VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

Your Gorgeous Late Summer Getaway at Off-Season Rates

You sent a message to this owner.

The cottage and its comfy deck


Last updated: 10/07/2014
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:2 nights
  • Internet:Yes
  • Pets considered:No
  • Wheel chair accessible:No

Cheshire cottage description

Late summer and early autumn are perfect times to escape to the Berkshires! From the moment you arrive, you'll fall in love with this perfect artist's retreat! Set behind a small fruit orchard and bounded behind by a lovely stream and woodland, the charming and cozy cottage offers plenty of privacy and an instant sense that you have arrived in a charmed space.

The cottage's bright interior has a main room, with windows looking out in every direction -- onto the orchard, stream and nearby woods -- a small kitchen with a coffee maker, small fridge, and a microwave for your convenience; and a bath sized just right for a maximum of two people. We've recently installed a wonderful outdoor shower (in addition to the one indoors) that faces the stream and the woods beyond. You'll also find seating out back where you can read or write or simply let your eyes close as the stream flows past.

A wide deck on two sides of the cottage allows for the pleasures of bird-watching, meal-taking, enjoying a drink at sunset and star-gazing after dark.

As for nearby activities, Cheshire Lake and the rail trail on its east side is just a short walk (5 minutes) and a shorter drive. Here you can bring your canoe or kayak and enjoy breathtaking views of Mount Greylock, the state's highest peak. Other hiking trails -- including those on Greylock -- can be found within a short drive where you can walk for hours without interruption.

In addition, the world of music, art, theatre and dance in the Berkshires is within a 30 minutes' drive. And when it comes to dining out, Berkshire County is unsurpassed. Let us know your preferences and we'll point you in the right direction! And if you have a hankering for a great massage, we can refer you to a wonderful masseuse just down the road.

Time and again our guests tell us it is the serenity and romance of the cottage and its surrounding landscape that makes their time here so magical. We invite you to experience the same enchantment.

Property Type

  • Cottage
  • 200 sq. ft.

Accommodation Type

      • Vacation Rental


          • Guests Provide Their Own Meals


          • Minimum Age Limit For Renters:


          • Limited Accessibility
          • Non Smoking Only
          • Not Suitable For Children
          • Pets Not Allowed:

            While we love dogs and cats, we are unable to allow them to stay at the cottage to avoid any allergy conditions for future guests....moreless

          Bedrooms: 1 Bedroom, Sleeps 2, Beds for 2

          • Bedroom 1: 1 queen


          • Queen bed, units for hanging clothes and storing luggage; new, quiet heater; sitting chairs; eating table; wifi....moreless

          Bathrooms: 1 Bathroom

          • Bathroom 1: toilet, shower, outdoor shower


          • Small bathroom with shower stall, toilet and sink.


              • Books:

                A small selection available; more, if guests inquire....moreless


              • Away From It All
              • Romantic
              • Tourist Attractions


              • Botanical Garden
              • Churches
              • Cinemas
              • Health/Beauty Spa
              • Library
              • Live Theater
              • Museums
              • Playground
              • Recreation Center
              • Restaurants
              • Synagogues
              • Winery Tours

              Local Services & Businesses

              • ATM/Bank
              • Fitness Center
              • Groceries
              • Hospital
              • Laundromat
              • Massage Therapist
              • Medical Services

              Leisure Activities

              • Antiquing
              • Bird Watching
              • Boating
              • Horseback Riding
              • Miniature Golf
              • Outlet Shopping
              • Paddle Boating
              • Photography
              • Scenic Drives
              • Shopping
              • Sight Seeing
              • Sledding
              • Walking
              • Wildlife Viewing

              Location Type

              • Lakefront:

                This gorgeous lake is in the nearby town of Lanesborough, has a small beach with beautiful views of mountains to the west. You may also rent canoes, kayaks, sailboats and houseboats....moreless

              • Mountain View:

                The cottage is virtually surrounded by mountains....moreless

              • Rural

              Sports & Adventure Activities

              • Cross Country Skiing
              • Cycling
              • Fishing
              • Freshwater Fishing
              • Golf
              • Golf Privileges Optional
              • Hiking
              • Hunting
              • Jet Skiing
              • Kayaking
              • Mountain Biking
              • Mountain Climbing
              • Mountaineering
              • Racquetball
              • Roller Blading
              • Sailing
              • Skiing
              • Snowboarding
              • Snowmobiling
              • Swimming
              • Tennis
              • Water Skiing
              • Whitewater Rafting
              • Wind-Surfing


              • Dining:

                Small eating area at the front of the main room...moreless

              • Dining Area
              • Seating for 2 people


              • Heating:

                Quiet propane heater, when necessary...moreless

              • Internet
              • Linens Provided
              • Parking:

                Parking is out front, at the main house. Sam is available to help carry bags from the parking area to the cottage. ...moreless

              • Towels Provided


              • Coffee Maker
              • Dishes & Utensils:

                We provide cups and saucers, cereal/soup bowls, wine and water glasses and silverware. Also a cutting board and a wine opener. ...moreless

              • Microwave
              • Refrigerator


              • Deck / Patio
              • Golf:

                Skyline Golf Course in Lanesboro is a few minutes drive, and the famous Waubeeka Springs course is about 20 minutes away. ...moreless

              • Lawn / Garden:

                Lawn area, small flower garden...moreless

              • Outdoor Grill:

                We'd be happy to provide a Weber grill for guest's use. ...moreless



              Write a review 5
              from 2 traveler reviews
              Rental basis: Per property
              Dates Nightly Weekend Night Weekly Monthly * Event
              My Standard Rate
              2 night min stay

              Additional information about rental rates


              • Taxes Not included


              Fifty percent deposit to hold the reservation, and final payment due on arrival.

