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Berkshires Highlands
Great Barrington, Massachusetts

Wander Berkshires Highlands

Wander Berkshires Highlands

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12 guests
7 beds
3 bathrooms
1/32
PropertyFull kitchenLarge TV
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.
Flexible check-in & out
Check-in after 4:00pm • Check-out before 10:00amNo pets 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

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. Newly renovated and thoughtfully designed, this spacious home features a grand great room with a cozy fireplace and TV, a welcoming basement game and media room, and a large deck overlooking the scenic grounds. Unwind in the soothing hot tub after a day of adventure or gather with loved ones in one of the beautifully appointed bedrooms spread across two floors, offering space and comfort for the entire family.

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

  • Ping pong table
  • TV

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
  • Shower
  • Shower gel
  • Shampoo
  • Bath linens
  • Toilet
  • Conditioner
  • Body soap

Bedroom 3

  • Bed linens
  • TV
  • Closet
  • Hangers

Bedroom 4

  • Bed linens
  • TV
  • Closet
  • Hangers

Bedroom 5

  • TV
  • Bed linens
  • Closet
  • Hangers

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

Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 queen bed
Bedroom 5
1 queen bed
Bedroom 6
2 full beds
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
1 queen bed
Bedroom 5
1 queen bed
Bedroom 6
2 full beds

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.
Great Barrington, Massachusetts, United States
42.2158641-73.4472783
Timezone: America/New_York

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.

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Guests love this place

Guests love the Property, Full kitchen, Large TV and more.
For group vacations, Wander hits all the right notes. Their rentals provide the perfect blend of communal areas for socializing and private spaces for downtime. The high-end finishes and attentive service make these trips feel like a real treat without losing that homey feel.
David from Salt Lake City, UT
David from Salt Lake City, UT
Stayed in Oct 2025
What we like about Wander is the variety of properties they offer. Whether we're looking for a beach house, a mountain cabin, or a downtown house, they seem to have options. The booking process is straightforward, and we've found their customer service to be helpful when we've had questions.
Jennifer from Sacramento, CA
Jennifer from Sacramento, CA
Stayed in Oct 2025
Staying with Wander was an absolute delight. The combination of luxury hotel service and the comfort of a vacation home was unparalleled. The 24/7 concierge service was a game-changer, ensuring every need was met promptly. Highly recommend!
David from New York, NY
David from New York, NY
Stayed in Oct 2025

Have a question?

24/7 Concierge
Talk with the concierge to ask any question you might have
Chat with Concierge
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Things to know

Here are some things which you should know before booking Wander Berkshires Highlands
HOUSE RULES
Check-in: after 4:00 pm
Check-out: before 10:00 am
12 guests maximum
No pets allowed
No smoking - fees will apply
Events require approval
CANCELLATION POLICY
Cancel within 24 hours for a full refund.

Before you book

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Oct 22, 2025$427Available
Oct 23, 2025$475Not Available
Oct 24, 2025$572Not Available
Oct 25, 2025$589Not Available
Oct 26, 2025$484Not Available
Oct 27, 2025$474Available
Oct 28, 2025$447Available
Oct 29, 2025$443Available
Oct 30, 2025$514Available
Oct 31, 2025$625Not Available
Nov 1, 2025$627Not Available
Nov 2, 2025$539Not Available
Nov 3, 2025$443Available
Nov 4, 2025$435Available
Nov 5, 2025$550Available
Nov 6, 2025$629Not Available
Nov 7, 2025$805Not Available
Nov 8, 2025$806Not Available
Nov 9, 2025$631Available
Nov 10, 2025$592Available
Nov 11, 2025$557Available
Nov 12, 2025$556Available
Nov 13, 2025$593Available
Nov 14, 2025$748Not Available
Nov 15, 2025$759Not Available
Nov 16, 2025$594Not Available
Nov 17, 2025$561Not Available
Nov 18, 2025$546Not Available
Nov 19, 2025$547Not Available
Nov 20, 2025$584Not Available
Nov 21, 2025$647Not Available
Nov 22, 2025$664Not Available
Nov 23, 2025$580Not Available
Nov 24, 2025$567Not Available
Nov 25, 2025$676Not Available
Nov 26, 2025$842Not Available
Nov 27, 2025$946Not Available
Nov 28, 2025$1090Not Available
Nov 29, 2025$964Not Available
Nov 30, 2025$658Not Available
Dec 1, 2025$550Not Available
Dec 2, 2025$525Available
Dec 3, 2025$419Available
Dec 4, 2025$572Available
Dec 5, 2025$710Not Available
Dec 6, 2025$698Not Available
Dec 7, 2025$565Not Available
Dec 8, 2025$527Available
Dec 9, 2025$406Available
Dec 10, 2025$415Available
Dec 11, 2025$575Available
Dec 12, 2025$684Not Available
Dec 13, 2025$694Not Available
Dec 14, 2025$574Not Available
Dec 15, 2025$523Not Available
Dec 16, 2025$509Available
Dec 17, 2025$407Available
Dec 18, 2025$435Available
Dec 19, 2025$700Available
Dec 20, 2025$695Not Available
Dec 21, 2025$672Not Available
Dec 22, 2025$725Not Available
Dec 23, 2025$729Not Available
Dec 24, 2025$876Not Available
Dec 25, 2025$938Not Available
Dec 26, 2025$1253Not Available
Dec 27, 2025$1283Not Available
Dec 28, 2025$1050Not Available
Dec 29, 2025$938Not Available
Dec 30, 2025$914Not Available
Dec 31, 2025$900Not Available
Jan 1, 2026$900Not Available
Jan 2, 2026$907Not Available
Jan 3, 2026$900Not Available
Jan 4, 2026$495Available
Jan 5, 2026$436Available
Jan 6, 2026$426Available
Jan 7, 2026$439Available
Jan 8, 2026$501Available
Jan 9, 2026$631Available
Jan 10, 2026$628Available
Jan 11, 2026$508Available
Jan 12, 2026$451Available
Jan 13, 2026$442Available
Jan 14, 2026$454Available
Jan 15, 2026$548Not Available
Jan 16, 2026$1264Not Available
Jan 17, 2026$1264Not Available
Jan 18, 2026$1264Not Available
Jan 19, 2026$533Not Available
Jan 20, 2026$470Available
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