Vacation rentals in the Berkshires make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals throughout the Berkshires. From vacation homes for rent to vacation apartment and condo rentals, each vacation rental offers a truly unique lodging experience. Below, you will find vacation home rentals in the Northern Berkshires, Central Berkshires and Southern Berkshires. Many vacation rentals are located within a short distance to one of our wonderful Berkshire attractions such as Tanglewood, MASS MoCA, The Colonial Theatre, Norman Rockwell Museum, Barrington Stage Company, Williamstown Theatre Festival, Clark Art, Ski Areas, Colleges and more!
Hancock, MA
Central Berkshire Area
Berkshire Vacation Rentals
Mountainside Condo Ski In Ski Out, Site Restaurants, Unit At The Base Of Jiminy Peak, Only One Adjacent Neighbor.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Hancock, MA
Central Berkshire Area
Berkshire Vacation Rentals
Must See Cabin Suite, Jiminy, Sleeps 4 – Mountainview-Ski On/Off Country Inn, Redone, Year Round Outdoor Heated Pool.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Hancock, MA
Central Berkshire Area
Berkshire Vacation Rentals
1st Floor Mountain View Suite, Ski On/Off At Jiminy, Jiminy Peak Is The Ultimate All Season Rental Vacation Resort.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pet
Hancock, MA
Central Berkshire Area
Berkshire Vacation Rentals
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 – Ski On/Off at Mountain Base, Lots Of Restaurants, Theaters, Shopping.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Hancock, MA
Central Berkshire Area
Berkshire Vacation Rentals
Jiminy Peak Mountain Resort, Slopeside Fun w/2 Restaurants & 2 Bars/Lounges, Outdoor Pool, Tennis Courts, Ski-In/Ski-Out Access.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Hancock, MA
Central Berkshire Area
Berkshire Vacation Rentals
Cozy 1BR Condo At Ski Resort w/WiFi, Fitness Room, Pool & Hottub, Complimentary Coffee Bar, Fantastic Eatery w/In Walking Distance.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Hancock, MA
Central Berkshire Area
Berkshire Vacation Rentals
Deluxe Mountain Fox Suite Jiminy Peak – Ski On Off – Fully Redone Decor, Privately Cleaned, Enjoy All The Amenities.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Hancock, MA
Central Berkshire Area
Berkshire Vacation Rentals
Disney Magic Suite At Jiminy – Ski On Off Sleeps 4- A Must See Mountain Retreat, Outdoor Heated Pool, Hot Tubs, Fitness Center.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Hancock, MA
Central Berkshire Area
Berkshire Vacation Rentals
Bentley Brook 1BR Mountainside Ski Resort In Charming Hancock, Sleeps 8, At The Base Of Jiminy Peak Ski Mountain.
Sleeps: 8
Bedrooms: 1
Bathrooms: 2
No Pets
Hinsdale, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshire Ashmere Lake Lodging, Quiet Room, Fantastic Sunsets, Private Front Entrance. Kayak, Swim, Feed The Ducks.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Hinsdale, MA
Central Berkshire Area
Berkshire Vacation Rentals
Beautiful 2BR + Loft w/6 Person Hot Tub At Lake Ashmere, 3 Min Walk To Lake Ashmere, Great Views, 25 Min From Jiminy Peak.
Sleeps: 8
Bedrooms: 3
Bathrooms: 1
No Pets
Hinsdale, MA
Central Berkshire Area
Berkshire Vacation Rentals
Quiet Lake House w/Beautiful Water Views, Porch, Boat Dock, 5 Minute Walk To Beach, Row Boat And Paddle Boat.
Sleeps: 8
Bedrooms: 2
Bathrooms: 2
Pets Welcome
Hinsdale, MA
Central Berkshire Area
Berkshire Vacation Rentals
Ashmere Lake Log Cabin w/Privacy/2BR, Private, Shared Beach, Try Your Skills At Ramblewild In Lanesboro.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Hinsdale, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshire Lake Access, Beautiful Offshore Lake House, Sun Room, Well Appointed Kitchen, Walking Distance To Beach.
Sleeps: 6
Bedrooms: 4
Bathrooms: 2
No Pets
Hinsdale, MA
Central Berkshire Area
Berkshire Vacation Rentals
Picturesque Cottage w/Sunroom On Ashmere Lake! Furnished Outdoor Deck, Water Views, Ashmere Lake Access.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Hinsdale, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lakefront Hinsdale Home ~ 10 Mi To Pittsfield! Canoe, 2 Kayaks, Fire pit, Ping-Pong Table, Incredible Sunset Views.
Sleeps: 8
Bedrooms: 3
Bathrooms: 4.5
No Pets
Hinsdale, MA
Central Berkshire Area
Berkshire Vacation Rentals
Beautiful Renovated Home, Close To Multiple Ski Mountains, Plenty Of Outdoor Space & Trails To Enjoy, Quiet Getaway.
Sleeps: 10
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Hinsdale, MA
Central Berkshire Area
Berkshire Vacation Rentals
Ashmere Lakefront Second Floor Apartment, Enjoy Kayaking Or Paddle Boarding, Beautiful Views, Biking & Hiking Trails.
Sleeps: 3
Bedrooms: 1
Bathrooms: 1
No Pets
Housatonic, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Great Barrington/Housatonic Getaway, Minutes To Tanglewood, Rockwell, Chesterwood, Lenox & Stockbridge.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Housatonic, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Newly Renovated Home w/All The Modern Amenities, Easy Drive To Great Barrington, Stockbridge, Lenox, Tanglewood.
