sheffield Covered Bridge back to the property line. brbrThe town of Sheffield has a charming Friday afternoon farmers' market in the summer, Dewey Hall music venue, bakeries and cafes, antique stores and casual restaurants within minutes. Catamount Mountain Ski Resort is 15 minutes away with winter and summer activities for the family.brbrOne of the best hikes in the Berkshires is 10 minutes away in Sheffield, Race Brook Falls. You can dine and have a drink at Race Brook Lodge after.brbrNo details are missed at River Orchard Meadow.

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$474.73

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Private Vacation Home

12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room

Sheffield, Massachusetts, United States

Beautiful country home with 3 bedrooms plus a kids loft, 6 minutes to Great Barrington with lots to discover. 12 minutes to Butternut Skiing, 15 minutes to Catamount Skiing. Electric car charger, hot tub, fire place, game room with pool table and pac man- loads of hiking, skiing, shopping, lakes and waterfalls, Sheffield is an amazing location in the Berkshires and a great vacation spot! We love our home and know you will too!

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$258.61

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Private Vacation Home

COME STAY AT THE SHEFFIELD CHALET!

Sheffield, Massachusetts, United States

Bring friends or the whole family to this cozy accessible Berkshire County Country getaway. Only 5 minutes to Great Barrington! Close to Butternut and Catamount ski areas, Twin Lakes for boating, fishing, skiing, boarding etc., state parks, Tanglewood, Jacobs Pillow, Shakespeare & Company, Mahaiwe Theatre for HD operas & prominent entertainment. Nearby distillery, breweries and restaurants are tasty. Bartholomew's Cobble is down the street for nature walks & talks, etc. You wont want to leave!brThe spacebrThis House sits on 6 beautiful acres in the heart of Sheffield. You can sit out on the back deck and get lost in nature. You're guaranteed to see the two resident rabbits hopping around along with the squirrels gathering their nuts. If you are quiet enough, you can see the deer pass by on their way to the corn fields across the way. After being done outside, you can walk up the steps or roll up the wheelchair accessible ramp and into the house. The entryway boasts radiant heated tile flooring, perfect for warming your feet after spending a day outside in the Berkshire's winter. There is a full wheelchair accessible bathroom conveniently located downstairs if needed as well. The newly remodeled open floorplan is perfect for entertaining family and friends, while the climate is controlled by efficiant quiet mini-splits. The large exposed beams and wood was all cut and processed on the property! The Lovely glass enclosed Porch across the front of the house is perfect for drinking coffee and watching the sunrise. The staircase leads to a cozy cherry floored 3 bedrooms and a full bath with a tub shower.brGuest accessbrThe house is on a one-way part of Route 7a, so entering and leaving driveways is simple. The stone driveway wraps around the house so you can park wherever is convenient.brbr There are security cameras on the exterior of the house for criminal deterrence, and insurance purposes. Thank you.br

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$327.28

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Private Vacation Home

Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!

Sheffield, Massachusetts, United States

Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. Warm nights by the fire & scenic views all in our fully stocked home 8 min from Great Barrington. Within literal steps of Sunset Meadows Winery, walking distance of Big Elm Brewery & Berkshire Mountain Distillery. Peloton included. Pet-Friendly. Minutes to hiking, skiing, antiquing & morebrSeasonal Hot Tub available May 15 until Oct 15br*WINTER RENTALS (Oct 15 -May 15) SEE BELOW*

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$510.35

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Private Vacation Home

Whitney by AvantStay | Private Berkshires Estate

Sheffield, Massachusetts, United States

Settle in among the beauty of the Berkshires at Whitney, a private retreat overflowing with comfort and charm. Enjoy the fresh mountain air and the surrounding foliage from a screened patio, complete with a foosball table and seating. Whitney features a large yard and sits next to a field, giving you a unique blend of privacy and open space. Inside, the cozy living room boasts a fireplace, while the quaint kitchen has everything you need to prepare everyone's favorites at home. After checking out the surrounding outdoor activities and views throughout the Berkshires, spread out between five comfortable bedrooms, each curated with chic decor. Whether you've come to relax or explore, Whitney is ready to show your group an unforgettable experience!brbrAvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team. Whether it’s fridge stocking or in-home massages, AvantStay offers a variety of upgrades & experiences to enhance your stay.brbrLocal Attractions: Beartown State Forest, East Mountain State Forest, Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain ResortbrbrA visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provide a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself!brbrHome Truths:br- This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- The grill is out of order for the rest of winter.br- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.br- This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects.brbrParking Details:br2 cars in the garage and 2 in the driveway.brNo parking on the grass.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed & sleeper sofabrBedroom 2 / Queen bedbrBedroom 3 / Bunk bedbrBedroom 4 / Queen bedbrBedroom 5 / Queen bedbr+ 2 twin size tri-fold sleeping matsbrbr---brbrAccidental Damage Protection: A non-refundable accidental damage protection plan has been included in the price of your reservation. Under this plan, you will not be held responsible to pay for accidental damage or loss to the rental property resulting from you or others in your party up to $2000. This plan does not cover intentional acts of a guest, gross negligence, or willful and wanton conduct, and/or damages caused by pets. This plan is not available for reservations 28 days or longer or reservations that require a security deposit.brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. All bookings over 30 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.

