At the waterfront, this 4-bedroom vacation home accommodates 10 guests and features 2 bathrooms. Enjoy lake views from the private boat dock while engaging in hiking, biking, or motorboating activities. The patio offers outdoor space for relaxation, and the property welcomes pets. Nearby attractions include Art et Industrie and Housatonic River.
Highlights
Centrally-located
You're never far from where you need to be with this convenient location.
Sleeps 10•4 bedrooms•6 beds
Popular amenities
Onsite parking available
Pet-friendly
Kitchen
Washing machine
Barbecue
Dock
Explore the area
Great Barrington, MA
Housatonic River
Place, Housatonic River
7 min drive
Art et Industrie
Place, Art et Industrie
7 min drive
Monument Mountain Reservation
Place, Monument Mountain Reservation
9 min drive
Pittsfield, MA (PSF-Pittsfield Municipal)
Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
29 min drive
Rooms & beds
4 bedrooms (sleeps 10)
Bedroom 1
1 Double Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 Double Bed
Bedroom 4 (Loft)
1 Single Bed, 1 Double Bed and 1 Double Sofa Bed
2 bathrooms
Full Bathroom
Full Bathroom
Spaces
Deck or patio
Kitchen
About this property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Leave your busy schedule behind for a life of leisure at this vacation rental hideaway. This rustic 4-bed, 2-bath home is complete with woodsy-style decor, contemporary furnishings, and space for 10. It's truly a sportsman's paradise - tucked away in the woods on Round Pond, where you can hike, fish, swim, boat, or admire it all from the deck and dock. Whether you're here for summers at the Symphony, winters on Ski Butternut, or leaf peeping in the fall, Great Barrington has it all.
-- THE PROPERTY --
Bedroom 1: Full Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed | Bedroom 4 (Loft): Twin Bed with Twin Pullout (Can be converted into a King), Full Bed
You'll find this rustic property hidden away in a semi-remote, wooded area, with very few neighbors nearby. Mornings here offer incredible views and quiet surroundings - best enjoyed with a warm cup of coffee on the deck.
This property is located right on Round Pond. With crystal clear water untouched by busy beaches or motor boats, this lake is ideal for swimming and fishing! Take a dip off the dock, or venture out on the rowboat provided.
After a day on the lake, head inside to enjoy some downtime. The living room is complete with cathedral ceilings, floor-to-ceiling views, and a cozy wood-burning fireplace, altogether creating the perfect place to unwind.
End the day with a hearty meal made in the fully-equipped kitchen. Follow dinner with a sweet treat of s'mores by the outdoor fire pit!
When you're ready to retire for the night, 4 bedrooms offer space for up to 10 guests.
-- THE LOCATION --
Named as the #1 best place to live by Smithsonian Magazine, Great Barrington is a small-but-mighty town brimming with activities and charm.
Take some time to tour the Berkshires. Within 15 minutes you'll be able to hike across Monument Mountain, shop and dine in Great Barrington, stop by the Norman Rockwell Museum in Stockbridge, or test your winning streak at the Springfield Casino just 40 minutes away.
The famous Tanglewood lies just 10 miles away. Since 1937, Tanglewood has served as the summer home for the Boston Symphony Orchestra. Concerts here will take your breath away!
The Berkshires turn into a winter wonderland when the snow falls. You'll find multiple mountains within 10 minutes of the property, including Ski Butternut and Catamount Ski Area, with Bousquet Ski Area, Jiminy Peak, and more just a short drive further!
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- Massachusetts Tax ID: C0198611130 - No smoking - Pet friendly w/ $75 fee (+ fees & taxes, dogs only) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: There is a completely separate unit located next door with its own private entrance. Other guests will not be present however the separate unit is off limits - NOTE: This unit also has exterior-facing cameras, but they do not look into any interior spaces of the vacation rental - NOTE: The property requires stairs to access - NOTE: The property does not have air conditioning
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
About the area
Great Barrington
Located in Great Barrington, this holiday home is on the waterfront. Chesterwood and Mission House are local landmarks, and some of the area's activities can be experienced at Ski Butternut and Greenock Country Club. Hoffman's Pottery and Berkshire Botanical Garden are also worth visiting. Discover the area's water adventures with nearby power boating, or enjoy the great outdoors with hunting and hiking/biking trails.
Monument Mountain Reservation - 9 min drive - 6.8 km
Norman Rockwell Museum - 13 min drive - 10.3 km
Berkshire Botanical Garden - 14 min drive - 11.7 km
Getting around
Pittsfield Intermodal Transportation Center - 28 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 27 min drive
Restaurants
McDonald's - 12 min drive
Guido’s Kitchen - 15 min drive
Dunkin' - 14 min drive
Café Holli - 12 min drive
Berkshire Mountain Bakery - 6 min drive
Frequently asked questions
Is Lakefront Berkshires Retreat w/ Deck, Dock & Boat! pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Lakefront Berkshires Retreat w/ Deck, Dock & Boat!?
As of 25 August 2026, prices found for a 1-night stay for 2 adults at Lakefront Berkshires Retreat w/ Deck, Dock & Boat! on 15 September 2026 start from NZ$1,531, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Lakefront Berkshires Retreat w/ Deck, Dock & Boat!?
On-site parking is available at the property.
What time is check-in at Lakefront Berkshires Retreat w/ Deck, Dock & Boat!?
Check-in begins at 4:00 PM.
What time is check-out at Lakefront Berkshires Retreat w/ Deck, Dock & Boat!?
Checkout is at 10:00 AM.
Where is Lakefront Berkshires Retreat w/ Deck, Dock & Boat! located?
Situated on the waterfront, this holiday home is 2.5 mi (4 km) from Housatonic River and 2.6 mi (4.2 km) from Art et Industrie. Monument Mountain Reservation and Lake Mansfield Park are also within 6 miles (10 km).