Berkshire Area Rentals
From $283 per night (USD)VRBO
Immaculate Berkshires home! Close to museums, colleges, and outdoor activities.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Comfortably sleeping 6 with a large yard, screened in porch, and newly renovated bathroom, this charming 3-bedroom house ...
From $283 per night (USD)VRBO
From $552 per night (USD)VRBO
Spacious & Family-Ready Home w/ Fenced Yard in Lee
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Indulge in the ultimate getaway and experience comfort, style, and convenience in our enchanting home. Step into an open ...
From $552 per night (USD)VRBO
From $805 per night (USD)VRBO
Luxurious, Family Friendly, Nature Retreat at Meadows Edge!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Meadows Edge! A charming 3 bedroom (plus 1BR guest suite) home nestled in the heart of the Berkshires that sl ...
From $805 per night (USD)VRBO
From $369 per night (USD)VRBO
Beautiful Lake Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relax with the whole family at this peaceful & quiet retreat close to Lake Garfield, Skiing and the best of the Berkshi ...
From $369 per night (USD)VRBO
From $483 per night (USD)VRBO
Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Hummingbird Haven is a thoughtfully designed 3,100-square-foot home crafted for comfort, creativity, and connection—with ...
From $483 per night (USD)VRBO
From $336 per night (USD)VRBO
Artistic Nature Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home at this quiet, private ...
From $336 per night (USD)VRBO
From $307 per night (USD)VRBO
Cozy Becket Cottage Minutes from Lake Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in nature and surrounded by wildlife, this Becket vacation rental offers the perfect setting for your dream outd ...
From $307 per night (USD)VRBO
From $502 per night (USD)Expedia
Grandparent’s Cottage 250 steps to the lake
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
4 bedrooms, sleeps 7, 2 living rooms, 2 full bathrooms, fully stocked kitchen; lawn chairs, beach towels, games, and bic ...
From $502 per night (USD)Expedia
From $345 per night (USD)VRBO
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 3
Perfect for budget-conscious travelers, our Basic Queen rooms provide a welcoming and practical space to rest and rechar ...
From $345 per night (USD)VRBO
From $385 per night (USD)Expedia
Cozy Carriage House room with a double bed and private balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Teddy Room (C24) at The Cornell Inn is a cozy and inviting retreat in the historic Carriage House, offering a peacef ...
From $385 per night (USD)Expedia
From $599 per night (USD)VRBO
\"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Emily Dickinson Junior Suite at The Cornell Inn offers a refined and tranquil retreat inspired by the beloved poet. ...
From $599 per night (USD)VRBO
From $674 per night (USD)Expedia
Elegant suite with a king bed, fireplace, and kitchenette.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
C23 - The Cleopatra Suite at The Cornell Inn is a spacious, two-floor retreat offering a blend of modern convenience and ...
From $674 per night (USD)Expedia
From $674 per night (USD)VRBO
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Lady Cicely Grand Suite (M27) - A Luxurious Escape at The Cornell Inn Indulge in elegance and comfort at The Lady C ...
From $674 per night (USD)VRBO
From $571 per night (USD)Expedia
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Niles Johnson Room (M11) - A Cozy & Elegant Retreat at The Cornell Inn Welcome to The Niles Johnson Room (M11) at T ...
From $571 per night (USD)Expedia
From $436 per night (USD)VRBO
Elegant Carriage House room with a queen bed and private patio.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Silver Thistle Room (C12) at The Cornell Inn is a charming and tranquil retreat in the historic Carriage House. This ...
From $436 per night (USD)VRBO
From $405 per night (USD)Expedia
Historic Susan B. Anthony Room - Cozy & Charming Stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Susan B. Anthony Room at The Cornell Inn offers a charming and cozy retreat in the heart of the Berkshires. This inv ...
From $405 per night (USD)Expedia
From $345 per night (USD)VRBO
Experience Timeless Elegance in The Edith Wharton Room!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Edith Wharton Room offers a refined and elegant retreat inspired by classic charm and modern comfort. This beautiful ...
From $345 per night (USD)VRBO
From $627 per night (USD)VRBO
Williamstown Stay, Minutes To Williams College
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Modern home in a quiet neighborhood, minutes from Williams College and an easy drive to top restaurants, the C ...
