Wander Stockbridge Woods
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8 guests
5 beds
2.5 bathrooms
Outdoor dining area•Mountain view•Fire place
8 guests
4 bedrooms
5 beds
2.5 bathrooms
2732 sq. ft.
Wander Stockbridge Woods is a picturesque retreat where New England charm meets modern luxury in the heart of the Berkshires.
The Wander Guarantee
Book with confidence. Read more.
Check-in & out
Check-in after 4:00pm • Check-out before 11:00am • 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
- Free parking
- Wifi
- Hot water
- Fire extinguisher
- Mountain view
- Pack n play
- Carbon monoxide detector
- Smoke detector
- First aid kit
- Air conditioning
- Washer
- Dryer
Patio
- Patio
- BBQ Area
- Outdoor seating
- Outdoor dining area
- BBQ Utensils
Living room
- TV
- Fire place
Dining room
- Dining table
Kitchen
- Dishes
- Dishwasher
- Kitchen
- Stove
- Microwave
- Fridge
- Coffee maker
- Cooking basics
- Oven
- Freezer
- Coffee
- Kettle
- Tea
- Spices
- Silverware
- Cleaning supplies
- Wine glasses
- Breakfast nook
- Baking sheet
- High chair
Bedroom 1
- Hangers
- Bed linens
Ensuite Bathroom
- Hair dryer
- Bath linens
- Toilet
- Shower gel
- Shampoo
- Conditioner
- Body soap
- Ensuite bathroom
- Shower
- Bathtub
Bedroom 2
- Bed linens
- Ceiling fan
Bedroom 3
- Bed linens
Bedroom 4
- Bed linens
Bathroom
- Bathtub
- Body soap
- Bath linens
- Toilet
- Shower gel
- Shampoo
- Conditioner
- Shower
Half Bath
- Bathtub
- Toilet
- Body soap
- Bath linens
- Half bath
Where you’ll sleep
Where you’ll be
Immerse yourself in the cultural heart of the Berkshires, where Gilded Age elegance meets the timeless charm of Stockbridge. Visit The Mount, Edith Wharton’s historic estate, stroll the vibrant Berkshire Botanical Garden, or explore the renowned grounds of Naumkeag.
Restaurants
Alta
Alta is a live-fire Spanish restaurant in London's Soho that brings the essence of Navarra's culinary traditions to life, with everything cooked over an open flame and featuring seasonal British produce in a theatrical, convivial setting that balances stunning design with serious food.
Bistro Zinc
Bistro Zinc is a cozy modern French bistro in the heart of Lenox, MA, serving classic fare like steak frites and escargot in a refined, art-filled space with welcoming vibes. Since 1999, it's been a Berkshires gem for lunch or dinner.
Starving Artist Creperie and Cafe
Discover the Starving Artist Creperie & Cafe, where sweet and savory crepes crafted from fresh, local Berkshire ingredients shine alongside organic salads, smoothies, and vegan delights. Savor the artistic vibe with live music, local artwork, and cozy seating in a welcoming spot for breakfast or lunch.[2][4]
Roses Restaurant
Nestled in South Coast Winery Resort & Spa, The Vineyard Rose Restaurant offers contemporary California cuisine with fresh, local ingredients in an elegant Tuscan-inspired dining room and vineyard-view terrace. Pair your steak, seafood, or vegan dishes with award-winning wines for a perfect Temecula escape.[1][2]
Once Upon a Table
Nestled in the heart of Stockbridge's Berkshires, Once Upon a Table is an intimate farm-to-table gem offering modern American dishes crafted from daily-changing, seasonal local ingredients. Enjoy cozy, homey vibes and fresh flavors in this refreshed hidden retreat.[1][2][3]
51 Park Restaurant & Tavern
Nestled in a historic 1800s Victorian house with stunning woodwork and a relaxing porch, 51 Park Restaurant & Tavern serves fresh, scratch-made tavern fare like wood-fired pizzas, juicy burgers, and unique entrees paired with craft beers and signature cocktails.[1][2][5]
Haven
Haven is a sophisticated yet welcoming South Tampa restaurant blending refined American cuisine with an eclectic small-plates concept, featuring artisanal charcuterie, craft cocktails, and an extensive wine selection in a stylish, convivial atmosphere that celebrates locally sourced ingredients.