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$180.1

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Apartment

Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

Sheffield, Massachusetts, United States

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. brbrYour 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.brbrNearby Amenities:br- A mere 7 minutes from the center of scenic Great Barrington, offering delightful shops, restaurants, theatre, and opera house.br- 10 minutes from Racebrook Falls, Bartholomew's Cobble, Ashley House Museum (oldest house standing in Berkshire County - perfectly preserved) br- Less than 15 minutes away from both Butternut Ski Resort and Catamount Ski Resort, ideal for winter sports enthusiasts. br- Conveniently located 2 miles from Guido's Supermarket and Big Y for all your grocery needs.br- 20 minutes away from the Berkshire Botanical Gardens, Norman Rockwell Museum, Bash Bish Falls, br- 30 minutes away from Tanglewood, Shakespeare & Co. , The Mount (home of Edith Wharton)br- brMore to Explore:brThe 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.brbrHistorical Significance:brDeacon 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.brbrSilas 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.brbrDespite 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.brbrThe 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.br

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$513.82

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Private Vacation Home

Family Friendly in Sheffield, private yet close to everything!

Sheffield, Massachusetts, United States

Your perfect country escape. Clean, spacious, light and airy home set in the middle of a meadow on 20 acres. Complete privacy, yet 10 minutes to downtown Great Barrington. Close to skiing at both Catamount and Butternut. There is room for everyone, with 4 bedrooms, including two master suites. The first floor features an open concept kitchen/living/dining, along with a powder room, spacious mudroom and a gorgeous newly added 4 season sun room with radiant heat. There is also a queen bedded master suite on the first floor with a walk in closet and bathroom featuring a Jacuzzi tub. The second floor has 3 additional bedrooms including a second master suite that has both a king sized bed and a twin bed, and a bathroom with a walk in shower (no tub). An additional bedroom features a full size bed, and the last bedroom has a twin over full bunk. An additional bathroom with tub completes the second floor. Luxury bamboo sheets on all beds. Both a travel crib and extra large playpen are available. The lower level bonus space gives the kids a place to play and also features a television. The very private house sits at the end of a long driveway and is charmingly situated in a park like setting, with a meadow filled with birdsong, specimen plantings, a fruit orchard, and garden (more in-season photos coming soon!) Conveniently located in Sheffield, MA, close to South Egremont, Great Barrington, Salisbury/Lakeville, CT area and all of the restaurants, skiing and cultural attractions in Berkshire County. All appliances in the home are less than 5 years old. Dogs are considered. It is our number one priority to ensure you have a truly special and relaxing stay at our property, so please let us know if you have any questions. Sorry, no events at this time.

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$417.76

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Private Vacation Home

Beautiful and Private Setting to Enjoy Spring

Sheffield, Massachusetts, United States

Summary:brBeautiful home with private yard and heated pool. Exquisite summer setting and breathtaking fall foliage in the town of Sheffield Massachusetts. Perfectly centered between Butternut and Catamount for winter activities!brbrThe Space:brHome offers three bedroom with amazing living /entertaining space. Accommodates up to 6 guests in private setting. Enjoy time with friends and family with beautiful entertaining space and luxurious heated inground pool. Open floor plan and beautiful design offer relaxation and ultimate entertaining. Home is private with beautiful setting to truly relax and enjoy time with loved ones in the breathtaking Berkshires.brbr*Pool Closed after Labor Day*br brbrbrFor Skiers!brbrbrButternut is 10.6 mi West.brbrbrCatamount is 11.2 mi East.brbrbrWe recently upgraded our system to enhance the heating/cooling system in the house. Please excuse the appearance of some baseboard areas. Upgrades are in progress! Pricing reflects the updates in progress.brbrGuest Access:brPrivate entrancebrbrThe Neighborhood:brVery quite neighborhood. House is in a private setting down a long driveway. Short drive to downtown Sheffield.brbrGetting Around:brRurual area brbrGood for driving brbrNo tradficbrbrOther Things to Note:brI'll email additional info on the house and BetkshiresbrbrInteraction with Guests:brSelf check inbrbrCall me if you need anything

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$563.57

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Private Vacation Home

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Sheffield, Massachusetts, United States

