Wander Berkshires Highlands
Saved to wishlist
12 guests
7 beds
3 bathrooms
Hot tub•Forest view•Game Room
12 guests
6 bedrooms
7 beds
3 bathrooms
2900 sq. ft.
Wander Berkshires Highlands is a peaceful mountain retreat set on four acres of rolling countryside, just minutes from skiing at Catamount and the vibrant dining scene of Great Barrington.
The Wander Guarantee
Book with confidence. Read more.
Check-in & out
Check-in after 4:00pm • Check-out before 10:00am • Dogs allowed
Easy cancellation
Cancel within 24 hours for a full refund.
Pristine homes, no to-do lists
Arrive to five star cleaning • No chores at checkout • Just lock up and go
About the property
Hotel-grade amenities
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.
Common Amenities
- Patio
- Free parking
- Long term stays allowed
- Hot tub
- Forest view
- Game Room
- Wifi
- Carbon monoxide detector
- Hot water
- Fire extinguisher
- Balcony
- First aid kit
- Air conditioning
- Smoke detector
Patio
- Outdoor seating
- BBQ Area
- BBQ Utensils
Living Room
- TV
- Fire place
Dining Room
- Dining table
Kitchen
- Oven
- Cooking basics
- Stove
- Microwave
- Freezer
- Fridge
- Dishwasher
- Dishes
- Coffee maker
- Coffee
- Kettle
- Tea
- Spices
- Silverware
- Cleaning supplies
- Wine glasses
Game Room
- TV
- Ping pong table
Bedroom 1
- Bed linens
- TV
- Closet
- Hangers
Ensuite Bathroom 1
- Shower
- Bathtub
- Shampoo
- Bath linens
- Toilet
- Shower gel
- Body soap
- Ensuite bathroom
- Conditioner
Bedroom 2
- Bed linens
- TV
- Closet
- Hangers
Ensuite Bathroom 2
- Ensuite bathroom
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Bedroom 3
- Bed linens
- TV
- Closet
- Hangers
Bedroom 4
- TV
- Closet
- Hangers
- Bed linens
Bedroom 5
- TV
- Closet
- Hangers
- Bed linens
Bedroom 6
- Bed linens
- TV
- Closet
- Hangers
Bathroom
- Bath linens
- Toilet
- Shower
- Shower gel
- Shampoo
- Conditioner
- Body soap
Laundry Room
- Washer
- Dryer
- Cleaning supplies
- Extra pillows
- Extra blankets
- Iron
Where you’ll sleep
Where you’ll be
Surrounded by the natural beauty of the Berkshires, this home offers easy access to the best of Western Massachusetts. Spend your days skiing or hiking at nearby Catamount Mountain, exploring the charming shops and art galleries of Great Barrington, or discovering local treasures like Bash Bish Falls and the Mahaiwe Performing Arts Center.
Restaurants
Hy's Fried
Hy's Fried serves addictive, hormone-free fried chicken with a crispy, sweet-savory crust in a vibrant, cozy space that turns into a lively dance club on weekends. Most dishes are gluten-free, making it a unique community hub with great food and fun vibes.
The Well Restaurant + Bar
The Well Restaurant + Bar offers a cozy atmosphere with a diverse menu featuring classic American cuisine made from quality ingredients, perfect for a relaxed dining experience. Guests enjoy its welcoming vibe and flavorful dishes.
Little Cat Lodge
Little Cat Lodge offers a cozy alpine-inspired retreat at the foot of Catamount, featuring seasonal, locally inspired dishes and a warm, rustic ambiance perfect for relaxing after a day on the slopes. Its inviting tavern and expansive terrace create a charming mountain getaway.
Bizen Gourmet Japanese Restaurant and Sushi Bar
Bizen Gourmet Japanese Restaurant and Sushi Bar offers fresh, vibrant Japanese cuisine with standout sushi and authentic dishes in a cozy, inviting atmosphere perfect for an intimate or casual meal. Its blend of traditional flavors and thoughtful presentation makes it a local favorite in Great Barrington.
GB Eats
GB Eats offers a vibrant dining experience with creative American cuisine, featuring locally sourced ingredients and a warm ambiance. This Great Barrington spot serves breakfast all day, with options for vegetarians, vegans, and gluten-free diners.
The Prairie Whale
The Prairie Whale in Great Barrington blends rustic Berkshire charm with Brooklyn-inspired flair, serving ever-changing farm-to-table dishes crafted from local produce and house-butchered meats in a cozy, reclaimed-wood setting—think candlelit comfort indoors and lively outdoor seating when the weather’s right.
