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 $557 per night (USD)
VRBO
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
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 $557 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Artist's Camp on Lake Mahkeenac
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Newly refurbished cottage, perfect for a family vacation or couples getaway. This retreat is tastefully decorated with w ...
From $253 per night (USD)
Expedia
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VRBO
The Lodge @ America's Switzerland - The Mountains Are Calling!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Breathtaking views of mountains of three states from the most gorgeous lodge in the Berkshires! Indescribably beautiful ...
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VRBO
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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 ...
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Expedia
From $460 per night (USD)
VRBO
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Bedrooms:
2
Bathrooms:
2
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 $460 per night (USD)
VRBO
$Modern Victorian Walk to Town \/ Close to 2 Ski Resorts!$
From $562 per night (USD)
VRBO
Modern Victorian Walk to Town \/ Close to 2 Ski Resorts!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Lovely 4 bedroom, sleeps 10. 3-story classic Victorian home in family-friendly neighborhood. Clean modern interiors and ...
From $562 per night (USD)
VRBO
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VRBO
Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Our beautiful, spacious, comfortable, light filled contemporary home, set on 5 acres, is a nature lover’s delight, is be ...
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VRBO
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Expedia
Secluded 19th century Farmhouse with mountain views
Bedrooms:
5
Bathrooms:
8
Sleeps:
15
Mayunsook Farm has been cherished by our family for seven generations. Once a working dairy farm, providing our family w ...
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Expedia
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VRBO
Park Model Single Family double lofted private heaven on a pond
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
You can't beat this place for location. It is close to all things Berkshires - Tanglewood, Close to Apalachian trail, L ...
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VRBO
$4Br\/3bath Lakefront\/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi$
From $304 per night (USD)
Expedia
4Br\/3bath Lakefront\/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Lakefront property with own dock on Otis Reservoir with beautiful views and garden. Great for fall foliage. For ski sea ...
From $304 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Dancing Horse Lodge
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Dancing Horse Lodge is located on Horse Farm in the heart of the beautiful Berkshire Mountains with plenty of room for f ...
From $168 per night (USD)
VRBO
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Expedia
Full Week of Ski-in,Ski-out @ Jiminy Peak Club Whyndam Bently Brook in Berkshire
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Full week rental only, Feb. 18 (in at 3pm) to Feb 25(check out 11am) @ Club Whyndham Bently Brook Resort @ Jiminy Peak ...
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Expedia
From $334 per night (USD)
VRBO
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard a ...
From $334 per night (USD)
VRBO
$East Otis Reservoir Cabin w\/ Porch - Walk to Lake!$
From $287 per night (USD)
Expedia
East Otis Reservoir Cabin w\/ Porch - Walk to Lake!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in the woods of East Otis, this cozy 2-bedroom, 1-bathroom vacation rental has everything you need for a peacefu ...
From $287 per night (USD)
Expedia
From $750 per night (USD)
VRBO
Perfect for Winter Skiing!!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Perfect family home for all Winter activities with 4 Bedrooms and 3.5 baths, plus it is central to all the cultural act ...
From $750 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Bedrooms:
2
Bathrooms:
4
Sleeps:
4
Escape to the serene beauty of the Berkshires and stay at this bright and cozy 2-bed, 2-bath cabin! Nestled just a few s ...
From $447 per night (USD)
Expedia
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VRBO
Private Apartment in the Heart of Downtown Lenox
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the heart of downtown Lenox on a beautiful side street. Two minute walk to concerts at Lilac Park, shops and ...
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VRBO
$Beautiful Timber Frame Home in the Berkshires \/Available for Long Term$
From $469 per night (USD)
Expedia
Beautiful Timber Frame Home in the Berkshires \/Available for Long Term
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The house is a newly constructed cruck timber frame designed by Jack Soban made from naturally treated local pine with c ...
From $469 per night (USD)
Expedia
From $259 per night (USD)
VRBO
Quiet rustic cottage with shared lake access
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Lake Buel! This recently renovated cottage has been an old favorite for generations since the 1950’s. Abuttin ...
