Wander Stockbridge Valley
Saved to wishlist
6 guests
3 beds
2 bathrooms
Forest view•BBQ Area•Fire pit
6 guests
3 bedrooms
3 beds
2 bathrooms
2119 sq. ft.
Wander Stockbridge Valley is a serene, modern retreat tucked into the Berkshire woodlands, featuring floor-to-ceiling windows, a cozy fireplace, and a spacious deck with lounge seating and a BBQ for effortless indoor-outdoor living.
The Wander Guarantee
Book with confidence. Read more.
Flexible check-in & out
Check-in after 4:00pm • Check-out before 10:00am • Pets not 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
- Wifi
- Free parking
- Pack n play
- Board games
- Carbon monoxide detector
- Fire extinguisher
- Smoke detector
- First aid kit
- Balcony
- Hot water
- Outdoor dining area
- Fire pit
- Garden
Deck
- Patio
- BBQ Area
- BBQ Utensils
- Outdoor seating
Living room
- Heating
- Air conditioning
- TV
- Fire place
- Ceiling fan
Dining Room
- Dining table
Kitchen
- Cooking basics
- Dishes
- Dishwasher
- Kettle
- Kitchen
- Stove
- Microwave
- Toaster
- Fridge
- Coffee maker
- Ice maker
- Oven
- Freezer
- Coffee
- Tea
- Spices
- Silverware
- Cleaning supplies
- Wine glasses
- Countertop oven
Sun Room
- Dining table
Bedroom 1
- Bed linens
- Ensuite bathroom
- Closet
- Ceiling fan
- TV
- Patio
- Hangers
Ensuite Bathroom 1
- Ensuite bathroom
- Bath linens
- Shower
- Body soap
- Toilet
- Shower gel
- Shampoo
- Conditioner
Bedroom 2
- Bed linens
- TV
Bedroom 3
- Bed linens
- TV
- Air conditioning
- Forest view
Bathroom 2
- Toilet
- Shower gel
- Shampoo
- Conditioner
- Body soap
- Bath linens
- Shower
- Hair dryer
Laundry room
- Cleaning supplies
- Iron
- Dryer
- Washer
Where you’ll sleep
Where you’ll be
Set in the heart of the Berkshires, this peaceful hideaway is just minutes from Great Barrington’s dining, cultural attractions, and outdoor adventures, offering a perfect balance of seclusion and convenience year-round.
Restaurants
No Comply Foods
No Comply Foods in Great Barrington rebels against restaurant norms with its retro skate-punk vibe, counter ordering, and rotating menu of chef-driven comfort food like golden milk lattes, falafel salads, and pop-up feasts. Dive into sustainable, creative bites in a casual, unhurried space that feels like a DIY daydream.
The Prairie Whale
Nestled in Great Barrington, The Prairie Whale blends Brooklyn flair with Berkshire farm-to-table magic, serving ever-changing savory dishes from on-site produce and whole animals in a cozy, reclaimed-wood space with low-lit cabin vibes.[1][2]
Barrington Brewery & Restaurant
Nestled in a converted Berkshire barn since 1995, Barrington Brewery crafts solar-brewed beers and scratch-made pub fare like cheddar ale soup and beer-steamed brats. Enjoy the rustic ambiance, friendly vibes, and eco-friendly edge in Great Barrington.[1][2][3][4]
Once Upon a Table
Nestled in Stockbridge's charming Mews, Once Upon a Table offers an intimate, cozy escape with modern American farm-to-table dishes crafted from fresh, seasonal local ingredients—like pan-seared salmon and flavorful lamb lollipops—that taste like home-cooked perfection.[1][2][3]
GB Eats
GB Eats is a beloved Great Barrington neighborhood diner serving all-day breakfast favorites like fluffy omelets, French toast with local compote, and hearty salads in a funky, comfortable spot. Friendly service, generous portions, and fair prices keep locals and visitors coming back.
