Operated by a Wander partner
Trusted operators, vetted by Wander
Highland Amenities: 4 Bedrooms, 2.5 baths, Sleeps 10. Pet friendly with a fully fenced yard (pet fees apply), hot tub (year round) propane grill, outdoor seating w/ sun umbrella on patio + chaises for sun deck, lovely gardens, high speed internet, mini split AC, ice maker, wood stove (wood included), Smart TV, washer/dryer, games, all linens included, attached garage. Gate access to McAllister Park for hiking and swimming and close to Lake Mansfield, Butternut, GB Busking in Summer! No Smoking.
Bedroom 1
1 king bed
Bedroom 2
1 queen bed
Bedroom 3
1 queen bed
Bedroom 4
1 queen bed
Bedroom 1
1 king bed
Bedroom 2
1 queen bed
Bedroom 3
1 queen bed
Bedroom 4
1 queen bed
Great Barrington, MA 1230, US
Great Barrington, MA, USThe Bistro Box is a charming roadside drive-in in Great Barrington, MA, serving classic American shack fare like juicy burgers, hand-cut truffle fries, and pressed Cubanos with modern, homemade twists. Enjoy fresh picnic eats at umbrella-shaded tables in a scenic field, perfect for summer vibes.
Discover Barrington Brewery & Restaurant, a solar-powered Berkshire gem brewing fresh ales since 1995 amid rustic converted barns. Savor scratch-made American pub fare like beer-infused Cheddar Ale Soup and Chocolate Stout Cake, paired with local ingredients and vibrant brews.[1][2][3][4]
Nestled in Great Barrington, The Prairie Whale blends Brooklyn flair with Berkshire farm-to-table magic in a cozy, reclaimed-wood space. Savor ever-changing dishes from on-site produce and nose-to-tail meats, perfect for a rustic, flavorful escape.[1][2][5]
Great Barrington Bagel is an authentic New York-style bagel shop that has been crafting fresh, chewy bagels daily since 1996, complemented by 17 cream cheese flavors, smoked fish specialties, and homemade soups in a welcoming deli atmosphere.
No Comply Foods is a skate-punk-inspired restaurant in Great Barrington serving globally influenced, seasonally sourced comfort food with a daily-changing menu, zero alcohol, no tipping, and a refreshingly DIY ethos that prioritizes community and culinary creativity over traditional restaurant conventions.
Perched dramatically atop Bald Head Cliff, The Tiller Restaurant at Cliff House Maine delivers immersive coastal cuisine with fresh lobster, local seafood, and inventive dishes like bacon-habanero jam burgers, all while offering breathtaking ocean views.
Marketplace Kitchen Table is a welcoming, cafeteria-style restaurant in Great Barrington that serves creative, made-from-scratch American cuisine with globally inspired flavors, from gourmet sandwiches and burgers to fresh salads and housemade pastries, all prepared daily in their Sheffield kitchen.
Nestled in South Egremont, Hy's Fried serves addictive, gluten-free fried chicken with a crisp tapioca crust, juicy free-range meat, and hot honey sambal kick—blending Southern and Korean vibes. This vivid red roadhouse turns into a raucous dance party after dinner.
Discover Ski Butternut, a family-friendly gem in the Berkshires with 22 groomed trails for all levels, thrilling terrain parks, and tubing fun amid stunning mountain views. Perfect for beginners building confidence, experts seeking challenges, and families craving affordable, uncompetitive winter adventures.
Conquer the steep trails of Monument Mountain Reservation to reach its 1,642-foot summit, where breathtaking views of the Housatonic Valley, eagles soaring overhead, and dramatic cliffs like Devil's Pulpit await. Nature lovers and adventure seekers craving a rewarding hike with history and wildlife will love it.[1][2][6]
Discover Thom Reed UFO Park, site of America's first officially recognized UFO encounter in 1969, validated by Massachusetts' historical society and governor with a monumental plaque near a scenic covered bridge. UFO enthusiasts and mystery seekers will love this quirky, historically endorsed hotspot.[1][3][5]
Lake Mansfield offers a perfect blend of water recreation and nature exploration, with a pristine sandy beach for swimming and paddling alongside easy, accessible forest trails ideal for families and wildlife enthusiasts seeking a serene Berkshire escape.
Soar through New England's largest aerial adventure park at Catamount Mountain Resort, tackling 9 treetop courses with bridges, ladders, obstacles, and thrilling zip lines. Perfect for thrill-seekers, families, and groups of all skill levels seeking an exhilarating tree canopy escape.
Discover serene Benedict Pond at Beartown State Forest, where you can kayak, fish, or hike the Appalachian Trail amid deer, bears, and stunning ledges views. Nature lovers and outdoor adventurers will relish this tranquil Massachusetts escape.[1][3][4][5]
Soar through New England's largest aerial adventure park at Catamount, tackling 9 treetop courses with over 150 ziplines, bridges, and obstacles for all skill levels. Thrill-seekers, families, and first-timers will love the safe, exhilarating 3-hour challenge under the forest canopy.[1][3][4]
The San Antonio River Walk is a stunning 15-mile urban waterway offering something for everyone—from leisurely boat cruises and world-class dining to vibrant arts, historic landmarks, and outdoor adventures. Whether you're seeking culture, relaxation, or family fun, this iconic destination delivers unforgettable experiences around every bend.
