•
54 reviews
Operated by a Wander partner
Trusted operators, vetted by Wander
Highland: Epic GB location: walk-to the Green River, fully fenced yard, with hot tub. 4 Bedroom, 2.5 baths, Sleeps 8 in beds, or 10 Max
Amenities: Main floor bedroom, AC throughout, attached garage, hot tub, fenced backyard, patio and deck seating with grill, umbrella, lovely gardens, fruit orchard (in season) direct access to a premier pet-friendly hike, cable internet, good cell service. Smart TV, wood stove (wood included) stainless appliances, gas range, freezer/fridge with filtered water and ice maker, dishwasher, microwave, drip coffee maker, toaster, blender. Washer/dryer and all linens included. Games, puzzles, and books, Delivered spotlessly clean! Pet Friendly, pet fees apply. No Smoking.
4 Bedrooms and 2.5 Bathrooms at a glance:
Main floor Queen bed in Guest room #4 (sleeps 2)
Main Floor: 1/2 bathroom, just off the kitchen.
Second Floor Primary with King bed, and full bathroom (ensuite) with double sinks, step in shower, and walk-in closet (Sleeps 2)
Second Floor: Guest room #2 has a queen bed (sleeps 2)
Second Floor: Guest room #3 has a Queen bed + queen fold out sofa bed (sleeps 4)
Second Floor Bathroom: Guest rooms #2 and #3 shared a full bathroom with tiled tub/shower
The Living Space: Simple Scandinavian features that are comforting and minimalist
Outside:
Location:
ADDITIONAL INFO:
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
Sara
•
May 2026
Kathy
•
December 2025
Catherine
•
September 2025
Great Barrington, MA 01230, 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.
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.
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]
Free cancellation up to 14 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 |
|---|---|---|
| Sep 2, 2026 | $525 | Not Available |
| Sep 3, 2026 | $525 | Not Available |
| Sep 4, 2026 | $525 | Not Available |
| Sep 5, 2026 | $525 | Not Available |
| Sep 6, 2026 | $525 | Not Available |
| Sep 7, 2026 | $525 | Not Available |
| Sep 8, 2026 | $490 | Not Available |
| Sep 9, 2026 | $490 | Not Available |
| Sep 10, 2026 | $490 | Available |
| Sep 11, 2026 | $490 | Available |
| Sep 12, 2026 | $490 | Available |
| Sep 13, 2026 | $490 | Available |
| Sep 14, 2026 | $490 | Available |
| Sep 15, 2026 | $490 | Available |
| Sep 16, 2026 | $490 | Available |
| Sep 17, 2026 | $490 | Available |
| Sep 18, 2026 | $490 | Available |
| Sep 19, 2026 | $490 | Available |
| Sep 20, 2026 | $490 | Available |
| Sep 21, 2026 | $490 | Available |
| Sep 22, 2026 | $490 | Available |
| Sep 23, 2026 | $490 | Available |
| Sep 24, 2026 | $490 | Available |
| Sep 25, 2026 | $490 | Not Available |
| Sep 26, 2026 | $490 | Not Available |
| Sep 27, 2026 | $490 | Available |
| Sep 28, 2026 | $490 | Available |
| Sep 29, 2026 | $490 | Available |
| Sep 30, 2026 | $490 | Available |
| Oct 1, 2026 | $490 | Available |
| Oct 2, 2026 | $490 | Available |
| Oct 3, 2026 | $490 | Available |
| Oct 4, 2026 | $490 | Available |
| Oct 5, 2026 | $490 | Available |
| Oct 6, 2026 | $490 | Available |
| Oct 7, 2026 | $490 | Available |
| Oct 8, 2026 | $490 | Not Available |
| Oct 9, 2026 | $490 | Not Available |
| Oct 10, 2026 | $490 | Not Available |
| Oct 11, 2026 | $490 | Available |
| Oct 12, 2026 | $490 | Available |
| Oct 13, 2026 | $490 | Available |
| Oct 14, 2026 | $490 | Available |
| Oct 15, 2026 | $490 | Available |
| Oct 16, 2026 | $490 | Not Available |
| Oct 17, 2026 | $490 | Not Available |
| Oct 18, 2026 | $490 | Available |
| Oct 19, 2026 | $490 | Available |
| Oct 20, 2026 | $490 | Available |
| Oct 21, 2026 | $490 | Available |
| Oct 22, 2026 | $490 | Available |
| Oct 23, 2026 | $490 | Not Available |
| Oct 24, 2026 | $490 | Not Available |
| Oct 25, 2026 | $395 | Available |
| Oct 26, 2026 | $395 | Available |
| Oct 27, 2026 | $395 | Available |
| Oct 28, 2026 | $395 | Available |
| Oct 29, 2026 | $395 | Available |
| Oct 30, 2026 | $395 | Available |
| Oct 31, 2026 | $395 | Available |
| Nov 1, 2026 | $395 | Available |
| Nov 2, 2026 | $395 | Available |
| Nov 3, 2026 | $395 | Available |
| Nov 4, 2026 | $395 | Available |
| Nov 5, 2026 | $395 | Available |
| Nov 6, 2026 | $395 | Available |
| Nov 7, 2026 | $395 | Available |
| Nov 8, 2026 | $395 | Available |
| Nov 9, 2026 | $395 | Available |
| Nov 10, 2026 | $395 | Available |
| Nov 11, 2026 | $395 | Available |
| Nov 12, 2026 | $395 | Available |
| Nov 13, 2026 | $395 | Available |
| Nov 14, 2026 | $395 | Available |
| Nov 15, 2026 | $395 | Available |
| Nov 16, 2026 | $395 | Not Available |
| Nov 17, 2026 | $395 | Not Available |
| Nov 18, 2026 | $395 | Not Available |
| Nov 19, 2026 | $395 | Not Available |
| Nov 20, 2026 | $395 | Not Available |
| Nov 21, 2026 | $395 | Not Available |
| Nov 22, 2026 | $500 | Not Available |
| Nov 23, 2026 | $500 | Available |
| Nov 24, 2026 | $500 | Not Available |
| Nov 25, 2026 | $500 | Not Available |
| Nov 26, 2026 | $500 | Not Available |
| Nov 27, 2026 | $500 | Not Available |
| Nov 28, 2026 | $500 | Available |
| Nov 29, 2026 | $395 | Available |
| Nov 30, 2026 | $395 | Available |
| Dec 1, 2026 | $395 | Available |