From $259 per night (USD)
VRBO
$Lovely Berkshire Home 1\/10 mile from Town on 11 acres$
From $602 per night (USD)
VRBO
Lovely Berkshire Home 1\/10 mile from Town on 11 acres
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Summary: "Feels good staying here! We built this house with our own hands. We chose materials and a design that we loved ...
From $602 per night (USD)
VRBO
From $1114 per night (USD)
VRBO
Stunning Modern Home - For Your Graduation Celebration
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Experience the charm of New England at our beautiful House in Williamstown, MA! Our cozy and open space offers a perfect ...
From $1114 per night (USD)
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 $219 per night (USD)
VRBO
Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This updated vintage 1900 home in North Adams is just a 10 minute walk to MASS MoCA, one of the country's largest contem ...
From $219 per night (USD)
VRBO
From $281 per night (USD)
Expedia
Lakefront Bungalow
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to our lakefront bungalow located on Massachusetts largest recreational lake. Otis Reservoir is ideal for boatin ...
From $281 per night (USD)
Expedia
From $1497 per night (USD)
VRBO
Luxury Ski Retreat on Jiminy Peak Mountain, Berkshires, MA
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to Jiminy Peak Mountain Resort in the Berkshire Mountains! Our newly-renovated mountain retreat "The Lazy Bear" ...
From $1497 per night (USD)
VRBO
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Expedia
Berkshires Retreat! in the woods, yet in town!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
About this space We are happy to share our piece of heaven in the Berkshires! Newly renovated 4-bedroom 2-1/2-bathroom v ...
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Expedia
$Escape to The Berkshires w\/Pool by Evergreen Home$
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VRBO
Escape to The Berkshires w\/Pool by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This 4Br home is filled with cheeky pop art, stylish comfortable spaces and all the amenities you need for the ideal Ber ...
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VRBO
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Expedia
Berkshire Retreat- Stone's throw to downtown Lenox
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Berkshire Retreat - A stone's throw to downtown Lenox Our calendar is updated in real-time & our nightly rates are accu ...
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Expedia
$Romantic Boutique Hotel \/ B&B - Deluxe Firespa Suite$
From $1276 per night (USD)
VRBO
Romantic Boutique Hotel \/ B&B - Deluxe Firespa Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our romantic "Firespa" suite with a Jacuzzi for two with a smokey mirrored surround, terry cloth robes and slippers, hea ...
From $1276 per night (USD)
VRBO
$Romantic Boutique Hotel \/ Bed and Breakfast - Standard King With Gas Fireplace$
From $1276 per night (USD)
Expedia
Romantic Boutique Hotel \/ Bed and Breakfast - Standard King With Gas Fireplace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
La Chambrette is our economy oriented "Little Chamber," a room as charming as its name. Its private bath with a whirlpoo ...
From $1276 per night (USD)
Expedia
$Romantic Boutique Hotel \/ Bed and Breakfast - Deluxe Schoolhouse Suite$
From $1276 per night (USD)
VRBO
Romantic Boutique Hotel \/ Bed and Breakfast - Deluxe Schoolhouse Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The exquisite Deluxe Schoolhouse Suite provides an impeccable setting for your holiday. Lounge next to the gas-operated ...
From $1276 per night (USD)
VRBO
$Romantic Boutique Hotel \/ Bed and Breakfast - SchoolHouse Suite$
From $1276 per night (USD)
Expedia
Romantic Boutique Hotel \/ Bed and Breakfast - SchoolHouse Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The regal king-sized canopy bed and the charming sitting area merge with modern amenities - a gas-operated fireplace, te ...
From $1276 per night (USD)
Expedia
$Deluxe Mountain View Nautical Suite Jiminy Ski On\/Off- Fully Redone Decor$
From $225 per night (USD)
VRBO
Deluxe Mountain View Nautical Suite Jiminy Ski On\/Off- Fully Redone Decor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA off lobby Unit has som ...
From $225 per night (USD)
VRBO
From $617 per night (USD)
Expedia
1 Bedroom Deluxe Condo, Sleeps 6, Skiing at Jiminy Peak Mountain, Bentley Brook!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This spacious one-bedroom resort suite measures approximately 780 to 880 square feet. You will enjoy two queen beds in t ...
