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 $209 per night (USD)
VRBO
Garfield Townhouse in the Berkshires on Main St
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozy Townhouse on Main St in Lee , the entrance to the Berkshires. The townhouse is two stories with 2 Bedrooms, 1 1/2 ...
From $209 per night (USD)
VRBO
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Expedia
Cozy two-bedroom ranch 15 minutes from Butternut Ski Resort - 90-day minimum
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy our comfortable, cozy, fully furnished two-bedroom, two-bathroom ranch (1,500 square-feet) in the Berkshires (Mont ...
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Expedia
$Berkshire Ski House \/ Pittsfield$
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VRBO
Berkshire Ski House \/ Pittsfield
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Close to several popular family friendly Berkshire ski areas. Theaters restaurants and shopping are all walking distan ...
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VRBO
From $469 per night (USD)
Expedia
Rustic Getaway with Extraordinary Vista
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
With exceptional lighting, Sky House overlooks a gorgeous , sloping yard in peaceful Monterey. Close to Lake Garfield an ...
From $469 per night (USD)
Expedia
From $563 per night (USD)
VRBO
Great Barrington Get Away
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Charming home steps away from downtown Great Barrington. Lots of modern amenities, close to all the fantastic cultural ...
From $563 per night (USD)
VRBO
From $558 per night (USD)
Expedia
Art House! Spacious Getaway By Mass Moca
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
This newly renovated Victorian curated by the local Grant Larkin Design Team is a great space for large groups, with eas ...
From $558 per night (USD)
Expedia
From $233 per night (USD)
VRBO
mountain refuge
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Extended stays are welcome! Stay in our little Mobile Home, clean, sweet and unique. The house is adjacent to Breakshir ...
From $233 per night (USD)
VRBO
From $303 per night (USD)
Expedia
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Spacious living/kitchen area, located on a quiet street and central location walkable to campus and restaurants, museums ...
From $303 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Stockbridge Home: Walk to Town Beach!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Escape to a lake retreat with this 3-bedroom, 1-bathroom vacation rental home in Stockbridge. Stockbridge Bowl's grassy ...
From $302 per night (USD)
VRBO
From $1117 per night (USD)
Expedia
ONTARA....
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ONTARA, Place of the New Light...in the Berkshires...on the mountainside, with the back of the property on the New York ...
From $1117 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Home in Great Barrington
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Central and Private!! Just steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy su ...
From $341 per night (USD)
VRBO
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Expedia
Restored Historic Home Half Mile to Ski Resort!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to The Berkshires and explore endless adventures in the area’s mountains, forests, and arts venues! This 4-bedroo ...
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Expedia
From $1575 per night (USD)
VRBO
Charming 6 Bdrm Countryside Stay, Sauna & HotTub
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
This stunning 6 bedroom, 5.5 bath home is the perfect blend of charm, privacy, and modern comfort. Thoughtfully designed ...
From $1575 per night (USD)
VRBO
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Expedia
River Orchard Meadow
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Tasteful, comfortable & tidy family Berkshire home located on the Housatonic River minutes from all the Berkshire offeri ...
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Expedia
From $721 per night (USD)
VRBO
Berkshires Lakefront Retreat by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your serene retreat nestled on 4 private acres. This newly renovated 4BR/2.5BA home offers breathtaking views ...
From $721 per night (USD)
VRBO
$1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On\/Off, Fully Redone Count$
From $250 per night (USD)
Expedia
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On\/Off, Fully Redone Count
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to the Woodlands. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn. 1st Fl ...
From $250 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Cozy Home on 17 acres in W Stockbridge. Close to the Pike, Slopes, Tanglewood
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Enjoy your stay in heart of the Berkshires! This 3 bedroom, 2 bath ranch vacation house in set on 17 private acres. En ...
From $274 per night (USD)
VRBO
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Expedia
Family fun @ The Ponds at Foxhollow Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Ponds at Foxhollow is a distinctive residential community in Lenox, MA. The community features elegantly designed ho ...
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Expedia
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VRBO
BERKSHIRES CHARM! Lenox, Tanglewood! SUMMER ONLY, or LongTerm Rental. Location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LOCATION! **Enjoy the culture and beauty of a Berkshires/Tanglewood summer from cozy furnished apartments of this 1840 ...
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VRBO
From $611 per night (USD)
Expedia
Linden by AvantStay | Countryside Berkshire Escape
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to Linden! Surrounded by tons of space and trees, this 4BR retreat gives your group the style, room, and privacy ...
