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 $638 per night (USD)
VRBO
Renovated, Five Bedrooms In Historic Williamstown
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Summary: Spacious and renovated, this large family home in Williamstown offers over 3400 square feet of living space. Wi ...
From $638 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Waterview Home in the Berkshires: Near Hiking
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Take a break from the city and relax at this charming Sheffield vacation rental in the Berkshires! The 3-bedroom, 2-bath ...
From $324 per night (USD)
Expedia
$Great Barrington\/Housatonic Village Getaway—bring your dog!$
From $291 per night (USD)
VRBO
Great Barrington\/Housatonic Village Getaway—bring your dog!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Three second-floor bedrooms, two baths (one up, one down), in my sweet, cozy village home in a quiet, safe, and walkable ...
From $291 per night (USD)
VRBO
From $828 per night (USD)
Expedia
Perfect location in the heart of downtown Lenox
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
If you want to feel like you're truly away, but still have access to a great lifestyle, this is the rental for you! St ...
From $828 per night (USD)
Expedia
From $363 per night (USD)
VRBO
Cozy Cabin on Lake Mahkeenac
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy cabin located in the popular Beachwood community which is 2 miles from Tanglewood on Stockbridge Bowl, close to Kr ...
From $363 per night (USD)
VRBO
$Charming Cottage w\/ Sauna, close to hiking trails, ski lodges & Great Barrington$
From $326 per night (USD)
VRBO
Charming Cottage w\/ Sauna, close to hiking trails, ski lodges & Great Barrington
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Perfect Refuge in a Charming Berkshire Cottage with Vaulted Ceilings, Two-Person Sauna, Wrap Around Deck, Amazing Sunlig ...
From $326 per night (USD)
VRBO
From $513 per night (USD)
VRBO
Charming cottage in Norman Rockwell's Stockbridge with two decks!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Light, sunny, charming 3-4 bedroom cottage built in 1832 in Norman Rockwell's Stockbridge, a five minute walk to the Red ...
From $513 per night (USD)
VRBO
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Expedia
sweet dreams retreat
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located near York Lake National Park and many other lakes. Equipped with everything you need for leisure or work. Includ ...
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Expedia
From $301 per night (USD)
VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $301 per night (USD)
VRBO
From $537 per night (USD)
Expedia
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This hotel/resort is at the base of the ski lift for Jiminy Mountain. And, when you are not on the slopes, it features a ...
From $537 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Summary: You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Styli ...
From $292 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Fox Hollow Luxury Ranch Laurel Lake
Bedrooms:
5
Bathrooms:
4
Sleeps:
11
Awesome Berkshire Location. 1000 feet of Laurel Lake frontage shared with private dock , 2 canoes and 2 kayaks. Large o ...
From $509 per night (USD)
Expedia
From $644 per night (USD)
VRBO
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Prior guests of this charming house next to the forest trails have already reserved their return stay for next year to e ...
From $644 per night (USD)
VRBO
$The Meadows House @ Otis Ridge w\/ 7-person hot tub$
From $295 per night (USD)
Expedia
The Meadows House @ Otis Ridge w\/ 7-person hot tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax in a beautiful mountain setting at this 4-season ski house within walking distance of the slopes at Otis Ridge Ski ...
From $295 per night (USD)
Expedia
From $569 per night (USD)
VRBO
Wildlife Retreat in the Forest
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contem ...
From $569 per night (USD)
VRBO
From $591 per night (USD)
VRBO
Great Barrington 4BR home on 3 wooded acres walking distance to town!
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Bring the whole family to our Great Barrington home on 'The Hill'. With 4 bedrooms, 4 bathrooms, outdoor deck, screened ...
From $591 per night (USD)
VRBO
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VRBO
The Wampanoag Cabin @ The Wigwam Western Summit
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Wampanoag cabin has a queen size bed, a full bath, a mini fridge, a writing desk, wood floor, AC and heat but the ma ...
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VRBO
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Expedia
Mahican Cabin - A Private Nature's Reserve For 2
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
The Mahican Cabin is at the highest peak of the Hoosac Range known as western summit and borders 750 acres of protected ...
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Expedia
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VRBO
The Bear’s Den @ America's Switzerland
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Own the sunset when you book the Bear's Den! The property is part of the Wigwam Western Summit which operates a seasonal ...
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VRBO
From $614 per night (USD)
Expedia
Private Island - Largest Fresh Water Reservoir in Mass....