From $617 per night (USD)
Expedia
From $818 per night (USD)
VRBO
2 Bedroom Condo, Sleeps 8, Skiing, Jiminy Peak Mountain, Bentley Brook Resort!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This spacious two-bedroom resort suite measures approximately 843 to 953 square feet. You will enjoy a king bed in the m ...
From $818 per night (USD)
VRBO
$A-Frame Cabin w\/ Furnished Deck in Becket!$
From $242 per night (USD)
Expedia
A-Frame Cabin w\/ Furnished Deck in Becket!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Built in 1974 | Private Acreage & Scenic Surroundings | Fireside Relaxation | EV Charger Embrace a slower pace of life ...
From $242 per night (USD)
Expedia
From $1199 per night (USD)
VRBO
Wellspring by AvantStay | Indoor Pool + Views
Bedrooms:
5
Bathrooms:
7
Sleeps:
12
Wellspring is a sprawling Berkshire escape with unparalleled views of the surrounding mountains. The crown jewel of this ...
From $1199 per night (USD)
VRBO
$Pittsfield Home w\/ Deck - 12 Mi to Jiminy Peak!$
From $290 per night (USD)
Expedia
Pittsfield Home w\/ Deck - 12 Mi to Jiminy Peak!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Great for outdoor enthusiasts, this 3-bedroom, 2.5-bathroom vacation rental home features a balcony, a deck, a patio, an ...
From $290 per night (USD)
Expedia
$1st Floor Mountain View Suite Ski On\/Off At Jiminy- Fully Redone Decor$
From $227 per night (USD)
VRBO
1st Floor Mountain View Suite Ski On\/Off At Jiminy- Fully Redone Decor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charm ...
From $227 per night (USD)
VRBO
From $1072 per night (USD)
Expedia
Find your Sanctuary at The Rectory at Stockbridge
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
In the heart of Stockbridge, Massachusetts, the rectory at St. Joseph's Church offers guests a truly divine retreat. Thi ...
From $1072 per night (USD)
Expedia
$2 Bedroom Deluxe - Club Wyndham Bentley Brook\n\n$
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VRBO
2 Bedroom Deluxe - Club Wyndham Bentley Brook\n\n
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
At the base of Jiminy Peak Ski Mountain, this resort is an exceptional choice for mountainside play. The area delivers a ...
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VRBO
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Expedia
10 Minutes to Ski Butternut! Dogs Welcome!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Close to Butternut and Catamount Ski Areas! This is a 3 month winter rental for $3,300 per month including utilities. Fa ...
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Expedia
From $894 per night (USD)
VRBO
Guesthouse Cabin vacation rentals in Berkshire County
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Undermountain Lodge offers an escape to a serene cabin, nestled between pristine natural spring lakes with panoramic mou ...
From $894 per night (USD)
VRBO
$house with view in the berkshires\n$
From $297 per night (USD)
Expedia
house with view in the berkshires\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience the charm of this newly renovated home with a wrap-around deck with vistas of a lake and mountains. Airy ope ...
From $297 per night (USD)
Expedia
From $728 per night (USD)
VRBO
Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Our airy, renovated farmhouse sits on a peaceful 8.5 acres on a quiet road, yet in close proximity to the towns of Lenox ...
From $728 per night (USD)
VRBO
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Expedia
Berkshire apartment on Green River; in ground pool; walking trail - pet friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to tranquility at this country home nestled among the picturesque Berkshires of Massachusetts. Located in North E ...
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Expedia
From $693 per night (USD)
VRBO
Spectacular views and close to Great Barrington.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Main floor bedroom with private bath, 2 car garage, electric vehicle charging, screened porch, pool, and Koi pond with v ...
From $693 per night (USD)
VRBO
From $493 per night (USD)
VRBO
Private Lakehouse in the heart of the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our lakehouse in the Berkshires! Chat GPT wants you to know this tranquil & picturesque getaway offers a perf ...
From $493 per night (USD)
VRBO
From $453 per night (USD)
VRBO
Berkshire Chalet: Walk to Lenox. Mobility friendly, Amazing Views.Dog Friendly!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in a private area of Lenox, right behind Kennedy Park, this chalet has the advantage of combining a peaceful fee ...
