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

$4Br\/3bath Lakefront\/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi$
From $335 per night (USD)
VRBO
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 $335 per night (USD)
VRBO
From $174 per night (USD)
Expedia
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 $174 per night (USD)
Expedia
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VRBO
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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VRBO
From $342 per night (USD)
Expedia
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 $342 per night (USD)
Expedia
$East Otis Reservoir Cabin w\/ Porch - Walk to Lake!$
From $197 per night (USD)
VRBO
East Otis Reservoir Cabin w\/ Porch - Walk to Lake!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Fireplace | Grill | Board Games & Puzzles Nestled in the woods of East Otis, this 2-bedroom, 1-bathroom vacation rental ...
From $197 per night (USD)
VRBO
From $760 per night (USD)
Expedia
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 $760 per night (USD)
Expedia
$Beautiful Timber Frame Home in the Berkshires \/Available for Long Term$
From $457 per night (USD)
VRBO
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 $457 per night (USD)
VRBO
From $407 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 $407 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
From $241 per night (USD)
Expedia
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 $241 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Now Featuring Spring Specials
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 $515 per night (USD)
VRBO
$General Williams Estate House Lenox\/Stockbridge$
From $1238 per night (USD)
Expedia
General Williams Estate House Lenox\/Stockbridge
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
The General Williams house is located 2 miles from Stockbridge Center and 5 miles from Lenox Center. Only 7 miles from ...
From $1238 per night (USD)
Expedia
From $1002 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 $1002 per night (USD)
VRBO
From $285 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 $285 per night (USD)
VRBO
From $599 per night (USD)
VRBO
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 $599 per night (USD)
VRBO
From $722 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 $722 per night (USD)
VRBO
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VRBO
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 ...
Click For Pricing
VRBO
$Escape to The Berkshires w\/Pool by Evergreen Home$
From $680 per night (USD)
Expedia
Escape to The Berkshires w\/Pool by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
8 MINUTES FROM BOSQUET SKI This 4Br home is filled with cheeky pop art, stylish comfortable spaces and all the amenitie ...
From $680 per night (USD)
Expedia
From $461 per night (USD)
VRBO
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 ...
From $461 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
$Pittsfield Home w\/ Deck - 12 Mi to Jiminy Peak!$
From $283 per night (USD)
VRBO
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 $283 per night (USD)
VRBO
$1st Floor Mountain View Suite Ski On\/Off At Jiminy- Fully Redone Decor$
From $207 per night (USD)
Expedia
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 $207 per night (USD)
Expedia
$Deluxe Mountain View Nautical Suite Jiminy Ski On\/Off- Fully Redone Decor$
From $195 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 $195 per night (USD)
VRBO
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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 ...
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Expedia
$A-Frame Cabin w\/ Furnished Deck in Becket!$
From $246 per night (USD)
VRBO
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 $246 per night (USD)
VRBO
$Indoor Pool & Lofted Game Area | Sunroom w\/ Sweeping Mountain Views | Wellspring$
From $1236 per night (USD)
Expedia
Indoor Pool & Lofted Game Area | Sunroom w\/ Sweeping Mountain Views | Wellspring
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 $1236 per night (USD)
Expedia
From $704 per night (USD)
VRBO
Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Discover a unique getaway in the heart of Stockbridge, Massachusetts, at the historic rectory of St. Joseph's Church. Pe ...
From $704 per night (USD)
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 $701 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 $701 per night (USD)
VRBO
$house with view in the berkshires\n$
From $327 per night (USD)
VRBO
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 $327 per night (USD)
VRBO
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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 ...
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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 $618 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 $618 per night (USD)
VRBO
From $298 per night (USD)
Expedia
Quiet 3BR Home, Near Tanglewood in Stockbridge
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Modern family home moments from Tanglewood, the Stockbridge Bowl, the Norman Rockwell and Chesterwood Museums. Just a 10 ...
From $298 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Experience Lenox near Tanglewood - 7 min drive - Peaceful Chalet in the Woods!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Nestled in the heart of Lenox, this charming vacation rental offers a tranquil escape for travelers seeking a memorable ...