Fuel Coffee
Fuel Coffee offers a cozy atmosphere with quality coffee and a variety of pastries, often blending a library-like setting with a vibrant coffee culture. The unique ambiance and delicious offerings make it a charming spot for both coffee and book lovers.
Roe Jan Brewing Co.
Roe Jan Brewing Co. in Hillsdale offers a warm, inviting brewpub experience with craft beers, a wood-fired open kitchen serving fresh, seasonal dishes, and a lively atmosphere enhanced by live music and spacious indoor and outdoor seating.
Twisted Sisters Coffee House
Twisted Sisters Coffee House offers expertly brewed specialty coffees, fresh-baked pastries, and a cozy, welcoming atmosphere perfect for relaxing or catching up with friends in a charming historic setting.
Heirloom Lodge
Heirloom Lodge offers a refined farm-to-table dining experience in a sleek lodge setting, featuring locally sourced seasonal dishes paired with exceptional wines from family-run vineyards. Its open kitchen and elegant simplicity create a warm, inviting atmosphere perfect for savoring the Berkshires' finest flavors.
Attractions
French Park
French Park offers a vibrant playground, scenic lake activities, and trails, making it perfect for families and outdoor enthusiasts. Its creative play area and beautiful surroundings ensure a fun-filled day for all ages.
River Walk
The San Antonio River Walk offers a vibrant mix of scenic strolls, lively dining, rich history, and unique cultural attractions, perfect for explorers, food lovers, and families seeking a memorable urban adventure along a beautiful 15-mile waterway.
Catamount Aerial Adventure Park
Catamount Aerial Adventure Park offers thrilling ropes courses and zip lines set high in the trees, perfect for adventurers aged 7 and up seeking a fun, active challenge in a beautiful forest setting. It’s ideal for families, friends, and groups of all skill levels.
Catamount Mountain Resort
Catamount Mountain Resort offers year-round adventure with thrilling ziplines, one of the largest aerial parks in New England, and scenic chairlift rides—perfect for families, thrill-seekers, and anyone looking to enjoy the outdoors on both sides of the New York–Massachusetts border.
Monument Mountain Reservation
Monument Mountain Reservation offers a steep but rewarding hike with stunning 360-degree views from its 1,642-foot summit, perfect for adventurous hikers who enjoy rocky trails, scenic overlooks, and a touch of local history and wildlife. Ideal for those seeking both challenge and natural beauty.
Guthrie Center
The Guthrie Center offers a unique blend of cultural, educational, and spiritual experiences, perfect for those seeking community and artistic expression. It's ideal for music enthusiasts and history buffs looking for a meaningful connection.
Lake Mansfield Beach and Conservation Forest Trails
Lake Mansfield Beach and Conservation Forest Trails offer a refreshing escape with swimming, shaded walking paths, and peaceful picnicking—perfect for families, nature lovers, and anyone seeking a relaxing day by the water or a gentle stroll through the woods.
Roeliff Jansen Park
Roeliff Jansen Park offers peaceful trails, a dog run, a community garden, and a lively farmers market, making it perfect for families, nature lovers, and anyone seeking outdoor fun and local culture in a scenic setting. Kids enjoy activity packs and live music on market days.
Jug End State Reservation
Jug End State Reservation offers a peaceful 3-4 mile loop through scenic Berkshires meadows and forests, perfect for families and nature lovers seeking wildlife, wildflowers, and stunning mountain views. It’s ideal for hiking, picnicking, and connecting with the Appalachian Trail.
Monument Mountain Reservation Parking
Monument Mountain Reservation offers a short but steep hike through lush forests and dramatic rock ledges, rewarding you with sweeping views of the Berkshires—perfect for adventurous hikers seeking a quick challenge and anyone who loves panoramic mountain vistas. Families, nature lovers, and history buffs will all find something memorable here.
Select dates in Wander Berkshires Highlands
Choose your check-in & check-out dates
5
based on 4 reviews
Guests love the home for its relaxing hot tub, sauna and lively game room with ping pong. They praise the peaceful woodland location yet easy access to downtown and outdoor activities. Visitors also note sparkling cleanliness, thoughtful host communication and roomy, comfortable layout.
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Things to know
Here are some things which you should know before booking Wander Berkshires Highlands
Check-in: after 4:00 pm
Check-out: before 10:00 am
12 guests maximum
Dogs allowed
No smoking - fees will apply
Events require approval
Cancel within 24 hours for a full refund.