Marketplace Kitchen Table
Marketplace Kitchen Table serves up creative, made-to-order American fare like hearty egg dishes, fresh salads, burgers, and house-made pies in a family-friendly, fast-casual spot with indoor and outdoor seating. Savor healthy, globally inspired options with vegan and gluten-free choices amid the Berkshires charm.
Main Street Cafe
Main Street Cafe is an eccentric yet stylish haven in Invercargill, specializing in wholesome home-style kai made with fresh, locally sourced ingredients for breakfast, lunch, or dinner.[1] Enjoy authentic flavors in a warm atmosphere, from irresistible coffees to custom cakes and private dining.[1]
Heirloom Lodge
Heirloom Lodge serves seasonal, wine-focused farm-to-table cuisine in a sleek yet cozy lodge setting, pairing locally sourced produce and sustainable proteins with curated wines from family-run vineyards. The intimate, rustic-modern ambiance makes it a relaxed destination for elegant, ingredient-driven meals.
GB Eats
GB Eats is a vibrant Great Barrington cafe serving all-day breakfast favorites like fluffy omelets, French toast with local compote, and hearty salads, all in an upbeat, art-lined space with top-notch coffee and house-baked treats. Expect generous portions, friendly service, and a welcoming vibe that keeps locals coming back.[1][2][3]
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 relaxed dinners or brunch.[1][2][3]
GB Eats
GB Eats is a vibrant Great Barrington cafe serving all-day breakfast favorites like fluffy omelets, French toast with local compote, and hearty salads in a funky, upbeat space adorned with bold art. Friendly service and house-made treats make it a must-visit neighborhood gem.
Barrington Brewery & Restaurant
Discover Barrington Brewery & Restaurant, a solar-powered Berkshire gem brewing fresh ales since 1995 in a cozy converted barn. Savor scratch-made American pub fare like cheddar ale soup and beer-infused dishes paired with their crisp, flavorful brews.[1][2][3]
Marketplace Kitchen Table
Marketplace Kitchen Table serves up creative, made-to-order American fare like hearty egg dishes, fresh sandwiches, salads, and house-made pies in a family-friendly, fast-casual spot with indoor-outdoor seating. Savor healthy, locally crafted bites from Berkshires pros, perfect for brunch or lunch.
Main Street Cafe
Nestled in a historic Victorian-style setting, Main Street Cafe serves up homemade Southern classics like crispy fried chicken and slow-smoked pulled pork, crafted fresh daily with local ingredients in a warm, inviting atmosphere.
Once Upon a Table
Once Upon a Table is an intimate Berkshires gem serving modern American comfort food crafted from seasonal, locally-sourced ingredients, where warm hospitality and a cozy atmosphere make every meal feel like a homecooked dinner prepared by a talented chef.
Fuel Coffee
Fuel Coffee Works is a charming coffee shop housed in a renovated gas station, blending automotive vibes with friendly service and top-notch brews. Savor excellent espresso, fresh pastries, and cozy seating that draws locals and travelers alike.[2][6]
Heirloom Lodge
Heirloom Lodge redefines farm-to-table dining in a charming 18th-century Berkshires lodge, pairing fresh local seafood, meats, and produce with exceptional wines from family-run vineyards. Savor elegant yet unpretentious dishes like roasted bavette steak or Atlantic halibut in a mesmerizing open kitchen ambiance.
No Comply Foods
No Comply Foods is a mission-driven Great Barrington restaurant that breaks traditional dining rules with hand-drawn decor, a rotating menu ordered at the counter, and chef-driven dishes like golden milk lattes and globally-inspired small plates served in a casual, retro-hip atmosphere.[2][3][5]
Michaels Restaurant
Michael's On East is an award-winning fine dining establishment in Sarasota offering inventive contemporary American cuisine and an exceptional wine selection in a sophisticated 1940s supper club atmosphere, with live piano music and impeccable service that has earned it consecutive AAA Four-Diamond Awards since 1990.