Sleeps: 7
Bedrooms: 3
Bathrooms: 1.5
No Pets
Housatonic, MA
Southern Berkshire Area
Berkshire Vacation Rentals
10 Min To Ski Butternut & Catamount Ski Areas! 1870’s Farmhouse, Outdoor Pizza Oven w/Grill, Close To A Park, Trails, Hikes.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Housatonic, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Soulful, Light-Filled Berkshire Home w/Gardens, 5 Min From Lenox, Shakespeare and Co., Barrington Stage & Tanglewood.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshire Village Carriage House – Super Private!! Walk The Ashuwillticock Rail Trail, It’s The Back Half Of The Main House.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Cozy Rustic Studio Apt In 18th c Berkshire Farmhouse, 6 Min To Jiminy Peak Ski Resort, Walking Trails Full Of Wildlife.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Hearts Desire Is A Furnished Whole House In A Small, Colorful Garden Center, Furnished Kitchen, Hot Tub, Fire Pit, Horseshoes.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Charming Historic Cottage On Scenic Road To Mt. Greylock, Situated Amidst Horse Farms, 5 Miles From Jiminy Peak Ski Area.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Entire Cottage In Berkshire Vlg., Perfect Location For Your Berkshire Getaway, Views Of The Pond, Nautical Books & Artifacts.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1.5
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Bright Boho Apt In 18th c Berk Farmhouse, Located On A Flower Farm Converted Into 4 Cute Apartments, 6 Min To Jiminy
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Wildlife Lakeside Cottage, Screened In Porch, Running, Biking, Fishing, Boating Are An Easy Walk Away, Great Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
Pets Welcome
Lanesborough, MA
Central Berkshire Area
Berkshire Vacation Rentals
Cozy Cottage In Berkshires: Min. To Jiminy Peak, Close To Hiking, Biking, Skiing, Fishing, Lake Activities, Cultural Venues & More.
Sleeps: 6
Bedrooms: 4
Bathrooms: 1.5
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Upstairs On Main w/Private Bath, Entire Top Floor, Awesome Spot On The North End Of Main Street, Walk To Downtown.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Deluxe Queen Room w/2 Queen Beds, Perfect For A Tranquil Night’s Sleep, Relax & Unwind, Short Walk To Downtown Lee.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Studio Mini Home Away From Home In The Berkshires, Front Room Of An Historic House Right On Main Street Lee.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Garfield Townhouse In The Berkshires On Main St, Back Yard w/Private Porch, Grill, Walk To Rest., Shops, Yoga, Churches.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Villa w/Access To Amazing Amenities! 2 Indoor Pools, 2 On-Site Bars, 18-Hole Mini Golf Course, Fitness Center, Hiking Trails.
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
South Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
1500 Sq Ft Private Entrance w/Beautiful Views Of The Berkshire Mountains, Enjoy A Quiet Getaway, Private Deck, Fire Pit.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
South Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4BR Home w/Yard & BBQ, 5 Min Walk To Downtown Lee, Tantalizing Mix Of Comfort & Adventure, Hammock, Firepit, BBQ Grill.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Centrally Located Historical Home, Private, Country Escape, Min To Tanglewood, Shakespeare and Co, & More.
Sleeps: 4
Bedrooms: 2
Bathrooms: 3
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Relax Between Your Berkshire Adventures! Easy Walk To Town! Basement Theatre & Game Room, Laurel Lake Up The Road.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy 2BR Apartment w/WiFi, Pools, Gym, Movie Theater & Mini Golf, Beautiful Place To Stay, Great Location!!
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stunning Lake Views & Privacy, Mins. To Lenox, Stockbridge, Lee. Ideal For Family Gatherings Or Romantic Getaways.
Sleeps: 14
Bedrooms: 3
Bathrooms: 3.5
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Berkshires Home Makeover ~ Lakefront Getaway ~ Dreamy Sunsets! On Laurel Lake, Rooftop Deck, Hot Tub & Kayaks.
Sleeps: 8
Bedrooms: 4
Bathrooms: 6
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Laurel Lake Luxury 4BR, 4.5BA, Ranch On Fox Hollow Estate, Private Dock w/2 Canoes, 2 Kayaks & Rowboat, Hot Tub & Fire Pit.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4.5
Pets Welcome
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spacious Comfortable Charming Family Farmhouse, Great Location, Tanglewood: 10 Min, Priv. Entrance, Glassed In Front Porch.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Enjoy Spring In The Berkshires At This Lovely Home, Truly One Of A Kind Craftsmen Inspired Home, Cozy, Clean & Comfortable.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spacious 4BR Central-Berkshires Home w/POOL! Performing Arts, Museums, Skiing, Hiking, Dining, Shopping, Pool.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2.5
No Pets
Lee, MA
Sothern Berkshire Area
Berkshire Vacation Rentals
The Playhouse: 7k Sq Ft of Berkshires Modern Luxury & History, In-House Yoga Studio, 2 Kitchens, Amazing Location.
Sleeps: 20
Bedrooms: 6
Bathrooms: 5
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stylish Mid-Century Modern Berkshire Cape, Chef’s Kitchen, 3 Season Sunroom, Veggie Garden, Close To Laurel Lake.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Freckled Hen’s Berkshire Nest, Sweet, Cozy, Private, Clean, Bird Watcher’s Delight, Small And Yet Spacious, Great Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
* Private Berkshire Escape* Located Between Lenox & Stockbridge, Walking Trails, Above Ground Pool, Great House!
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
No Pets
Lee, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Berkshire Mountain Retreat w/Urban Eco-Luxuries, Relaxation In The Mountains, Firepit, Screened In Back Porch, Patio.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets