# Highland
https://www.wander.com/property/wander-great-barrington-highlands

> Luxury vacation rental in Great Barrington, MA

## Property Overview
- **Sleeps**: 10 guests
- **Bedrooms**: 4
- **Bathrooms**: 2.5
- **Square Footage**: 1,000 sq ft


## Pricing & Availability
- **Nightly Rate**: $475 - $500 (before taxes and fees)
- **Next Available**: September 10, 2026
- **Available Days**: 33 days in the next 90 days
- **Daily Pricing (Next 90 Days)**:
  - 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)
  - Oct 12, 2026: $500 (Available)


## Location
- **Address**: Great Barrington, MA, US
- **Coordinates**: 42.1935411, -73.3772016
- **Timezone**: America/New_York
- **Local Area**: Beautiful destination with local attractions




## Amenities
- Fire pit
- Hot tub
- Wood stove
- Dining table
- Patio
- Dryer
- Extra blankets
- Body soap
- Board games
- Hot water
- Ceiling fan
- Hangers
- Freezer
- Bathtub
- Shampoo
- Shower gel
- Toilet
- Extra pillows
- Closet
- Hair dryer
- Cleaning supplies
- Wine glasses
- Blender
- Free parking
- Cooking basics
- Baking sheet
- Conditioner
- Long term stays allowed
- Safe
- Balcony
- Garden
- Bbq area
- Outdoor seating
- Air conditioning
- Fire place
- Heating
- Wifi
- Bed linens
- Tv
- Bath linens
- Washer
- Dishes
- Dishwasher
- Kitchen
- Microwave
- Oven
- Fridge
- Spices
- Stove
- Toaster
- Carbon monoxide detector
- Fire extinguisher
- First aid kit
- Smoke detector
- Coffee maker

## Dining Recommendations
- **The Bistro Box**: The 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.
- **Barrington Brewery & Restaurant**: 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]
- **The Prairie Whale**: 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**: 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**: 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.
- **The Cliff House**: 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**: 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.
- **Hy's Fried**: 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.

## Activities & Attractions
- **River Walk**: 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.
- **Ski Butternut**: 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.
- **Monument Mountain Reservation**: 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]
- **Thom Reed - UFO Park**: 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 Beach and Conservation Forest Trails**: 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.
- **Catamount Mountain Resort**: 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.
- **Beartown State Forest**: 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]
- **Catamount Aerial Adventure Park**: 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]

## Local Services
- **Berkshire Food Co-op**: Discover Berkshire Food Co-op, where every item shines with top-quality local produce, organic essentials, sustainable meats, specialty wines, and bulk goods—if it's not local, it's organic. Friendly staff and a vibrant deli cafe make it a community hub for thoughtful, delicious shopping.
- **Big Y**: Discover Big Y, your go-to grocery haven boasting fresh World Class pies, premium gourmet meats, and an unbeatable selection of local produce that elevates every meal. Shop where quality and flavor collide!
- **Market 32**: Discover Market 32, where fresh local Northeast produce, Boar's Head deli meats, artisan baked breads, and exclusive PICS brands deliver exceptional flavor and value every visit.
- **Domaney's Liquors and Fine Wines**: Discover Domaney's Liquors and Fine Wines, where a temperature-controlled room hides rare vintages and a deli tempts with gourmet cheeses and meats. Family-owned since 1973, it's your Berkshire go-to for fine spirits, craft beers, cigars, and perfect pairings.
- **Dollar General**: Discover Dollar General, where budget meets bold flavors with standout steals like Bibigo Korean mini wontons, Duke's mayo, Nutella spreads, and Crystal hot sauce—all under one roof for everyday indulgence.[2]
- **bear butter | fortified almond butter, acai bowls, smoothies, superfoods**: Discover Bear Butter, where fortified almond butter packs superfoods like cacao nibs, goji berries, and hemp seeds into every chunky bite—perfect for acai bowls and smoothies. Try the innovative foraged mushroom blend with reishi, chaga, and lion's mane for an immune-boosting twist.
- **CVS**: Discover CVS's grocery haven for healthy snacks like SkinnyPop, Late July, and Well Market trail mixes, plus indulgent frozen treats from Ben & Jerry's and Jeni's. Order online for same-day pickup or delivery and skip the crowds.
- **Cumberland Farms**: Discover Cumberland Farms, where crave-worthy Farmhouse Premium chocolates, salty snacks, bakery treats, and creamy ice cream steal the show, alongside fresh pizza slices and specialty coffee for any craving.[1]
- **Guido's Fresh Marketplace**: Guido's Fresh Marketplace delights with direct-imported Italian pastas, pestos, and French cheeses you won't find elsewhere, plus house-made mozzarella, creative smoothies, and gourmet prepared foods. This family-owned gem in the Berkshires blends specialty imports with fresh, craveable eats for every craving.
- **The Marketplace Specialty Foods**: Discover The Marketplace Specialty Foods, where over 140 cheese varieties, unpasteurized olives, house-roasted meats, and scratch-made pastries from our Sheffield Kitchen await. Grab gourmet entrees, artisan breads, and charcuterie for an irresistible taste of Berkshire excellence.



## Additional Information
- **Shipping to**: <p><strong>Shipping Items to the House</strong><br>Can I ship some gear to the house before my stay? Absolutely! However, please note that deliveries are at your own discretion; Wander will not be held liable for lost, stolen, or tampered items or packages.<br><br>IMPORTANT: Please ensure that delivery will fall during your stay dates in order to prevent disturbing the guests at the house before and after your trip. Should your package arrive on a day that doesn’t fall during your trip, a $50 fee will be charged for our runner's fee.</p><p><br><strong>Need Something at the Home? </strong><br>If there is anything you want in your Wander Home that you can’t find, simply let Concierge know so they can help out (no need to buy anything). You may contact them through the app or by texting&nbsp;<a target="_blank" rel="noopener noreferrer" class="notion-link-token notion-focusable-token notion-enable-hover" href="tel:+17373773205">+1-737-377-3205</a>.</p>
- **Occupancy notice**: <p>This home follows a strict maximum occupancy rule. Please make sure that the total number of guests accompanying you (including both children and adults) doesn't exceed the indicated maximum occupancy above to avoid cancellation of your stay and additional fees.</p>
- **No smoking**: <p>Smoking is not permitted anywhere on the property.</p>

## Guest Services
- **24/7 Concierge**: Available through the Wander app
- **Housekeeping**: Professional cleaning service
- **Maintenance**: On-call support for any issues
- **Local Recommendations**: Dining, activities, and experiences

## Property Details
- **Property ID**: 636377540046358380
- **Hero Image**: https://assets.wander.com/650274482027499084/640.webp

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*Last modified: 2026-07-14*