From $468 per night (USD)
VRBO
From $1027 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 $1027 per night (USD)
Expedia
From $567 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 $567 per night (USD)
VRBO
From $380 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 $380 per night (USD)
Expedia
From $371 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 $371 per night (USD)
VRBO
From $470 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 $470 per night (USD)
Expedia
From $684 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 $684 per night (USD)
VRBO
From $274 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 $274 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 $465 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 $465 per night (USD)
Expedia
From $268 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 $268 per night (USD)
VRBO
From $339 per night (USD)
Expedia
Berkshires' best! Tanglewood, Jacob's Pillow and 400 feet from a pristine lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This newly renovated house in the woods on a private road in Lee is an ideal summer or fall retreat. Our little communit ...
From $339 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
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 $333 per night (USD)
VRBO
From $485 per night (USD)
Expedia
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)
Expedia
From $545 per night (USD)
VRBO
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 $545 per night (USD)
VRBO
$Family-Friendly Richmond Cottage w\/ Private Yard$
From $416 per night (USD)
Expedia
Family-Friendly Richmond Cottage w\/ Private Yard
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Plan your next family getaway at this waterfront vacation rental in Richmond. Surrounded by the beauty of the Berkshires ...
From $416 per night (USD)
Expedia
From $438 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 $438 per night (USD)
VRBO
From $219 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 $219 per night (USD)
VRBO
From $452 per night (USD)
VRBO
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 $452 per night (USD)
VRBO
From $466 per night (USD)
Expedia
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 $466 per night (USD)
Expedia
From $1798 per night (USD)
VRBO
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 $1798 per night (USD)
VRBO
From $207 per night (USD)
Expedia
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 $207 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
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 $181 per night (USD)
VRBO
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Expedia
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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Expedia
$All Season Adventures, Ski In\/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.$
From $171 per night (USD)
VRBO
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 $171 per night (USD)
VRBO
$Charming 1 Bedroom - 4 Star Resort w\/ heated pool, gym, wi-fi, lot's more!$
From $169 per night (USD)
Expedia
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 $169 per night (USD)
Expedia
$Becket Home w\/ 3-Season Porch: Walk to Lake Access$
From $227 per night (USD)
VRBO
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 $227 per night (USD)
VRBO
From $470 per night (USD)
Expedia
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 $470 per night (USD)
Expedia
From $333 per night (USD)
VRBO
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 $333 per night (USD)
VRBO
From $288 per night (USD)
Expedia
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 $288 per night (USD)
Expedia
Click For Pricing
VRBO
Stylish Retreat; Pool & Hot Tub By:Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
2 MINUTES FROM CATAMOUNT MOUNTAIN RESORT Newly renovated 4BR, 3BA home just 2 minutes from Catamount. Enjoy a heated poo ...
Click For Pricing
VRBO
From $630 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 $630 per night (USD)
Expedia
From $321 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 $321 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 $787 per night (USD)
VRBO
New!! Lovely Post & Beam home minutes from Lenox & Williamstown, lakes & 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 $787 per night (USD)
VRBO
From $177 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 $177 per night (USD)
Expedia
From $365 per night (USD)
VRBO
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 $175 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 $175 per night (USD)
VRBO
From $1410 per night (USD)
Expedia
Serene 5-BR Retreat 9-Min to Catamount
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Summary: Gather your friends and family at this a luxurious 5-BR retreat. Nestled in the serene woodlands of the Berkshi ...
From $1410 per night (USD)
Expedia
From $198 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 $198 per night (USD)
VRBO
$4 Mi to Skiing: Cottage w\/ Fire Pit in Richmond!$
From $256 per night (USD)
Expedia
4 Mi to Skiing: Cottage w\/ Fire Pit in Richmond!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Furnished Outdoor Space | Walk to Richmond Pond | Peaceful Surroundings Your New England escape awaits at this 3-bedroo ...
From $256 per night (USD)
Expedia
From $447 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 $447 per night (USD)
VRBO
From $385 per night (USD)
Expedia
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 $385 per night (USD)
Expedia
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VRBO
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, ...