Family or couples getaway! 3 bedrooms plus library, Sleeps 6-8 A beautiful 3050 Sq. Ft., 2-Story Colonial and attached 2 car garage. Large, upscale chefs kitchen where everything is first class. Marble counters. Professional Blue Star (6 burner) gas range. Fully stocked kitchen with all kitchen utensils.brClose to Great Barrington, Stockbridge & Lee Outlet Mall! Enjoy Tanglewood Music in Lenox! Gorgeous drive to the Clark Museum in N Adams and Mass MOCA. brClose to Butternut & Catamount & Jiminy Peak! Enjoy the steam shower & soaking tub after a day of hiking or skiing. Relax in from of the granite fireplace…. brMaster bedroom can accommodate our portable quality twin bed or sleep mats or be a romantic couples room with its adjoining luxury bathroom. The other 2 bedrooms are the Country Lavender room & the Red Renaissance themed room… both with top quality Queen beds, that sleep two and can accommodate the extra bedding. brMagnificent chandeliers, and both modern furniture and mixed antiques make this a warm and charming home.brGreat home near all Berkshire attractions - Tanglewood, Berkshire Theatre, Shakespeare & Co., Berkshire Choral Festival and the Norman Rockwell Museum in nearby Stockbridge & the famous Red Lion Inn! Lime Rock car racing in Ct is only 20 minutes away! Enjoy sports from Zip-lining at Catamount. Hike the Appalachian Trail & many others! Canoe & Kayak rentals nearby., or launch your own at launch sites nearby. Top bike riding roads. Winter skiing at Butternut & Catamount nearby.brThis 8 acre property runs to the Housatonic river and is 5 minutes from Rt. 7 !brbr

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$313.03

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Private Vacation Home

Skiing & Hiking: Water-View Home in the Berkshires

Sheffield, Massachusetts, United States

2,262 Sq Ft | Ping-Pong Table | Nestled on Mill Pond | 7 Mi to Dwtn Great BarringtonbrbrTake a break from the city and book this Sheffield vacation rental in the Berkshires! The 3-bed, 2-bath house boasts a retro interior, a full kitchen, an enclosed porch, and stellar pond and fall color views! Conveniently located near Great Barrington, Butternut Ski Area, the Appalachian Trail, and more, this home is the perfect choice for active families seeking all-season adventure.brbr-- THE PROPERTY --brbrC0383872670brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 full bedbr- Bedroom 3: 2 twin bedsbrbrINDOOR LIVINGbr- Smart TV w/ cable, dining tablebr- Wood-burning fireplacebr- Board games, booksbr- Dining table, ping-pong tablebr- En-suite bathroom, natural lightbrbrOUTDOOR LIVINGbr- Waterfront, Solo Stove Yukon fire pitbr- Private yard, enclosed porchbr- Small covered deck, dining setbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Dishware/flatware, cooking basics, spicesbr- Drip coffee maker, microwave, toasterbrbrGENERALbr- Free WiFibr- Central heating, window A/C units, ceiling fansbr- Linens/towels, washer/dryerbr- Complimentary toiletries, hair dryerbrbrFAQbr- Exterior security camera (facing out)brbrACCESSIBILITYbr- Single-story home, 2 steps to enterbrbrPARKINGbr- Garage (2 vehicles)br- Driveway (2 vehicles)brbr-- THE LOCATION --brbr- Near waterfalls, hiking & skiingbr- 4 miles to Appalachian Trailbr- 9 miles to Mill River Historic Districtbr- 10 miles to Butternut Ski Area and Tubing Centerbr- 49 miles to Bradley International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- Your safety matters. This property features 1 exterior security camera located on the garage, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion. It will record when it first senses motion and 30 seconds after the last motion is detectedbr- This single-story home requires 2 steps to enter

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$1349.15

/ Nightly

Private Vacation Home

Historic (updated)1812 Federal brick house well situated in Berkshires with pool

Sheffield, Massachusetts, United States

Historic fully updated brick house originally built in 1812 in the Berkshires in Western Massachusetts on one of the prettiest roads in the area. Minutes from Great Barrington and close to borders of Connecticut and New York, the spacious house sits on 10 quiet acres with swimming pool and patio, large deck with retractable awning, seating for many, chaise lounges, dining table, grill.brbrThe house contains four bedrooms, including a two-bedroom private wing with full bath, a master bedroom with large ensuite bath, library/office, and large (650 sq ft) enclosed rec. room with ping pong table. The remaining bedroom has it's own sitting area and private full bath.brbrThe downstairs contains a large kitchen with dining table that seats 8 as well as counter seating. There is a separate formal dining room, a very large living room/library with grand piano, an additional large double living room as well as a formal parlor.brbrThere is also a mudroom, large laundry room/pantry and powder room. Attached 1000 sq ft studio building has an art library, living room with large screen television, athletic equipment and an additional office/work area.

