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 $205 per night (USD)
VRBO
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You want to pop out of bed, walk outside, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charmin ...
From $205 per night (USD)
VRBO
From $655 per night (USD)
Expedia
Wildlife Retreat in the Forest
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contem ...
From $655 per night (USD)
Expedia
From $429 per night (USD)
VRBO
Berkshire Lake at the Pillow, and EV!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
At the intersection of New York. CT and MA, enjoy a newly finished Four Season Home with your own boat dock. Included 2 ...
From $429 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Perfect Holiday Retreat, Completely Renovated, Central Location
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Our completely renovated farmhouse is set upon a hilltop overlooking downtown Lee. It is a perfect spot for culture, sp ...
From $434 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Ashintully Cottage in spectacular setting
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
This bright cottage sits between Ashintully Gardens (landscaped public gardens with winding brook, fountain, paths and h ...
From $346 per night (USD)
VRBO
From $304 per night (USD)
VRBO
Shingle style, Timber Frame, Berkshire Cottage beside babbling brook
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Colesbrook Manor is a timber frame, shingle-style cottage. A true retreat destination in and of itself anytime of the ye ...
From $304 per night (USD)
VRBO
From $432 per night (USD)
VRBO
Spacious, In-Town, Steinway grand
Bedrooms:
5
Bathrooms:
4
Sleeps:
6
Our home is lovely, large and comfortable. It is located "On The Hill" in Great Barrington, MA. which means we are virtu ...
From $432 per night (USD)
VRBO
From $244 per night (USD)
VRBO
Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
This charming and appropriately named "Little Cottage" was newly renovated in 2017. Enjoy a short walk (300 feet) down ...
From $244 per night (USD)
VRBO
$The Meadows House @ Otis Ridge w\/ 7-person hot tub$
From $303 per night (USD)
VRBO
The Meadows House @ Otis Ridge w\/ 7-person hot tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax in a beautiful mountain setting at this 4-season ski house within walking distance of the slopes at Otis Ridge Ski ...
From $303 per night (USD)
VRBO
From $468 per night (USD)
Expedia
Best of the Berkshires & Hudson Valley
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in Canaan, NY, less than a mile from the Massachusetts border, this wonderful 1700s post and beam farmhouse has ...
From $468 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Relax, Read, Entertain, Or Walk To West Lake From Our Berkshire Home.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2-bedroom, sun-filled, open floor plan that was recently renovated inside and out. Sits on lovely property with multipl ...
From $190 per night (USD)
VRBO
From $499 per night (USD)
Expedia
West Stockbridge Sanctuary by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy a getaway to the Berkshires in this magnificent post & beam home; newly renovated and nestled on 1 acre of land - ...
From $499 per night (USD)
Expedia
From $160 per night (USD)
VRBO
Vacation Village in the Berkshires 5 Star Resort - Suite A
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Gold Crown Resort! Spectacular mountain views, clubhouse, fitness center, indoor pool, outdoor jacuzzi, outdoor pool, ga ...
From $160 per night (USD)
VRBO
From $466 per night (USD)
Expedia
Minutes from downtown Great Barrington, Convenient location
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Built in 2015, this lovely 4 bedroom, 2500 sq.ft. home on a knoll is set back 175 feet from the street. This charming ...
From $466 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Charming historic cottage on scenic road to Mt. Greylock
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room scho ...
From $227 per night (USD)
VRBO
From $728 per night (USD)
VRBO
Berkshires Year-Round Home-Great mountain & lake views, sunsets, close to Lenox
Bedrooms:
4
Bathrooms:
10
Sleeps:
10
NEWLY RENOVATED This house has some of the most amazing views in the Berkshires, looking west over Queechy Lake; incred ...
From $728 per night (USD)
VRBO
Click For Pricing
VRBO
Cottage Retreat in Heart of the Berkshires
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LIVING ROOM: Bright light and high ceilings with new couch, chairs, Sonos speakers, and more. KITCHEN: Fully-outfitted k ...