From $611 per night (USD)
Expedia
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VRBO
Eastbungalow
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
About this space Welcome to the Berkshires!!! A very large duplex apartment with own entrance and a porch to relax in. T ...
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VRBO
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Expedia
Charming Ashley Falls Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
About this space The home is set back from the road in a quiet rural neighborhood, nestled among stately pines. There is ...
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Expedia
From $538 per night (USD)
VRBO
Moores · Berkshire Mountain Top Chalet
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Summary: Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fi ...
From $538 per night (USD)
VRBO
From $474 per night (USD)
Expedia
Treetop Hideaway in Tyringham
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
Summary: For your upcoming stay, look no further than this airy, secluded log cabin overlooking the beautiful Tyringham ...
From $474 per night (USD)
Expedia
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VRBO
Cabin in the woods w cedar Hot Tub + private pond
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
About this space The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests ...
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VRBO
From $398 per night (USD)
Expedia
Great Barrington Farmhouse near Lake Mansfield
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
72 CHill Road is a cozy 1860’s farm house with mid-century modern flair. A 7-minute drive to downtown or Butternut, this ...
From $398 per night (USD)
Expedia
From $1362 per night (USD)
VRBO
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
Renovations just finished on this unique home, that originally dates to the 1700s. Great for families and big groups, wi ...
From $1362 per night (USD)
VRBO
From $341 per night (USD)
Expedia
Park Street Penthouse Apartment
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Stay in one of the best preserved historical home that's now a private art galley in downtown Adams. Walk to Adams Thea ...
From $341 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Wake up to spectacular sunrise lake views from the deck or while soaking in the hot tub. Close to all the year round a ...
From $396 per night (USD)
VRBO
From $496 per night (USD)
Expedia
New home in the Berkshires. Fire pit, Hot tub, gas grill, private & quiet.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with the whole family or escape with your partner for a romantic getaway to Lovers Lane. Surrounded by trees and s ...
From $496 per night (USD)
Expedia
From $559 per night (USD)
VRBO
Spring time fun time. Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
***Spring Time is here. Stroll the town or enjoy a scenic walk then warm right up in our OUTDOOR Hot Tub after a long da ...
From $559 per night (USD)
VRBO
$Serene Berkshires Cabin w\/ Deck & Fire Pit!$
From $367 per night (USD)
Expedia
Serene Berkshires Cabin w\/ Deck & Fire Pit!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Discover the charm, beauty, and fun of the Berkshires from this 4-bedroom, 3-bath Otis cabin. Featuring a peaceful woode ...
From $367 per night (USD)
Expedia
$Gorgeous Mountain View Suite Ski On\/Off At Jiminy - Fully Redone Decor$
From $250 per night (USD)
VRBO
Gorgeous Mountain View Suite Ski On\/Off At Jiminy - Fully Redone Decor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Welcome to modern country comfort. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn ...
From $250 per night (USD)
VRBO
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Expedia
Quaint Single Story 1Bd with Vintage Charm, Walk to Downtown Restaurants & Shops
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to our charming 1 bedroom, 1 bath single-level duplex, located just 2 town blocks from the heart of downtown Lee ...
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Expedia
From $1272 per night (USD)
VRBO
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldw ...
From $1272 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Quiet Cabin On Over 12 Acres Of Woods!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: This home features both modern finishes & New England charm. Large open great room, chef's kitchen & brick fire ...
From $329 per night (USD)
Expedia
From $302 per night (USD)
VRBO
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Stay at the heart of it all. Walk to lifts, restaurants, shopping and amenities right from your door. It doesn’t get an ...
From $302 per night (USD)
VRBO
From $227 per night (USD)
Expedia
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village ...
From $227 per night (USD)
Expedia
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VRBO
1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village.
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Our home is located in the beautiful village of New Marlborough - 15/20 min. from Gt. Barrington & Sheffield. The porch ...
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VRBO
$Stockbridge Retreat w\/ Pool & Hot Tub!$
From $1624 per night (USD)
Expedia
Stockbridge Retreat w\/ Pool & Hot Tub!
Bedrooms:
4
Bathrooms:
8
Sleeps:
10
Escape to the Berkshires and indulge in the ultimate experience at this luxurious 4-bedroom, 3.5-bathroom house. Situate ...
From $1624 per night (USD)
Expedia
From $439 per night (USD)
VRBO
A cozy home nestled in the Green Mountains of Vermont!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Our cozy home is great in all seasons! Comfortably furnished, it is a great place to read in front of the fire, set out ...
