We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Berkshires Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $274 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travelers to Berkshires are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 369 Rentals in Berkshires
    Sort by:
    Default
    Wyndham Bentley Brook1 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    2200sf Country House on 16 Acres-2 Miles to Jiminy1 / 14
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are...
    View all property information
    Location Information
    Tyringham, Berkshires 01264
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    4 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Washer
    • Patio
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lots of space, great yard, walk to everything: restaurants, museums, Williams College, theater, night life, etc. Plus, nearby ski and tubing areas. This beautifully maintained historic House On Main Street was known as the Victorian Tourist & Antique House in a by-gone era. It was originally...
    View all property information
    Location Information
    Williamstown, Berkshires 01267
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 16
    Make Inquiry
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Yard
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our cottage is situated in a private lake community. Short walk to lake and private beach. Minutes from Tanglewood, Kripalu, Stockbridge town center and Lenox town center. Convenient to many cultural institutions, hiking, skiing. Our cottage has plenty of outdoor space for relaxing and dining....
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Sauna
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Booking stays under 3 days may be possible. Please inquire for more information Bentley Brook is a colorful resort located in Hancock, Massachusetts. This spacious hotel also has the majestic Bershire Mountains, which is apart of the Appalachians, at it’s front door. This resort offers scenic...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Lake House in the Berkshires1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect...
    View all property information
    Location Information
    North Egremont, Berkshires 01230
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the...
    View all property information
    Location Information
    Monterey, Berkshires 01245
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Shared Yard
    • Parking
    • Mountain Views
    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the second floor of the barn. this is ver rustic, literally a barn! Open cathedral ceiling. Wooden interior with open floor plan. Big queen sized bed with canopy . 2 twin beds. Great for traveling with family or friends. Kitchen area has microwave, mini fridge, induction cooktop, hot...
    View all property information
    Location Information
    Lee, Berkshires 01238
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    Perfect Getaway for Body, Mind and Soul1 / 24
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Satellite TV
    • Washer
    • Hot Tub
    • Internet Access
    • Porch
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat...
    View all property information
    Location Information
    Lee, Berkshires 01238
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Private Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You can join us for horseback...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A bright, lovely and comfortable room with queen bed in a charming country farmhouse with adjoining private bath. Located in Tyringham, a bucolic, rural village on a scenic country road the beautiful and magical 'Hop Brook' valley. The house is surrounded by farmland surrounding it on all sides. A...
    View all property information
    Location Information
    Tyringham, Berkshires 01264
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Cozy and clean in Gt Barrington- 1 week in summer!1 / 10
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Lake House1 / 19
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Air Conditioning
    • Grill
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home has 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located...
    View all property information
    Location Information
    Lee, Berkshires 01238
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 9
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.<BR><BR>The Space:<BR><BR>Quaint cottage with wood burning stove. Ideal base for...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Berkshires Vacation Rental - Bentley Brook Resort Suite1 / 16
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Hot Tub
    • Internet Access
    • Shared Indoor Pool
    • DVD Player
    • Sauna
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1762 farmhouse features wide board floors, kitchen, dining and living room areas along with a spacious front porch. Agritour gardens, horseback riding, and close proximity to Tanglewood and the Norman Rockwell Museum make for an adventure filled visit. Larry prepares a great fresh egg...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Inquiry
    Heart of Lenox1 / 10
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just rated Best Small Town in the Northeast by USA Today, our home is located in the heart of Lenox MA! Come relax in our lovely home, situated in a quiet neighborhood just steps from downtown. Walk to Zagat rated restaurants, shop unique boutique shops, hike in Kennedy Park. Whether you love the...
    View all property information
    Location Information
    Lenox, Berkshires 01240
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed across from the community...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Terrace
    • Central Heating
    • DVD Player
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whitman Woods offers privacy with proximity to excellent skiing at Jiminy Peak (less than 5 minutes away) and to many cultural attractions of the Berkshires including Williamstown Theater Festival and Tanglewood. For outdoor lovers, Whitman Woods is near Mount Greylock Reservation, Audubon's...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed...
    View all property information
    Location Information
    Richmond, Berkshires 01254
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great little house in a very convenient location. Set nicely back from the street with a spacious back and side yard. 8 minutes drive to tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Almost an acre of land with large trees and garden....
    View all property information
    Location Information
    Lenox, Berkshires 01240
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Shared Indoor Pool
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please email or call to confirm availability. Ski-In/Ski-Out Resort! Wyndham Bentley Brook is located right at the base of Jiminy Peak ski mountain, with ski lifts only 200 feet from the resort's front door. In winter, you can ski right out the door to the lifts. In spring, summer and fall,...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • Patio
    • Internet Access
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities in Stockbridge. This quaint vacation rental home features 2 bedrooms and 2 bathrooms, accommodating 6 guests. From this property, you'll be central to all the...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Washer
    • Balcony
    • Shared Indoor Pool
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our home on Jiminy Peak! This beautiful, luxury unit was just renovated for the 2016 ski season. It is fully equipped with everything a family will need for the perfect Mountainside vacation. Two Bedrooms accommodates 6+ guests with all the comforts of home. 10 foot ceilings and crown...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Inquiry
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 6,700 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses)....
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Inquiry
    Golden Triangle in the Berkshires1 / 4
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    7 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Terrace
    • Washer
    • Balcony
    • Patio
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful 7 bedroom home with over 4000 sq. ft. of nicely furnished large rooms. Nestled in the heart of the Berkshire Mountains, between 2 lakes and located in a quiet family friendly neighborhood. Just minutes from the New York border. Our home is a fantastic deal for the wonderfully...