Antimony Brewing - Craft Brewery & Kitchen
Antimony Brewing is a vibrant brewpub in Lenox that crafts its own beers onsite while serving creative scratch-cooked cuisine in a newly renovated taproom with weekly live entertainment. With a diverse clientele and standout dishes like their signature Antimony burger and Dr. Pepper wings, it's a destination that expertly blends quality craft beer with exceptional food.
Attractions
The Mount, Edith Wharton's Home
Step into The Mount, Edith Wharton's 1902 masterpiece in the Berkshires, where the Pulitzer-winning author designed every elegant detail—from the classically inspired house to lush Italian gardens—as her ultimate creative haven. Literature lovers and design enthusiasts will adore this rare glimpse into her visionary world.
Naumkeag
Discover Naumkeag's enchanting 8-acre gardens and Gilded Age mansion, crowned by the iconic Blue Steps cascading through birch groves with stunning Berkshire views. Garden enthusiasts, history buffs, and families seeking scenic picnics will adore this timeless Stockbridge gem.[1][2][8]
Ventfort Hall Gilded Age Mansion & Museum
Step back into the opulent Gilded Age at Ventfort Hall, J.P. Morgan's sister's lavish Jacobean-Revival mansion, with its hand-carved oak, stained-glass wonders, and captivating guided tours revealing untold stories of wealth and restoration. History buffs, architecture lovers, and time-travel seekers will adore this Berkshires gem.
Norman Rockwell Museum
Step into Norman Rockwell's actual relocated studio at the Norman Rockwell Museum, where his easel and brushes evoke the magic behind iconic American scenes of humor, heart, and history. Art lovers, families, and nostalgia seekers will cherish this immersive journey through his world.[1][2][7]
Berkshire Botanical Garden
Discover the enchanting Berkshire Botanical Garden, where kids delight in fairy gardens, edible veggie patches, whimsical topiaries, and a tree bearing 40 fruits, amid 24 acres of vibrant seasonal blooms and wildlife. Families and nature lovers will adore this magical, interactive outdoor haven.[1][2][7]
Mass Audubon's Pleasant Valley Wildlife Sanctuary
Mass Audubon's Pleasant Valley Wildlife Sanctuary is a 1,100-acre nature haven featuring 7 miles of scenic trails through forests, meadows, and wetlands where visitors can spot beavers, birds, and other wildlife year-round. Perfect for families and outdoor enthusiasts of all abilities, it offers hiking, canoeing, guided programs, and a nature play area for kids.
October Mountain State Forest
Discover Massachusetts' largest state forest, October Mountain, where a 9-mile Appalachian Trail stretch winds through Schermerhorn Gorge and serene lakes, offering hikes, kayaking, and wildlife spotting year-round. Nature lovers, hikers of all levels, and outdoor adventurers will revel in its tranquil wilderness escape.
Olivia's Overlook at Yokun Ridge Reserve
Discover stunning vistas of Monument Mountain and tri-town borders from Olivia's Overlook, the heart of 734-acre Yokun Ridge Reserve with its historic charcoal pits and wildflower blooms. Hikers, birdwatchers, and nature lovers will relish this moderate 1.6-mile loop adventure.[1][2][4]
Chesterwood
Discover Chesterwood, the gilded-age estate and studio of sculptor Daniel Chester French, creator of the Lincoln Memorial and Minute Man statues, where stunning gardens blend with woodland trails featuring contemporary sculptures. Art lovers, history buffs, and nature enthusiasts will cherish this inspiring Berkshires retreat.[1][2][4]
Monument Mountain Reservation
Conquer Monument Mountain Reservation's steep trails and boulder scrambles to the thrilling Devil's Pulpit, where jaw-dropping views of the Housatonic Valley and soaring eagles await. Adventure seekers and nature lovers craving a rewarding Berkshires challenge will love this unforgettable hike.
