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 Cottages

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
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
    Location
    Any Distance
    from
    Price
    per night
    C$257 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Travellers to Berkshires are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    11 Matching Rentals in BerkshiresView all 143 rentals
    Sort by:
    Default
    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Stone School Cottage1 / 10
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Stockbridge Bowl Lake Beach Cottage near Tanglewood (1.8 miles away)1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Mountain Views
    • Balcony
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 26, 2018
    Great location, 2 minute walk to the beach with a view of the mountains and a very short drive to Tanglewood, Norman Rockwell Museum and all local attractions.Cindy and Paul are...
    See all reviews
    About this property
    The Stockbridge Bowl Lake Beach cottage is centrally located in Berkshire County in Stockbridge, MA. Walk across the street to Stockbridge Bowl Town Beach. We provide the beach chairs and towels. Lovely furnishings, fully equipped kitchen with new small appliances and amenities. Open cottage feel...
    View all property information
    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    PanoramicView1000 sq ft Guest Quarters Berkshires1 / 16
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Washer
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to aview of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
    See all reviews
    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer...
    View all property information
    Location Information
    Hancock, Berkshires 01237
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    Make Enquiry
    INTERIOR DESIGNERS BOTANICAL GARDENS1 / 30
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Patio
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 4, 2017
    We have been traveling to the Berkshires for several years to attend Shakespeare & Company plays. We have stayed at Inns and Hotels. This was our first time, in this area...
    See all reviews
    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING...
    View all property information
    Location Information
    Lenox, Berkshires 01240
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    Make Enquiry
    Romantic Berkshire Cottage on Storybook Estate1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Cable/satellite TV
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    What a wonderful, magical place, heaven on earth! From the moment we were greeted warmly by Denise and entered our Tiny House, we knew this was such a special place.The sound of...
    See all reviews
    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest...
    View all property information
    Location Information
    Tyringham, Berkshires 01264
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Lake House in Berkshires1 / 21
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Parking
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2017
    Robert was so thoughtful and courteous to make sure we had the best birthday weekend ever! He literally thought of everything such as bug spray, flash lights, birthday candles...
    See all reviews
    About this property
    Charming studio cottage on Windsor Lake, North Adams, MA. Great spot from which to explore MASS MoCa, attend Solid Sound or Fresh Grass, Clark Art Museum, Massachusetts College of Liberal Arts, Williamstown Theater Festival, Williams College, the Berkshires, and Southern Vermont. Hike, bike, swim...
    View all property information
    Location Information
    North Adams, Berkshires 01247
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Berkshire Getaway1 / 7
    (8)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Parking
    • Outdoor Dining Area
    • Grill
    • Porch
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2015
    Descriptions are accurate. The house and grounds are very well kept. Extremely clean especially bathroom and kitchen. It is located at the end of a hard pack dirt road with no...
    Reviewed August 24, 2015
    The minute we entered the cottage we felt at home. A perfect secluded, warm and cosy getaway. Our only sorrow was that we could only stay for one night. We prepared dinner in...
    See all reviews
    About this property
    Cozy cottage with complete privacy on 142 acres and borders Monroe State Forest. Cottage offers 2 bedrooms, 1 bathroom, large living room, eat in kitchen, deck with grill, TV and DVD. Hiking and biking is available right outside your door. The Dunbar Brook Trail boasts great hiking and a grove of...
    View all property information
    Location Information
    North Adams, Berkshires 01247
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Garden
    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. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying...
    View all property information
    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Save time - get the best Berkshires rentals sent straight to your email!
    Get the List
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Grill
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All New, renovated 400 sq. ft. cottage is located centrally in South Lee, / Stockbridge line. Only 1 mile from Stockbridge main street, nightly entertainment at the Red Lion's Den, close to everything, boutique shops, grocery stores, restaurants, and all Berkshire cultural attractions. Live...
    View all property information
    Location Information
    Lee, Berkshires 01260
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property
    Owner log in