From $627 per night (USD)VRBO
From $375 per night (USD)VRBO
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
550 Sq. Ft , Dogs *only* friendly A-Frame cabin amongst the forest located in private lake community with neighborhood g ...
From $375 per night (USD)VRBO
From $632 per night (USD)Expedia
Richmond Ranch w/ Hot Tub by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Evergreen Home Vacation Rentals invites you to this charming 3-bedroom, 2-bath ranch, perfect for comfortable one-level ...
From $632 per night (USD)Expedia
From $558 per night (USD)VRBO
Walk to Lenox Village - 1930s Cottage Charmer!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Autumn 2026 - Come enjoy the fall color in the Berkshires / Lenox in this walk-to- town vintage charmer. Positively frag ...
From $558 per night (USD)VRBO
From $478 per night (USD)VRBO
Private Mountain Retreat on 5 acres - Close to lakes and attractions
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a peaceful stay at this 4-bedroom house on the Monterey line. 5-10 minutes from Butternut Ski Area and Otis Ridge, ...
From $478 per night (USD)VRBO
From $334 per night (USD)VRBO
Lake View Cozy Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Pittsfield like a local in this 2-bedroom house. The bedrooms feature 2 queen beds, perfect for a tremendous ...
From $334 per night (USD)VRBO
From $147 per night (USD)VRBO
Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your Berkshires getaway starts at this sweet 1-bedroom, 1-den condo. The picture windows in the front sitting area look ...
From $147 per night (USD)VRBO
From $255 per night (USD)VRBO
Tranquil Lakeside Escape in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Retreat to this spacious 2-bedroom condo at The Ponds at Foxhollow, nestled in the scenic Berkshires of Massachusetts. P ...
From $255 per night (USD)VRBO
From $219 per night (USD)Expedia
Peaceful 1BR Condo with Pond View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to a serene retreat at this cozy 1-bedroom condo in The Ponds at Foxhollow, nestled in the heart of the Berkshire ...
From $219 per night (USD)Expedia
From $884 per night (USD)VRBO
Lakeside Estate: 2 Homes For Family Gatherings
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 18
Summary: Stay tonight and book two houses across the street from each other—perfect for large families! Together: 8 bed ...
From $884 per night (USD)VRBO
From $1365 per night (USD)VRBO
Stunning Estate w/Hot tub • New Pool • Huge porch!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Magnificent estate with charm, ideal for family gatherings, events, and retreats! This 5,300 sqft home offers ample sp ...
From $1365 per night (USD)VRBO
From $471 per night (USD)VRBO
Lakefront, Kayaks Included, Come Unwind In Lenox!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Newly renovated lakefront getaway on beautiful and serene Laurel Lake in Lenox! This spacious 4-bedroom, 3-bat ...
From $471 per night (USD)VRBO
From $574 per night (USD)VRBO
Charming 3-bedroom condo with WiFi in Williamstown, MA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This fabulous condo in Williamstown offers 3 adorable bedrooms with queen beds, 2 brilliant bathrooms featuring a bathtu ...
From $574 per night (USD)VRBO
From $590 per night (USD)VRBO
Spacious 5-bedroom house in charming Lee with WiFi
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Welcome to Lee Manor – Your Cozy Retreat in the Heart of the Berkshires. Located in the charming town of Lee, Massachuse ...
From $590 per night (USD)VRBO
From $221 per night (USD)Expedia
The Serendipity Spot
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Greetings from the Serendipity Spot where old meets new in this charming, elegant & peaceful space where you may rest, l ...
From $221 per night (USD)Expedia
From $367 per night (USD)VRBO
Cozy, welcoming Berkshires cottage – perfect home base & place to unplug!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Charming, comfortable cottage tucked away in a serene setting in Mahkeenac Heights. Step back to a time when things wer ...
From $367 per night (USD)VRBO
From $288 per night (USD)Expedia
Friendly Hills | Passive Home • EV Charger
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Friendly Hills, a one-of-a-kind Mid-Century home nestled on 6 private acres. Built in the 1950s by GE enginee ...
