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Wander is the best of both worlds. The quality of a luxury hotel with the comfort of a private vacation home just for you and your guests.
Near East Hill Road in New Marlborough, Massachusetts, there are plenty of activities to enjoy in the heart of the Berkshires. Outdoor enthusiasts can explore nearby hiking trails, including those at Beartown State Forest, perfect for nature walks, birdwatching, and picnics.
New Marlborough, Massachusetts, United StatesAn inviting farm-to-table restaurant, offering seasonal, globally-inspired dishes plus craft cocktails in a casual setting with lawn games, bonfires, and community-style or private seating. Reservations may be booked through Resy. Open 5 PM - 9 PM, Thursday-Sunday; closed Monday-Wednesday.
An intimate, historic inn offering a prix fixe menu with seasonal, locally sourced dishes crafted by Chef Peter Platt along with an extensive wine list. Guests can dine by candlelight in cozy, restored rooms or enjoy the canopied garden terrace in warmer months. Reservations can be made through OpenTable. Open 5:30 PM - 9 PM, Wednesday-Sunday; closed Monday-Tuesday.
A classic steakhouse in Great Barrington serving American and French favorites with a focus on locally sourced, sustainable ingredients. Diners can relax in the inviting dining room or lively bar, featuring an extensive American whiskey selection and live jazz. Open 5 PM - 8:30 PM daily.
An all-sourdough bakery crafting hand-shaped, naturally fermented breads, croissants, and take-and-bake pizzas in European style. Founded by Richard Bourdon, the bakery is known for its delicious, digestible breads made with traditional techniques. Online orders are accepted through their website. Open 7 AM - 6 PM daily.
This supermarket chain has house-brand groceries and organics, plus deli and bakery counters. Open 7 AM - 10 PM every day except Sundays (closes 9 PM).
An American, family-owned supermarket chain throughout Massachusetts and Connecticut. Open 7 AM - 9 PM daily.
An inclusive, accessible store that sells local, sustainable, and organic grocery essentials. Open 8 AM - 7 PM daily.
For pantry staples, fresh produce, fresh fruit, meat and seafood, or household essentials. Open 7 AM - 11 PM daily.
A family-owned grocery store in the heart of the Berkshires. Open 9 AM - 7 PM daily, except Sundays (closes 6 PM).
A family-friendly ski resort with over 10 acres of runs, 11 lifts, and artificial snowmakers on all trails, offering skiing, snowboarding, and tubing. Its popular Tubing Center features up to 10 lanes, hundreds of tubes, a Magic Carpet Lift, and 100% snow-making coverage, making it a top destination for tubing in New England. Hours vary seasonally.
An elegant blend of formal and natural landscapes, this tranquil Berkshires destination features sculptures, winding paths, and serene garden rooms. Open from dawn to dusk daily.
An inviting family-owned winery, offering tastings in a cozy setting in New Marlborough. Named after the owners' granddaughters, the winery features a selection of wines crafted on-site.
Hire a local chef to provide a meal from your kitchen. Consult with concierge to discuss menu options and to make aware of any dietary restrictions.
Opened to the public in 1955, the Clark has built upon this extraordinary group of works to become one of the most beloved and respected art museums in the world, known for its intimate galleries and stunning natural environment.
A 300-seat theater built in 1883 with a proscenium stage for music shows & a New American bistro. You can check their website for their calendar.
Jacob's Pillow is a dance center, school and performance space located in Becket, Massachusetts, in the Berkshires. The facility also includes a professional school and extensive archives as well as year-round community programs.
The Mahaiwe Block, located in downtown Great Barrington, Massachusetts, is a commercial and theater building dating back to 1905. It houses smaller businesses and the Mahaiwe Performing Arts Center, the town's primary performance venue.
The Norman Rockwell Museum showcases the world's largest collection of original works by Norman Rockwell, celebrating American illustration. It highlights the impact of illustration art in shaping society and promotes values of kindness, respect, and social equity depicted in Rockwell's work.
The Mount, located in Lenox, Massachusetts, is a country house designed by American author Edith Wharton, who considered it her "first real home." Now a National Historic Landmark, the estate is open to the public and sits in the scenic Berkshires.
Founded in 1991, Blue Riders Stables is a non-profit organization focused on providing holistic horseback riding experiences. Their mission is to foster growth in both students and horses while prioritizing safety for all involved.
Enjoy farm-fresh ice cream or an artisanal cheese board at our picnic tables while watching our Jersey cows graze in the fields. Take a stroll around the property, visit the milking area, and soak in the beautiful views of the Berkshires.
Naumkeag is a 48-acre public garden and historic home located in the Berkshires, Massachusetts. Seasonal programs and hours vary, so visitors are encouraged to check the "Hours and Admissions" page, with pre-registration required for events and recommended for summer general admission.
Noble Heart Sanctuary, set on an 8-acre property with various buildings, a swimming pool, pond, and trails to the Umpachene River, is an ideal venue for weddings or special events. Conveniently located between New York City and Boston, it welcomes all visitors by appointment.
