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Berkshire Vacation Rentals Page 4

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!

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Pittsfield Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Richmond Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Richmond Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Richmond Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Richmond Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Richmond Vacation Rentals, Central Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Savoy Vacation Rentals, Northern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sandisfield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sheffield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sheffield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sheffield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sheffield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sheffield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sheffield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sheffield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sheffield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Sheffield Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Stockbridge Vacation Rentals, Southern Berkshires Vacation Rentals

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

Berkshire Vacation Rentals, Vacation Home Rentals In The Berkshires, Stockbridge Vacation Rentals, Southern Berkshires Vacation Rentals

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