Operated by a Wander partner
Trusted operators, vetted by Wander
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!AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!Local 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 ResortA 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!Home Truths:- 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.- The grill is out of order for the rest of winter.- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.- This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects.Parking Details:2 cars in the garage and 2 in the driveway.No parking on the grass.---The room configuration is as follows:Primary Bedroom / King bed & sleeper sofaBedroom 2 / Queen bedBedroom 3 / Bunk bedBedroom 4 / Queen bedBedroom 5 / Queen bed+ 2 twin size tri-fold sleeping mats---This 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.As 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. Events 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. There 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.As 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.IDs will be requested for verification after booking. All bookings over 30 days require a security deposit.We report and prosecute all Credit Card Fraud.
Exterior
1 queen bed
Patio
1 queen bed
Dining Room
1 full sofa, 1 king bed
Kitchen
1 queen bed
Bedroom 1
1 king bed, 1 twin sofa
Bedroom 2
1 queen bed
Bedroom 3
1 queen bed
Bedroom 4
1 queen bed
Bedroom 5
2 twin bunk beds
Exterior
1 queen bed
Patio
1 queen bed
Dining Room
1 full sofa, 1 king bed
Kitchen
1 queen bed
Bedroom 1
1 king bed, 1 twin sofa
Bedroom 2
1 queen bed
Bedroom 3
1 queen bed
Bedroom 4
1 queen bed
Bedroom 5
2 twin bunk beds
Sheffield, Massachusetts 1257, US
Sheffield, Massachusetts, USThe Bistro Box is a seasonal roadside eatery in Great Barrington, MA, serving fresh, made-to-order classics like gourmet burgers, hand-cut fries, and creative sandwiches in a spacious outdoor setting with picnic tables—perfect for families and locals seeking quality comfort food with modern twists.
GB Eats is a beloved Great Barrington diner serving all-day breakfast favorites like fluffy omelets, French toast with local compote, and hearty schnitzel sandwiches alongside vegan and gluten-free options. Pet-friendly outdoor seating and incomparable customer care make it a community staple since 2000.[1][2][3]
Great Barrington Bagel crafts authentic New York-style bagels—chewy, golden, and baked fresh daily—with 17 cream cheese flavors, smoked fish, and hearty deli sandwiches.[1][2][3] Dive into this local favorite's inviting deli vibe for breakfast or lunch in the Berkshires.[2][3]
Bizen is a Japanese restaurant and sushi bar in Great Barrington, Massachusetts, frequently praised for its fresh, authentic sushi and vibrant Japanese cuisine served in an elegantly decorated setting that captures the beauty of Japanese culture.
The Well Restaurant + Bar serves up classic American cuisine like hand-packed, hormone-free burgers in a cozy spot perfect for lunch, dinner, and drinks. Gluten-free options and a welcoming vibe make it a Great Barrington favorite.
Nestled in Great Barrington, The Prairie Whale delivers farm-to-table American cuisine with seasonal, locally sourced dishes like grass-fed steaks and brick chicken in a cozy, rustic space of reclaimed wood and a glowing zinc bar. Its warm, inclusive vibe draws locals and visitors for unfussy yet inventive meals.
Fuel America is a welcoming coffeehouse fueling your day with gourmet espresso drinks, all-day breakfast, fresh açaí bowls, paninis, and protein-packed prolattas in a warm, unpretentious vibe that celebrates America's diverse spirit.[1][4]
Roberto's Pizzeria in Sandestin serves Sandestin's best gourmet pizzas, pastas, calzones, and strombolis with premium ingredients. Relax in casual indoor-outdoor seating with a full bar, big screens for the game, and friendly service perfect for families or delivery.
Discover Bartholomew's Cobble Reservation, a National Natural Landmark with twin rocky knolls, 5 miles of trails past caves, ferns, and the Housatonic River, culminating in panoramic mountain views from Hurlburt's Hill. Nature lovers, hikers, and birders will cherish its exotic biodiversity and serene escape.
Stroll the enchanting San Antonio River Walk, a vibrant 15-mile urban oasis blending lush gardens, public art, historic landmarks, and riverboat cruises past the Alamo and bat colonies. Perfect for families, culture lovers, and anyone craving a lively mix of adventure and serenity.[1][2][4][7]
Jug End State Reservation offers stunning Berkshire views with easy-to-moderate hiking trails through open meadows and forests, making it perfect for families and nature lovers seeking a peaceful outdoor escape with a touch of history from its former resort days.
Discover the hidden gem of Umpachene Falls Park, where cascading falls meet shallow wading pools and the serene Konkapot River, perfect for picnics, play, and peaceful nature immersion. Families, hikers, and relaxation seekers will love this easy-access Berkshires oasis.[1][2][3][4]
AsiaBarong Gallery is a museum-like wonderland nestled in the Berkshire hills featuring over 25,000 pieces of high-quality Asian art and antiques, from Buddha statues to hand-carved furniture. Perfect for culture enthusiasts and curious explorers who want to spend hours discovering rare ethnographic treasures while supporting fair-trade artisan families across Asia.
Discover Thom Reed UFO Park, site of the nation's first officially recognized UFO encounter in 1969—validated by historians, the governor, and shows like Ancient Aliens. UFO enthusiasts and mystery lovers will relish this quirky riverside memorial near a historic covered bridge.[1][3][4][6]
Discover the wild beauty of Mount Washington State Forest, where 30 miles of rugged trails lead hikers and mountain bikers to Alander Mountain's stunning 2,250-foot summit views amid blooming laurel and fern-carpeted woods. Perfect for adventure seekers craving backcountry thrills and nature immersion.