Click For Pricing
VRBO
From $1166 per night (USD)
Expedia
Secluded Estate: 5 Bedrooms, Hot Tub, Tranquil Mood
Bedrooms:
5
Bathrooms:
5
Sleeps:
16
Summary: Unparalleled views for miles and absolute killer location, built on Stone Hill Rd, which has a local walking pa ...
From $1166 per night (USD)
Expedia
From $79 per night (USD)
VRBO
Apartment Newly Remodeled Super Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Large 2nd floor fully furnished apartment in 2 story corner house with plenty of parking and separate back entrance/stai ...
From $79 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
This spacious, sunny condo at Foxhollow on the Lenox/Lee border is perfectly situated for you to enjoy the natural beaut ...
From $389 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Apartment in Gorgeous Stonybrook Farm
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This apartment is located in a renovated barn on a large private estate, centrally located in the heart of the Berkshire ...
From $192 per night (USD)
VRBO
From $392 per night (USD)
Expedia
Heart of Lenox!! - renovated downtown apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Completely renovated 2-bedroom downtown apartment with open floor plan, located in the picturesque historical town of Le ...
From $392 per night (USD)
Expedia
From $592 per night (USD)
VRBO
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Newly Renovated for 2023 Cape Cod Style ,4BR, 4BA, sleeps 10-12. New fully equipped kitchen w/ center island, indoor an ...
From $592 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Enjoy a renovated private home right in downtown Lenox
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our lovely home is literally a stones throw from Lenox's downtown shops and fabulous restaurants but also in a very quie ...
From $447 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Available for Winter Rental, Healthcare, Central
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
If you are coming to the area to help in one of our Hospitals or Healthcare facility please contact us for booking optio ...
From $192 per night (USD)
VRBO
From $842 per night (USD)
Expedia
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Bright and airy, cathedral ceiling, Post & Beam home situated in the heart of the Berkshires, minutes from Lenox, Tangle ...
From $842 per night (USD)
Expedia
From $614 per night (USD)
VRBO
Antique Farmhouse Totally Restored
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
This rambling farmhouse has a balanced mix of meticulous restoration with an eccentric flair. Undermountain Farm is a ho ...
From $614 per night (USD)
VRBO
$Charming Cottage w\/ Sauna, close to hiking trails, ski lodges & Great Barrington$
From $326 per night (USD)
VRBO
Charming Cottage w\/ Sauna, close to hiking trails, ski lodges & Great Barrington
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Perfect Refuge in a Charming Berkshire Cottage with Vaulted Ceilings, Two-Person Sauna, Wrap Around Deck, Amazing Sunlig ...
From $326 per night (USD)
VRBO
From $312 per night (USD)
VRBO
Little House in the Woods by Evergreen Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fresh, cozy & serene, the Little House is set back from the road with several acres of woods behind & a wildlife preserv ...
From $312 per night (USD)
VRBO
From $293 per night (USD)
Expedia
North Getaway Cottage
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
A great place for vacationers and those seeking a remote work or school location with three work areas and a guest print ...
From $293 per night (USD)
Expedia
From $335 per night (USD)
VRBO
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Our home is nestled on 2.6 acres in the heart of the Berkshires! We are within 2 miles to Tanglewood & Kripalu while ju ...
From $335 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Bright Boho Apt in 18th c Berkshire Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Bright and clean apartment on flower farm in the mountains This bright 1BR/1BA is located at the base of Mount Greylock ...
From $218 per night (USD)
Expedia
$Premiere Berkshire Country Estate w\/ Private Pool & Tennis Court - 5 mins to GB!$
From $1262 per night (USD)
VRBO
Premiere Berkshire Country Estate w\/ Private Pool & Tennis Court - 5 mins to GB!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
In 2016 Smithsonian Magazine deemed Great Barrington, "The Best Small Town in America." Manor Lane is a private French C ...
From $1262 per night (USD)
VRBO
From $517 per night (USD)
Expedia
Modern Cottage in the heart of the Berkshires with new exterior flex space!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Drive down our private road to find an adorable and spacious cottage, nestled on four secluded wooded acres, with every ...
From $517 per night (USD)
Expedia
From $599 per night (USD)
VRBO
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only a few minutes walk to the town's b ...
From $599 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Let this newly renovated 3-bedroom, 2-bathroom townhouse, with European finishes, sky lights and brand new kitchen, bath ...
From $377 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Private Woodland Getaway minutes from Ski Butternut
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Set in the heart of fifteen peaceful wooded acres and fronted by a private meadow, this beautiful chalet-style home with ...
From $547 per night (USD)
VRBO
$Modern Berkshires Cottage 🌲 Gas Stove, Large Deck & W\/D + 7 mins to Otis Ridge$
From $361 per night (USD)
Expedia
Modern Berkshires Cottage 🌲 Gas Stove, Large Deck & W\/D + 7 mins to Otis Ridge
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to our brand new cottage, which is nestled in one of the Berkshires’ best areas for skiing, hiking, and spending ...
From $361 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Equipped Villa with Access to Amazing Amenities!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy an awesome location and access to a number of exciting amenities including a fitness center, 2 pools, a hot tub, d ...
From $289 per night (USD)
VRBO
$IN\/OUT SKIING CONDO , POOL, MOVIE THEATER\/ KIDS ACTIVITIES$
From $384 per night (USD)
Expedia
IN\/OUT SKIING CONDO , POOL, MOVIE THEATER\/ KIDS ACTIVITIES
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
2BEDROOM and 2 BATH CONDO. Master Bath has large whirlpool tub. also has full sized pull out couch and portable cribs a ...
From $384 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Villa with Access to Various Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
When you stay in our villa, you'll have access to a number of exciting amenities including a fitness center, 2 pools, a ...
From $247 per night (USD)
VRBO
From $318 per night (USD)
Expedia
Spacious Villa with Access to Various Amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is the perfect villa for your group! Enjoy an awesome location and access to a number of exciting amenities includi ...
From $318 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Villa with Access to Amazing Amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sleeps 4 up to 6 people (Max 5 Adults) - Large and small outdoor pool - Two indoor pools: Open - Hot Tub - 2 on-site B ...
From $289 per night (USD)
VRBO
From $666 per night (USD)
Expedia
Superb Views -- Sunsets, Mountains, Valley
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Overview of availability in 2025 (as of 11/5/2024) : May 24-30 June 3-15 July 13 - August 17 Septe ...
From $666 per night (USD)
Expedia
From $648 per night (USD)
VRBO
Home with Pool on 10 Acres
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully furnished, recently renovated Stockbridge home centrally located 3 miles from Tanglewood, 1 mile from Norman ...
From $648 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Family Fun in The Berkshires at Beautiful Hygge House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Thank you for checking out Hygge House on Richmond Pond! Hygge (hoo-ga) is the Danish art of enjoying life's simple ple ...
From $461 per night (USD)
Expedia
From $1615 per night (USD)
VRBO
Morning Face - Berkshire estate with heated pool, views and privacy.
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Morning Face is a meticulously restored Italian villa with privacy and mature gardens. Set on 20 acres, the beautifully ...
From $1615 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Skiing & Hiking: Water-View Home in the Berkshires
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
2,262 Sq Ft | Ping-Pong Table | Nestled on Mill Pond | < 7 Mi to Dwtn Great Barrington Take a break from the city and b ...
From $324 per night (USD)
Expedia
From $517 per night (USD)
VRBO
Private Berkshires Getaway Minutes to Ski Butternut
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Newly renovated 4 bedroom and 2 full bath home set back from the road is a peaceful oasis. 2 minute drive to Ski Buttern ...
From $517 per night (USD)
VRBO
From $724 per night (USD)
Expedia
Renovated, Five Bedrooms In Historic Williamstown
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Summary: Spacious and renovated, this large family home in Williamstown offers over 3400 square feet of living space. Wi ...
From $724 per night (USD)
Expedia
From $1195 per night (USD)
VRBO
Luxury Berkshires Retreat in Lenox - Main House & Studio
Bedrooms:
5
Bathrooms:
7
Sleeps:
15
A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxu ...
From $1195 per night (USD)
VRBO
From $956 per night (USD)
Expedia
Berkshires Home Makeover ~ Immaculate Lakefront Getaway ~ Dreamy Sunsets!
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
This 4 bedroom, 6 bath home takes advantage of its prime location on Laurel Lake, offering breathtaking waterfront views ...
From $956 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Centrally Located Historical Home
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Summary: Come to enjoy views from this private, country escape. Decorated with many cool antiques and theatre related ob ...
From $369 per night (USD)
VRBO
From $539 per night (USD)
Expedia
Stonebridge Cabin: Modern Amenities, Enjoy Nature!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Our quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort ...
From $539 per night (USD)
Expedia
From $161 per night (USD)
VRBO
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built ...
From $161 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Lovely two bedroom river-view rental unit
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Comfortable, contemporary-styled, second-floor apartment with a view of the river. You'll have a great time relaxing ins ...
From $315 per night (USD)
Expedia
$Berkshires Apt w\/ Deck & Mtn Views!$
Click For Pricing
VRBO
Berkshires Apt w\/ Deck & Mtn Views!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Stream On-Site | Fire Pit | 6 Mi to Tanglewood Perfect for music enthusiasts, outdoorsy friends, or families seeking th ...
Click For Pricing
VRBO
From $255 per night (USD)
Expedia
Charming cedar shingle cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
A 3-bedroom lakefront cottage. Knotty pine interior with ample frontage on Big Pond. Dock available on property May - S ...
From $255 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Cozy Cabin on Lake Mahkeenac
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy cabin located in the popular Beachwood community which is 2 miles from Tanglewood on Stockbridge Bowl, close to Kr ...
From $309 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Rustic cottage on hill accessed by private lane Located in beautiful Berkshire Mountains of western, MA Simple, charming ...
From $369 per night (USD)
Expedia
$Great Barrington\/Housatonic Getaway—bring your dog!$
From $216 per night (USD)
VRBO
Great Barrington\/Housatonic Getaway—bring your dog!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome! Great location in the Housatonic village of Great Barrington with big yard, walkable streets and an excellent f ...
From $216 per night (USD)
VRBO
From $597 per night (USD)
Expedia
Perfect location in the heart of downtown Lenox
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
If you want to feel like you're truly away, but still have access to a great lifestyle, this is the rental for you! St ...
From $597 per night (USD)
Expedia
From $275 per night (USD)
VRBO
Remote and Relaxing Cabin in the Berkshires
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Wake up to a beautiful view from this A-frame home built by our family. Unpack and unwind! Spend the day hiking(or snow ...
From $275 per night (USD)
VRBO
From $518 per night (USD)
Expedia
Sophisticated Lenox Retreat by Evergreen Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautiful Dutch Gambrel is the ideal spot for your next New England getaway. So spacious- with four bedrooms, 2.5 ...
From $518 per night (USD)
Expedia
Click For Pricing
VRBO
Berkshire Get away
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Beautiful old home in Lee Massachusetts. Two bedrooms one bath on a quiet street in Lee Massachusetts. A front porch to ...
Click For Pricing
VRBO
From $181 per night (USD)
Expedia
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring ...
From $181 per night (USD)
Expedia
From $347 per night (USD)
VRBO
Main Street Delight 1bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located on Main Street in downtown Lenox. A beautifully space fully equipped for all your needs. The eat-in kitchen has ...
From $347 per night (USD)
VRBO
$Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On\/Off at Mountain Base$
From $196 per night (USD)
Expedia
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On\/Off at Mountain Base
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You want to pop out of bed, walk downstairs, and be right on the mountain - this is the place for you. This 1B ...