Barrington Brewery & Restaurant
Discover Barrington Brewery & Restaurant, a solar-powered Berkshire gem brewing fresh, unfiltered ales since 1995 in a cozy converted barn. Savor scratch-made pub fare like ale-infused Cheddar Ale Soup and grass-fed burgers paired with their crisp beers.
The Prairie Whale
Nestled in Great Barrington, The Prairie Whale blends Brooklyn flair with Berkshire farm-to-table magic, serving ever-changing dishes from on-site produce and whole animals in a cozy, reclaimed-wood space with low-lit, cabinesque charm.[1][2][5]
Marketplace Kitchen Table
Discover fresh, scratch-made American comfort food like juicy burgers, hearty soups, crisp salads, and house-baked treats at Marketplace Kitchen Table, a family-friendly fast-casual spot in the Berkshires with indoor-outdoor seating and vegan options.
Main Street Cafe
Nestled in a historic Victorian-style setting, Main Street Cafe serves up homemade Southern classics like crispy fried chicken and slow-smoked pulled pork, crafted fresh daily with local ingredients in a warm, inviting atmosphere.
Once Upon a Table
Nestled in the heart of the Berkshires, Once Upon a Table offers cozy, intimate dining with modern American farm-to-table fare crafted from seasonal local ingredients. Savor homestyle dishes like crab cakes and beef tenderloin in a warm, welcoming ambiance perfect for unwinding.[1][2][3]
Michaels Restaurant
Michaels Cuisine in Fort Worth's Cultural District delights with contemporary ranch cuisine, from peppercrusted fillet to jalapeño shrimp, in a relaxed, romantic ambiance adorned with contemporary art.[1][2]
Heirloom Lodge
Heirloom Lodge is a wine-focused farm-to-table gem in a historic 18th-century Berkshires lodge, serving artful rustic French-Italian dishes like exquisite trout, gouda, and chocolate cake amid a mesmerizing open kitchen and relaxing ambiance.[1][2][3][5]
Fuel Coffee
Fuel Coffee Shop in Great Barrington brews creative coffee and espresso alongside legendary sandwiches like the Arlo and McGuido, fresh pastries, and breakfast favorites. This welcoming bistro draws doctors, mechanics, and locals for lively chats in a cozy, community vibe.
Attractions
Benedict Pond Loop
Discover the serene Benedict Pond Loop, a gentle 1.7-mile trail in Beartown State Forest blending pondside strolls, Appalachian Trail views from rocky ledges, and vibrant hardwood forests. Perfect for families, casual hikers, and winter snowshoers seeking easy nature escapes.[1][2][5]
Chesterwood
Step into Daniel Chester French's gilded-age studio at Chesterwood, where original Lincoln Memorial molds and sculptures blend seamlessly with Berkshire gardens for an inspiring artistic journey. Art and history lovers, plus families with older kids, will cherish this National Historic Landmark's creative magic.[5][1][2]
TurnPark Art Space
Discover TurnPark Art Space, a magical 16-acre sculpture park in a former marble quarry blending bold Soviet nonconformist art with nature's serenity and live performances. Art lovers, families, and dog-walkers will adore its immersive trails and vibrant energy.[1][2][3][4][7][8]
Berkshire Botanical Garden
Wander 24 acres of whimsical gardens, living topiaries, and seasonal displays at Berkshire Botanical Garden — perfect for families, plant lovers, and anyone who enjoys peaceful outdoor art and hands-on nature activities.
Ski Butternut
Discover Ski Butternut, a charming Berkshire gem with 22 varied trails, two terrain parks, and a top-notch ski school perfect for families, beginners, and intermediates seeking affordable, fun-filled skiing since 1963.