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$324.55

/ Nightly

Private Vacation Home

Serene Berkshire Artist's House

Sheffield, Massachusetts, United States

Beautiful, comfortable artist's house, that is tastefully furnished. Located on a very quiet 5 acre property abutting Mt Everett State Reservation with Race Brook runs past the house. A 2.5 hour drive from New York City and Boston. You can just relax, hike, visit concerts in Tanglewood or go fine dining.brbrThis is a 3 bedroom (2 beds, 1 sofa-bed and 1 toddler bed) and 2,5 bathroom house. The living area is light and has an open floor plan with an open wood-burning fireplace and a gourmet kitchen. There is a large lawn with outside seating and BBQ. Fast cable internet allows for working fully remotely. Washer and dryer are in the basement.brbrLocal Attractions: 5 minutes from Appalachian Trail, 15 minutes from stores, restaurants, theaters and Lake Mansfield in Great Barrington, 10 minutes from Catamount Ski Center, 35 minutes from Metro North to Grand Central, 30 minutes from Tanglewood, Hancock Shaker Village, Berkshire Theater Festival and Jacobs Pillow, 60 minutes from Colonial Theater and Berkshire Museum, 75 minutes from Mass MOCA and Clark Art Institute. brbrChildren's Activities and Day Camps: Blue Rider Stables, Flying Cloud Institute, IS 183 Art School of the Berkshires, Berkshire Museum, Animagic – Museum of Animation Special Effects.

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$246.67

/ Nightly

Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield, Massachusetts, United States

Welcome to The Blue Elm - a cozy and historic Berkshire getaway located in Ashley Falls, MA.brbrSet on 3.5 tranquil acres, the cottage ties into an early 19th century barn and is nestled amongst old growth maple trees.brbrEnjoy 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.brbrThe SpacebrbrA 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.brbrEnjoy outdoor meals and relaxation on the large vaulted screened room with access to the back yard.brbrAt 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!brbrAmenity Highlights include:brbr✔ Off street parking for two vehiclesbrbr✔ Private Entrancebrbr✔ Numerous reclaimed accents, furniture and materials, including:brbr♥♥ Reclaimed church pews from Berkshire and Columbia Countiesbrbr♥♥ Reclaimed beams from a historic Canadian barnbrbr♥♥ Custom wood shelving salvaged from our 1826 farm housebrand other mid-19th century homesbrbr♥♥ Salvaged Cipollino marble from the Daily News Building in NYCbrbr✔ Bespoke reproduction MCM lighting in the Living and Dining Areasbrbr✔ Direct access to the Ashley Falls Wood hiking and walking trailsbrbr✔ Only a minutes drive to Bartholomew's Cobble Reservation, a 329-acrebrNational Natural Landmarkbrbr✔ Enjoy wild black berries that grow along our property in the summerbrmonthsbrbr✔ Only a minutes drive to the historic Ashley House - the birthplace of thebrSheffield Resolves, a direct precursor to the United States Constitution,brAND the former home of Elizabeth 'Mumbet Freeman, the first slave tobrwin a legal battle for her freedom in the state of Massachusetts!brbr✔ Lovely in-town walks amongst beautiful 18th-19th centurybrresidential architecturebrbr✔ Festive holiday atmosphere throughout the year, including:brbr♥♥ A beautiful Memorial Day parade and ceremony at the historic AshleybrFalls Burial Groundbrbr♥♥ A sought-after tree lighting ceremony each December with the tallestbrilluminated tree in Berkshire County!brbrGuest AccessbrbrGuests have access to clearly marked parking spaces in our shared driveway, along with full access to the 3.5 acres surrounding our home.brbrOther things to notebrbrPrivate architecture and sketch tours of nearby Great Barrington are available upon request. Please message Nick when booking The Blue Elm for more details.

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$191.09

/ Nightly

Apartment

Remodeled Unit #2, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

Sheffield, Massachusetts, United States

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. brbrYour 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.brbrThe 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.brbrNearby Amenities:br- A mere 7 minutes from the center of scenic Great Barrington, offering delightful shops, restaurants, theatre, and opera house.br- 10 minutes from Racebrook Falls, Bartholomew's Cobble, Ashley House Museum (oldest house standing in Berkshire County - perfectly preserved) br- Less than 15 minutes away from both Butternut Ski Resort and Catamount Ski Resort, ideal for winter sports enthusiasts. br- Conveniently located 2 miles from Guido's Supermarket and Big Y for all your grocery needs.br- 20 minutes away from the Berkshire Botanical Gardens, Norman Rockwell Museum, Bash Bish Falls, br- 30 minutes away from Tanglewood, Shakespeare & Co. , The Mount (home of Edith Wharton)br- brMore to Explore:brThe 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.brbrHistorical Significance:brDeacon 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.brbrSilas 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.brbrDespite 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.brbrThe 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.br

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