Berkshire Area, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Berkshire Area, Massachusetts on RentalSaver.com!

Berkshire Area Rentals

From $689 per night (USD)
VRBO
Luxury 3-Bedroom Retreat in Downtown Lenox & Minutes to Tanglewood
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your perfect Berkshires getaway! This beautifully appointed 3-bedroom home is located right in downtown Lenox ...
From $689 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Timpani Corners | Private Pond • AC
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Tucked beside a brook on a private quarry pond in Lenox adjacent to Pleasant Valley Wildlife Sanctuary, this rustic cabi ...
From $317 per night (USD)
Expedia
From $273 per night (USD)
VRBO
Country Charm condo with gym, pool, hot tub & ski-in/ski-out access and king bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Hancock adventure begins at this cozy condo. The resort offers adorable country charm you'll love! Equipped with a ...
From $273 per night (USD)
VRBO
From $442 per night (USD)
Expedia
3-bedroom duplex in Stockbridge on the river
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Come relax in this three bedroom space on two floors that occupies one side of a duplex in Stockbridge. Located on the H ...
From $442 per night (USD)
Expedia
From $290 per night (USD)
VRBO
stylish Berkshires Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience stylish comfort in our recently renovated two-bedroom home, thoughtfully designed for relaxation and connecti ...
From $290 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Lakeside. Enjoyable 4-bedroom house in quaint Hinsdale minutes from Pittsfield
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This Hinsdale house boasts 4 inviting bedrooms, including a king bed, 4 twin beds, and a full bed. Guests enjoy two bath ...
From $301 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Cozy cottage in the Berkshires
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your cozy getaway awaits in PITTSFIELD at this brilliant house. Guests will find one comfortable bedroom and a peaceful ...
From $268 per night (USD)
VRBO
From $536 per night (USD)
Expedia
Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy a peaceful stay at this 3-bedroom mountainside townhome located within Jiminy Peak resort. The space features thre ...
From $536 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Historical Housatonic Street apartment
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Located on Housatonic Street in downtown Lenox. A beautifully renovated space fully equipped for all your needs. The kit ...
From $367 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Suite: The loft-like second floor studio Suite has an upright piano for playing, a private balcony with a beautiful view ...
From $344 per night (USD)
Expedia
From $1070 per night (USD)
VRBO
Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Evergreen Home Vacation Rentals invites you to this refined log cabin featuring a heated saltwater pool, hot tub, and mo ...
From $1070 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Real Estate: Therapy - Lake, Laundry, Love it
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
This is what happens when a realtor and an expressive-therapist make a vacation home. You get a decent property, in a go ...
From $299 per night (USD)
Expedia
From $731 per night (USD)
VRBO
Charming 5-bedroom farmhouse in Lanesborough
Bedrooms:
2
Bathrooms:
5
Sleeps:
13
Relax with the whole family at this peaceful Historic Farmhouse Retreat with Modern Luxuries in the Berkshires. Welcome ...
From $731 per night (USD)
VRBO
From $323 per night (USD)
Expedia
Dharma Grove - Bask in the Light
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Set on sprawling open grounds in Richmond, this Berkshire retreat has a quiet magic to it. The home is bright and airy, ...
From $323 per night (USD)
Expedia
Click For Pricing
VRBO
Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Keep it simple at this peaceful and centrally-located apartment set on 17 private acres. Bright, clean and serene; you ...
Click For Pricing
VRBO
From $458 per night (USD)
VRBO
Berkshires 3BR Retreat in Lee, MA with Lake & Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the Berkshires like a local in this adorable 3-bedroom house. With two queen beds and twin trundle beds, it c ...
From $458 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Private Home in the Berkshires with Hot Tub
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your private country escape — a newly renovated 2-bedroom, 1-bath home surrounded by 2 acres of open lawn and ...
From $529 per night (USD)
VRBO
From $339 per night (USD)
Expedia
The Docent`s House - Honoring a Legacy
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to The Docent`s House, a home with a story worth staying for. For 18 years the woman who lived here walked visit ...
From $339 per night (USD)
Expedia
From $659 per night (USD)
VRBO
Historic, Modern Comforts, Walk To Downtown
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Summary: Spacious historic home in Downtown Great Barrington blending century-old charm with modern comforts. Sleeps up ...
From $659 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Lakefront Chalet | Dock, Sauna & Fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Escape to this peaceful lakefront chalet in the heart of the Berkshires. Set along the quiet shores of Long Bo ...
From $399 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Relax in this 3 bedroom Otis retreat in the woods!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Spacious and comfortable home in Otis. Relax on the wraparound porch or screened in patio while enjoying the peace and q ...
From $538 per night (USD)
VRBO
From $2546 per night (USD)
VRBO
Berkshire Estate In The Heart Of Lenox 10 Luxurius Bds, Indoor/Outdoor Pools
Bedrooms:
9
Bathrooms:
10
Sleeps:
17
This historic Rotch and Tilden designed 1889 mansion includes 10 bedrooms 9.5 baths to comfortably accomodate 17 guests. ...