Lake Mansfield Beach and Conservation Forest Trails
Discover the serene Lake Mansfield Beach and Conservation Forest Trails, where clean waters invite paddleboarding and kayaking, easy shaded paths wind through pristine woods, and picnic spots await amid stunning views. Families, nature lovers, and relaxed explorers will cherish this peaceful Berkshire gem.[1][2][3]
Norman Rockwell Museum
Step into Norman Rockwell’s warm, story-filled world—see original paintings, visit his restored studio, and enjoy family-friendly exhibits and scenic grounds; perfect for art lovers, history fans, and anyone who loves nostalgic, narrative American art.
Monument Mountain Reservation
Conquer Monument Mountain Reservation's steep trails to a 1,642-foot summit with jaw-dropping views of the Housatonic Valley, waterfalls, and soaring eagles. Adventure-loving hikers seeking thrilling scrambles and Berkshire beauty will love this rewarding escape.
Naumkeag
A charming Gilded Age estate with eight acres of artistically terraced gardens — including the famed Blue Steps — perfect for garden lovers, photographers, and anyone who enjoys peaceful scenic walks and seasonal events like the Pumpkin Show and Winterlights.
Norman Rockwell Museum
Discover the Norman Rockwell Museum's hands-on I-Spy games and Art Hunts that spark creativity and connection to iconic American art in a stunning 36-acre Berkshires setting. Young explorers, families, and art lovers will adore this playful, inspiring adventure.[1][2][3]
Berkshire Botanical Garden
Discover the enchanting Berkshire Botanical Garden, where kids delight in fairy gardens, topiary animals, edible veggie patches, and frog-filled ponds across 24 magical acres. Perfect for families seeking whimsical nature adventures and hands-on discovery.
Chesterwood
Step into the Gilded Age world of Daniel Chester French, sculptor of the Lincoln Memorial, at his enchanting Stockbridge estate, studio, and gardens. Art lovers and history buffs will adore exploring plaster models, woodland walks, and timeless sculptures amid stunning Berkshires views.
Berkshire Botanical Garden
Discover the enchanting Berkshire Botanical Garden, where kids adore the Children's Discovery Garden's fairy houses, chicken coop, and animal topiaries, plus edible veggies and a tree of 40 fruits. Families love its whimsical trails, ponds teeming with wildlife, and hands-on weekend nature crafts.[1][2]
Ski Butternut
Ski Butternut is a family-friendly mountain resort in Massachusetts's Berkshires offering 22 trails suited for all skill levels, with 100% snowmaking coverage and affordable rates perfect for beginners and intermediate skiers seeking a convenient Northeast getaway just 135 miles from New York City and Boston.
Norman Rockwell Museum
Immerse yourself in the world of one of America's most beloved artists at this 36-acre campus housing the world's largest collection of Norman Rockwell's original works, including his iconic Saturday Evening Post covers. Perfect for art enthusiasts and families alike, the museum offers interactive exhibits, a faithful recreation of Rockwell's studio, and engaging programs that bring his artistic legacy to life.
Naumkeag
Discover the gilded-age splendor of Naumkeag, a historic Berkshire estate famed for its terraced gardens, iconic Blue Steps, and sweeping valley views. Garden lovers, history buffs, and families seeking seasonal magic will adore this enchanting escape.[3][2][1]
Chesterwood
Step into Daniel Chester French's Gilded Age studio at Chesterwood, where the Lincoln Memorial sculptor crafted icons amid stunning gardens and woodland walks. Art lovers and history buffs will cherish exploring his home, plaster models, and mountain vistas on this National Historic Landmark estate.[1][3][5]
Monument Mountain Reservation
Conquer Monument Mountain's steep trails and boulder scrambles to reach the 1,642-foot summit, where sweeping views of the Housatonic Valley and soaring eagles await at Devil's Pulpit. Adventure-loving hikers seeking a rewarding Berkshires challenge will love it.