From $196 per night (USD)
Expedia
Click For Pricing
VRBO
Great mountain getaway
Bedrooms:
4
Bathrooms:
6
Sleeps:
8
Berkshire getaway, close to all activites. Easily accessible first floor. Master on main floor. Fully furnished two base ...
Click For Pricing
VRBO
From $1097 per night (USD)
Expedia
Perfect setting for Family Vacations Short and Long Term Stays Welcomed.
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Private Estate Centrally located to all Berkshire attractions and just mins. from the Mass Pike. Perfect for any event. ...
From $1097 per night (USD)
Expedia
$Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!$
From $139 per night (USD)
VRBO
Wyndham Bentley Brook-Ski In\/Out, Pool, Next to Jiminy Peak - Only 25% Deposit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
WHAT YOU’LL LOVE: Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley B ...
From $139 per night (USD)
VRBO
$In-Town Victorian 5 Bd Front House &\/or 6 Bd Back House w\/Beach Rights, Skiing$
From $912 per night (USD)
Expedia
In-Town Victorian 5 Bd Front House &\/or 6 Bd Back House w\/Beach Rights, Skiing
Bedrooms:
8
Bathrooms:
12
Sleeps:
24
The Front 5 Bedroom Norman Rockwell Feel Home offers a Living Room, Den, Fully Stocked Kitchen, lovely screened porch & ...
From $912 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Lakeside Retreat-Mt. Views, Museums, Paddling, Hiking- Best of the Berkshires!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Windsor Cottage is a relaxing, lakeside retreat located on Windsor Lake in North Adams, MA where you will enjoy your own ...
From $409 per night (USD)
VRBO
From $219 per night (USD)
Expedia
Cozy renovated cabin in Williamstown, steps from hiking trails
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Originally built in the early 1900s, this cabin has been owned and lovingly maintained by the same family for over 50 ye ...
From $219 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Beachwood Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unique small cottage in the sought-after Beachwood community situated 2 miles from Tanglewood on Stockbridge Bowl. Featu ...
From $306 per night (USD)
VRBO
From $1125 per night (USD)
Expedia
Historic Stockbridge Villa on 25 acres sleeps 23
Bedrooms:
7
Bathrooms:
11
Sleeps:
23
At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and ...
From $1125 per night (USD)
Expedia
$East Otis Vacation Rental w\/ Private Deck & BBQ!$
From $259 per night (USD)
VRBO
East Otis Vacation Rental w\/ Private Deck & BBQ!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Prepare for your Western Massachusetts lake escape by booking this welcoming 1-bathroom studio cottage in East Otis! Loc ...
From $259 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Berkshires Getaway! Family-friendly retreat near hiking, museums, and more!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
<b>Your Cozy Berkshires Getaway Awaits!</b> Escape to the serene beauty of the Berkshires! Nestled in a peaceful, fami ...
From $356 per night (USD)
Expedia
From $520 per night (USD)
VRBO
CABIN FEVER IN STOCKBRIDGE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hello hip, glamping cabin! Our 2 bedroom 1.5 bath cottage has been fully remodeled. The decor is chic & bohemian cool! E ...
From $520 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Konkapot Cottage, Pastoral Bliss With Wide Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly and totally renovated house, with modern appliances and bathrooms in the heart of the Berkshires. The house featur ...
From $338 per night (USD)
Expedia
From $941 per night (USD)
VRBO
Fabulous Renovated Log Cabin: the perfect family getaway
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Stunning log cabin in the Berkshires on 10 wooded acres complete with brand new 4 season hot tub, in-ground pool, pickle ...
From $941 per night (USD)
VRBO
From $503 per night (USD)
Expedia
Country Living just minutes from Everything!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
2 minutes to Bartlett's Apple Orchard, Richmond 5 minutes to Bousquet Ski Area, Pittsfield 6 minutes to Balderdash Cella ...
From $503 per night (USD)
Expedia
Click For Pricing
VRBO
Loft Style Cabin In West Stockbridge, Book Now!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
Summary: Custom built loft style home in beautiful West Stockbridge. You’ll love how the outdoors streams into the house ...