From $288 per night (USD)Expedia
From $408 per night (USD)VRBO
Mac Shores | 5 min to Tanglewood ! • Shared Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our funky little summer cottage! Tucked in a stone`s throw from the Stockbridge Bowl and just down the street ...
From $408 per night (USD)VRBO
From $399 per night (USD)Expedia
Pixley Forest | 15 Mins To Tanglewood • Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Get away to this peaceful Berkshire escape tucked into the woods of Pixley Hill in West Stockbridge! The home boasts 3 f ...
From $399 per night (USD)Expedia
From $439 per night (USD)VRBO
Stockbridge Landings | 3 Mins To Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our rustic summer cottage—quaint, quirky, and perfectly imperfect! Nestled right at the Stockbridge Bowl in ...
From $439 per night (USD)VRBO
From $817 per night (USD)Expedia
St Anne`s Manor | Walk to Downtown! • Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Step back in time into this beautifully curated victorian built in the late 1800`s right in downtown Lenox. If a simple ...
From $817 per night (USD)Expedia
From $713 per night (USD)VRBO
Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Imagine being in a brand new apartment on Main Street Stockbridge. Well imagine no more - this is available with one ca ...
From $713 per night (USD)VRBO
From $223 per night (USD)Expedia
Berkshire Mountain Cottage - Spectacular Views of Mount Greylock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This lovely cottage sits on 90 acres featuring gardens, fruit groves, forest, and the Hoosic River. Spectacular views o ...
From $223 per night (USD)Expedia
From $476 per night (USD)VRBO
Spacious Central Berkshires Home for Groups
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Laurel House, your beautifully renovated home in the charming town of Lee, the gateway to the Berkshires. Whe ...
From $476 per night (USD)VRBO
From $448 per night (USD)VRBO
All Season Escape | Four 2BR Rooms, Pools, Movie Nights & Game Room Galore
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 24
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $448 per night (USD)VRBO
From $448 per night (USD)VRBO
Play, Soak, Repeat | 4 Spacious Villas w/ Pools, Game Room, Trails & BBQ Decks
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 24
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $448 per night (USD)VRBO
From $223 per night (USD)VRBO
Two Spacious Villas | Indoor Pools, Game Nights & Nature Trails – All-in Escape
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $223 per night (USD)VRBO
From $1168 per night (USD)VRBO
Crossbridge Main House - Vintage Charm & Unique Character
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 7
Summary: Crossbridge is a spacious 4 bed, 5 bath property 2.5 hrs from Boston & under 3 hrs from NYC. It is a beautiful ...
From $1168 per night (USD)VRBO
From $1653 per night (USD)VRBO
Crossbridge - Vintage Charm & Unique Character
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 11
Summary: Crossbridge is a spacious 6 bed, 7 bath property 2.5 hrs from Boston & under 3 hrs from NYC featuring a main h ...
From $1653 per night (USD)VRBO
From $309 per night (USD)VRBO
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: You want to bring your whole family to Jiminy and be in ONE CONDO, with gorgeous views, a deck, BBQ, Backyard, ...
From $309 per night (USD)VRBO
From $618 per night (USD)Expedia
The Summerwood Hideout | Mins to Downtown! • Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Book your getaway today to Long Pond Luxe in the Berkshires! This recently renovated home features a 3bd / 3 bath main h ...
From $618 per night (USD)Expedia
From $669 per night (USD)VRBO
Beautiful House in the Woods: Huge Yard, Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the charm of country living year-round on 4+ acres of peaceful land, tucked away on a private lane just minut ...
From $669 per night (USD)VRBO
From $316 per night (USD)Expedia
The Reel Retreat | Theatre & Firepit • Game Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Movie buffs unite! This home comes designed specifically as the perfect getaway. Featuring three comfortable bedrooms, ...
From $316 per night (USD)Expedia
From $936 per night (USD)VRBO
Copper Kettle Farm - newly renovated farmhouse with spectacular views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to Copper Kettle Farm in southern Berkshire County, Massachusetts. This newly renovated farmhouse is designed fo ...
From $936 per night (USD)VRBO
From $559 per night (USD)Expedia
Prime Location, Recently Redesigned, Riverfront!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Stay in a 4-bedroom historic factory conversion in Great Barrington. Original wood beams, stonework, and leade ...
