4 bedrooms
•
9 beds
•
2.5 bathrooms
•
14 guests
•
3680 sq. ft.

Saved to wishlist
Bedroom 1
1 king bed
Bedroom 2
1 queen bed
Bedroom 3
1 queen bed
Bedroom 4
4 full bunk beds, 2 twin xl bunk beds
Bedroom 1
1 king bed
Bedroom 2
1 queen bed
Bedroom 3
1 queen bed
Bedroom 4
4 full bunk beds, 2 twin xl bunk beds
Sheffield, Massachusetts 1257, United States
Sheffield, Massachusetts, United StatesPicante's Canaan delights with a bold fusion of authentic Mexican and Italian cuisine, from spicy molcajetes and fresh ceviche to seafood ravioli and chicken parmigiana. This hidden gem serves up fresh, flavorful dishes in a welcoming spot perfect for lunch or dinner.
Roberto's Pizza in North Brunswick crafts diverse pies from deep dish classics to crispy Thin Sicilian and nostalgic Grandma styles, alongside pasta and subs. This cozy, family-friendly spot next to the bowling alley delivers welcoming service and Italian delights perfect for groups.[1]
Discover The Marketplace Kitchen and Cafe, a family-friendly Berkshire gem serving fresh salads, signature sandwiches, housemade soups, and decadent pastries in a fast-casual vibe. Grab-and-go specialties and lattes make it perfect for breakfast, lunch, or a quick treat.
Nestled beside a scenic nine-hole golf course along the Blackberry River, Canaan Country Club's Belted Cow Farmhouse Tavern offers hearty farmhouse fare like prime rib in a cozy, belted cow-themed space with expanded outdoor dining.[1][3][4]
Discover Big Elm Brewing's Sheffield taproom, where fresh ales, lagers, and hard seltzers flow alongside flights and growlers in a laid-back Berkshire spot perfect for families and leashed pets. Pair your pints with takeout from nearby gems like Roberto’s Pizza or food trucks, channeling the spirit of the historic Big Elm tree.
Industry Kitchen is a modern American restaurant featuring seasonal ingredients, wood-fired pizzas, and grilled meats in a striking industrial-chic space beneath the FDR Drive with views of the East River and Brooklyn skyline.
Nestled in Canaan, Blackberry River Bistro serves up fresh, from-scratch Mexican delights like tacos, burritos, and flavorful rice bowls in a cozy, casual vibe with excellent beer and wine. It's the perfect spot for simple, satisfying meals with friendly service.[1][2][3][4]
Discover Bartholomew's Cobble Reservation, a National Natural Landmark with twin rocky knolls, 5 miles of trails through caves, marshes, and wildflower meadows, plus stunning Housatonic River views from Hurlburt's Hill. Nature lovers, hikers, and birders will adore its rugged geology and 800+ plant species.
Discover Thom Reed UFO Park, site of the first UFO encounter officially recognized as historically true by Massachusetts historians and the governor, where Thom Reed's family witnessed insect-like beings after a glowing craft emerged from the Housatonic River in 1969. UFO enthusiasts, mystery lovers, and history buffs will relish this quirky riverside tribute near a scenic covered bridge.[1][2][3][5]
Discover over 500 sparkling vintage accordions—rhinestone-encrusted gems with stories from Lawrence Welk to Al Capone—at this hidden Connecticut gem in a historic train station. Music history buffs, polka lovers, and curious families will squeeze pure joy from Paul Ramunni's passionate tribute to the squeezebox.
Discover the timeless charm of Land of Nod Vineyard & Winery, a bicentennial farm in Connecticut's Berkshire foothills crafting grape and fruit wines amid serene mountain views and the Blackberry River since 1780. Wine lovers, history buffs, and nature seekers will savor tastings, farm-fresh yarns, and picnic bliss.[1][3][4]
Discover breathtaking 360-degree panoramas from Mount Everett's summit, the Dome of the Taconics, via scenic Appalachian Trail hikes for all levels, waterfalls, and serene Guilder Pond. Nature lovers, avid hikers, and birders will relish this stunning Massachusetts reservation year-round.
Discover the magic of Lime Kiln Farm Wildlife Sanctuary, where 2 miles of easy trails wind through diverse habitats teeming with butterflies, pileated woodpeckers, and stunning Mount Everett vistas, plus historic lime kilns and quarries. Nature lovers, birders, and families seeking serene hikes will love this Berkshires gem.
Discover the hidden gem of Campbell Falls State Park, where a stunning 50-foot waterfall thunders through a zig-zagging gorge in lush evergreen forest, reachable by a short, steep trail to a serene swimming pool. Nature lovers and solitude seekers will love this uncrowded Berkshires escape.[2][3]
Mount Riga State Park offers hikers an unforgettable adventure to Bear Mountain, Connecticut's highest peak, crowned with a stone pyramid and featuring panoramic views across three states. Nature enthusiasts and trail seekers will love the accessible Appalachian Trail connection and scenic forest walks through this 276-acre wilderness.