From $453 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Serenity Summit: Hot Tub, Mountain Views, Book Now
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Summary: Escape to this luxurious, sun-drenched, 5-bedroom retreat in Southfield, MA. Enjoy stunning views of Haystack M ...
From $626 per night (USD)
Expedia
From $658 per night (USD)
VRBO
Charming 7-BR 1800s Retreat 8-Min to Catamount
Bedrooms:
8
Bathrooms:
7
Sleeps:
14
Summary: Step into the past with this charming 7-BR 1800s retreat, just 8 minutes from Catamount. Amidst its historic ch ...
From $658 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Historic 2-BR 1800s Carriage House 8-Min to Catamount
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Step back in time within this historic 2-BR 1800s carriage house, just 8 minutes from Catamount. Embrace its al ...
From $350 per night (USD)
Expedia
From $511 per night (USD)
VRBO
18th century Berkshires farmhouse on 12 acres, impeccably updated.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Woods, stone walls, a wet bar, a swimming pool with chaise lounges, a wood burning stove, all 15-ish minutes from Great ...
From $511 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Woodland Zen by AvantStay | Modern Design + Patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Introducing Woodland Zen: where modern luxury meets secluded tranquility in the heart of the Berkshires. This sleek, co ...
From $522 per night (USD)
Expedia
From $240 per night (USD)
VRBO
Golf House by Mt Greylock - Walkable Adventures!
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Relax in our spacious 4-bedroom, 3-bath home, nestled at the end of a quiet dead-end road with a large yard and cozy spo ...
From $240 per night (USD)
VRBO
From $272 per night (USD)
Expedia
Stylish Newly Renovated 2-Bedroom Apartment Steps from Otis Reservoir
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our stylish, newly renovated 2-bedroom apartment, just steps from the beautiful Otis Reservoir! Located only ...
From $272 per night (USD)
Expedia
$Berkshires Lakefront Gem. Cozy home w\/ hiking, swimming & all things cultural!\n$
From $315 per night (USD)
VRBO
Berkshires Lakefront Gem. Cozy home w\/ hiking, swimming & all things cultural!\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The perfect getaway for people who want to unwind from the grind of everyday life. Little Robin Lake is located right in ...
From $315 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Bygone era Lake Buel cottage with access to shared dock and canoe
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Re-introducing a wonderful cottage built in the early 1900’s, one of the first privately owned constructions near the la ...
From $473 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Luxury on the River@Fish Camp-Close to Tanglewood
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax with the entire family in this beautiful new home built on the Farmington River. Enjoy luxurious, natural open spa ...
From $298 per night (USD)
VRBO
$Fall Berkshires Retreat! Dog friendly, Hot Tub, Hiking, Canoe!\n$
From $233 per night (USD)
Expedia
Fall Berkshires Retreat! Dog friendly, Hot Tub, Hiking, Canoe!\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
720 Sq. Ft, 2 Bed, 1 Bath cottage with HOT TUB amongst the forest located in a private, dirt road, lake community with n ...
From $233 per night (USD)
Expedia
From $485 per night (USD)
VRBO
Sophisticated and secluded Lenox Mt retreat minutes from Tanglewood. New listing
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this chic Lenox Mountain chalet in picturesque West Stockbridge, just minutes from Tanglewood. In a secluded w ...
From $485 per night (USD)
VRBO
From $539 per night (USD)
Expedia
Lake Haven with new dock and amazing views of Lake Garfield
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with the whole family at this peaceful lakeside home. Enjoy the lake-facing deck for dining and drinks. Swim/boat/ ...
From $539 per night (USD)
Expedia
$Family-Friendly Richmond Cottage w\/ Private Yard$
From $272 per night (USD)
VRBO
Family-Friendly Richmond Cottage w\/ Private Yard
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Plan your next family getaway at this waterfront vacation rental in Richmond. Surrounded by the beauty of the Berkshires ...
From $272 per night (USD)
VRBO
From $317 per night (USD)
VRBO
2 Comfortable Units! Indoor and Outdoor Pool, Short Drive to Tanglewood Town!
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 $317 per night (USD)
VRBO
From $159 per night (USD)
VRBO
Short Drive to Norman Rockwell Museum! Indoor and Outdoor Pool, Free Parking!
