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 $461 per night (USD)
VRBO
Waterfront Cottage 10 Min From Great Barrington
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A couple's getaway for the books awaits you at this Lake Buel vacation rental. Just 6 miles from Great Barrington's shop ...
From $461 per night (USD)
VRBO
$house with view in the berkshires\n$
From $335 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 $335 per night (USD)
VRBO
From $172 per night (USD)
VRBO
In-law studio in the heart of the Berkshires!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
In-law studio in a super location in the heart of the Berkshires. Fully furnished and equiped, this sweet private-entra ...
From $172 per night (USD)
VRBO
From $389 per night (USD)
VRBO
Saltbox-style residence in the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the allure of this enchanting Saltbox-style residence nestled in the picturesque town of Hillsdale, NY. With t ...
From $389 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Elegant Mountain View Retreat By Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Explore the best of the Berkshires at this private country retreat, minutes from the Williams campus, world-class museum ...
From $531 per night (USD)
VRBO
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Expedia
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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Expedia
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VRBO
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
VRBO
$Idyllic Retreat; Hot Tub\/Sauna by Evergreen Home$
From $708 per night (USD)
Expedia
Idyllic Retreat; Hot Tub\/Sauna by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Great Barrington 3BR / 3BA retreat nestled on 4.7 acres of park-like grounds. Relax in the inviting hot tub under the st ...
From $708 per night (USD)
Expedia
$Tanglewood Chalet - Majestic View of Mountains \nMinutes to Tanglewood & Theaters$
From $528 per night (USD)
VRBO
Tanglewood Chalet - Majestic View of Mountains \nMinutes to Tanglewood & Theaters
Bedrooms:
2
Bathrooms:
5
Sleeps:
7
Beautiful, newly renovated home, surrounded by nature and very close to hiking trails and cultural and historical sites ...
From $528 per night (USD)
VRBO
From $626 per night (USD)
Expedia
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 $626 per night (USD)
Expedia
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VRBO
Berkshires Tranquil Retreat With Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Escape to your very own serene haven in Great Barrington with a private, in-ground pool on a 4-acre property. T ...
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VRBO
From $396 per night (USD)
VRBO
Light-filled family home. Book now for the summer!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Light-filled modern 4 bedroom, 3.5 bath home in the Berkshires. This lovely two story home features a master bedroom on ...
From $396 per night (USD)
VRBO
From $1077 per night (USD)
VRBO
Large, comfortable house and yard located on a beautiful lake.
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Bring extended family or a group of friends to this great house with lots of room for fun, on a beautiful lake, just min ...
From $1077 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Gateway to the Berkshires - Renovated downtown apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Completely renovated downtown second floor apartment with open floor plan, located in historical downtown Lee. This apar ...
From $238 per night (USD)
Expedia
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VRBO
Adorable Berkshires Loft on Quiet Dirt Road. Close to Tanglewood.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sweet loft on quiet dirt road. First floor has kitchen, eating area, living room, bathroom with laundry, three season p ...
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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 $475 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 $475 per night (USD)
VRBO
From $1033 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 $1033 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 $388 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 $388 per night (USD)
VRBO
From $516 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 $516 per night (USD)
Expedia
From $2670 per night (USD)
VRBO
***Your Own B&B*** Su
Bedrooms:
13
Bathrooms:
13
Sleeps:
36
Summary: **Please message us prior to booking and talking with your group to confirm pricing and availability** Interio ...
From $2670 per night (USD)
VRBO
From $333 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 $333 per night (USD)
Expedia
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VRBO
Spacious 4 bedroom, big pool & outdoor space. Close for local summer activities!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Less than 2 miles from Williams College, this a great homebase for the upcoming Williams events or other summer events i ...
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VRBO
From $263 per night (USD)
Expedia
Luxury 2 Bedroom 2 Bathroom Loft Apartment In Williamstown With Great Amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxury two-bedroom loft apartment for in the prestigious Cable Mills building in Williamstown, Massachusetts. A five-min ...
From $263 per night (USD)
Expedia
From $147 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
1
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $147 per night (USD)
VRBO
From $147 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $147 per night (USD)
VRBO
From $147 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $147 per night (USD)
VRBO
From $147 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $147 per night (USD)
VRBO
From $473 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 $473 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 $307 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 $307 per night (USD)
Expedia
From $440 per night (USD)
VRBO
Baldwin Hill Retreat Guest House
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
In one of the most sought after destinations in New England, located just outside Great Barrington near the top of Baldw ...
From $440 per night (USD)
VRBO
$Berkshires Summer Chalet w\/ Pool + Private Hiking Trails$
From $835 per night (USD)
VRBO
Berkshires Summer Chalet w\/ Pool + Private Hiking Trails
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Nestled in the foothills of East Mountain, just minutes from the center of Great Barrington, this woodsy pine cabin has ...
From $835 per night (USD)
VRBO
From $182 per night (USD)
VRBO
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Nestled in history and nature, The Historic Kellogg House, built in 1739, is the third oldest house in the Berkshires. R ...
From $182 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Delightful Stockbridge House, Walk to Town!
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
Within walking distance to Main Street in Stockbridge, 38 Church St. offers a large backyard and gardens which boarder p ...
From $238 per night (USD)
VRBO
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 $108 per night (USD)
VRBO
1br Deluxe Condo Jiminy Peak Skiing!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $108 per night (USD)
VRBO
From $108 per night (USD)
VRBO
1br Deluxe Condo Jiminy Peak Skiing!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $108 per night (USD)
VRBO
From $118 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $118 per night (USD)
VRBO
From $118 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $118 per night (USD)
VRBO
From $108 per night (USD)
VRBO
1br Deluxe Condo Jiminy Peak Skiing!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $108 per night (USD)
VRBO
From $118 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $118 per night (USD)
VRBO
From $118 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $118 per night (USD)
VRBO
From $108 per night (USD)
VRBO
1br Deluxe Condo Jiminy Peak Skiing!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $108 per night (USD)
VRBO
From $118 per night (USD)
VRBO
Studio Condo Outdoor Adventures
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $118 per night (USD)
VRBO
From $108 per night (USD)
VRBO
1br Deluxe Condo Jiminy Peak Skiing!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $108 per night (USD)
VRBO
From $147 per night (USD)
VRBO
2br DX Condo Ski & Berkshire County!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $147 per night (USD)
VRBO
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 $527 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 $527 per night (USD)
Expedia
From $445 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 $445 per night (USD)
VRBO
From $567 per night (USD)
Expedia
Fully Renovated Jiminy Peak Townhouse, walk to all
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Fully renovated in 2022. On-site at ski mountain Jiminy Peak A-frame townhouse with 4 stories of fun for the whole famil ...
From $567 per night (USD)
Expedia
From $222 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 $222 per night (USD)
VRBO
$3 Bedroom home w\/ lake and mountain views near skiing, and cultural attractions!$
From $532 per night (USD)
Expedia
3 Bedroom home w\/ lake and mountain views near skiing, and cultural attractions!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Conveniently located near a lake, off of Route 7 on the way to attractions in both North Berkshire County and Southern B ...
From $532 per night (USD)
Expedia
From $456 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 $456 per night (USD)
VRBO
$Hilltop: Panoramic Views w\/ Pool near Catamount$
From $648 per night (USD)
VRBO
Hilltop: Panoramic Views w\/ Pool near Catamount
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: With 360-degree views of the Catskill and Berkshire Mountains from the highest point in Hillsdale, Hilltop is a ...
From $648 per night (USD)
VRBO
$Silver Ridge: Hilltop Chalet w\/ Sweeping Views$
From $630 per night (USD)
VRBO
Silver Ridge: Hilltop Chalet w\/ Sweeping Views
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Summary: Perched high on the hills above Hillsdale, Silver Ridge is a perfectly-sited contemporary mountain lodge offeri ...