From $2546 per night (USD)
VRBO
From $423 per night (USD)
VRBO
Stoneridge Landing | Hot Tub • Fire Pit
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to Hillside Haven, a cozy Berkshire retreat perfect for families. This spacious 4BR, 2.5BA home features an open ...
From $423 per night (USD)
VRBO
From $491 per night (USD)
VRBO
7 minute walk to Tanglewood! Beautifully renovated 2BR Berkshire home.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your Berkshires escape, where elevated design, privacy, and an unbeatable location come together just steps f ...
From $491 per night (USD)
VRBO
From $233 per night (USD)
VRBO
Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Relax and enjoy at this peaceful 1 bedroom, 1 bath condo with pullout couch and pullout sleeper chair (unit sleeps 5) at ...
From $233 per night (USD)
VRBO
From $843 per night (USD)
VRBO
Berkshire Waterfront Private Escape– 5BR, 3 Bath, Hot Tub, Firepit & Kayak
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Hayden’s Hideaway Escape to Hayden’s Hideaway — a peaceful lakefront home in the heart of the Berkshires, pe ...
From $843 per night (USD)
VRBO
From $314 per night (USD)
VRBO
Charming Retreat by Mass MoCA
Bedrooms:
1
Bathrooms:
4
Sleeps:
9
The perfect weekend retreat, this charming country home with an antique vibe is centrally located by all the arts and cu ...
From $314 per night (USD)
VRBO
From $451 per night (USD)
VRBO
Nature Retreat Near Prospect Lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
Summary: Spacious Berkshires getaway, come enjoy nature, with easy access to Prospect Lake! Enjoy a large granite kitch ...
From $451 per night (USD)
VRBO
From $1526 per night (USD)
VRBO
Expansive Mountainside Escape by Evergreen Home
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Evergreen Home Vacation Rentals invites you to this sprawling 6-bedroom, 4.5-bathroom retreat featuring sweeping mountai ...
From $1526 per night (USD)
VRBO
From $1109 per night (USD)
VRBO
Large Mountainside Condo with Private Trail to Grouse Run
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Your All-Season Berkshires Getaway — Ski, Relax & Reconnect! Welcome to your home away from home in the heart of the Be ...
From $1109 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Single family home, nice neighborhood with fenced in back yard. Pet friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
North Adams is waiting for you at this charming 2-bedroom house. Inside, guests find two comfortable queen beds and 1.5 ...
From $208 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Cozy 1-bedroom studio in serene Great Barrington with AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This Great Barrington studio boasts one welcoming bedroom featuring a cozy bunk bed and a comfortable sofa bed. Guests e ...
From $165 per night (USD)
Expedia
From $472 per night (USD)
VRBO
Light-filled Carpenter's Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to this charming cottage in picturesque Stockbridge. Guests will enjoy a serene retreat featuring one cozy bedroo ...
From $472 per night (USD)
VRBO
From $547 per night (USD)
VRBO
Hot Tub, Lake Views! All-Season Hinsdale Haven
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Lindal Home | 5 Mi to the Appalachian Trail | Near Ski Resorts Tucked into the peaceful winter landscapes of Hinsdale, ...
From $547 per night (USD)
VRBO
From $251 per night (USD)
VRBO
Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This fabulous house is the perfect home base for your trip to Berkshires. With three cozy bedrooms featuring two queen b ...
From $251 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Misty Pines Cabin | Wood Stove • Sauna
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Misty Mountain Camp — a cozy 3-bedroom, 3-bath escape surrounded by peaceful woods and Berkshire charm. Enjoy ...
From $306 per night (USD)
Expedia
From $619 per night (USD)
VRBO
Heated Pool & Hot Tub • Ideal Berkshires / Hudson Valley Getaway
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
A stylish 4-bedroom farmhouse thoughtfully designed with modern comfort and historic charm. Located where the Berkshire ...
From $619 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Cozy Pittsfield Gem w/ Deck, Gazebo & Fireplace!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Find peace and adventure at this inviting Pittsfield escape, just minutes from ski slopes and forest trails. This cozy 3 ...
From $430 per night (USD)
Expedia
From $355 per night (USD)
VRBO
2-bedroom cottage close to hiking and swimming with AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the beauty of the Southern Berkshires in the quaint village of Mill River in the town of New Marlborough, MA, f ...
From $355 per night (USD)
VRBO
From $702 per night (USD)
VRBO
3-Bedroom Victorian home within walking distance of downtown Great Barrington.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Higgins House: A 1920 Folk Victorian Retreat Close to the Town Center Welcome to Higgins House, a beautifully restored ...
From $702 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Lots of snow! Ski, snowshoe/ heated pool - fabulous in beautiful Stockbridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to the Garden House in picturesque Stockbridge. Fifteen minutes to three ski areas. Fully furnished and equipped ...
From $230 per night (USD)
VRBO
From $792 per night (USD)
Expedia
The Belden House - WALK to Tanglewood !
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Step into the Belden House, circa 1881. Stop and imagine reading a book beside the vintage Steinway in the music parlor, ...