From $439 per night (USD)
VRBO
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Expedia
Serene Acreage - Pond - Hiking Trails Nearby
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hawks Eye Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
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Expedia
From $625 per night (USD)
VRBO
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Autumn Hill Lakehouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $625 per night (USD)
VRBO
$Monterey Haven < 1\/2 Mi to Lake Garfield w\/ Kayaks$
From $276 per night (USD)
Expedia
Monterey Haven < 1\/2 Mi to Lake Garfield w\/ Kayaks
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Get carried away to this quaint 3-bedroom, 1-bath vacation rental in beautiful Monterey, Massachusetts. Surrounded by sc ...
From $276 per night (USD)
Expedia
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VRBO
Large Country farmhouse in the Berkshires.
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to Brookside Farm, a 5000sqft one level farmhouse on 70 acres of woodlands and fields with a large pond that yie ...
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VRBO
From $508 per night (USD)
Expedia
Shales Brook Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Shales Brook Cottage is a newly renovated 2 bedroom and 2 bath, fantastic place. Vintage Malm wood burning stove for coo ...
From $508 per night (USD)
Expedia
From $259 per night (USD)
VRBO
COME STAY AT THE SHEFFIELD CHALET!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Bring friends or the whole family to this cozy accessible Berkshire County Country getaway. Only 5 minutes to Great Barr ...
From $259 per night (USD)
VRBO
$Ashley Falls Home w\/ Fire Pit: Hike & Ski!$
From $439 per night (USD)
Expedia
Ashley Falls Home w\/ Fire Pit: Hike & Ski!
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Game Room | 2,734 Sq Ft | ~6 Mi to Campbell Falls State Park Whether you’re chasing waterfalls in the summer, leaf-peep ...
From $439 per night (USD)
Expedia
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VRBO
Berkshires Log Cabin by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The ultimate escape to peace & tranquility in the Berkshires! Set on 1.3 private acres, this cozy log cabin getaway is c ...
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VRBO
From $390 per night (USD)
Expedia
Lenox - Walk to Town - Berkshire Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Come, enjoy the Berkshires! This cottage built in the 1950's has recently been completely renovated from stem to stern ...
From $390 per night (USD)
Expedia
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VRBO
Long term vacation rental. Quiet clean and comfortable all one level
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a all one level, 1st floor, 1bedroom & 1bathroom in a 2 family home. The property has been recently updated with ...
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VRBO
From $674 per night (USD)
Expedia
Imagine Being Lakeside This Summer! Book Now!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Summary: This two story lake home has all the room needed for you and your guests to experience the serenity of lake liv ...
From $674 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Charming Apt in 18th c Berkshire Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This lovely studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in t ...
From $208 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Chic Berkshire Retreat by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Feel like you have entered your own oasis in this charming retreat. A hidden gem set far back from the road, tucked away ...
From $458 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Ski Season Rental!
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Charming cottage on "The Hill," within walking distance of Lake Mansfield and the shops and restaurants of downtown Grea ...
From $372 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Berkshires Cabin Steps to Lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This cabin is across the street from Little Robin Lake and is big enough to spread out with lots of quiet spaces. Living ...
From $232 per night (USD)
Expedia
From $182 per night (USD)
VRBO
Renovated Private Guest House by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Your perfect Berkshire getaway awaits in this 2 BR, 1.5 BA guest house on Long Pond Rd in Great Barrington. Hiking is j ...
From $182 per night (USD)
VRBO
From $525 per night (USD)
Expedia
Whitney by AvantStay | Private Berkshires Estate
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Settle in among the beauty of the Berkshires at Whitney, a private retreat overflowing with comfort and charm. Enjoy the ...
From $525 per night (USD)
Expedia
$Lenox House w\/ Screened Patio & Mountain View$
From $222 per night (USD)
VRBO
Lenox House w\/ Screened Patio & Mountain View
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Head to Massachusetts for the holiday and stay at this inviting 1-bedroom, 1.5-bathroom vacation rental house in Lenox. ...
From $222 per night (USD)
VRBO
$Charming Farmhouse; 2 Bed \/ 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.$
From $267 per night (USD)
Expedia
Charming Farmhouse; 2 Bed \/ 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come experience the charms of our 18th century family farmhouse, where old meets new to combine into a cozy weekend geta ...
From $267 per night (USD)
Expedia
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VRBO
Spacious & Serene Berkshires Retreat In The Woods
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
Summary: Unplug from city life and retreat to our spacious home in beautiful West Stockbridge. Minutes away from all the ...
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VRBO
From $835 per night (USD)
Expedia
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Bedrooms:
7
Bathrooms:
7
Sleeps:
15
This charming former tavern and stage coach inn makes the perfect four season getaway. You'll feel like you've taken ove ...
