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 $716 per night (USD)
VRBO
Perfect for Winter Skiing!!
Bedrooms:
3
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 $716 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Bedrooms:
2
Bathrooms:
2
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 $330 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $457 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 $457 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Quiet rustic cottage with shared lake access
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Lake Buel! This recently renovated cottage has been an old favorite for generations since the 1950’s. Abuttin ...
From $296 per night (USD)
VRBO
From $565 per night (USD)
VRBO
Just a min from Downtown Stockbridge on 11 Acres
Bedrooms:
4
Bathrooms:
4
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 $565 per night (USD)
VRBO
From $1216 per night (USD)
VRBO
General Williams Estate House Lenox/Stockbridge
Bedrooms:
5
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 $1216 per night (USD)
VRBO
From $1114 per night (USD)
VRBO
Stunning Modern Home - For Your Graduation Celebration
Bedrooms:
2
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 $262 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 $262 per night (USD)
VRBO
From $602 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 $602 per night (USD)
Expedia
From $940 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 $940 per night (USD)
VRBO
From $741 per night (USD)
Expedia
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 ...
From $741 per night (USD)
Expedia
From $470 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 $470 per night (USD)
VRBO
From $276 per night (USD)
Expedia
Pittsfield Home w/ Deck - 12 Mi to Jiminy Peak!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Great for outdoor enthusiasts, this 3-bedroom, 2.5-bathroom vacation rental home features a balcony, a deck, a patio, an ...
From $276 per night (USD)
Expedia
From $189 per night (USD)
VRBO
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Bedrooms:
1
Bathrooms:
1
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 $189 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Bedrooms:
1
Bathrooms:
1
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 $191 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $889 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 $889 per night (USD)
VRBO
From $227 per night (USD)
VRBO
A-Frame Cabin w/ Furnished Deck in Becket!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Built in 1974 | Private Acreage & Scenic Surroundings | Fireside Relaxation | EV Charger Embrace a slower pace of life ...
From $227 per night (USD)
VRBO
From $1255 per night (USD)
Expedia
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Wellspring is a sprawling Berkshire escape with unparalleled views of the surrounding mountains. This gorgeous home has ...
From $1255 per night (USD)
Expedia
From $838 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 $838 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $573 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 $573 per night (USD)
VRBO
$house with view in the berkshires\n$
From $346 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 $346 per night (USD)
VRBO
Click For Pricing
VRBO
Renovated Berkshires Farmhouse - minutes from hiking, swimming, and Tanglewood
Bedrooms:
2
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 ...
Click For Pricing
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Spectacular views and close to Great Barrington.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Main floor bedroom with private bath, 2 car garage, electric vehicle charging, screened porch, pool, and Koi pond with v ...
Click For Pricing
VRBO
From $298 per night (USD)
Expedia
Quiet 3BR Home, Near Tanglewood in Stockbridge
Bedrooms:
2
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 $446 per night (USD)
VRBO
Luxury Cabin Fall Views & Deck besides Kennedy Park, Walk to Lenox.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegant, light-filled cabin blending modern comfort with rustic charm, nestled beside Kennedy Park. Enjoy mesmerizing ...
From $446 per night (USD)
VRBO
From $558 per night (USD)
Expedia
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 $558 per night (USD)
Expedia
From $501 per night (USD)
VRBO
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
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 $501 per night (USD)
VRBO
From $275 per night (USD)
Expedia
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 $275 per night (USD)
Expedia
From $274 per night (USD)
VRBO
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)
VRBO
$Berkshires Lakefront Gem. Cozy home w/ hiking, swimming & all things cultural!\n$
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
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
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 $312 per night (USD)
VRBO
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 $312 per night (USD)
VRBO
From $393 per night (USD)
Expedia
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 $393 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 $513 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 $513 per night (USD)
Expedia
From $331 per night (USD)
VRBO
Two 2BR Villas l From Sauna to Sports Courts – Comfort & Fun for Everyone
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 $331 per night (USD)
VRBO
From $165 per night (USD)
VRBO
Resort Stay with Arcade, Heated Pool, Sports Courts & Family Perks
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 $165 per night (USD)
VRBO
From $442 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 $442 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Perfect Nature Haven In Great Barrington
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Welcome to your home for the week in Great Barrington—a spacious, nature-surrounded retreat. Just a 2-minute dr ...
From $464 per night (USD)
Expedia
From $1821 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 $1821 per night (USD)
VRBO
From $201 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 $201 per night (USD)
Expedia
From $211 per night (USD)
Expedia
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 $211 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
Expedia
From $143 per night (USD)
VRBO
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round ...
From $143 per night (USD)
VRBO
From $175 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 $175 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Becket Home w/ 3-Season Porch: Walk to Lake Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Unwind and embrace nature at this charming Becket vacation rental! With views of Lake Robinhood and a screened porch for ...
From $215 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Lakefront Jewel By: Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Breathtaking lakefront jewel with stunning, unparalleled views & central AC. Relax and unwind at our stunning 3BR / 2BA ...
From $457 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Treat your family to the ultimate getaway in the Berkshires at this beautiful vacation rental on Lake Ashmere! The 3-bed ...
From $469 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Berkshire Holiday Home with Hot Tub & A+ Amenities
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Book your next vacation at our special Berkshire Holiday home set on several acres in the beautiful Berkshire Mountains ...
From $314 per night (USD)
Expedia
From $425 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 $425 per night (USD)
VRBO
From $308 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 $308 per night (USD)
Expedia
From $177 per night (USD)
VRBO
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)
VRBO
From $875 per night (USD)
Expedia
New!! Lovely Post & Beam home minutes from Lenox & Williamstown, lakes & hiking
Bedrooms:
2
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 $875 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 $172 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 $172 per night (USD)
VRBO
From $1318 per night (USD)
VRBO
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 $1318 per night (USD)
VRBO
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
Click For Pricing
Expedia
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Furnished Outdoor Space | Walk to Richmond Pond | Peaceful Surroundings Your New England escape awaits at this 3-bedroo ...
Click For Pricing
Expedia
From $542 per night (USD)
VRBO
Lakefront Home on Pontoosuc Lake, the Berkshires
Bedrooms:
2
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 $542 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
Click For Pricing
VRBO
The Berkshires Basecamp
Bedrooms:
3
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 $431 per night (USD)
Expedia
Solomon Ely Homestead - Charming Pittsfield Stay
Bedrooms:
1
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 $431 per night (USD)
Expedia
From $574 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 $574 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 $510 per night (USD)
VRBO
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 $510 per night (USD)
VRBO
From $435 per night (USD)
Expedia
Lake Views & Dock Access - Pittsfield Cottage!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Waterfront Yard | Furnished Sunroom | Boat Dock | Beach Gear Provided Nestled in the serene town of Pittsfield, 'Pontoo ...
From $435 per night (USD)
Expedia
Click For Pricing
VRBO
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
VRBO
From $1930 per night (USD)
VRBO
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
Bedrooms:
7
Bathrooms:
6
Sleeps:
14
Welcome to Moose Lodge – A 7,500 Sq. Ft. Berkshires Luxury Retreat Experience the pinnacle of comfort and entertainment ...
From $1930 per night (USD)
VRBO
From $246 per night (USD)
VRBO
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 $246 per night (USD)
VRBO
From $184 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 $184 per night (USD)
Expedia
From $1134 per night (USD)
VRBO
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Stunning 5BR/5.5BA 4,500 sq ft home with soaring 25-ft ceilings, modern finishes, pearched in the trees with sparkeling ...
From $1134 per night (USD)
VRBO
$Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool\n\n$
From $231 per night (USD)
Expedia
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 $231 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Cozy Family Cottage in Peaceful New Marlborough
Bedrooms:
1
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 $296 per night (USD)
Expedia
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 $296 per night (USD)
Expedia
From $255 per night (USD)
VRBO
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 $255 per night (USD)
VRBO
From $297 per night (USD)
Expedia
Rustic 3bd Lake Front Country Cottage
Bedrooms:
1
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 $297 per night (USD)
Expedia
From $228 per night (USD)
VRBO
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 $228 per night (USD)
VRBO
From $356 per night (USD)
Expedia
- Lake Front 4 Bdr w/ Fast Internet! -
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Enjoy this spacious 4 bed, 4 bath home nestled on Lake Garfield in the beautiful Berkshires. Well-curated, clean, and pe ...
From $356 per night (USD)
Expedia
From $621 per night (USD)
VRBO
Spacious 4Bd Just a Block from Lake Mansfield!
Bedrooms:
2
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 $621 per night (USD)
VRBO
From $418 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 $418 per night (USD)
Expedia
From $414 per night (USD)
VRBO
Pet Friendly Oasis on 5 Private Acres, 10 min to Tanglewood
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Escape to this peaceful retreat on 5 private acres. Large picture windows envelope you in the gorgeous surroundings, and ...
From $414 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Spacious 4BR Central-Berkshires Home with POOL!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Spacious and comfortable home in a serene setting and ideal location. Whether you are coming for performing arts, museu ...
From $351 per night (USD)
Expedia
From $574 per night (USD)
VRBO
Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Available February 17-21 - President’s week 2025! Condo Resort at Jiminy Peak Ski Mountain's Base Enjoy ski retreat at ...
From $574 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Trail Access: Berkshires Gem w/ Rooftop Deck!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Walk to Restaurants | Pet Friendly w/ Fee | 6 Mi to Tanglewood Get the most out of your next Berkshires getaway when yo ...
From $232 per night (USD)
Expedia
From $738 per night (USD)
VRBO
Grand Berkshire Manor By Evergreen Home
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Welcome to The Manor – your refined escape to the tranquil beauty of the Berkshires. Discover a perfectly situated, spa ...
From $738 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Grandparent’s Cottage 250 steps to the lake
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
4 bedrooms, sleeps 7, 2 living rooms, 2 full bathrooms, fully stocked kitchen; lawn chairs, beach towels, games, and bic ...
From $454 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Bedrooms:
3
Bathrooms:
3
Sleeps:
3
Perfect for budget-conscious travelers, our Basic Queen rooms provide a welcoming and practical space to rest and rechar ...
From $301 per night (USD)
VRBO
From $405 per night (USD)
Expedia
Walk to Ski Slopes: Jiminy Peak Resort Getaway!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Private Ski Locker On-Site | 2 Living Rooms | In-Unit Laundry | Forest Views | WFH Friendly The beauty and adventure of ...
From $405 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Cozy Carriage House room with a double bed and private balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Teddy Room (C24) at The Cornell Inn is a cozy and inviting retreat in the historic Carriage House, offering a peacef ...
From $341 per night (USD)
VRBO
$\Elegant Emily Dickinson Junior Suite with King Bed & Fireplace$
From $499 per night (USD)
Expedia
\"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Emily Dickinson Junior Suite at The Cornell Inn offers a refined and tranquil retreat inspired by the beloved poet. ...
From $499 per night (USD)
Expedia
From $559 per night (USD)
VRBO
Elegant suite with a king bed, fireplace, and kitchenette.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
C23 - The Cleopatra Suite at The Cornell Inn is a spacious, two-floor retreat offering a blend of modern convenience and ...
From $559 per night (USD)
VRBO
From $559 per night (USD)
Expedia
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Lady Cicely Grand Suite (M27) - A Luxurious Escape at The Cornell Inn Indulge in elegance and comfort at The Lady C ...
From $559 per night (USD)
Expedia
From $457 per night (USD)
VRBO
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Niles Johnson Room (M11) - A Cozy & Elegant Retreat at The Cornell Inn Welcome to The Niles Johnson Room (M11) at T ...
From $457 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Elegant Carriage House room with a queen bed and private patio.
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Silver Thistle Room (C12) at The Cornell Inn is a charming and tranquil retreat in the historic Carriage House. This ...
From $321 per night (USD)
Expedia

Search Your Destination Now!

Berkshire Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 988 Rentals