From $559 per night (USD)Expedia
From $375 per night (USD)VRBO
Cheshire Cove | Waterfront • Kayak • Firepit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this charming lakeside oasis on Cheshire Lake in the heart of The Berkshires. This nicely appointed 2-bedroom, ...
From $375 per night (USD)VRBO
From $575 per night (USD)Expedia
1 Mi to Vineyard: Serene Berkshires Country Escape
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Built in the 1770s | Writer’s Workspace | Wooded Setting | 8 Mi to Stockbridge Bowl Breathe in the fresh air and let cr ...
From $575 per night (USD)Expedia
From $268 per night (USD)VRBO
Rustic 4-bedroom farmhouse in bucolic Hinsdale, MA
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Step back into the 1800's in this rustic post-and-beam farmhouse with original wide pine flooring. Hinsdale is the perfe ...
From $268 per night (USD)VRBO
From $936 per night (USD)VRBO
Best Berkshire “Readaway” Stay! New reno, stunning private acreage, cultural gem
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Pastoral Views | Luxe Furnishings | Cultural Center This Great Barrington area rental, which comfortably sleeps up to ...
From $936 per night (USD)VRBO
From $781 per night (USD)VRBO
Large open floor plan. Private yet close to everything. Lovely meadow views
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Get ready to relax in this 6-bedroom house in Pittsfield. This welcoming property boasts 4 queen beds, 1 king bed, 1 twi ...
From $781 per night (USD)VRBO
From $681 per night (USD)Expedia
Charming Barn Home Near Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to the Berkshires and enjoy this beautiful rustic barn home set on 7+ private acres overlooking Beaver Pond. The ...
From $681 per night (USD)Expedia
From $211 per night (USD)VRBO
Berkshires Barn Stay on Working Homestead
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is more than just a place to stay — it’s a working homestead experience. Depending on the season, guests may enjoy ...
From $211 per night (USD)VRBO
From $703 per night (USD)Expedia
Cozy. Clean. Free bagel shop. 3 Fireplaces.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Three reasons to stay: 1) The Bagels – enjoy a complimentary breakfast bagel and hot beverage from the Great Barringto ...
From $703 per night (USD)Expedia
From $1413 per night (USD)VRBO
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Luxury 4-Bedroom Retreat | Hot Tub • Pool Table • Gym • Spacious deck & lawn. Welcome to your private getaway — a beauti ...
From $1413 per night (USD)VRBO
From $437 per night (USD)VRBO
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the heart of the Berkshires at this stunning high-end retreat, designed for comfort, relaxation, and unforgett ...
From $437 per night (USD)VRBO
From $317 per night (USD)VRBO
Riverside Retreat in the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Stay in our charming historic home nestled along the Housatonic River, where peaceful river views and classic character ...
From $317 per night (USD)VRBO
From $511 per night (USD)Expedia
Lakes & Leisure! Spacious Berkshire Getaway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Spacious 4BR home in the Berkshires, sleeping up to 12 guests. Features two full baths, a well-equipped kitche ...
From $511 per night (USD)Expedia
From $1515 per night (USD)VRBO
Country Castle-Total privacy-just a few minutes from center of Great Barrington
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
Welcome to the Country Castle! This expansive home, boasting 7000 square feet, sits on 20 private acres less than five ...
From $1515 per night (USD)VRBO
From $270 per night (USD)Expedia
Pine & Paddle | Pond Access • Kayaks
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come enjoy all The Berkshires have to offer at our chic country cottage! Imagine relaxing by the cozy wood stove after a ...
From $270 per night (USD)Expedia
From $331 per night (USD)VRBO
Jiminy Peak Slopeside Getaway • Ski & Adventure
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Jiminy Peak Slopeside Getaway • Ski & Adventure ★☆ ABOUT THIS SPACE ☆★ Welcome to Jiminy Peak Slopeside Getaway, your a ...
From $331 per night (USD)VRBO
From $484 per night (USD)VRBO
Log Cabin w/ fire pit, close to Ski Catamount, Butternut Ski, Great Barrington
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hillside Haus is a modern log cabin on 4 private wooded acres close to Catamount Mountain & Ski Butternut. Enjoy soari ...