From $792 per night (USD)
Expedia
From $363 per night (USD)
VRBO
1 BR | Vacation Village In The Berkshires
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Please Do Not Forget to Check for important information about Additional Fees that may be collected at the Resort. Th ...
From $363 per night (USD)
VRBO
From $334 per night (USD)
VRBO
1 BR | Vacation Village In The Berkshires
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Please Do Not Forget to Check for important information about Additional Fees that may be collected at the Resort. Th ...
From $334 per night (USD)
VRBO
From $631 per night (USD)
VRBO
2 BR | Vacation Village In The Berkshires
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Please Do Not Forget to Check for important information about Additional Fees that may be collected at the Resort. Th ...
From $631 per night (USD)
VRBO
From $640 per night (USD)
Expedia
Meadow`s Edge: A Modern Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Meadow`s Edge, a modern 4 bed, 3.5 bath luxury retreat in historic Stockbridge, MA, just 5 minutes from Tangl ...
From $640 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Berkshire's Family Gathering & Mountain Escape!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Newly Renovated Berkshires home on 10 acres of private land. Immerse yourself in nature and explore the property in all ...
From $540 per night (USD)
VRBO
From $444 per night (USD)
VRBO
3-bedroom furnished townhome near Lenox, beautiful views, 3 month min rental
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
New on the rental market for 2026, this fully-furnished 3-bedroom, 2-car garage townhome features 3 1/2 bathrooms, a lei ...
From $444 per night (USD)
VRBO
From $236 per night (USD)
VRBO
Charming & Bright Berkshires Field House
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy our sun drenched and cozy Berkshires retreat! Our duplex is newly renovated with updated bathrooms and new applian ...
From $236 per night (USD)
VRBO
From $1082 per night (USD)
Expedia
Woodland - Stunning 5 bedroom home in GB!
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Sparkling Renovation, top to bottom, on quiet cul-du-sac: 5 bedrooms, 3.5 baths, sleeps 14 in beds. Max of 9 adults, pre ...
From $1082 per night (USD)
Expedia
From $429 per night (USD)
VRBO
Updated and inviting home in Lenoxdale
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to this thoughtfully renovate half duplex in the village on Lenoxdale. Neat as a pin, this unit offers an inviti ...
From $429 per night (USD)
VRBO
From $606 per night (USD)
VRBO
Charming in-town Lenox Cottage with AC and fire pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Walk to Downtown & just minutes to Tanglewood! Enjoy a lovely, historic cottage in the heart of Lenox, just steps from ...
From $606 per night (USD)
VRBO
From $318 per night (USD)
VRBO
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay comfortably in Lenox at this charming 1-bedroom apartment. The space features a cozy queen bed, perfect for a restf ...
From $318 per night (USD)
VRBO
From $214 per night (USD)
VRBO
Cozy Berkshire Retreat Near Skiing & Culture
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in this cozy 1-bedroom condo nestled in the heart of the Berkshires, comfortably sleeping up to 4 guests. The uni ...
From $214 per night (USD)
VRBO
From $766 per night (USD)
VRBO
Spacious 5BR Farmhouse • Sleeps 10 • Perfect for Families • Near Two Lakes
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Brady’s Croft, a beautifully restored farmhouse in the heart of the Berkshires. Set on 3 peaceful acres, our ...
From $766 per night (USD)
VRBO
Click For Pricing
Expedia
Luxury, Romantic, Timeless Berkshires: Sleeps 18!
Bedrooms:
4
Bathrooms:
8
Sleeps:
18
Hartfield: Sprawling Designer Colonial with 8 Bedrooms, 4.5 baths - sleeps 18 Max. High Speed internet and Wi-Fi, 2 wood ...
Click For Pricing
Expedia
From $421 per night (USD)
VRBO
Charming Berkshire Retreat-Minutes to Williamstown
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Beautifully renovated home on a former farm with the Green River running through the backyard. Between Williamstown & Ne ...
From $421 per night (USD)
VRBO
From $817 per night (USD)
Expedia
Fall Weekends, Lake Buel Dock Sunsets: Sleeps 8!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Immaculate Waterfront Lake House with Direct Access to Lake Buel. This charming, spotless, 4-season lake cottage is per ...
From $817 per night (USD)
Expedia
From $893 per night (USD)
VRBO
Shaker Pine Cabin: your cozy Berkshires retreat in the middle of it all!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to Shaker Pine Cabin in the heart of charming West Stockbridge! Set on 4 peaceful acres, this newly renovated lo ...
From $893 per night (USD)
VRBO
From $259 per night (USD)
Expedia
Cozy 1-Bedroom Guesthouse in Beautiful Southfield
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step into a beautifully preserved piece of Berkshire history. Originally built in the 1880s, this renovated one-bedroom ...
From $259 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Modern Berkshire Retreat on 8 Peaceful Acres Near Tanglewood & Trails
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to a true Berkshire mountain retreat on nearly eight peaceful acres in one of the Berkshires’ most beautiful hill ...
From $407 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located in North Adams, this inviting apartment offers a peaceful home base for your Berkshires getaway. Designed for co ...
From $232 per night (USD)
Expedia

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Berkshire Area Rentals

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Results: 562 Rentals