From $835 per night (USD)
Expedia
From $322 per night (USD)
VRBO
Cozy retreat in beautiful country setting
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled at the base of October Mountain, this cozy retreat has all the comforts of home. Sit out on the deck and sip you ...
From $322 per night (USD)
VRBO
From $179 per night (USD)
Expedia
Upstairs on Main with private bathroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This is our newest and most exciting unit. Before, it was a one bedroom with two small business offices on the same floo ...
From $179 per night (USD)
Expedia
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VRBO
Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. W ...
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VRBO
From $296 per night (USD)
Expedia
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
This ski-in, ski-out condo is located right at the base of the mountain in JJ’s Lodge in the heart of the village at Jim ...
From $296 per night (USD)
Expedia
From $642 per night (USD)
VRBO
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Open and bright retreat in beautiful setting with privacy and stunning lake views. Centrally located between Lenox and S ...
From $642 per night (USD)
VRBO
From $339 per night (USD)
Expedia
COZY CABIN IN BERKSHIRES RESORT
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
PERFECT COZY MOUNTAIN CABIN for a couple's getaway, a fun little trip with friends or with family to enjoy all offered b ...
From $339 per night (USD)
Expedia
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VRBO
Stylish cottage close to great hiking trails and great art museums
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The cabin on Florida Mountain has a covered porch and a south facing terrace providing ample outdoor space in complete p ...
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VRBO
$Half Moon by AvantStay | 4BR Cabin w\/ Large Deck & Yard$
From $513 per night (USD)
Expedia
Half Moon by AvantStay | 4BR Cabin w\/ Large Deck & Yard
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Kick back among the wooded hills of the Berkshires at Half Moon. The rustic exterior of this log cabin gives way to natu ...
From $513 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: The most unique Suite in the Berkshires - This gorgeous Disney Themed Hotel Room will bring Mickey Magic to our ...
From $250 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
FULLY RENOVATED FALL 2023. Beautiful Berkshire home with modern furnishings. This fabulous multi-level 3 bedroom house ...
From $509 per night (USD)
Expedia
$Williamstown Rustic & Spacious Estate w\/ 4 Master Suites in Berkshire County$
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VRBO
Williamstown Rustic & Spacious Estate w\/ 4 Master Suites in Berkshire County
Bedrooms:
5
Bathrooms:
4
Sleeps:
14
This historic 3300 sq/ft mountain home has 4 master suites and 4.5 baths. It is perfectly set up for 2-3 families or one ...
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VRBO
From $807 per night (USD)
Expedia
Family-Friendly Hancock Home: Walk to Slopes!
Bedrooms:
3
Bathrooms:
6
Sleeps:
15
Situated in the town of Hancock, 'Whistling Birches' offers guests 4 bedrooms, 3 bathrooms, a prime location just steps ...
From $807 per night (USD)
Expedia
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VRBO
Beautiful Berkshire rental, rustic elegance, August through fall
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
4.5 acres overlooking Juniper pond, private setting, 11 minutes to Gt.Barrington, 35 minutes to Tanglewood. Charming lar ...
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VRBO
From $706 per night (USD)
Expedia
Catamount, Zip Line, Private Setting, Book Now!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Summary: Expertly renovated four bedroom house with views of Catamount, post and beam wood ceilings and a lovely centerp ...
From $706 per night (USD)
Expedia
From $548 per night (USD)
VRBO
Jiminy Peak Mountainside Getaway in the Berkshires, Massachusetts Lodging Tax
Bedrooms:
6
Bathrooms:
3
Sleeps:
8
This beautiful 3 bedroom, 3 full bath condo nestled in a quiet cul-de-sac is a short hop to the bunny ski lift! Newly re ...
From $548 per night (USD)
VRBO
$Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On\/Off at Mtn$
From $250 per night (USD)
Expedia
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On\/Off at Mtn
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: This is the MOST UNIQUE suite in the Berkshires, specially designed for an incredible experience. The Master B ...
From $250 per night (USD)
Expedia
From $581 per night (USD)
VRBO
Spacious & Modern Berkshires Getaway
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Absolutely stunning 2018 build less than 1 mile from downtown Stockbridge and an 8 minute drive to Ski Butternut and dow ...
From $581 per night (USD)
VRBO
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Expedia
Soulful, light-filled Berkshire home with gardens
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our beautifully renovated Victorian is located in Housatonic, a hamlet of Great Barrington and only 10 minutes to the ce ...
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Expedia
From $395 per night (USD)
VRBO
Pristine Home In Becket Woods
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Summary: Peaceful home on two acres to come and enjoy nature and each other's company. The house features high ceilings, ...