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Rustic.. Not fancy... It's a cabin... 2 bedroom, one with Queen the other with twin bunkbeds... 2 couches could sleep ex ...
From $614 per night (USD)
Expedia
From $173 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 $173 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 $491 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 $491 per night (USD)
Expedia
From $510 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 $510 per night (USD)
VRBO
From $257 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 $257 per night (USD)
Expedia
From $220 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 $220 per night (USD)
VRBO
From $259 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 $259 per night (USD)
Expedia
From $261 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 $261 per night (USD)
VRBO
From $1097 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 $1097 per night (USD)
Expedia
From $294 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 $294 per night (USD)
VRBO
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Expedia
Wyndham Bentley Brook ~ Winter Recess
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
DVD Player Television Wi-Fi Internet Access Hairdryer Washer/Dryer In Unit Balcony/Patio Wyndham Bentley Brook. Locate ...
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Expedia
From $221 per night (USD)
VRBO
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 ...
From $221 per night (USD)
VRBO
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Expedia
Rockspring by AvantStay | Huge Berkshires Estate
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
This charming Berkshires estate consists of a beautiful main house, an ample separate recreation space, and a private po ...
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Expedia
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Expedia
Guaranteed President's Day Ski Weekend for 4 Guests - 4 Nights - pay for 3!
Bedrooms:
1
Bathrooms:
0
Sleeps:
4
A fantastic opportunity to ski from Thursday until next Monday of President's Day weekend! This is an amazing bargain ...
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Expedia
$1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On\/Off, Fully Redone Count$
From $227 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 $227 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Private Home on 17 acres 10 minutes to Tanglewood and other Berkshire Attraction
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 $381 per night (USD)
VRBO
From $634 per night (USD)
Expedia
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 ...
From $634 per night (USD)
Expedia
From $109 per night (USD)
VRBO
Mountain living, Hot Tub, 1 bedroom apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Relax and enjoy nature at it's finest at this tranquil, one-bedroom unit down the block from Mt. Greylock, highest mount ...
From $109 per night (USD)
VRBO
From $670 per night (USD)
Expedia
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 $670 per night (USD)
Expedia
From $477 per night (USD)
VRBO
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 $477 per night (USD)
VRBO
$Lenox House w\/ Screened Patio & Mountain View$
From $235 per night (USD)
Expedia
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 $235 per night (USD)
Expedia
$Charming Farmhouse; 2 Bed \/ 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.$
From $262 per night (USD)
VRBO
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 $262 per night (USD)
VRBO
From $237 per night (USD)
VRBO
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 $237 per night (USD)
VRBO
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VRBO
Woodfall by AvantStay | Tons of Outdoor Space
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
- Huge yard with a swing set and lawn for families - Natural fire pit area tucked in the trees - Large deck with a BBQ/g ...
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VRBO
From $182 per night (USD)
Expedia
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)
Expedia
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VRBO
Family-Centric Berkshire Getaway by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This renovated 4 BR ranch located just minutes from Lenox has everything your family needs for a relaxing getaway! Ideal ...
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VRBO
From $433 per night (USD)
VRBO
Private and Cheerful Berkshire Oasis in Dalton with in-ground pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Take a break and unwind at this peaceful Centrally located Berkshire oasis. Single-family 3 BR/2 full bath Cape with de ...
From $433 per night (USD)
VRBO
From $965 per night (USD)
VRBO
Moose Lodge by AvantStay | Luxe Berkshires Escape
Bedrooms:
7
Bathrooms:
6
Sleeps:
18
Welcome to Moose Lodge! This expansive home has everything your group needs to enjoy quality time together among the bea ...
From $965 per night (USD)
VRBO
From $526 per night (USD)
Expedia
Private Access To Laurel Lake, Enjoy Lake Life
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 $526 per night (USD)
Expedia
From $217 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 $217 per night (USD)
VRBO
From $356 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 $356 per night (USD)
Expedia
From $354 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 $354 per night (USD)
VRBO
From $144 per night (USD)
Expedia
Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $144 per night (USD)
Expedia
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VRBO
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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VRBO
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Expedia
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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Expedia
From $625 per night (USD)
VRBO
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 $625 per night (USD)
VRBO
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Expedia
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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Expedia
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VRBO
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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VRBO
From $144 per night (USD)
Expedia
Ski-In, Ski-Out at Wyndham Bentley Brook-2 Bedroom Deluxe
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent ...