From $484 per night (USD)VRBO
From $452 per night (USD)VRBO
Play, Soak, Repeat | 4 Spacious Villas w/ Pools, Game Room, Trails & BBQ Decks
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 24
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $452 per night (USD)VRBO
From $339 per night (USD)VRBO
Three Villas, Endless Play | Indoor Pools, Trails, Games & BBQ Decks
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $339 per night (USD)VRBO
From $452 per night (USD)VRBO
Four 2BR Rooms, Fitness Center, Pools, Movie Nights & Game Room Galore
- Bedrooms:
- 8
- Bathrooms:
- 8
- Sleeps:
- 24
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $452 per night (USD)VRBO
From $113 per night (USD)VRBO
Scenic Escape: Full Kitchen, Pools, Game Room & Outdoor Fun
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $113 per night (USD)VRBO
From $226 per night (USD)VRBO
Two Spacious Villas | Indoor Pools, Game Nights & Nature Trails – All-in Escape
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $226 per night (USD)VRBO
From $226 per night (USD)VRBO
Two 2BR Villas l From Sauna to Sports Courts – Comfort & Fun for Everyone
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Muse ...
From $226 per night (USD)VRBO
From $537 per night (USD)VRBO
Beautiful Berkshire Home - in the heart of Southfield, Ma. -The Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience New Marlborough like a local in this 3-bedroom house. Each bedroom features a lovely queen bed for a comforta ...
From $537 per night (USD)VRBO
From $370 per night (USD)VRBO
New Listing!! Berkshire Flat Overlooking Rising Pond!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Two cozy bedrooms featuring brand new queen and king beds, plus a living room with a comfortable sofa bed, Each bedroo ...
From $370 per night (USD)VRBO
From $542 per night (USD)VRBO
Lenox Interlude Stylish Retreat Views, Central Air, Walk to Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Lenox Interlude is nestled on a quiet cul-de-sac, an easy, seven-minute walk from Lenox village. Designed for guests se ...
From $542 per night (USD)VRBO
From $507 per night (USD)Expedia
Hawthorne House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy the Berkshires at our peaceful and centrally-located home. This well appointed, spacious stay is just down the roa ...
From $507 per night (USD)Expedia
From $1450 per night (USD)VRBO
Fernbrook - Contemporary Getaway with Private Home Gym near Great Barrington
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Fernbrook is a stylish 5 bed, 4.5 bath Scandinavian-inspired sanctuary 2.5 hrs from Boston & under 3 hrs from ...
From $1450 per night (USD)VRBO
From $553 per night (USD)Expedia
Kayak on Prospect Lake, Paddle Boards, Swim Dock+!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Amenities: 3 bedroom, 1 bath, sleeps 4 or 5, max. waterfront cottage on Prospect Lake with a sun deck, bar, 2 kayaks, 2 ...
From $553 per night (USD)Expedia
From $234 per night (USD)VRBO
Fall Weekends and Ski Season is here!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This light and bright home has been beautifully remodeled to be the perfect rental for you to enjoy the Berkshires! Whet ...
From $234 per night (USD)VRBO
From $1253 per night (USD)Expedia
Berkshires Mid-Century Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to this one-of-a-kind sanctuary, nestled on 14 pristine acres in the mountains of the Berkshires, just minutes fr ...
From $1253 per night (USD)Expedia
From $494 per night (USD)VRBO
Cozy Duplex in Pittsfield: 1 Mile to Onota Lake – Near Bousquet & Jiminy Peak
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Pittsfield at this perfect duplex with 3 rooms and 1.5 bath; enclosed porch with yard views and spac ...
From $494 per night (USD)VRBO
From $1369 per night (USD)VRBO
Comfortable & Casual Stockbridge Retreat with View & Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Relax by the pool or on the shaded porch and enjoy the light breeze, and open views of the Berkshire Mountains. Enjoy t ...
From $1369 per night (USD)VRBO
From $371 per night (USD)VRBO
Prime Berkshires–2 Bed Garden Home–Private Entry–Walk to Town & Lake!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this quaint apartment in picturesque Great Barrington. With two cozy bedrooms—one featuring a queen bed and th ...