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 $159 per night (USD)
VRBO
From $440 per night (USD)
Expedia
Urban Peak Escape, Lenox, MA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover Urban Peak Escapes in Lenox, MA—a charming New England town in the Berkshires. Just 1 mile from Tanglewood and ...
From $440 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Perfect Nature Retreat In Great Barrington
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Welcome to your home for the week in Great Barrington—a spacious, nature-surrounded retreat. Just a 2-minute dr ...
From $447 per night (USD)
VRBO
From $2074 per night (USD)
Expedia
Peaceful Compound Perfect for Groups 12 Minutes from Great Barrington!
Bedrooms:
5
Bathrooms:
7
Sleeps:
17
In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldw ...
From $2074 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dreaming of waking up, heading downstairs, and being right on the mountain? This is the place for you. Conveniently loca ...
From $208 per night (USD)
VRBO
From $163 per night (USD)
Expedia
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Hancock with commanding views of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless ...
From $163 per night (USD)
Expedia
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VRBO
Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your cozy getaway awaits in Lee at this delightful Oak n'Spruce Resort. With 2 bedrooms, including a king bed and a quee ...
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VRBO
$All Season Adventures, Ski In\/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.$
From $173 per night (USD)
Expedia
All Season Adventures, Ski In\/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round ...
From $173 per night (USD)
Expedia
$Charming 1 Bedroom - 4 Star Resort w\/ heated pool, gym, wi-fi, lot's more!$
From $173 per night (USD)
VRBO
Charming 1 Bedroom - 4 Star Resort w\/ heated pool, gym, wi-fi, lot's more!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Berkshire Mountain Lodge features one-bedroom condominiums equipped with modern amenities such as full kitchens an ...
From $173 per night (USD)
VRBO
$Becket Home w\/ 3-Season Porch: Walk to Lake Access$
From $231 per night (USD)
Expedia
Becket Home w\/ 3-Season Porch: Walk to Lake Access
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Unwind and embrace nature at this charming Becket vacation rental! With views of Lake Robinhood and a screened porch for ...
From $231 per night (USD)
Expedia
From $425 per night (USD)
VRBO
Lakefront Jewel By: Evergreen Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Breathtaking lakefront jewel with stunning, unparalleled views & central AC. Relax and unwind at our stunning 3BR / 2BA ...
From $425 per night (USD)
VRBO
From $318 per night (USD)
Expedia
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bagels & Slopes: Start Your Day Deliciously, Hit the Powder Perfectly! Welcome to the ultimate ski getaway where comfor ...
From $318 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Mid Century Modern home with distant views of Mount Greylock Summit.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step back into the mid 20th century with this tastefully updated mid-mod home. Two bedrooms with in suite full baths mak ...
From $308 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Charming 4-bedroom house in Great Barrington with secluded garden
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Located walking distance to Main Street in Great Barrington, enjoy what this lovely art filled 4-bedroom house has to of ...
From $307 per night (USD)
Expedia
From $822 per night (USD)
VRBO
Stylish Retreat; Pool & Hot Tub By:Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Newly renovated 4BR, 3BA home just 2 minutes from Catamount. Enjoy a heated pool, hot tub, and screened-in porch, all ne ...
From $822 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Treat your family to the ultimate getaway in the Berkshires at this beautiful vacation rental on Lake Ashmere! The 3-bed ...
From $626 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Berkshire Holiday Home with A+ Amenities
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Book your next vacation at our special Berkshire Holiday home set on several acres in the beautiful Berkshire Mountains ...
From $409 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Historic home Nestled on a quiet street in downdown Great Barrington, just steps from the River Walk path, this enchanti ...
From $177 per night (USD)
Expedia
From $852 per night (USD)
VRBO
New!! Breathtaking Post & Beam home minutes from skiing, music, arts and hiking
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
New listing from the owners of Sunny Pines!! Bright and spacious, 25 ft ceiling, Post & Beam home nestled in the middle ...
From $852 per night (USD)
VRBO
From $168 per night (USD)
Expedia
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Just bring your clothes and food! Everything else is here. Everything to cook with, clean, shower, even linens and extra ...
