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!
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
3BR Home w/Lake & Mountain Views, Near Skiing, And Cultural Attractions! New Deck To Enjoy w/BBQ Grill, Great Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Apt. Newly Remodeled Super Location, Large Covered Porch, Close To Lakes And 5 Minutes From Bousquet Ski Area.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
House w/View In The Berkshires, Deck, Tanglewood, The Mount, Naumkeag, Mass Moca, Clark, Hancock Village, Etc.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Charming Apartment In Berkshire Victorian Home, 3rd Floor Penthouse, Rooftop Deck, Short & Long-Term Rental, Great Location.
Sleeps: 8
Bedrooms: 3
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Pittsfield Home w/Deck – 12 Mi To Jiminy Peak! Great For Outdoor Enthusiasts, Balcony, Deck, Patio, Gazebo. Park Square.
Sleeps: 10
Bedrooms: 3
Bathrooms: 2.5
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Centrally Located In The Berkshires – Cozy Bungalow In SE Pittsfield! 5 Minutes From Bousquet Ski Resort, 20 To Jiminy.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Country Living Just Min. From Everything! Home Office, Lg. Deck, ENORMOUS Yard, Mountain Views, Beautiful Sunrises.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
The Ponds At Foxhollow, Indoor And Outdoor Pool, Tennis Court, Sauna, Fitness Center, Perfect Location, Beautiful Grounds.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Beautiful 8BR, Walk To Lake, Jetted Hot Tub, Fireplace, & Pool Table, Swimming, Boating, Fishing, Picnicking And More.
Sleeps: 28
Bedrooms: 8
Bathrooms: 3
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Stylish, Centrally Located Berkshires Home-Base, 15 Minutes To Lenox & Tanglewood, Theater Room, Corn Hole Game.
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Elegant Pittsfield Home Near Downtown & Skiing! Foosball Table, Screened Porch, Catch Live Music At Tanglewood.
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lake Front Home In Heart Of The Berkshires, Near Jiminy Peak, Amazing Location, Close To Skiing, Hiking, Restaurants.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Beautiful Waterfront Home w/Deep Water Dock On Onota Lake, Sun Room, Covered Deck, Water Sports, Kayaking, Fishing.
Sleeps: 10
Bedrooms: 3
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Renovated Pittsfield Colonial By Evergreen Home, Museums, Tanglewood, Theaters, Hiking, Skiing, Golf, Shopping & Dining.
Sleeps: 12
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Tranquil Lake House Getaway On Onota Lake, 3 Miles To The City, 2 Canoes, 5 Kayaks And A Stand-Up Paddleboard.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Solomon Ely Homestead – Charming Pittsfield Stay, Steps From Pittsfield, Wraparound Porch, Filled w/Historic Charm.
Sleeps: 7
Bedrooms: 4
Bathrooms: 1.5
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Hidden Oasis In This Mnt. Home, Hidden Oasis, Hot Tub, Fire Pit, Overlooking October Mountain, Great Location.
Sleeps: 10
Bedrooms: 5
Bathrooms: 3
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Fully Equipped Spacious Family Home In The Berkshires, 3.5 Miles To Downtown Lenox, Tanglewood, Kripalu, Ideal Location.
Sleeps: 7
Bedrooms: 3
Bathrooms: 3
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Cape Home In The Beautiful Berkshires – Near Lenox & Bousquet, Wild Acres, Tanglewood, Lenox, Museums, Shopping.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Spacious Luxury Berkshire’s Estate On 21 Acres, Pool Table, Air Hockey Table, Foosball Table, Rowing Machine, Sauna Room.
Sleeps: 14
Bedrooms: 6
Bathrooms: 4.5
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Slopeside View: Airy, Luxury Condo w/Pool. Minutes From It All! Miraval, Canyon Ranch, Shakespeare & Co, Tanglewood.
Sleeps: 10
Bedrooms: 5
Bathrooms: 4.5
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lakeside Home w/Heated Outdoor Pool-Completely Renovated, On Beautiful Lake Pontoosuc, Perfect For Family Gatherings.
Sleeps: 16
Bedrooms: 6
Bathrooms: 4.5
No Pets
Richmond, MA
Central Berkshire Area
Berkshire Vacation Rentals
Pet Friendly Oasis On 5 Private Acres, 10 Min To Tanglewood, Gorgeous Surroundings, Utter Tranquility, Jacuzzi Tub.
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
Pets Welcome
Richmond, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshires Sanctuary w/Outdoor Living Area & Firepit. 8 Min To Tanglewood! Peaceful Country House, Amazing Location.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2.5
Pets Welcome
Richmond, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lovely Ranch Home Getaway In The Berkshires- 6 Miles To Tanglewood, Lg Private Deck, Apple Orchards.