    View all property information
    Location Information
    Pittsfield, Berkshires 01201
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 18
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Washer
    • Satellite TV
    • Private Yard
    • DVD Player
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water...
    View all property information
    Location Information
    Becket, Berkshires 01223
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 2
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Grill
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury Condo in Beaver Pond, Hancock, Mass. Three bedrooms, loft, 2 baths, living room, kitchen with dining area, deck w/grill. Near Clark Art Museum, MassMoca. Williams College with schedule of sports open to the public: swimming, tennis, squash, basketball, skating and fitness room. Indoor...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY...
    View all property information
    Location Information
    Otis, Berkshires 01255
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!...
    View all property information
    Location Information
    Lee, Berkshires 01238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Grill
    • Air Conditioning
    • Mountain Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedrooms and five and a half baths. The six hundred square foot great room has a soaring ceiling, fireplace, interior balcony, and multiple French doors and windows to overlook the...
    View all property information
    Location Information
    Lenox, Berkshires 01240
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Make Inquiry
    Apple Cottage1 / 10
    (4)Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Balcony
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and...
    View all property information
    Location Information
    Sheffield, Berkshires 01257
    Rental Home - 3 Bedrooms, 6 Bathrooms, Sleeps 8
    Make Inquiry
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Terrace
    • Balcony
    • Private Yard
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding.<BR>Near Center pond where there are many boating...
    View all property information
    Location Information
    Becket, Berkshires 01223
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • Air Conditioning
    • Parking
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located along the Appalachian trail and 3 miles to Great Barrington, this designer home is central to all the Berkshires has to offer, not to mention being 35 minutes to Hudson you are really in the center of of it all. This completely separate designer home is located on the 2nd and 3rd floors...
    View all property information
    Location Information
    Sheffield, Berkshires 01257
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated vacation home with state of the art kitchen and marble baths, centrally located in the Berkshires 3 miles from Tanglewood, on 10 acres on a quiet country road. New in-ground pool surrounded by patio and expansive deck and pool house nestled in the woods. Central air...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    The perfect Southern Berkshire winter vacation esc1 / 14
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Wi-Fi
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the...
    View all property information
    Location Information
    Sheffield, Berkshires 01257
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Balcony
    • Patio
    • Mountain Views
    • Central Heating
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This turn of the century cottage is located on a 130 acre property, and is stocked with linens. Three and a half baths, three full bedrooms, kitchen, living room, dining room, screened porches, a deck, and washer dryer. The house is across the brook and up a stone staircase (30 steps) from the...
    View all property information
    Location Information
    Tyringham, Berkshires 01264
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Inquiry
    3 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share a beautifully renovated home in the Berkshire Mountains of Western MA. I would prefer a long-term housemate, but will be glad to do weekend or short term stays. Long-term pricing can be negotiable. Cable TV (in your room), internet, washer and dryer, big eat-in kitchen, well-lit living room....
    View all property information
    Location Information
    Lee, Berkshires 01238
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 2
    Make Inquiry
    Enjoy Summer in The Berkshires1 / 20
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. Visit our web-site aberkshirehome. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is...
    View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays and Sundays only. Commanding a stunning view of the Jiminy Peak ski area, your luxury resort home at Vacation Village will also serve as your gateway to all that the Berkshires has to offer. The...
    View all property information
    Location Information
    Hancock, Berkshires 01267
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Mountain Views
    • Washer
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Restored 1940's log cabin, amazing undisturbed 30 mile, 180 degree views. Hilltop location, walking distance to the village of South Egremont, ideal for hiking, Appalachian trail nearby, minutes to all major Berkshire attractions, very private & quiet, abundant wildlife, deer, fox, hawks, turkey....
    View all property information
    Location Information
    Great Barrington, Berkshires
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Waterfront
    • Mountain Views
    • Parking
    • DVD Player
    • Central Heating
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this serene lakefront Great Barrington area cottage in New Marlborough, within the Berkshires, serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and room to comfortably sleep 4 guests, this property is an excellent choice for people who are looking for either a...
    View all property information
    Location Information
    New Marlborough, Berkshires 01230
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,...
    View all property information
    Location Information
    Lee, Berkshires 01238
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Inquiry
    3 Bedrooms, 1 Bathroom, Sleeps 15 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located at the end of a dead end street. It has a huge, private backyard with 2 firepits, hammock, portable bar, grill and ample seating. Under one mile to downtown North Adams and about a 5 minute drive to Williamstown. This is a 3 bedroom, upstairs apartment (one bedroom has a...
    View all property information
    Location Information
    North Adams, Berkshires 01247
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 15
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have this in both 1 and 2Br, so please confirm which you want. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which week you choose. This is for 1 full week only. Check in is Friday, Saturday, or Sunday, depending upon which week you choose. This is for a...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Berkshires Spacious Comfortable Charming Farmhouse1 / 11
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Parking
    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock...
    View all property information
    Location Information
    Lee, Berkshires 01238
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Gartner House, a charming home in Lenox1 / 21
    (25)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Washer
    • Parking
    • Internet Access
    • Central Heating
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore...
    View all property information
    Location Information
    Lenox, Berkshires 01240
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Make Inquiry
    Berkshires Flight and Weather Info
    Airports nearby (1)
    Plan your day of travel
    ALB
    Albany Intl Airport
    41.6 miles from Berkshires
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    70° 48°
    June
    74° 51°
    July
    73° 51°
    August

    Additional Berkshires Info

    View Map
    • Local time: 01:22 PM (EDT)
    List your property
    Owner log in