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Things to know
Here are some things which you should know before booking Wander Stockbridge Woods
Check-in: after 4:00 pm
Check-out: before 11:00 am
8 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 11:00 am
8 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 |
|---|---|---|
| Feb 16, 2026 | $223 | Not Available |
| Feb 17, 2026 | $223 | Not Available |
| Feb 18, 2026 | $152 | Not Available |
| Feb 19, 2026 | $139 | Not Available |
| Feb 20, 2026 | $416 | Not Available |
| Feb 21, 2026 | $428 | Not Available |
| Feb 22, 2026 | $319 | Not Available |
| Feb 23, 2026 | $139 | Available |
| Feb 24, 2026 | $139 | Available |
| Feb 25, 2026 | $139 | Available |
| Feb 26, 2026 | $186 | Not Available |
| Feb 27, 2026 | $252 | Not Available |
| Feb 28, 2026 | $156 | Available |
| Mar 1, 2026 | $202 | Available |
| Mar 2, 2026 | $197 | Available |
| Mar 3, 2026 | $224 | Available |
| Mar 4, 2026 | $224 | Available |
| Mar 5, 2026 | $232 | Available |
| Mar 6, 2026 | $339 | Not Available |
| Mar 7, 2026 | $348 | Not Available |
| Mar 8, 2026 | $208 | Available |
| Mar 9, 2026 | $197 | Available |
| Mar 10, 2026 | $203 | Available |
| Mar 11, 2026 | $203 | Available |
| Mar 12, 2026 | $235 | Available |
| Mar 13, 2026 | $248 | Available |
| Mar 14, 2026 | $355 | Not Available |
| Mar 15, 2026 | $276 | Not Available |
| Mar 16, 2026 | $261 | Not Available |
| Mar 17, 2026 | $202 | Available |
| Mar 18, 2026 | $202 | Available |
| Mar 19, 2026 | $240 | Available |
| Mar 20, 2026 | $269 | Available |
| Mar 21, 2026 | $276 | Available |
| Mar 22, 2026 | $216 | Available |
| Mar 23, 2026 | $205 | Available |
| Mar 24, 2026 | $205 | Available |
| Mar 25, 2026 | $205 | Available |
| Mar 26, 2026 | $239 | Available |
| Mar 27, 2026 | $344 | Not Available |
| Mar 28, 2026 | $352 | Not Available |
| Mar 29, 2026 | $199 | Not Available |
| Mar 30, 2026 | $230 | Not Available |
| Mar 31, 2026 | $270 | Not Available |
| Apr 1, 2026 | $249 | Not Available |
| Apr 2, 2026 | $291 | Not Available |
| Apr 3, 2026 | $333 | Not Available |
| Apr 4, 2026 | $342 | Not Available |
| Apr 5, 2026 | $270 | Not Available |
| Apr 6, 2026 | $255 | Not Available |
| Apr 7, 2026 | $187 | Not Available |
| Apr 8, 2026 | $187 | Not Available |
| Apr 9, 2026 | $297 | Not Available |
| Apr 10, 2026 | $339 | Not Available |
| Apr 11, 2026 | $347 | Not Available |
| Apr 12, 2026 | $217 | Available |
| Apr 13, 2026 | $206 | Available |
| Apr 14, 2026 | $206 | Available |
| Apr 15, 2026 | $206 | Available |
| Apr 16, 2026 | $227 | Available |
| Apr 17, 2026 | $298 | Not Available |
| Apr 18, 2026 | $305 | Not Available |
| Apr 19, 2026 | $239 | Not Available |
| Apr 20, 2026 | $262 | Available |
| Apr 21, 2026 | $221 | Available |
| Apr 22, 2026 | $220 | Available |
| Apr 23, 2026 | $255 | Available |
| Apr 24, 2026 | $288 | Available |
| Apr 25, 2026 | $296 | Available |
| Apr 26, 2026 | $231 | Available |
| Apr 27, 2026 | $218 | Available |
| Apr 28, 2026 | $218 | Available |
| Apr 29, 2026 | $218 | Available |
| Apr 30, 2026 | $254 | Available |
| May 1, 2026 | $271 | Available |
| May 2, 2026 | $278 | Available |
| May 3, 2026 | $232 | Available |
| May 4, 2026 | $221 | Available |
| May 5, 2026 | $221 | Available |
| May 6, 2026 | $221 | Available |
| May 7, 2026 | $259 | Available |
| May 8, 2026 | $292 | Available |
| May 9, 2026 | $299 | Available |
| May 10, 2026 | $235 | Available |
| May 11, 2026 | $224 | Available |
| May 12, 2026 | $225 | Available |
| May 13, 2026 | $225 | Available |
| May 14, 2026 | $263 | Available |
| May 15, 2026 | $299 | Available |
| May 16, 2026 | $307 | Available |
| May 17, 2026 | $242 | Available |