Discover Beartown State Forest's serene Benedict Pond for swimming, kayaking, and fishing, surrounded by miles of hiking trails including the Appalachian Trail, alive with deer, bears, and bobcats. Nature lovers and outdoor adventurers seeking peaceful wilderness escapes will love it.[1][3][4]
Discover Ski Butternut, the Berkshires' family gem with 1,000 feet of vertical drop across 22 groomed trails, terrain parks, and tubing fun for all ages. Perfect for beginners building confidence and experts seeking affordable thrills amid stunning views.[2][4][6]
Discover the serene Lake Mansfield Beach and Conservation Forest Trails, where clean, accessible paths wind through shaded woods to a pristine lakeside beach perfect for relaxing, paddling, or picnicking amid stunning Berkshire scenery. Families, nature lovers, and casual walkers will cherish its peaceful vibes and wildlife spotting.
If canceling with 30–59 days before check-in: 50% refund (cancellation charge 50% of total). If canceling with 0–29 days before check-in: 0% refund (cancellation charge 100% of total).
Pets allowed with fee
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 11:00 am
10 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jun 18, 2026 | $231 | Not Available |
| Jun 19, 2026 | $274 | Not Available |
| Jun 20, 2026 | $446 | Not Available |
| Jun 21, 2026 | $345 | Not Available |
| Jun 22, 2026 | $281 | Not Available |
| Jun 23, 2026 | $283 | Not Available |
| Jun 24, 2026 | $290 | Not Available |
| Jun 25, 2026 | $340 | Not Available |
| Jun 26, 2026 | $258 | Available |
| Jun 27, 2026 | $517 | Not Available |
| Jun 28, 2026 | $417 | Not Available |
| Jun 29, 2026 | $336 | Not Available |
| Jun 30, 2026 | $339 | Not Available |
| Jul 1, 2026 | $398 | Not Available |
| Jul 2, 2026 | $564 | Not Available |
| Jul 3, 2026 | $564 | Not Available |
| Jul 4, 2026 | $564 | Not Available |
| Jul 5, 2026 | $564 | Not Available |
| Jul 6, 2026 | $291 | Available |
| Jul 7, 2026 | $283 | Available |
| Jul 8, 2026 | $287 | Available |
| Jul 9, 2026 | $306 | Available |
| Jul 10, 2026 | $377 | Available |
| Jul 11, 2026 | $515 | Not Available |
| Jul 12, 2026 | $398 | Not Available |
| Jul 13, 2026 | $324 | Not Available |
| Jul 14, 2026 | $325 | Not Available |
| Jul 15, 2026 | $325 | Not Available |
| Jul 16, 2026 | $386 | Not Available |
| Jul 17, 2026 | $504 | Not Available |
| Jul 18, 2026 | $525 | Not Available |
| Jul 19, 2026 | $402 | Not Available |
| Jul 20, 2026 | $325 | Not Available |
| Jul 21, 2026 | $325 | Not Available |
| Jul 22, 2026 | $325 | Not Available |
| Jul 23, 2026 | $386 | Not Available |
| Jul 24, 2026 | $510 | Not Available |
| Jul 25, 2026 | $526 | Not Available |
| Jul 26, 2026 | $403 | Not Available |
| Jul 27, 2026 | $327 | Not Available |
| Jul 28, 2026 | $327 | Not Available |
| Jul 29, 2026 | $327 | Not Available |
| Jul 30, 2026 | $389 | Not Available |
| Jul 31, 2026 | $512 | Not Available |
| Aug 1, 2026 | $626 | Not Available |
| Aug 2, 2026 | $488 | Not Available |
| Aug 3, 2026 | $485 | Not Available |
| Aug 4, 2026 | $483 | Not Available |
| Aug 5, 2026 | $478 | Not Available |
| Aug 6, 2026 | $463 | Not Available |
| Aug 7, 2026 | $609 | Not Available |
| Aug 8, 2026 | $623 | Not Available |
| Aug 9, 2026 | $477 | Not Available |
| Aug 10, 2026 | $385 | Not Available |
| Aug 11, 2026 | $385 | Not Available |
| Aug 12, 2026 | $385 | Not Available |
| Aug 13, 2026 | $459 | Not Available |
| Aug 14, 2026 | $535 | Available |
| Aug 15, 2026 | $573 | Available |
| Aug 16, 2026 | $427 | Available |
| Aug 17, 2026 | $380 | Available |
| Aug 18, 2026 | $438 | Available |
| Aug 19, 2026 | $409 | Available |
| Aug 20, 2026 | $466 | Available |
| Aug 21, 2026 | $603 | Available |
| Aug 22, 2026 | $531 | Available |
| Aug 23, 2026 | $414 | Available |
| Aug 24, 2026 | $372 | Available |
| Aug 25, 2026 | $368 | Available |
| Aug 26, 2026 | $372 | Available |
| Aug 27, 2026 | $416 | Not Available |
| Aug 28, 2026 | $536 | Not Available |
| Aug 29, 2026 | $552 | Not Available |
| Aug 30, 2026 | $503 | Not Available |
| Aug 31, 2026 | $340 | Available |
| Sep 1, 2026 | $319 | Available |
| Sep 2, 2026 | $320 | Available |
| Sep 3, 2026 | $361 | Available |
| Sep 4, 2026 | $411 | Available |
| Sep 5, 2026 | $395 | Available |
| Sep 6, 2026 | $334 | Available |
| Sep 7, 2026 | $256 | Available |
| Sep 8, 2026 | $250 | Available |
| Sep 9, 2026 | $251 | Available |
| Sep 10, 2026 | $272 | Available |
| Sep 11, 2026 | $312 | Available |
| Sep 12, 2026 | $316 | Available |
| Sep 13, 2026 | $273 | Available |
| Sep 14, 2026 | $251 | Available |
| Sep 15, 2026 | $250 | Available |
| Sep 16, 2026 | $251 | Available |