From $144 per night (USD)
Expedia
From $419 per night (USD)
VRBO
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 $419 per night (USD)
VRBO
From $477 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 $477 per night (USD)
VRBO
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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 $502 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 $502 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
From $3086 per night (USD)
Expedia
The Winthrop Estate - 12K SF 32 Acres
Bedrooms:
11
Bathrooms:
11
Sleeps:
24
The Winthrop Estate is a registered Great Estate built in 1875 for Henri Braem, US Ambassador to Denmark and Partner in ...
From $3086 per night (USD)
Expedia
$Ashley Falls Home w\/ Fire Pit: Hike & Ski!$
From $325 per night (USD)
VRBO
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 $325 per night (USD)
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
From $287 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 $287 per night (USD)
VRBO
From $387 per night (USD)
Expedia
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 ...
From $387 per night (USD)
Expedia
From $410 per night (USD)
VRBO
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 $410 per night (USD)
VRBO
$Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On\/Off at Mtn$
From $227 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 $227 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Tastefully Restored Berkshire Farmhouse Available October 15th - 31st 2024
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Lovingly restored, sunny 1890s farmhouse situated on two verdant, private acres, filled with perennial flowers and matur ...
From $290 per night (USD)
VRBO
From $544 per night (USD)
Expedia
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 $544 per night (USD)
Expedia
From $452 per night (USD)
VRBO
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 ...
From $452 per night (USD)
VRBO
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Expedia
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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Expedia
From $503 per night (USD)
VRBO
Gorgeous Deck Views at this Serene Berkshires Cabin
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Discover why everyone is flocking to the Berkshires with a stay in this charming 5-bedroom, 3-bathroom Richmond mountain ...
From $503 per night (USD)
VRBO
From $259 per night (USD)
Expedia
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)
Expedia
From $55 per night (USD)
VRBO
Nature retreat by Brook
Bedrooms:
2
Bathrooms:
2
Sleeps:
2
Long term rental November through May This Rustic contemporary cabin with barn beams/boards has a loft master bedroom su ...
From $55 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Loft Style Cabin In West Stockbridge, Book Now!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Summary: Custom built loft style home in beautiful West Stockbridge. You’ll love how the outdoors streams into the house ...
From $416 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Stylish Mid-century Modern Berkshires Cape
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Stylish, fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires! Enjoy the large, sunny yard an ...
From $495 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our property is a renovated 1770s stage coach stop. The upstairs of our home (with separate entrance) is our rental apar ...
From $290 per night (USD)
Expedia
From $406 per night (USD)
VRBO
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 $406 per night (USD)
VRBO
From $713 per night (USD)
Expedia
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 $713 per night (USD)
Expedia
From $429 per night (USD)
VRBO
Cozy Cabin on resort property in Cultural Berkshires.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Perfect cozy mountain house for a couple's getaway, a fun little trip with friends or with family to enjoy all the arts ...
From $429 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
$Half Moon by AvantStay | 4BR Cabin w\/ Large Deck & Yard$
From $619 per night (USD)
VRBO
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 $619 per night (USD)
VRBO
From $225 per night (USD)
Expedia
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 $225 per night (USD)
Expedia
From $563 per night (USD)
VRBO
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 $563 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Little Longbow Lakefront Chalet
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to your Berkshire Oasis! This rustic lakefront chalet is ideally located right in the heart of the Berkshires in ...
From $300 per night (USD)
Expedia
From $528 per night (USD)
VRBO
Elegant Pittsfield Home Near Downtown & Skiing!
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Experience a fun-filled group getaway at this Pittsfield vacation rental! Named 'The Duchess of Pomeroy' for its charmin ...
From $528 per night (USD)
VRBO
From $858 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 $858 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
$Williamstown Rustic & Spacious Estate w\/ 4 Master Suites in Berkshire County$
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $753 per night (USD)
VRBO
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 $753 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $456 per night (USD)
VRBO
New! Inspired Country Retreat in Lenox Sleeps 8
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Looking for a centrally located destination for a ski weekend? Cozy up by the fireplace for at this stylish winter count ...
From $456 per night (USD)
VRBO
$Upstairs on Main \n$
From $126 per night (USD)
Expedia
Upstairs on Main \n
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 $126 per night (USD)
Expedia
From $309 per night (USD)
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 ...
From $309 per night (USD)
VRBO
From $512 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 $512 per night (USD)
Expedia

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