From $371 per night (USD)VRBO
From $691 per night (USD)VRBO
All new mountain retreat near Great Barrington.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kick back and relax in this calm, stylish space. Amazing restaurants, hiking and biking trails, fishing, and ski mounta ...
From $691 per night (USD)VRBO
From $668 per night (USD)VRBO
Spacious Lenox Home Near Tanglewood
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Experience the beauty of the Berkshires in this spacious historic home overlooking a wildflower meadow with mo ...
From $668 per night (USD)VRBO
From $345 per night (USD)Expedia
Family Cabin w/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Great Barrington=25min Tanglewood=34min Otis Reservoir=13min Appala Trail=13min Jacobs Pillow=15min Welcome to The Owl ...
From $345 per night (USD)Expedia
From $773 per night (USD)VRBO
Berkshire Lake Hideaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Tucked on a quiet little lake, Berkshire Lake Hideaway is a cozy 3BR/3BA cottage sleeping 6 (7 w/ child) — minutes from ...
From $773 per night (USD)VRBO
From $335 per night (USD)Expedia
Fall Fun in the Berkshires: Yard, Patio, Playset
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Near Trails & Lake Access | Fire Pit & Grill | Fall Foliage & Apple Picking Pack up the crew for a cozy Berkshires geta ...
From $335 per night (USD)Expedia
From $232 per night (USD)VRBO
Cozy Camper tucked into the woods
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RV turned cozy tiny house on a small homestead. There’s 50 private acres that connect you to state forest trails that go ...
From $232 per night (USD)VRBO
From $818 per night (USD)Expedia
Chic, Mid Century 3+ Bedroom with Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Amenities Include: 3 bedrooms and 3 full bathrooms (sleeps 8 in beds), bonus finished basement game room, high speed int ...
From $818 per night (USD)Expedia
From $602 per night (USD)VRBO
Direct on Lake Garfield: Book Fall Weekends!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Lake Garfield Waterfront is a dynamic, adorable, cozy and exhilarating rental experience directly on the water! Ameniti ...
From $602 per night (USD)VRBO
From $751 per night (USD)Expedia
Colorful Fall Weekends with River Views! Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Riverside Amenities: 4 bedrooms (King, Queen, Queen, King), 2.5 baths. sleeps 8 guests in beds, with a max of 10 guests. ...
From $751 per night (USD)Expedia
From $745 per night (USD)VRBO
Fall Weekends: Hot Tub, Green River Hike, Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Highland: Epic GB location: walk-to the Green River, fully fenced yard, with hot tub. 4 Bedroom, 2.5 baths, Sleeps 8 in ...
From $745 per night (USD)VRBO
From $918 per night (USD)Expedia
Light-filled, Stylish, Farmhouse Colonial, Egremont MA
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
span style="font-family:Verdana,Geneva,sans-serif;">Seventeen is a beautifully Updated light-filled Berkshire Farmhouse ...
From $918 per night (USD)Expedia
From $1004 per night (USD)VRBO
5 Stars w/ Hot Tub, Sunny Patio, Game Room, Views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
White Birch amenities include 4 bedrooms, 3 baths, Sleep 12+ a main floor master suite with a large walk in shower, hot ...
From $1004 per night (USD)VRBO
From $546 per night (USD)Expedia
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Amenities: 3 bedrooms, 1.5 baths, (sleeps 6 in beds or 8 Max.) WIFI, AC, SmartTVs with Spectrum cable, local phone, good ...
From $546 per night (USD)Expedia
From $450 per night (USD)VRBO
Timber-Frame Retreat + Chef's Kitchen + Game Room | 3.5 Acres | Bow & Beam
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The drive ends at a wide green lawn, and then the house: shingled, gabled, and quietly substantial, with woods drawing a ...
From $450 per night (USD)VRBO
From $1073 per night (USD)Expedia
Grand Berkshire Manor By Evergreen Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Evergreen Home Vacation Rentals invites you to The Manor, a refined five-bedroom, 4.5-bathroom retreat in the heart of t ...
From $1073 per night (USD)Expedia