Check-in: after 4:00 pm
Check-out: before 10:00 am
12 guests maximum
Dogs allowed
No smoking - fees will apply
Events require approval
Before you book
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Feb 3, 2026 | $387 | Available |
| Feb 4, 2026 | $399 | Available |
| Feb 5, 2026 | $420 | Available |
| Feb 6, 2026 | $511 | Not Available |
| Feb 7, 2026 | $516 | Not Available |
| Feb 8, 2026 | $452 | Available |
| Feb 9, 2026 | $397 | Available |
| Feb 10, 2026 | $430 | Available |
| Feb 11, 2026 | $445 | Not Available |
| Feb 12, 2026 | $518 | Not Available |
| Feb 13, 2026 | $786 | Not Available |
| Feb 14, 2026 | $871 | Not Available |
| Feb 15, 2026 | $828 | Not Available |
| Feb 16, 2026 | $765 | Not Available |
| Feb 17, 2026 | $662 | Not Available |
| Feb 18, 2026 | $640 | Not Available |
| Feb 19, 2026 | $699 | Not Available |
| Feb 20, 2026 | $814 | Not Available |
| Feb 21, 2026 | $802 | Not Available |
| Feb 22, 2026 | $584 | Not Available |
| Feb 23, 2026 | $418 | Available |
| Feb 24, 2026 | $417 | Available |
| Feb 25, 2026 | $523 | Available |
| Feb 26, 2026 | $570 | Not Available |
| Feb 27, 2026 | $781 | Not Available |
| Feb 28, 2026 | $804 | Not Available |
| Mar 1, 2026 | $550 | Not Available |
| Mar 2, 2026 | $511 | Available |
| Mar 3, 2026 | $409 | Available |
| Mar 4, 2026 | $395 | Available |
| Mar 5, 2026 | $542 | Available |
| Mar 6, 2026 | $747 | Not Available |
| Mar 7, 2026 | $762 | Not Available |
| Mar 8, 2026 | $558 | Not Available |
| Mar 9, 2026 | $533 | Available |
| Mar 10, 2026 | $416 | Available |
| Mar 11, 2026 | $524 | Available |
| Mar 12, 2026 | $564 | Not Available |
| Mar 13, 2026 | $747 | Not Available |
| Mar 14, 2026 | $757 | Not Available |
| Mar 15, 2026 | $646 | Not Available |
| Mar 16, 2026 | $654 | Available |
| Mar 17, 2026 | $540 | Available |
| Mar 18, 2026 | $560 | Available |
| Mar 19, 2026 | $602 | Available |
| Mar 20, 2026 | $887 | Available |
| Mar 21, 2026 | $903 | Available |
| Mar 22, 2026 | $587 | Available |
| Mar 23, 2026 | $528 | Available |
| Mar 24, 2026 | $520 | Available |
| Mar 25, 2026 | $520 | Available |
| Mar 26, 2026 | $565 | Not Available |
| Mar 27, 2026 | $805 | Not Available |
| Mar 28, 2026 | $823 | Not Available |
| Mar 29, 2026 | $567 | Not Available |
| Mar 30, 2026 | $518 | Available |
| Mar 31, 2026 | $486 | Available |
| Apr 1, 2026 | $486 | Available |
| Apr 2, 2026 | $584 | Available |
| Apr 3, 2026 | $847 | Available |
| Apr 4, 2026 | $847 | Available |
| Apr 5, 2026 | $615 | Available |
| Apr 6, 2026 | $546 | Available |
| Apr 7, 2026 | $604 | Available |
| Apr 8, 2026 | $604 | Available |
| Apr 9, 2026 | $654 | Available |
| Apr 10, 2026 | $913 | Available |
| Apr 11, 2026 | $923 | Available |
| Apr 12, 2026 | $699 | Available |
| Apr 13, 2026 | $547 | Available |
| Apr 14, 2026 | $502 | Available |
| Apr 15, 2026 | $482 | Available |
| Apr 16, 2026 | $554 | Available |
| Apr 17, 2026 | $809 | Available |
| Apr 18, 2026 | $808 | Available |
| Apr 19, 2026 | $659 | Available |
| Apr 20, 2026 | $544 | Available |
| Apr 21, 2026 | $496 | Available |
| Apr 22, 2026 | $521 | Available |
| Apr 23, 2026 | $854 | Not Available |
| Apr 24, 2026 | $854 | Not Available |
| Apr 25, 2026 | $854 | Not Available |
| Apr 26, 2026 | $600 | Not Available |
| Apr 27, 2026 | $538 | Available |
| Apr 28, 2026 | $522 | Available |
| Apr 29, 2026 | $536 | Available |
| Apr 30, 2026 | $582 | Available |
| May 1, 2026 | $1260 | Available |
| May 2, 2026 | $1267 | Available |
| May 3, 2026 | $890 | Available |
| May 4, 2026 | $690 | Available |