Click For Pricing
VRBO
$The Great Escape Ski Cottage w\/HOT TUB @ Great Barrington$
From $1043 per night (USD)
Expedia
The Great Escape Ski Cottage w\/HOT TUB @ Great Barrington
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Well appointed Vacation Cottage, newly renovated by the Owners; An Architect and an Interior Designer as a Modern Farmho ...
From $1043 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Pleasant on Pleasant
Bedrooms:
2
Bathrooms:
2
Sleeps:
1
Modern conveniences and fresh decor make this Victorian the perfect spot for your North Adams stay. Our "Pleasant House" ...
From $245 per night (USD)
VRBO
$Berkshires Summer Rental - Lee\/Lenox$
From $266 per night (USD)
Expedia
Berkshires Summer Rental - Lee\/Lenox
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Sunny three bedroom condo available for summer rental , with two full baths. Shaded front porch and sunny rear deck wi ...
From $266 per night (USD)
Expedia
From $706 per night (USD)
VRBO
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Enjoy total privacy at this cozy mountain home on 40 acres, just minutes from ski resorts and charming shops. With floo ...
From $706 per night (USD)
VRBO
Click For Pricing
Expedia
Luxury Berkshire Estate: Proximity to all the best the Berkshires has to offer!
Bedrooms:
7
Bathrooms:
6
Sleeps:
14
"Words can't describe the incredible experience our family had during the holiday season at this magnificent property." ...
Click For Pricing
Expedia
From $510 per night (USD)
VRBO
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Welcome to the beautiful Lakeside Condominiums at Fox Hollow in Lenox/Lee, MA. This newly furnished condo is spacious a ...
From $510 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Mountainside: Large 3-level Jiminy Peak Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
From our easily accessible, newly renovated, fully equipped spacious home you can walk to the ski trails, hike and explo ...
From $460 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: You want to pop out of bed, walk downstairs, and be right on the mountain This 1BR 1 BA Ground Floor Unit righ ...
From $247 per night (USD)
VRBO
From $281 per night (USD)
Expedia
Hearts Desire is a furnished whole house in a small, colorful garden center.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Newly renovated, one level house with 2 rooms with king sized beds, 1 queen size sleeper sofa. Fully furnished kitchen ...
From $281 per night (USD)
Expedia
Click For Pricing
VRBO
Great house in Stockbridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Three bedroom house, one en suite on first floor(can be twin or king), two (both queen) on second floor sharing a bathro ...
Click For Pricing
VRBO
From $428 per night (USD)
Expedia
Berkshires Retreat: Firepit, Grill, Screened Deck!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to where comfort meets convenience in the heart of the Berkshires! Just 1.5 miles from Tanglewood, 5 minutes to ...
From $428 per night (USD)
Expedia
From $745 per night (USD)
VRBO
11 acre mid-century estate, newly renovated, seasonally available pool.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Rare 11 acre private estate close to the center of town. Designed by renowned NYC architect David Todd in the late 60s, ...
From $745 per night (USD)
VRBO
From $680 per night (USD)
Expedia
Ski on ski off 1 Br loft condo in the village center with private gated parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Completely remodeled 1 Br loft condo with pull out sleeper sofa located steps from everything Jiminy has to offer.Unit f ...
From $680 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
This 3 bedroom, 1 bathroom home of 1000 square feet with an additional 200 square foot screened in porch with a table fo ...
From $391 per night (USD)
VRBO
From $605 per night (USD)
Expedia
Stylish Mid-century Modern Berkshires Cape
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Stylish, fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires! Enjoy the large, sunny yard an ...
From $605 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our property is a renovated 1770s stage coach stop, with original wood floors. The upstairs of our home (with separate e ...
From $302 per night (USD)
VRBO
From $278 per night (USD)
Expedia
5 Minutes from Catamount Ski Area
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Cozy house conveniently located in a quiet area near the village of South Egremont. Fresh air, natures beauty all togeth ...
From $278 per night (USD)
Expedia

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