Guthrie Center
Join the uplifting Praise Sunday at the Guthrie Center, a non-denominational interfaith spiritual service in the historic Old Trinity Church from Arlo Guthrie's "Alice's Restaurant" legend. Spiritual seekers and music lovers of all faiths will cherish this welcoming, soul-nourishing gathering.[1][5]
TurnPark Art Space
Discover the magic of TurnPark Art Space, a 16-acre former marble quarry transformed into an immersive sculpture park blending bold art, architecture, and nature, with live performances and galleries. Art lovers, families, and serenity seekers will adore wandering its quirky paths and stone amphitheater.[1][2][3][6][8]
Lake Mansfield Beach and Conservation Forest Trails
Discover the serene Lake Mansfield Beach and Conservation Forest Trails, where clean waters invite paddleboarding and kayaking, easy shaded paths wind through pristine woods, and picnic spots await amid stunning Berkshire views. Families, nature lovers, and relaxed adventurers will cherish this peaceful, accessible escape.[1][2][3]
Ski Butternut
Discover Ski Butternut's 22 groomed trails and two terrain parks in the scenic Berkshires, perfect for intermediates with beginner and expert options too. Families, learners, and East Coast skiers love its affordable, historic charm since 1963.[1][2][3][8]
Naumkeag
Discover the enchanting Gilded Age splendor of Naumkeag, where Fletcher Steele's iconic Blue Steps cascade through lush terraced gardens amid breathtaking Berkshires views. Garden lovers, history buffs, and families seeking timeless beauty will adore this Stockbridge gem.
Monument Mountain Reservation Parking
Discover Monument Mountain's thrilling 3-mile loop from the Reservation Parking, tackling steep climbs, rocky scrambles to Devil's Pulpit, and sweeping valley views with waterfalls and wildlife. Perfect for adventure-loving hikers seeking a rewarding Berkshires challenge.
Lake Mansfield Beach and Conservation Forest Trails
Discover the serene Lake Mansfield Beach and Conservation Forest Trails, where clean waters invite paddleboarding and kayaking, a small sandy beach beckons for relaxation, and easy, shaded trails wind through pristine woods teeming with wildlife. Families, nature lovers, and anyone seeking peaceful outdoor fun will adore this accessible Berkshire gem.
TurnPark Art Space
Discover TurnPark Art Space, a magical 16-acre sculpture park in a former marble quarry blending bold outdoor art, live performances, and stunning natural landscapes. Art enthusiasts, families, and nature lovers will adore wandering its immersive paths, galleries, and amphitheater.[1][2][5][7]
Monument Mountain Reservation
Conquer Monument Mountain Reservation's steep, rocky trails to epic Berkshire vistas, Devil's Pulpit thrills, and unique rock formations like the fern-draped 'floating' boulder. Adventure hikers and nature lovers craving rewarding challenges will love this 2-3 hour loop.[1][3][4][7]
Select dates in Wander Stockbridge Valley
Choose your check-in & check-out dates
Guests love Wander
Wander's average ratings
Have a question?
24/7 Concierge
Ask AI
Get quick answers with our AI-powered search for property info.