Explore Connecticut's best-preserved industrial landmark, where you can hike scenic trails past historic slag piles, learn how 19th-century ironworks operated, and enjoy picnicking and fishing in a picturesque park setting—perfect for history enthusiasts and nature lovers alike.
Umpachene Falls Park is a hidden gem where cascading waterfalls meet peaceful river pools, offering the perfect blend of scenic beauty and family-friendly recreation. Whether you're swimming in the cool Konkapot River, wading through shallow falls, or picnicking on the grassy field, this tucked-away Berkshires treasure appeals to nature lovers, photographers, and families alike.
Cancel within 24 hours for a full refund.
Pets not allowed
No smoking - fees will apply
Events require approval
Check-in after 4:00 pm
Check-out before 11:00 am
14 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Apr 7, 2026 | $167 | Available |
| Apr 8, 2026 | $167 | Available |
| Apr 9, 2026 | $167 | Available |
| Apr 10, 2026 | $279 | Available |
| Apr 11, 2026 | $279 | Available |
| Apr 12, 2026 | $213 | Available |
| Apr 13, 2026 | $195 | Available |
| Apr 14, 2026 | $197 | Available |
| Apr 15, 2026 | $200 | Available |
| Apr 16, 2026 | $260 | Available |
| Apr 17, 2026 | $289 | Available |
| Apr 18, 2026 | $293 | Available |
| Apr 19, 2026 | $279 | Available |
| Apr 20, 2026 | $253 | Available |
| Apr 21, 2026 | $263 | Available |
| Apr 22, 2026 | $267 | Available |
| Apr 23, 2026 | $283 | Available |
| Apr 24, 2026 | $292 | Available |
| Apr 25, 2026 | $296 | Available |
| Apr 26, 2026 | $292 | Available |
| Apr 27, 2026 | $269 | Available |
| Apr 28, 2026 | $264 | Available |
| Apr 29, 2026 | $272 | Available |
| Apr 30, 2026 | $286 | Available |
| May 1, 2026 | $310 | Available |
| May 2, 2026 | $316 | Available |
| May 3, 2026 | $299 | Available |
| May 4, 2026 | $274 | Available |
| May 5, 2026 | $270 | Available |
| May 6, 2026 | $276 | Available |
| May 7, 2026 | $298 | Available |
| May 8, 2026 | $323 | Available |
| May 9, 2026 | $314 | Available |
| May 10, 2026 | $308 | Available |
| May 11, 2026 | $282 | Available |
| May 12, 2026 | $278 | Available |
| May 13, 2026 | $284 | Available |
| May 14, 2026 | $301 | Available |
| May 15, 2026 | $811 | Not Available |
| May 16, 2026 | $840 | Not Available |
| May 17, 2026 | $290 | Available |
| May 18, 2026 | $272 | Available |
| May 19, 2026 | $269 | Available |
| May 20, 2026 | $515 | Not Available |
| May 21, 2026 | $571 | Not Available |
| May 22, 2026 | $839 | Not Available |
| May 23, 2026 | $839 | Not Available |
| May 24, 2026 | $428 | Available |
| May 25, 2026 | $419 | Available |
| May 26, 2026 | $373 | Available |
| May 27, 2026 | $339 | Available |
| May 28, 2026 | $366 | Available |
| May 29, 2026 | $388 | Available |
| May 30, 2026 | $390 | Available |
| May 31, 2026 | $417 | Available |
| Jun 1, 2026 | $391 | Available |
| Jun 2, 2026 | $391 | Available |
| Jun 3, 2026 | $391 | Available |
| Jun 4, 2026 | $475 | Available |
| Jun 5, 2026 | $475 | Available |
| Jun 6, 2026 | $475 | Available |
| Jun 7, 2026 | $432 | Available |
| Jun 8, 2026 | $391 | Available |
| Jun 9, 2026 | $391 | Available |
| Jun 10, 2026 | $391 | Available |
| Jun 11, 2026 | $475 | Available |
| Jun 12, 2026 | $475 | Available |
| Jun 13, 2026 | $475 | Available |
| Jun 14, 2026 | $446 | Available |
| Jun 15, 2026 | $421 | Available |
| Jun 16, 2026 | $414 | Available |
| Jun 17, 2026 | $423 | Available |
| Jun 18, 2026 | $587 | Available |
| Jun 19, 2026 | $589 | Available |
| Jun 20, 2026 | $610 | Available |
| Jun 21, 2026 | $587 | Available |
| Jun 22, 2026 | $517 | Available |
| Jun 23, 2026 | $507 | Available |
| Jun 24, 2026 | $515 | Available |
| Jun 25, 2026 | $570 | Available |
| Jun 26, 2026 | $624 | Available |
| Jun 27, 2026 | $717 | Available |
| Jun 28, 2026 | $655 | Available |
| Jun 29, 2026 | $589 | Available |
| Jun 30, 2026 | $589 | Available |
| Jul 1, 2026 | $781 | Available |
| Jul 2, 2026 | $1035 | Available |
| Jul 3, 2026 | $1035 | Available |
| Jul 4, 2026 | $1035 | Available |
| Jul 5, 2026 | $1035 | Available |
| Jul 6, 2026 | $794 | Available |