From $630 per night (USD)
VRBO
$Mountain View: Airy + Secluded w\/Panoramic Views$
From $628 per night (USD)
VRBO
Mountain View: Airy + Secluded w\/Panoramic Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Welcome to Mountain View, a beautifully appointed 3-bed, 2.5-bath home perched on the mountainside—just 2.5 hrs ...
From $628 per night (USD)
VRBO
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 $260 per night (USD)
VRBO
Charming 2-bedroom apartment in Lee with fitness room, WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $260 per night (USD)
VRBO
From $463 per night (USD)
Expedia
Perfect Nature Haven 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 $463 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $265 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $261 per night (USD)
VRBO
Click For Pricing
VRBO
Central Berkshire Craftsman - Long Terms Welcome!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This cute as a button cottage in a walkable residential neighborhood, is the perfect home base to explore the Berkshires ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Lakefront 3-bedroom house in lower Berkshires with WiFi, AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to this delightful mid-century lake-front house on Twin Lakes in the foothills of the Berkshires. This relaxing v ...
Click For Pricing
Expedia
From $454 per night (USD)
VRBO
Charming 3-bedroom in-town house with AC and WiFi in tranquil West Stockbridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This light filled; in-town home is a short walk to the picturesque Village of West Stockbridge. In town you'll find anti ...
From $454 per night (USD)
VRBO
From $181 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 $181 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $261 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $261 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
$All Season Adventures, Ski In\/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.$
From $200 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 $200 per night (USD)
Expedia
$Charming 1 Bedroom - 4 Star Resort w\/ heated pool, gym, wi-fi, lot's more!$
From $169 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 $169 per night (USD)
VRBO
$Becket Home w\/ 3-Season Porch: Walk to Lake Access$
From $235 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 $235 per night (USD)
Expedia
From $492 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 $492 per night (USD)
VRBO
$All Season Adventures, Ski In\/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.$
From $322 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 $322 per night (USD)
VRBO
From $630 per night (USD)
VRBO
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)
VRBO
From $347 per night (USD)
Expedia
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 $347 per night (USD)
Expedia
From $1272 per night (USD)
VRBO
Newly renovated private 3 bedroom house on a dead end road.13 acres & 360 views
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your dream upstate country escape! This newly remodeled 3-bedroom, 3-bathroom home offers a perfect blend of ...
From $1272 per night (USD)
VRBO
From $333 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 $333 per night (USD)
Expedia
From $288 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 $288 per night (USD)
VRBO
Click For Pricing
Expedia
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
Expedia
$Berkshires Lakefront Retreat\n$
From $547 per night (USD)
VRBO
Berkshires Lakefront Retreat\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Catch your breath…and let nature take it away again... Private and serene, our beautiful lakefront home is your idylli ...
From $547 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 $793 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 $793 per night (USD)
VRBO
From $798 per night (USD)
Expedia
Fabulous modern home with pool & separate guest house . Pet-friendly!
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Sunny modern home with separate luxury guest house. 3 lovely bedrooms in main house, 2 with en-suite bathrooms, tasteful ...
From $798 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Cozy Comfortable Three Bedroom Home in charming Williamstown
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Your Williamstown adventure begins at this 3-bedroom house. Each bedroom features a cozy king, queen, or full bed, ensur ...
From $400 per night (USD)
VRBO
From $179 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 $179 per night (USD)
Expedia
$All Season Adventures, Ski In\/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.$
From $296 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 $296 per night (USD)
VRBO
From $462 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 $462 per night (USD)
VRBO
From $385 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 $385 per night (USD)
VRBO
Click For Pricing
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, ...
Click For Pricing
Expedia
$Berkshire Hideaway w\/ Fire Pit & Playground!$
From $212 per night (USD)
VRBO
Berkshire Hideaway w\/ Fire Pit & Playground!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Near Wineries & Historical Sites | Screened Porch | Peaceful Location Fine wines, scenic landscapes, and quality family ...
From $212 per night (USD)
VRBO
From $466 per night (USD)
Expedia
Beautiful Berkshire family home
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
This is a beautiful 5 bedroom Berkshire, post and beam private house nestled in the woods just off the Appalachian trail ...
From $466 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

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