Chat with Concierge
Talk with the concierge to ask any question you might have
Things to know
Here are some things which you should know before booking Wander Stockbridge Valley
Check-in: after 4:00 pm
Check-out: before 10:00 am
6 guests maximum
Pets not 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
6 guests maximum
Pets not allowed
No smoking - fees will apply
Events require approval
Before you book
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jan 6, 2026 | $102 | Available |
| Jan 7, 2026 | $102 | Available |
| Jan 8, 2026 | $102 | Available |
| Jan 9, 2026 | $254 | Not Available |
| Jan 10, 2026 | $262 | Not Available |
| Jan 11, 2026 | $192 | Not Available |
| Jan 12, 2026 | $136 | Not Available |
| Jan 13, 2026 | $139 | Not Available |
| Jan 14, 2026 | $138 | Not Available |
| Jan 15, 2026 | $216 | Not Available |
| Jan 16, 2026 | $391 | Not Available |
| Jan 17, 2026 | $411 | Not Available |
| Jan 18, 2026 | $273 | Not Available |
| Jan 19, 2026 | $193 | Not Available |
| Jan 20, 2026 | $194 | Not Available |
| Jan 21, 2026 | $137 | Not Available |
| Jan 22, 2026 | $176 | Not Available |
| Jan 23, 2026 | $243 | Not Available |
| Jan 24, 2026 | $251 | Not Available |
| Jan 25, 2026 | $184 | Not Available |
| Jan 26, 2026 | $131 | Not Available |
| Jan 27, 2026 | $131 | Not Available |
| Jan 28, 2026 | $131 | Not Available |
| Jan 29, 2026 | $166 | Not Available |
| Jan 30, 2026 | $245 | Not Available |
| Jan 31, 2026 | $253 | Not Available |
| Feb 1, 2026 | $199 | Not Available |
| Feb 2, 2026 | $140 | Not Available |
| Feb 3, 2026 | $237 | Available |
| Feb 4, 2026 | $237 | Available |
| Feb 5, 2026 | $283 | Available |
| Feb 6, 2026 | $339 | Available |
| Feb 7, 2026 | $316 | Not Available |
| Feb 8, 2026 | $273 | Not Available |
| Feb 9, 2026 | $222 | Not Available |
| Feb 10, 2026 | $222 | Not Available |
| Feb 11, 2026 | $243 | Available |
| Feb 12, 2026 | $357 | Available |
| Feb 13, 2026 | $411 | Available |
| Feb 14, 2026 | $503 | Available |
| Feb 15, 2026 | $337 | Not Available |
| Feb 16, 2026 | $287 | Not Available |
| Feb 17, 2026 | $287 | Not Available |
| Feb 18, 2026 | $160 | Not Available |
| Feb 19, 2026 | $325 | Available |
| Feb 20, 2026 | $364 | Available |
| Feb 21, 2026 | $373 | Available |
| Feb 22, 2026 | $305 | Available |
| Feb 23, 2026 | $247 | Available |
| Feb 24, 2026 | $247 | Available |
| Feb 25, 2026 | $246 | Available |
| Feb 26, 2026 | $289 | Available |
| Feb 27, 2026 | $342 | Available |
| Feb 28, 2026 | $348 | Available |
| Mar 1, 2026 | $235 | Available |
| Mar 2, 2026 | $192 | Available |
| Mar 3, 2026 | $191 | Available |
| Mar 4, 2026 | $191 | Available |
| Mar 5, 2026 | $224 | Available |
| Mar 6, 2026 | $267 | Available |
| Mar 7, 2026 | $283 | Available |
| Mar 8, 2026 | $240 | Available |
| Mar 9, 2026 | $195 | Available |
| Mar 10, 2026 | $195 | Available |
| Mar 11, 2026 | $194 | Available |
| Mar 12, 2026 | $227 | Available |
| Mar 13, 2026 | $284 | Available |
| Mar 14, 2026 | $292 | Available |
| Mar 15, 2026 | $239 | Available |
| Mar 16, 2026 | $194 | Available |
| Mar 17, 2026 | $193 | Available |
| Mar 18, 2026 | $193 | Available |
| Mar 19, 2026 | $227 | Available |
| Mar 20, 2026 | $284 | Available |
| Mar 21, 2026 | $278 | Available |
| Mar 22, 2026 | $239 | Available |
| Mar 23, 2026 | $193 | Available |
| Mar 24, 2026 | $193 | Available |
| Mar 25, 2026 | $194 | Available |
| Mar 26, 2026 | $227 | Available |
| Mar 27, 2026 | $284 | Available |
| Mar 28, 2026 | $292 | Available |
| Mar 29, 2026 | $239 | Available |
| Mar 30, 2026 | $218 | Available |
| Mar 31, 2026 | $219 | Available |
| Apr 1, 2026 | $194 | Available |
| Apr 2, 2026 | $227 | Available |
| Apr 3, 2026 | $273 | Available |
| Apr 4, 2026 | $283 | Available |
| Apr 5, 2026 | $240 | Available |
| Apr 6, 2026 | $195 | Available |