Cheshire, Massachusetts
Renovated Historic Berkshire Gem w/Hot Tub • Pool
About the property
<p><br></p> <p>Fully-renovated architectural gem in the heart of the Berkshires! Perfect for family gatherings, weddings, or wellness escapes. Our Cheshire home is nestled on an idyllic 4-acre property and features a gigantic 50’x25’ pool, large hot tub, fire pit and more. Located in the heart of the Berkshires, local attractions such as Tanglewood, skiing at Jiminy Peak, and MASS MoCA are only a short-drive away.</p> <p>Home layout by floor:</p> <p>The house includes 6 bedrooms, 3 full bathrooms, and multiple common areas. Here’s the layout:</p> <p>First Floor:</p> <p>Bedroom #1: Master bedroom with King Bed and en-suite full bathroom with shower.</p> <p>Front staircase off of front entryway leading up to Bedrooms #2, #3, and #4.</p> <p>Living room with large windows to soak in the nature of the private yard.</p> <p>The Dining Area has a large dining table perfect for groups.</p> <p>Kitchen is fully equipped with everything you need to make a large family meal, including two ovens!</p> <p>Large deck off the dining room/kitchen with lots of seating, BBQ, and in-ceiling speakers.</p> <p>Laundry room.</p> <p>The back staircase off of the laundry room up to second floor leading to Bedrooms #5 & #6.</p> <p>Full bathroom with shower off the laundry room/back staircase.</p> <p>Off the living room, there is a small staircase down to the door leading out to the hot tub and the pool.</p> <p>Second Floor:</p> <p>Bedroom #2: Full Bed.</p> <p>Bedroom #3: King Bed.</p> <p>Bedroom #4: Full Bed and Twin Bunk Bed.</p> <p>Bendroom #5: Queen Bed. (Bedrooms #4 and #5 have a connecting door).</p> <p>Bedroom #6: Queen bed.</p> <p>Full bathroom across from Bedrooms #2, #3, and #4. Has a tub with showerhead.</p> <p>Bedrooms #5 and #6 are across from 2 staircases: one leading downstairs to the full bathroom that is off the laundry room/kitchen, the other leading up to the 3rd floor family room.</p> <p>The hall leading to Bedrooms #2, #3, and #4 has a door that opens to the staircase leading up to the other “3rd floor” space, which is the dedicated office space.</p> <p>Third floor:</p> <p>There are two separate third floor spaces:</p> <p>One in the front of the house, accessed through the staircase coming off the hallway to Bedrooms #2, #3, and #4. This one goes up to the “Eagle’s Nest,” which is set up as an office space with a wooden desk and PC monitor.</p> <p>The other space is in the back of the house, accessed through the staircase coming off the landing off of Bedrooms #5 and #6. This one is a den / kids play room with TV, toys, a bean bag, a large couch and lots of fun!</p> <p>TEMPORARY NOTICE ABOUT THE TWO FIREPLACES: As of January 2026 our fireplaces are being renovated by a specialized vendor. Until it is complete, the fireplaces in the living room and dining room will not be available for guests to use. We apologize for the inconvenience. We will post updates as we have them!</p> <p>Parking: Up to 2 vehicles can be parked along the left side of the house, and up to 4-5 vehicles can fit along the U-shaped drive depending on how they're laid out. So, parking is available for up to 6-7 vehicles in total!</p> <p>Driveway: Even though our driveway is flat and the home is easily accessible, it is always helpful to have 4WD to drive in the area in the winter.</p> <p>Pets: Pups are welcome with a $100 for one dog, $150 for two pups, and $200 for three. If you plan on bringing more than three pups, please reach out to us as additional approval may be required. We ask that dogs are kept on a leash while outside the property and about the neighborhood, for everyone's comfort. Please remember to clean up after your pets and mind that additional fees for pup-related damages may apply! Dogs are not allowed in the pool. Finally, unfortunately we cannot host cats or other furry animals due to potential allergy issues.</p> <p>Heat and air conditioning: There's steam radiators for heat and AC window units at the house. Please mind that cooling is seasonal. For the two fireplaces, we typically leave a few logs to get you started!</p> <p>Outdoor pool: The pool typically opens after Memorial Day and closes around the beginning of October. Please mind that pool availability may change, depending on weather conditions!</p> <p>The hot tub outside fits 6 guests comfortably!</p> <p>Coffee maker: There's a 12-cup drip pot coffee maker at the house.</p> <p>Strict no smoking, no parties, no fireworks. Please mind the noise ordinance in Town is 10 PM. Other house rules will be on arrival guide.</p> <p>Please mind that you must be 25 years old to book, and at least one person 25 years old must remain during the stay.</p> <p>Cancellation Policy: We cannot make any exceptions to our cancellation policy. Please consider traveler's insurance.</p>
<p><br></p> <p>Fully-renovated architectural gem in the heart of the Berkshires! Perfect for family gatherings, weddings, or wellness escapes. Our Cheshire home is nestled on an idyllic 4-acre property and features a gigantic 50’x25’ pool, large hot tub, fire pit and more. Located in the heart of the Berkshires, local attractions such as Tanglewood, skiing at Jiminy Peak, and MASS MoCA are only a short-drive away.</p> <p>Home layout by floor:</p> <p>The house includes 6 bedrooms, 3 full bathrooms, and multiple common areas. Here’s the layout:</p> <p>First Floor:</p> <p>Bedroom #1: Master bedroom with King Bed and en-suite full bathroom with shower.</p> <p>Front staircase off of front entryway leading up to Bedrooms #2, #3, and #4.</p> <p>Living room with large windows to soak in the nature of the private yard.</p> <p>The Dining Area has a large dining table perfect for groups.</p> <p>Kitchen is fully equipped with everything you need to make a large family meal, including two ovens!</p> <p>Large deck off the dining room/kitchen with lots of seating, BBQ, and in-ceiling speakers.</p> <p>Laundry room.</p> <p>The back staircase off of the laundry room up to second floor leading to Bedrooms #5 & #6.</p> <p>Full bathroom with shower off the laundry room/back staircase.</p> <p>Off the living room, there is a small staircase down to the door leading out to the hot tub and the pool.</p> <p>Second Floor:</p> <p>Bedroom #2: Full Bed.</p> <p>Bedroom #3: King Bed.</p> <p>Bedroom #4: Full Bed and Twin Bunk Bed.</p> <p>Bendroom #5: Queen Bed. (Bedrooms #4 and #5 have a connecting door).</p> <p>Bedroom #6: Queen bed.</p> <p>Full bathroom across from Bedrooms #2, #3, and #4. Has a tub with showerhead.</p> <p>Bedrooms #5 and #6 are across from 2 staircases: one leading downstairs to the full bathroom that is off the laundry room/kitchen, the other leading up to the 3rd floor family room.</p> <p>The hall leading to Bedrooms #2, #3, and #4 has a door that opens to the staircase leading up to the other “3rd floor” space, which is the dedicated office space.</p> <p>Third floor:</p> <p>There are two separate third floor spaces:</p> <p>One in the front of the house, accessed through the staircase coming off the hallway to Bedrooms #2, #3, and #4. This one goes up to the “Eagle’s Nest,” which is set up as an office space with a wooden desk and PC monitor.</p> <p>The other space is in the back of the house, accessed through the staircase coming off the landing off of Bedrooms #5 and #6. This one is a den / kids play room with TV, toys, a bean bag, a large couch and lots of fun!</p> <p>TEMPORARY NOTICE ABOUT THE TWO FIREPLACES: As of January 2026 our fireplaces are being renovated by a specialized vendor. Until it is complete, the fireplaces in the living room and dining room will not be available for guests to use. We apologize for the inconvenience. We will post updates as we have them!</p> <p>Parking: Up to 2 vehicles can be parked along the left side of the house, and up to 4-5 vehicles can fit along the U-shaped drive depending on how they're laid out. So, parking is available for up to 6-7 vehicles in total!</p> <p>Driveway: Even though our driveway is flat and the home is easily accessible, it is always helpful to have 4WD to drive in the area in the winter.</p> <p>Pets: Pups are welcome with a $100 for one dog, $150 for two pups, and $200 for three. If you plan on bringing more than three pups, please reach out to us as additional approval may be required. We ask that dogs are kept on a leash while outside the property and about the neighborhood, for everyone's comfort. Please remember to clean up after your pets and mind that additional fees for pup-related damages may apply! Dogs are not allowed in the pool. Finally, unfortunately we cannot host cats or other furry animals due to potential allergy issues.</p> <p>Heat and air conditioning: There's steam radiators for heat and AC window units at the house. Please mind that cooling is seasonal. For the two fireplaces, we typically leave a few logs to get you started!</p> <p>Outdoor pool: The pool typically opens after Memorial Day and closes around the beginning of October. Please mind that pool availability may change, depending on weather conditions!</p> <p>The hot tub outside fits 6 guests comfortably!</p> <p>Coffee maker: There's a 12-cup drip pot coffee maker at the house.</p> <p>Strict no smoking, no parties, no fireworks. Please mind the noise ordinance in Town is 10 PM. Other house rules will be on arrival guide.</p> <p>Please mind that you must be 25 years old to book, and at least one person 25 years old must remain during the stay.</p> <p>Cancellation Policy: We cannot make any exceptions to our cancellation policy. Please consider traveler's insurance.</p>
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Mar 31, 2026 | $592 | Available | 2 |
| Apr 1, 2026 | $592 | Available | 2 |
| Apr 2, 2026 | $592 | Available | 2 |
| Apr 3, 2026 | $592 | Not Available | 2 |
| Apr 4, 2026 | $592 | Not Available | 2 |
| Apr 5, 2026 | $592 | Not Available | 2 |
| Apr 6, 2026 | $592 | Available | 2 |
| Apr 7, 2026 | $592 | Available | 2 |
| Apr 8, 2026 | $592 | Available | 2 |
| Apr 9, 2026 | $592 | Available | 2 |
| Apr 10, 2026 | $592 | Available | 2 |
| Apr 11, 2026 | $592 | Available | 2 |
| Apr 12, 2026 | $592 | Available | 2 |
| Apr 13, 2026 | $592 | Available | 2 |
| Apr 14, 2026 | $592 | Available | 2 |
| Apr 15, 2026 | $592 | Available | 2 |
| Apr 16, 2026 | $592 | Available | 2 |
| Apr 17, 2026 | $592 | Available | 2 |
| Apr 18, 2026 | $592 | Available | 2 |
| Apr 19, 2026 | $592 | Available | 2 |
| Apr 20, 2026 | $592 | Available | 2 |
| Apr 21, 2026 | $592 | Available | 2 |
| Apr 22, 2026 | $592 | Available | 2 |
| Apr 23, 2026 | $592 | Available | 2 |
| Apr 24, 2026 | $592 | Available | 2 |
| Apr 25, 2026 | $592 | Available | 2 |
| Apr 26, 2026 | $592 | Available | 2 |
| Apr 27, 2026 | $592 | Available | 2 |
| Apr 28, 2026 | $592 | Available | 2 |
| Apr 29, 2026 | $592 | Available | 2 |
| Apr 30, 2026 | $592 | Available | 2 |
| May 1, 2026 | $621 | Available | 2 |
| May 2, 2026 | $617 | Available | 2 |
| May 3, 2026 | $592 | Available | 2 |
| May 4, 2026 | $592 | Available | 2 |
| May 5, 2026 | $592 | Available | 2 |
| May 6, 2026 | $592 | Available | 2 |
| May 7, 2026 | $592 | Available | 2 |
| May 8, 2026 | $640 | Available | 2 |
| May 9, 2026 | $612 | Available | 2 |
| May 10, 2026 | $592 | Available | 2 |
| May 11, 2026 | $592 | Available | 2 |
| May 12, 2026 | $592 | Available | 2 |
| May 13, 2026 | $592 | Available | 2 |
| May 14, 2026 | $626 | Available | 2 |
| May 15, 2026 | $723 | Available | 2 |
| May 16, 2026 | $763 | Available | 2 |
| May 17, 2026 | $626 | Available | 2 |
| May 18, 2026 | $592 | Available | 2 |
| May 19, 2026 | $592 | Available | 2 |
| May 20, 2026 | $592 | Available | 2 |
| May 21, 2026 | $610 | Available | 2 |
| May 22, 2026 | $851 | Available | 2 |
| May 23, 2026 | $852 | Available | 2 |
| May 24, 2026 | $851 | Available | 2 |
| May 25, 2026 | $625 | Available | 2 |