From $168 per night (USD)
Expedia
From $365 per night (USD)
VRBO
20% off thru Nov 30th..Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Nestled on picturesque grounds, this modern and updated 3-bedroom home offers the perfect blend of comfort and luxury. E ...
From $365 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Charming 3-bedroom Salt Box house in quaint Williamstown Mass with WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
2
WILLIAMSTOWN MASSACHUSETTS RENTAL 18 THORNLIEBANK ROAD FURNISHED 3 BEDROOM 2 CAR GARAGE ...
From $452 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Pittsfield at this charming corporate apartment. With AC, a washing machine, and WiFi, guests can enjoy a marv ...
From $222 per night (USD)
VRBO
From $1148 per night (USD)
Expedia
Serene 5-BR Retreat 9-Min to Catamount
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: Gather your friends and family at this a luxurious 5-BR retreat. Nestled in the serene woodlands of the Berkshi ...
From $1148 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Large 3-bedroom house with WiFi and AC in Great Barrington
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in Great Barrington, this superb house boasts 3 cozy bedrooms - one with a king bed, one with two twin beds, and ...
From $202 per night (USD)
VRBO
$Richmond Cottage w\/ Fire Pit & Furnished Deck!$
From $203 per night (USD)
Expedia
Richmond Cottage w\/ Fire Pit & Furnished Deck!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Your New England escape awaits at this 3-bedroom, 2-bathroom vacation rental in Richmond. In the warmer months, bask in ...
From $203 per night (USD)
Expedia
From $487 per night (USD)
VRBO
Lakefront Home on Pontoosuc Lake, the Berkshires
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Stunning Lakehouse: Lakefront property & house on 1-acre on Pontsoosuc Lake in western MA, 2600 sq.ft., 3 bedrooms / 2 ...
From $487 per night (USD)
VRBO
From $255 per night (USD)
Expedia
Private 1-bedroom apartment in enchanting North Adams with WiFi.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your home away from home in North Adams with 1 bedroom. This apartment offers a soothing atmosphere with a full bed, iro ...
From $255 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience Stockbridge like a local in this 3-bedroom apartment. Great location on Main Street Stockbridge await you fro ...
From $382 per night (USD)
VRBO
From $605 per night (USD)
Expedia
The Berkshires Basecamp
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
7min to Bear Town SF/Butternut Ski 26min to Tanglewood Solo Stove, 2 decks, screened porch 2-65in+55in Roku TVs, Arcade, ...
From $605 per night (USD)
Expedia
From $433 per night (USD)
VRBO
Solomon Ely Homestead - Charming Pittsfield Stay
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy your stay at this 1847 New England farmhouse located just steps from downtown Pittsfield. Make yourself at home wi ...
From $433 per night (USD)
VRBO
$Cozy Home in Lenox\n\n\n$
From $344 per night (USD)
Expedia
Cozy Home in Lenox\n\n\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Enjoy a stylish experience at this cozy newly renovated two-bedroom mobile home in the Berkshires of Lenox, Massachusett ...
From $344 per night (USD)
Expedia
From $838 per night (USD)
VRBO
The Race Mountain House
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
High on the slopes of Race Mountain, this spacious 4-bedroom villa offers sweeping east-facing views. In the early hours ...
From $838 per night (USD)
VRBO
From $225 per night (USD)
VRBO
Charming studio loft in The Berkshires surrounded by 20 acres of nature
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This studio loft in historic Tyringham, Massachusetts (a Hinterland Settlement) boasts an inviting bedroom area, kitchen ...
From $225 per night (USD)
VRBO
From $398 per night (USD)
VRBO
Large four-bedroom house in prime location
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
New construction, custom house with no visible neighbors. Cape Cod style. Garage parking for at least two cars. Three ...
From $398 per night (USD)
VRBO
From $230 per night (USD)
VRBO
Cozy 1-bedroom condo at ski resort with WiFi, fitness room, pool & hottub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Relax in a comfortable and cozy space after a winter day on the ski slopes. Enjoy all of the amenities of the on premise ...
From $230 per night (USD)
VRBO

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