From $395 per night (USD)
VRBO
From $582 per night (USD)
Expedia
Stockbridge Home, Come Experience The Berkshires!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Beautifully renovated three bedroom in Stockbridge with a great layout and energy throughout the home. In addi ...
From $582 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Elegant Mountain View Retreat By Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Explore the best of the Berkshires at this private country retreat, minutes from the Williams campus, world-class museum ...
From $561 per night (USD)
VRBO
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Expedia
Berkshires Tranquil Retreat With Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Escape to your very own serene haven in Great Barrington with a private, in-ground pool on a 4-acre property. T ...
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Expedia
From $356 per night (USD)
VRBO
Light-filled family home. Book now for the summer!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Light-filled modern 4 bedroom, 3.5 bath home in the Berkshires. This lovely two story home features a master bedroom on ...
From $356 per night (USD)
VRBO
$Idyllic Retreat; Hot Tub\/Sauna by Evergreen Home$
From $807 per night (USD)
Expedia
Idyllic Retreat; Hot Tub\/Sauna by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Great Barrington 3BR / 3BA retreat nestled on 4.7 acres of park-like grounds. Relax in the inviting hot tub under the st ...
From $807 per night (USD)
Expedia
From $847 per night (USD)
VRBO
LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy this very private, super comfortable, 1925 lake cottage, waterfront boathouse and dock for an entire Berkshire Sum ...
From $847 per night (USD)
VRBO
From $442 per night (USD)
Expedia
Waterfront Cottage 10 Min From Great Barrington
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A couple's getaway for the books awaits you at this Lake Buel vacation rental. Just 6 miles from Great Barrington's shop ...
From $442 per night (USD)
Expedia
From $1079 per night (USD)
VRBO
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Located near Lenox, Stockbridge, and Lee, this private and peaceful country house with modern amenities offers a relaxin ...
From $1079 per night (USD)
VRBO
From $1079 per night (USD)
Expedia
Mountain Blossom Retreat by Evergreen Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This centrally located property at the base of Mount Greylock offers luxury and tranquility on 60 private acres with swe ...
From $1079 per night (USD)
Expedia
From $146 per night (USD)
VRBO
Pet friendly, cozy, modest cape, two bedrooms
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You, those in your party and your pet(s) will have this modest, quirky, cozy, cape style, home all to yourself. There ar ...
From $146 per night (USD)
VRBO
From $1003 per night (USD)
Expedia
6-BR Expansive Berkshires Estate w Pool
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
(7/19/24): POOL RENOVATION UPDATE! We have just installed a BRAND NEW 15 x 30-foot pool, and she's ready for summer vi ...
From $1003 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Gateway to the Berkshires - Renovated downtown apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Completely renovated downtown second floor apartment with open floor plan, located in historical downtown Lee. This apar ...
From $265 per night (USD)
VRBO
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Expedia
Adorable Berkshires Loft on Quiet Dirt Road. Close to Tanglewood.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sweet loft on quiet dirt road. First floor has kitchen, eating area, living room, bathroom with laundry, three season p ...
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Expedia
Click For Pricing
VRBO
Central Berkshire Craftsman - Long Terms Welcome!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This cute as a button cottage in a walkable residential neighborhood, is the perfect home base to explore the Berkshires ...
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VRBO
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Expedia
Overlooking the city in a quiet 7 unit building
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
This is a quiet, 7 unit, newly renovated condominium building. We welcome quiet guests who will appreciate a relaxing st ...
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Expedia
From $245 per night (USD)
VRBO
Lakefront Cottage in the Berkshires
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
5 North Lake is a seasonal cottage situated yards from the shore. The property has panoramic views of the largest recrea ...
From $245 per night (USD)
VRBO
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Expedia
Farmhouse on Otis Pond
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
A spacious farmhouse with room for 10 has a large porch with rocking chairs, access to the pond, large yard, fire pit. ...
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Expedia
From $251 per night (USD)
VRBO
Cozy Cottage in the Berkshires on 1.6 Acres
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to our Modern Rustic Cottage in the Berkshires! The Accommodations: Bedroom 1: A comfortable queen-sized bed. Be ...
From $251 per night (USD)
VRBO
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Expedia
Cozy and large 2 Bedroom 2 Full Bath ski in, ski out condo Unit with balcony.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Family friendly resort with indoor/outdoor heated pool, 2 hot tubs, fitness gym, game room, ski/equip rentals, daily act ...
Click For Pricing
Expedia

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Results: 975 Rentals