50% refund up to 30 days before check-in. No refund after that.
Pets allowed with fee
No smoking - fees will apply
Events not allowed
Check-in after 3:00 pm
Check-out before 11:00 am
10 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jul 13, 2026 | $433 | Not Available |
| Jul 14, 2026 | $433 | Not Available |
| Jul 15, 2026 | $433 | Not Available |
| Jul 16, 2026 | $433 | Not Available |
| Jul 17, 2026 | $433 | Not Available |
| Jul 18, 2026 | $433 | Not Available |
| Jul 19, 2026 | $433 | Not Available |
| Jul 20, 2026 | $433 | Not Available |
| Jul 21, 2026 | $433 | Not Available |
| Jul 22, 2026 | $433 | Not Available |
| Jul 23, 2026 | $433 | Not Available |
| Jul 24, 2026 | $433 | Not Available |
| Jul 25, 2026 | $433 | Not Available |
| Jul 26, 2026 | $433 | Not Available |
| Jul 27, 2026 | $433 | Not Available |
| Jul 28, 2026 | $433 | Not Available |
| Jul 29, 2026 | $433 | Not Available |
| Jul 30, 2026 | $433 | Not Available |
| Jul 31, 2026 | $433 | Not Available |
| Aug 1, 2026 | $433 | Not Available |
| Aug 2, 2026 | $433 | Not Available |
| Aug 3, 2026 | $433 | Not Available |
| Aug 4, 2026 | $433 | Not Available |
| Aug 5, 2026 | $433 | Not Available |
| Aug 6, 2026 | $433 | Not Available |
| Aug 7, 2026 | $433 | Not Available |
| Aug 8, 2026 | $433 | Not Available |
| Aug 9, 2026 | $433 | Not Available |
| Aug 10, 2026 | $433 | Not Available |
| Aug 11, 2026 | $433 | Not Available |
| Aug 12, 2026 | $433 | Not Available |
| Aug 13, 2026 | $433 | Not Available |
| Aug 14, 2026 | $433 | Not Available |
| Aug 15, 2026 | $433 | Not Available |
| Aug 16, 2026 | $433 | Not Available |
| Aug 17, 2026 | $433 | Not Available |
| Aug 18, 2026 | $433 | Not Available |
| Aug 19, 2026 | $433 | Not Available |
| Aug 20, 2026 | $433 | Not Available |
| Aug 21, 2026 | $433 | Not Available |
| Aug 22, 2026 | $433 | Not Available |
| Aug 23, 2026 | $433 | Not Available |
| Aug 24, 2026 | $433 | Not Available |
| Aug 25, 2026 | $433 | Not Available |
| Aug 26, 2026 | $433 | Not Available |
| Aug 27, 2026 | $433 | Not Available |
| Aug 28, 2026 | $433 | Not Available |
| Aug 29, 2026 | $433 | Not Available |
| Aug 30, 2026 | $433 | Not Available |
| Aug 31, 2026 | $433 | Not Available |
| Sep 1, 2026 | $575 | Not Available |
| Sep 2, 2026 | $575 | Not Available |
| Sep 3, 2026 | $575 | Not Available |
| Sep 4, 2026 | $575 | Not Available |
| Sep 5, 2026 | $575 | Not Available |
| Sep 6, 2026 | $575 | Not Available |
| Sep 7, 2026 | $575 | Not Available |
| Sep 8, 2026 | $475 | Not Available |
| Sep 9, 2026 | $475 | Not Available |
| Sep 10, 2026 | $475 | Available |
| Sep 11, 2026 | $475 | Available |
| Sep 12, 2026 | $475 | Available |
| Sep 13, 2026 | $475 | Available |
| Sep 14, 2026 | $475 | Available |
| Sep 15, 2026 | $475 | Available |
| Sep 16, 2026 | $475 | Available |
| Sep 17, 2026 | $475 | Available |
| Sep 18, 2026 | $475 | Available |
| Sep 19, 2026 | $475 | Available |
| Sep 20, 2026 | $475 | Available |
| Sep 21, 2026 | $475 | Available |
| Sep 22, 2026 | $475 | Available |
| Sep 23, 2026 | $475 | Available |
| Sep 24, 2026 | $475 | Available |
| Sep 25, 2026 | $475 | Available |
| Sep 26, 2026 | $475 | Available |
| Sep 27, 2026 | $475 | Available |
| Sep 28, 2026 | $475 | Available |
| Sep 29, 2026 | $475 | Available |
| Sep 30, 2026 | $475 | Available |
| Oct 1, 2026 | $475 | Available |
| Oct 2, 2026 | $475 | Available |
| Oct 3, 2026 | $475 | Available |
| Oct 4, 2026 | $475 | Available |
| Oct 5, 2026 | $475 | Available |
| Oct 6, 2026 | $475 | Available |
| Oct 7, 2026 | $475 | Available |
| Oct 8, 2026 | $475 | Available |
| Oct 9, 2026 | $500 | Available |
| Oct 10, 2026 | $500 | Available |
| Oct 11, 2026 | $500 | Available |