Click For Pricing
VRBO
From $436 per night (USD)
Expedia
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 $436 per night (USD)
Expedia
From $550 per night (USD)
VRBO
Cozy Home in Lenox
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 $550 per night (USD)
VRBO
From $838 per night (USD)
Expedia
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)
Expedia
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
$1 Mi to Dtwn: Cottage w\/ Large Yard in Stockbridge$
From $433 per night (USD)
Expedia
1 Mi to Dtwn: Cottage w\/ Large Yard in Stockbridge
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Dog Friendly w/ Fee | Furnished Deck for Coffee Moments | Fireside Relaxation Nestled in the heart of Stockbridge, with ...
From $433 per night (USD)
Expedia
From $496 per night (USD)
VRBO
Lake Views & Dock Access - Pittsfield Cottage!
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Waterfront Yard | Furnished Sunroom | Boat Dock | Beach Gear Provided Nestled in the serene town of Pittsfield, 'Pontoo ...
From $496 per night (USD)
VRBO
Click For Pricing
Expedia
Bentley Brook, Charming 2-bedroom with WiFi, at Jiminy Peak Ski Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape to this peaceful ski in/out 2-bedroom resort retreat in Hancock at Jiminy Peak. Unwind in the welcoming living ro ...
Click For Pricing
Expedia
From $2606 per night (USD)
VRBO
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
Welcome to Moose Lodge – A 7,500 Sq. Ft. Berkshires Luxury Retreat Experience the pinnacle of comfort and entertainment ...
From $2606 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
From $351 per night (USD)
Expedia
From $1254 per night (USD)
VRBO
New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
We have been renting out the Taggart House estate for over 10 years. The "guest house" has always been our primary home ...
From $1254 per night (USD)
VRBO
From $267 per night (USD)
VRBO
Cozy Family Cottage in Peaceful New Marlborough
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Birdwatcher's Paradise! Experience acres of unspoiled wilderness as far as you can see while being surrounde ...
From $267 per night (USD)
VRBO
From $434 per night (USD)
VRBO
Family Ski House at Catamount !
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the ultimate family ski getaway at this spacious 4-bedroom, 3-bath home across from Catamount Ski Area. With ...
From $434 per night (USD)
VRBO
From $351 per night (USD)
Expedia
A Writer's Retreat at The Barn
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to a renovated barn that blends rustic charm with modern comfort. Enjoy airy, open spaces with vaulted ceilings a ...
From $351 per night (USD)
Expedia
From $275 per night (USD)
VRBO
Rustic 3bd Lake Front Country Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Take a step out of everyday life and enjoy some rest and relaxation at this cozy home on the lake nestled in the hills o ...
From $275 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Bougie B’s Mountainside Getaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick ...
From $280 per night (USD)
Expedia
$- Lake Front 4 Bdr w\/ Fast Internet! -$
From $482 per night (USD)
VRBO
- Lake Front 4 Bdr w\/ Fast Internet! -
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Take a step out of busy life and enjoy this large well curated lake front property in the heart of The Berkshires. Ente ...
From $482 per night (USD)
VRBO
Click For Pricing
Expedia
The Eddy - Apres Ski Sanctuary
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to The Eddy, a stylish retreat in the hills of The Berkshires, just a stone's throw from Otis Ridge! This home ...
Click For Pricing
Expedia
From $583 per night (USD)
VRBO
Spacious 4Bd Just a Block from Lake Mansfield!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming four bedroom house on the hill with convenient access to downtown Great Barrington. Just a few blocks to the b ...
From $583 per night (USD)
VRBO
From $521 per night (USD)
Expedia
Charming 3-BR Berkshires Timber Cottage
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Gather your family and friends and experience the charm of this 3-BR cabin in Becket, MA. Featuring three bedro ...
From $521 per night (USD)
Expedia
$Family-Friendly Mountain Retreat at Jiminy Peak, ski on\/off, fitness, pool\n\n$
From $230 per night (USD)
VRBO
Family-Friendly Mountain Retreat at Jiminy Peak, ski on\/off, fitness, pool\n\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Create unforgettable memories in this charming, one-bedroom, one-bathroom rental, perfectly located right on the mountai ...
From $230 per night (USD)
VRBO
From $491 per night (USD)
VRBO
Charming 3-bedroom chic farmhouse within walking distance of great barrington
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Your cozy getaway awaits in Great Barrington at this marvelous farmhouse. With 3 bedrooms including 2 queen beds and 2 t ...
From $491 per night (USD)
VRBO

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