Windy Hill Farm is a diverse horticultural business serving Berkshire, Litchfield, and Columbia counties, featuring an apple orchard, blueberry field, specialty ornamental nursery stock, and a retail garden center. It also offers a Holiday Shop and a full-service landscape department.
Embark on the ultimate off-road adventure in the scenic landscapes of East Canaan, Connecticut, for an unforgettable thrill. It's the perfect way to cap off an incredible weekend with Backyard Adventures.
This 12,000-acre forest offers a perfect escape year-round. Enjoy swimming, boating, or fishing at Benedict Pond in warmer months, and cross-country skiing or snowmobiling in the winter.
The Berkshire Botanical Garden, located on 15 acres in Stockbridge, Massachusetts, is home to over 3,000 species and varieties of plants. The garden focuses on showcasing plants that thrive in the unique climate of the Berkshires.
Campbell Falls is one of Massachusetts' top waterfalls, offering a stunning sight with its zigzagging plunge through a gorge. The short, easy hike makes it an ideal spot for both visiting and photographing.
Haystack Mountain State Park in Norfolk, Connecticut, features a twisting road and a rugged trail that lead to a 34-foot stone tower at the summit. The peak offers stunning views of the Berkshires, New York, and Vermont, with fall foliage and summer mountain laurel enhancing the experience.
Here you'll find three short trails, each less than three miles, offering a picturesque introduction to the mountain’s striking pale quartzite formations. Along these routes, you'll be treated to breathtaking views of Mount Greylock and the distant Catskill Mountains.
Mount Everett State Reservation, located in the towns of Mount Washington and Sheffield, Massachusetts, offers stunning panoramic views from the 2,624-foot summit of Mount Everett. From the top, you can enjoy vistas stretching across Massachusetts, Connecticut, and New York.
Mt. Washington State Forest's re-grown red oak northern hardwood forest features over 30 miles of trails for hiking and mountain biking. Hike the South Taconic Trail to the 2,250-foot summit of Alander Mountain for breathtaking panoramic views.
The Land Trust trailhead serves as a key entry point into Cookson State Forest, offering a variety of hikes ranging from easy to challenging. Explore diverse trails suited to different skill levels and experience the natural beauty of the forest.
York Lake, one of five sister lakes in the state forest, offers a sandy beach, grassy play area, and convenient changing and bathroom facilities. Shady picnic areas with grills make it a perfect spot for a relaxing day outdoors.
Berkshire Hills Country Club in Pittsfield, Massachusetts, is the only original A.W. Tillinghast-designed golf course in the state. With a meticulously groomed 18-hole course, a large swimming pool, panoramic Berkshire views, and year-round dining at the Members Tavern, it’s a top choice for families, voted "Best of the Berkshires" in 2016.
At the world-renowned Canyon Ranch in Lenox, MA, indulge in exceptional spa and beauty services, ranging from integrative massage to transformative skincare. Lenox Spa Day passes are available for $350 and can be redeemed Monday through Thursday.
Miraval Berkshires Resort and Spa is an award-winning wellness destination focused on fostering balance in life. Offering a device-free environment, it features a wide range of activities including meditation, creative expression, water activities, Pilates, and cuisine classes to help guests fully engage with their surroundings.
Quarry View Golf Course offers a distinctive experience, combining the feel of two different types of courses. Each hole features fairways lined with fescue reminiscent of a links course, while the surrounding woods provide the charm of a classic New England setting.
Located in the heart of downtown Stockbridge at 7 South Street, across from the historic Red Lion Inn, the Seven Salon Spa is your premier destination for exceptional haircare, skincare, and bodywork. Discover their specialty massages, including Hot Stones, Reflexology, and CranioSacral, alongside a full range of standard spa treatments.
The 18-hole "Wyantenuck" course at Wyantenuck Country Club in Great Barrington, Massachusetts spans 6,403 yards from the longest tees, with a par of 72. The course has a rating of 70.6 and a slope rating of 120, featuring well-maintained Bent grass fairways.
Bousquet Mountain is the premier ski resort in the Berkshires, offering family-friendly skiing, snow tubing, dining, and lodging, with a shared Summit pass for Berkshire East and Catamount Ski Area. With over 100 tubes, group lanes, and 100% snow-making coverage, it's perfect for snow tubing and fun family activities, even when there's no snow at home.
Catamount Mountain Resort is a four-season destination located on the New York-Massachusetts border, just 2.5 hours from NYC and easily accessible to Western Massachusetts, Connecticut, and the Hudson Valley. Known for its diverse terrain suited for all skiing and snowboarding levels, Catamount also offers activities like the longest zipline in North America and one of New England’s largest aerial adventure parks during the warmer months.
An idyllic spot in New Marlborough, featuring scenic waterfalls, picnic areas, and shallow pools for wading. It’s a perfect place for a peaceful afternoon in nature, with easy trails and relaxing views. Open from dawn to dusk daily.
Here are some things which you should know before booking Wander Berkshires Retreat
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Oct 15, 2025 | $3265 | Not Available |
| Oct 16, 2025 | $3265 | Not Available |
| Oct 17, 2025 | $3564 | Not Available |
| Oct 18, 2025 | $3564 | Not Available |
| Oct 19, 2025 | $2995 | Available |
| Oct 20, 2025 | $2995 | Available |
| Oct 21, 2025 | $2995 | Available |
| Oct 22, 2025 | $2995 | Available |
| Oct 23, 2025 | $2995 | Available |
| Oct 24, 2025 | $3564 | Not Available |
| Oct 25, 2025 | $3564 | Not Available |
| Oct 26, 2025 | $3265 | Not Available |
| Oct 27, 2025 | $3265 | Not Available |
| Oct 28, 2025 | $3265 | Not Available |
| Oct 29, 2025 | $3265 | Not Available |
| Oct 30, 2025 | $3265 | Not Available |
| Oct 31, 2025 | $3564 | Not Available |
| Nov 1, 2025 | $3474 | Available |
| Nov 2, 2025 | $3175 | Available |
| Nov 3, 2025 | $3175 | Available |
| Nov 4, 2025 | $3175 | Available |
| Nov 5, 2025 | $3175 | Available |
| Nov 6, 2025 | $3175 | Available |
| Nov 7, 2025 | $3474 | Available |
| Nov 8, 2025 | $3474 | Available |
| Nov 9, 2025 | $3175 | Available |
| Nov 10, 2025 | $3175 | Available |
| Nov 11, 2025 | $3175 | Available |
| Nov 12, 2025 | $3175 | Available |
| Nov 13, 2025 | $3175 | Available |
| Nov 14, 2025 | $3474 | Not Available |
| Nov 15, 2025 | $3474 | Not Available |
| Nov 16, 2025 | $2995 | Available |
| Nov 17, 2025 | $2995 | Available |
| Nov 18, 2025 | $2995 | Available |
| Nov 19, 2025 | $3175 | Not Available |
| Nov 20, 2025 | $3175 | Not Available |
| Nov 21, 2025 | $4223 | Available |
| Nov 22, 2025 | $4223 | Available |
| Nov 23, 2025 | $4223 | Available |
| Nov 24, 2025 | $4223 | Available |
| Nov 25, 2025 | $4223 | Available |
| Nov 26, 2025 | $4500 | Not Available |
| Nov 27, 2025 | $4500 | Not Available |
| Nov 28, 2025 | $4500 | Not Available |
| Nov 29, 2025 | $4500 | Not Available |
| Nov 30, 2025 | $4223 | Available |
| Dec 1, 2025 | $2995 | Available |
| Dec 2, 2025 | $2995 | Available |
| Dec 3, 2025 | $2995 | Available |
| Dec 4, 2025 | $2995 | Available |
| Dec 5, 2025 | $3504 | Not Available |
| Dec 6, 2025 | $3504 | Not Available |
| Dec 7, 2025 | $3205 | Not Available |
| Dec 8, 2025 | $2995 | Available |
| Dec 9, 2025 | $2995 | Available |
| Dec 10, 2025 | $2995 | Available |
| Dec 11, 2025 | $3205 | Not Available |
| Dec 12, 2025 | $3504 | Not Available |
| Dec 13, 2025 | $3504 | Not Available |
| Dec 14, 2025 | $3205 | Not Available |
| Dec 15, 2025 | $3205 | Not Available |
| Dec 16, 2025 | $3205 | Available |
| Dec 17, 2025 | $3205 | Available |
| Dec 18, 2025 | $3205 | Available |
| Dec 19, 2025 | $3504 | Available |
| Dec 20, 2025 | $4500 | Available |
| Dec 21, 2025 | $4500 | Available |
| Dec 22, 2025 | $4500 | Available |
| Dec 23, 2025 | $4500 | Available |
| Dec 24, 2025 | $4500 | Available |
| Dec 25, 2025 | $4500 | Available |
| Dec 26, 2025 | $4500 | Available |
| Dec 27, 2025 | $4500 | Available |
| Dec 28, 2025 | $4500 | Available |
| Dec 29, 2025 | $4500 | Available |
| Dec 30, 2025 | $4500 | Available |
| Dec 31, 2025 | $4500 | Not Available |
| Jan 1, 2026 | $4500 | Not Available |
| Jan 2, 2026 | $4500 | Not Available |
| Jan 3, 2026 | $4500 | Available |
| Jan 4, 2026 | $3175 | Available |
| Jan 5, 2026 | $3175 | Available |
| Jan 6, 2026 | $3175 | Available |
| Jan 7, 2026 | $3175 | Available |
| Jan 8, 2026 | $3175 | Available |
| Jan 9, 2026 | $3474 | Available |
| Jan 10, 2026 | $3474 | Available |
| Jan 11, 2026 | $3175 | Available |
| Jan 12, 2026 | $3175 | Available |
| Jan 13, 2026 | $3175 | Available |