Sleeps: 3
Bedrooms: 2
Bathrooms: 2
No Pets
Richmond, MA
Central Berkshire Area
Berkshire Vacation Rentals
Cheever Hollow Farm An Essential Retreat, Close To Lenox & The Berkshires, Expansive Gardened Wooded Areas.
Sleeps: 7
Bedrooms: 4
Bathrooms: 3
No Pets
Richmond, MA
Central Berkshire Area
Berkshire Vacation Rentals
4 Mi To Skiing: Cottage w/Fire Pit In Richmond! Furnished Deck, Beach Chairs And Towels, Safe And Private Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cabin w/3 Acres, Tennis Courts: By 4 Ski Mtns., Unplug, Unwind, And Spend Time In The Outdoors, Wraparound Deck.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Relaxing Retreat In The Berkshires! Perfect For Outdoor Enthusiast! Unique & Tranquil Cabin, Hiking & Mountain Bike Trails.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Waterfront Oasis In Heart Of The Berkshires, Steps From A Private Pond, Furnished Patio, 2 Firepits, Canoes And Kayaks.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Relax, Read, Entertain, Or Walk To West Lake From Our Berkshire Home. Screened-In Porch, 20 Minute To Great Barrington.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Cabin In The Berkshires, Tranquility & Natural Beauty, Butternut Is 25 Mins Away, Pool Table And Dart Board.
Sleeps: 8
Bedrooms: 2
Bathrooms: 2
Pets Welcome
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Berkshires, Lakefront Home, 3BR, Beach, Pool, Tennis & More…Screened In Deck, Canoe & Kayak, Just Come & Enjoy.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Family Friendly Farmhouse In The Berkshires, Pool, 5 Min Drive To Butternut Ski Lodge, 40 Min To Tanglewood.
Sleeps: 10
Bedrooms: 5
Bathrooms: 2
No Pets
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Beautiful Berkshire Classic Home Nestled In A Quiet Peaceful Area, Located Near York Lake National Park & Many Other Lakes.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Iconic Cabin In The Berkshires, Massive Stone Fireplace, Yoga And Indoor Endless Swimming Pool Located In The Spa Room.
Sleeps: 12
Bedrooms: 6
Bathrooms: 2.5
Pets Welcome
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Luxury On The River @ Fish Camp – Close To Tanglewood, Jacobs Pillow, Kripalu, Norman Rockwell Museum, Farmington River.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Savoy, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Retreat In The Woods, Hiking Trail And Wetlands, It’s In The Woods, It’s Quiet, It’s Warm, Great Escape Into Nature!
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Blue Elm – A Historic Berkshire Cottage, 15 Minute Drive To Catamount Ski Area, Large Vaulted Screened Room.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1.5
No Pets
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
“Elterwater”-Swan lake. Your Own Lakefront Oasis, A True Berkshire Getaway, Jacob’s Pillow & Tanglewood, Screened In Porch.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
Pets Welcome
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cheerful 3BR Cottage w/Woodstove, Easy Access To All The Area Has To Offer, Enjoy Peace & Quiet Of The Surrounding Woods.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Berkshire Getaway Walk To Winery, Brewery Or Distillery w/Peloton! Total Privacy, Scenic Views, Min To Hiking & Skiing.
Sleeps: 5
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Skiing & Hiking: Water-View Home In The Berkshires, Solo Stove Yukon Fire Pit, Small Covered Deck, 4 Miles To Appalachian Trail.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts, Private Luxurious Guest House, 10 Miles To Ski Resorts.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4 Mi To Gr Barrington: Berkshires Retreat! Catch A Show At Tanglewood, Activities On The Hudson River, Fire Pit w/Seating.
Sleeps: 8
Bedrooms: 2
Bathrooms: 3
No Pets
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Peaceful & Private Setting, Pool, Perfectly Centered Between Butternut & Catamount For Winter Activities! Great Location.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Race Mountain House, High On The Slopes Of Race Mountain, Pool, Hiking Trails, Great Location, Baby Grand Piano.
Sleeps: 12
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Family Friendly In Sheffield, Private Yet Close To Everything! Your Perfect Country Escape, 4 Season Sun Room, Wonderful Spot.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3.5
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Location!!! Location!!! Berkshire Glamour (And Comfort) Meets Town And Country, Clean, Well Stocked And Very Comfortable.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Artist’s Camp On Lake Mahkeenac, Perfect For A Couples Getaway, Nestled into the forest, Great Location, Comfortable.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Stockbridge Cabin – Walk To Beach & Lake! Lake Activities, Tanglewood, Norman Rockwell Museum, Hiking Trails.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets