Pittsfield, MA

Pine & Paddle | Pond Access • Kayaks

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4 guests
2 bedrooms
1 bathrooms
1000 sqft

Come enjoy all The Berkshires have to offer at our chic country cottage!

  • Fire pit
  • Fire place
  • BBQ Area
4 guests
2 bedrooms
1 bathrooms
1000 sqft

  • Flexible check-in & out

    Check-in after 3:00 PM • Check-out before 11:00 AM

  • Easy cancellation


About this property

Come enjoy all The Berkshires have to offer at our chic country cottage! Imagine relaxing by the cozy wood stove after a day spent exploring. With two bedrooms and a fresh bathroom, it’s perfect for a peaceful getaway. A short walk brings you to a private community beach on Richmond Pond, or enjoy music at nearby Tanglewood and winter skiing and tubing at Bousquet. Whether you’re here for relaxation or adventure, our inviting home is perfectly located to make your stay memorable. ✔ High-speed Wi-Fi ✔ TV ✔ Fully equipped kitchen ✔ Washer & dryer ✔ Free parking ✔ Wood-burning fireplace ✔ Kayak & Lake access ✔ BBQ Grill ✔ Pet-friendly ✔ Pack n Play Travel Crib (Upon request) ➥ 3 mins to Lenox Mountain ➥ 5 mins to Bousquet Mountain Ski Area ➥ 7 mins to Hancock Shaker Village ➥ 9 mins to The Colonial Theatre: Berkshire Theatre Group ➥ 9 mins to Berkshire Museum ➥ 9 mins to Olivia's Overlook at Yokun Ridge Reserve ➥ 12 mins to Tanglewood ➥ 14 mins to Stockbridge Bowl ➥ 16 mins to The Mount, Edith Wharton's Home ➥ 17 mins to Shakespeare & Company ✦BEDS & BATHS✦ Inside we have 2 bedrooms and 1 bathroom, all decorated tastefully to give the full nostalgic Berkshire travel experience. Room Breakdown: Main Bedroom - 1 Queen bed Bedroom 2 - 1 Queen bed All Berkshire Vacation Rental Co.™ Properties include: - Support from full-time local team available daily from 9am to 9pm - Professional housekeeping & property inspection prior to guest arrival - Towels, linens, and bath products - At least a mornings worth of coffee to get you started - Learn more @berkshirevacationrental Cleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property. • DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 1 dog. No other types of animals are authorized. To provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn't rectified. There is space for parking two cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.