| May 26, 2026 | $633 | Available | 2 |
| May 27, 2026 | $592 | Available | 2 |
| May 28, 2026 | $675 | Available | 2 |
| May 29, 2026 | $692 | Available | 2 |
| May 30, 2026 | $716 | Available | 2 |
| May 31, 2026 | $710 | Available | 2 |
| Jun 1, 2026 | $592 | Available | 2 |
| Jun 2, 2026 | $597 | Available | 2 |
| Jun 3, 2026 | $607 | Available | 2 |
| Jun 4, 2026 | $752 | Available | 2 |
| Jun 5, 2026 | $895 | Available | 2 |
| Jun 6, 2026 | $922 | Available | 2 |
| Jun 7, 2026 | $799 | Available | 2 |
| Jun 8, 2026 | $636 | Available | 2 |
| Jun 9, 2026 | $620 | Available | 2 |
| Jun 10, 2026 | $832 | Available | 2 |
| Jun 11, 2026 | $1,324 | Available | 2 |
| Jun 12, 2026 | $1,339 | Available | 2 |
| Jun 13, 2026 | $1,339 | Available | 2 |
| Jun 14, 2026 | $845 | Available | 2 |
| Jun 15, 2026 | $825 | Available | 2 |
| Jun 16, 2026 | $817 | Available | 2 |
| Jun 17, 2026 | $692 | Available | 2 |
| Jun 18, 2026 | $842 | Available | 2 |
| Jun 19, 2026 | $970 | Available | 2 |
| Jun 20, 2026 | $961 | Not Available | 2 |
| Jun 21, 2026 | $818 | Not Available | 2 |
| Jun 22, 2026 | $710 | Not Available | 2 |
| Jun 23, 2026 | $698 | Not Available | 2 |
| Jun 24, 2026 | $650 | Available | 2 |
| Jun 25, 2026 | $1,095 | Available | 2 |
| Jun 26, 2026 | $1,339 | Not Available | 2 |
| Jun 27, 2026 | $1,339 | Not Available | 2 |
| Jun 28, 2026 | $1,339 | Not Available | 2 |
| Jun 29, 2026 | $824 | Available | 3 |
Where you'll sleep
Amenities
Where you'll be
Cheshire, Massachusetts, 01225, United States
Immerse yourself in the rugged natural beauty of the Berkshires, where outdoor exploration meets quiet New England charm. A short drive takes you to the expansive Mount Greylock State Reservation and its visitor center, where you can hike scenic trails or ascend to the Veterans War Memorial Tower for panoramic views. Within easy reach, cycle the Ashuwillticook Rail Trail, discover the cascading beauty
Immerse yourself in the rugged natural beauty of the Berkshires, where outdoor exploration meets quiet New England charm. A short drive takes you to the expansive Mount Greylock State Reservation and its visitor center, where you can hike scenic trails or ascend to the Veterans War Memorial Tower for panoramic views. Within easy reach, cycle the Ashuwillticook Rail Trail, discover the cascading beauty
Things to know
Cancellation policy
Refundable Bookings
Cancellation deadlines:
- For stays under 15 nights, you may cancel or reschedule up to 14 days before check-in for a full refund. For stays 15 nights or longer, the cancellation window is 60 days.
- For some homes, a 30-day deadline applies — this will be clearly shown before you book.
- Cancellations must be submitted before 4 PM EST on the deadline day to qualify.
Fair-Refund Policy
If you cancel after the deadline:
- Berkshire Stream will relist your dates and automatically refund you for any nights that rebook.
- The refund per night will be the lower of the original price or the rebooking rate. Nights that do not rebook are non-refundable.
Half-Now, Half-Later Bookings
- The first half of your payment is non-refundable.
- The second half may be refunded according to the standard cancellation policy above.
Non-Refundable Bookings
If you selected a Non-Refundable rate at checkout, the booking cannot be changed or canceled, and no refund will be issued.
Date Changes & Rebooking
Once a stay is canceled, you can't rebook the same dates yourself. If you need help choosing new dates, our Concierge team is happy to assist.
Transfers to Another Guest
You may transfer your booking to someone else at no charge. Just contact the Concierge with the new guest's name and email. The new guest must accept the transfer for it to take effect.
Policy Match Guarantee
If a better price is available for the same property on Airbnb or the owner's site, contact the Concierge — Berkshire Stream will match it.
By completing your booking, you acknowledge and agree to Berkshire Stream's cancellation policy.