              Please wait... Travel with confidence

              Pay with an approved method (credit card, check, or bank transfer) to protect your payment up to $1,000. Before making a payment always call the owner at the number listed on our website, and never use instant money transfer services such as Western Union and MoneyGram.

              Don't forget your vacation protection! Get protected now

              Adding our Vacation Protection services can make sure your getaway goes smoothly, no matter what. We offer Cancellation Protection, Carefree Rental Guarantee, and Damage Protection so you can truly relax.

              Protect your payments in case you need to cancel.
              Guarantee the rental meets your expectations.
              Ensure you're prepared in case of accidental damage.


              Last updated: 10/07/2014
              Check availability
              23 Available
              21 Unavailable
              22 Today
              23 Selected dates


              40 Miles
              Nearest Airport
              Albany, NY
              1 Miles
              Nearest Barpub
              Basswater Grill
              3 Miles
              Nearest Golf
              40 Miles
              Nearest Train
              Hudson, NY
              0.25 Miles
              Nearest Motorway
              Route 8
              1 Miles
              Nearest Restaurant
              Basswater Grill
              8 Miles
              Nearest Ski
              Jiminy Peak
              5 Miles
              Nearest Beach
              Pontoosuc Lake

              Car: Necessary

              Our lovely cottage is located in an area of great natural beauty that offers a huge array of cultural activities -- notably dance, music and theatre festivals from June through September. These include Tanglewood, Jacobs Pillow, Berkshire Theatre Festival, Williamstown Theatre Festival, the Barrington Stage, and many other music venues. Museums include the world famous Mass MoCA and Clark Art Institutes, plus the Norman Rockwell and Berkshire Museums. There are numerous cinemas in the area, and a huge variety of dining opportunities -- in every price range. The cottage is within a short driving distance of a mall and several shopping centers, and yet is tucked away in its own little private nook. We are within walking distance of a wonderful lake (Cheshire Reservoir) that features boating, canoeing, kayaking and sailing. Yet another lake that offers the same water sports, plus swimming and jet-skiing is ten minutes away.


              Owner info

              Year Purchased: 1986

              About the owner: I am a writer, lanscaper and gardener. My wife, Maggie, and I grew up in New York, and when our children were still young moved to the Berkshires to do some farming. Maggie is a psychotherapist with a practice in Lenox. We currently live in the main house on the property which is about 250 feet from the cottage. Our goal is to provide our guests with the utmost privacy while offering any assistance we can to make their stay as pleasant as possible. We can offer you suggestions for where to hike, eat, go to the movies, see a play, attend a music recital, and visit any number of museums within a half-hour drive of the cottage.

              Why the Owner Chose Cheshire:
              Cottage 22 is a perfect getaway for spring, summer and fall. It is a splendid retreat for an artist or writer who needs a level of solitude to complete his or her work. The bedroom is charming and comfortable -- with a brand new queen bed, bedding, and an eating table that looks onto the orchard. We had this lovely structure moved to our property from a nearby guest farm in the late 1980s ... its unknown connection to family and friends -- both from the area and outside -- are nothing short of amazing!

              The Unique Benefits at this Cottage:
              Our guests discover that the Cheshire country location, which is half-way between the attractions of both north and south Berkshire County, is away from the hullaballoo of summer traffic and crowds, but near enough to get anywhere within thirty minutes.

              Contact us

              Speaks: english, french, german, spanish, Yiddish



              • The cottage and its comfy deck

                The cottage and its comfy deck

              VRBO #463468

              There have been  visitors to this page since the counter was last reset in .

              This listing was first published here in 2013.

              Date last modified - Monday, October 13, 2014

              $135 per night (USD)

              1 Bedroom / 1 Bathroom
              Sleeps 2

              View calendar: Updated 10/07/14
              Minimum stay: 2 nights
              Dates are unavailable
              Please stay a bit longer. A stay of nights or more is required for these dates.
              This listing requires that rentals start on a .
              Get an instant quote
              Member since: 2013
              Speaks: english, french, german, spanish, Yiddish
              • Calendar last updated 10/07/2014
              Email owner

              ++1 413.329.8591

              Please wait... Travel with confidence Guaranteed, secure, with no booking fees Learn how to pay safely
              Add vacation protection services to your booking

              Three services to protect your trip:

              Protect your payments in case you need to cancel.

              Guarantee the rental meets your expectations.

              Ensure you're prepared in case of accidental damage.

              Get it now


              Share this property via Email

              Your Gorgeous Late Summer Getaway at Off-Season Rates

              Cheshire #463468

              1 BR  1 BA  Sleeps 2

              You must be signed in to share this property by e-mail

              Share this property via Email

                Please correct the following errors and resend:
              • Enter one or more valid email addresses separated by commas.
              • Oops! You have exceeded the limit of 10 email addresses.
              • Your message may not contain markup. Please remove the markup and try again.