Come enjoy all The Berkshires have to offer at our chic country cottage! Imagine relaxing by the cozy wood stove after a day spent exploring. With two bedrooms and a fresh bathroom, it’s perfect for a peaceful getaway. A short walk brings you to a private community beach on Richmond Pond, or enjoy music at nearby Tanglewood and winter skiing and tubing at Bousquet. Whether you’re here for relaxation or adventure, our inviting home is perfectly located to make your stay memorable. ✔ High-speed Wi-Fi ✔ TV ✔ Fully equipped kitchen ✔ Washer & dryer ✔ Free parking ✔ Wood-burning fireplace ✔ Kayak & Lake access ✔ BBQ Grill ✔ Pet-friendly ✔ Pack n Play Travel Crib (Upon request) ➥ 3 mins to Lenox Mountain ➥ 5 mins to Bousquet Mountain Ski Area ➥ 7 mins to Hancock Shaker Village ➥ 9 mins to The Colonial Theatre: Berkshire Theatre Group ➥ 9 mins to Berkshire Museum ➥ 9 mins to Olivia's Overlook at Yokun Ridge Reserve ➥ 12 mins to Tanglewood ➥ 14 mins to Stockbridge Bowl ➥ 16 mins to The Mount, Edith Wharton's Home ➥ 17 mins to Shakespeare & Company ✦BEDS & BATHS✦ Inside we have 2 bedrooms and 1 bathroom, all decorated tastefully to give the full nostalgic Berkshire travel experience. Room Breakdown: Main Bedroom - 1 Queen bed Bedroom 2 - 1 Queen bed All Berkshire Vacation Rental Co.™ Properties include: - Support from full-time local team available daily from 9am to 9pm - Professional housekeeping & property inspection prior to guest arrival - Towels, linens, and bath products - At least a mornings worth of coffee to get you started - Learn more @berkshirevacationrental Cleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property. • DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 1 dog. No other types of animals are authorized. To provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn't rectified. There is space for parking two cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Feb 19, 2026$199Available2
Feb 20, 2026$199Available2
Feb 21, 2026$199Available2
Feb 22, 2026$199Available2
Feb 23, 2026$199Available2
Feb 24, 2026$199Available2
Feb 25, 2026$199Available2
Feb 26, 2026$199Available2
Feb 27, 2026$199Available2
Feb 28, 2026$199Available2
Mar 1, 2026$199Available2
Mar 2, 2026$199Available2
Mar 3, 2026$199Available2
Mar 4, 2026$199Available2
Mar 5, 2026$199Available2
Mar 6, 2026$199Available2
Mar 7, 2026$199Available2
Mar 8, 2026$199Available2
Mar 9, 2026$199Available2
Mar 10, 2026$199Available2
Mar 11, 2026$199Available2
Mar 12, 2026$199Available2
Mar 13, 2026$199Available2
Mar 14, 2026$199Available2
Mar 15, 2026$199Available2
Mar 16, 2026$199Available2
Mar 17, 2026$199Available2
Mar 18, 2026$199Available2
Mar 19, 2026$199Available2
Mar 20, 2026$199Available3
Mar 21, 2026$199Available3
Mar 22, 2026$199Available3
Mar 23, 2026$199Available3
Mar 24, 2026$199Available3
Mar 25, 2026$199Available3
Mar 26, 2026$199Available3
Mar 27, 2026$201Available3
Mar 28, 2026$203Available3
Mar 29, 2026$199Available3
Mar 30, 2026$199Available3
Mar 31, 2026$199Available3
Apr 1, 2026$199Available3
Apr 2, 2026$199Available3
Apr 3, 2026$222Available3
Apr 4, 2026$219Available3
Apr 5, 2026$220Available3
Apr 6, 2026$202Available3
Apr 7, 2026$199Available3
Apr 8, 2026$200Available3
Apr 9, 2026$210Available3
Apr 10, 2026$238Available3
Apr 11, 2026$229Available3
Apr 12, 2026$210Available3
Apr 13, 2026$199Available3
Apr 14, 2026$199Available3
Apr 15, 2026$204Available3
Apr 16, 2026$206Available3
Apr 17, 2026$219Available3
Apr 18, 2026$218Available3
Apr 19, 2026$214Available4
Apr 20, 2026$212Available4
Apr 21, 2026$207Available4
Apr 22, 2026$206Available4
Apr 23, 2026$212Available4
Apr 24, 2026$240Available4
Apr 25, 2026$238Available4
Apr 26, 2026$211Available4
Apr 27, 2026$199Available4
Apr 28, 2026$199Available4
Apr 29, 2026$200Available4
Apr 30, 2026$199Available4
May 1, 2026$232Available4
May 2, 2026$226Available4
May 3, 2026$199Available4
May 4, 2026$199Available4
May 5, 2026$199Available4
May 6, 2026$199Available4
May 7, 2026$201Available4
May 8, 2026$236Available4
May 9, 2026$244Available4
May 10, 2026$202Available4
May 11, 2026$199Available4
May 12, 2026$202Available4
May 13, 2026$210Available4
May 14, 2026$227Available4
May 15, 2026$242Available4
May 16, 2026$259Available4
May 17, 2026$243Available4
May 18, 2026$219Available4
May 19, 2026$224Available5
May 20, 2026$260Available5

Top notch amenities

GUEST FAVORITES

Fire pit
Fire place
BBQ Area
Patio
Balcony
Lake view
Wood Stove
Air hockey
Arcade machine

Where you'll sleep



Explore Pittsfield, MA

Explore the cultural heart of the Berkshires from this scenic setting in Pittsfield, where year-round outdoor adventure meets historic charm. Discover world-class skiing a short drive away at Bousquet Mountain Ski Area or step back in time at the nearby Hancock Shaker Village for a fascinating glimpse into regional history. Uncover natural beauty at Mass Audubon's Pleasant Valley Wildlife Sanctuary and take in the vistas

Things to know

Here are some things which you should know before booking Pine & Paddle | Pond Access • Kayaks

House rules

Check-in after 3:00 PM
Check-out before 11:00 AM
4 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval

Cancellation policy

This property follows Berkshire Vacation Rental’s standard cancellation policy.