Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Great Barrington, Massachusetts
$381 avg/night Minimum Stay 2 Nights
Bed 4

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 2 nights

Min Stay

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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 2000 Sq Ft (186 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking
  • INTERNET

    Internet Access
  • OUTDOORS

    Barbecue Grill Dock Firepit Patio
  • BATHROOMS

    2 Bathrooms Hair Dryer Towels Provided
  • LANGS SPOKEN

    English French German Spanish
  • THINGS TO DO

    Boat On Site Hiking Nearby Hiking/biking Trails Nearby Hunting Nearby Power Boating Nearby
  • ENTERTAINMENT

    Books DVD Player Stereo TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Wood Stove
  • CLIMATE CONTROL

    Heating
  • LOCATION HIGHLIGHTS

    On The Lake On The Waterfront
  • SERVICES AND CONVENIENCES

    Housekeeping (on Request) Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Katelyn

    Submitted Nov 8, 2022

    Stayed Dec 31, 1969

    This property was a great size for our group of 8, plus two little ones. The kitchen was stocked with all appliances and utensils we needed, and there was plenty of seating for lounging and eating meals together. The large deck and fire pit were also great spaces for the whole group to gather. The bathrooms were a little bit dated, but the host provided a wonderful variety of toiletries and soap products! We really enjoyed this quiet location; we were close to hiking trails, breweries, grocery stores, and small bakeries/ coffee shops. We had a very nice stay!

  • Michael Z.

    Submitted Feb 8, 2026

    Stayed Jan 23, 2026

    I don’t like to leave negative reviews. I know owners of rental properties have a lot to deal with and also manage quite a bit of wear and tear. But this property needs work. On the positive side, it could be a great spot - good location, great views and a really nice frame for the house to take it all in. The owners were courteous, got us plowed out of the snow storm, offered a late check out, and disclosed some of the issues in advance. On the negative side:1. Snow made the entries difficult to get into when we arrived.2. Cob webs and dust caked over much of the furniture and fixtures (undisclosed)3. Wood stove disconnected, plastic and duct tape covering the ceiling exhaust (partially disclosed)4. Tree damage on the ceiling interior (disclosed), large plastic and duct tape section of the internal ceiling (undisclosed).5. External roof damage from a tree on the back porch - a chunk of wood with a nail on it flew off and landed a foot next to us while we were on the porch (undisclosed).6. A window screen in the loft was off the window and laying on the floor when we arrived. That same window was broken and wouldn’t shut properly, swinging open in the middle of the winter.Having a rustic stay is fine. It’s a matter of taste I guess. But the broken loft bedroom window, the plastic and duct tape on the ceiling, and the chunks of wood flying off a damaged roof…. Probably time to pull the rental property off market for a bit and put some shine on it.

  • Aidan W.

    Submitted Sep 8, 2025

    Stayed Aug 29, 2025

    Great spot for a weekend getaway to the lake!

  • Carol W.

    Submitted Aug 8, 2025

    Stayed Jul 24, 2025

    Lovely lakefront, but the house was not comfortable. Many broken items (shower, door) dirty, very unpleasant smell downstairs in the bedrooms.

  • Carol

    Submitted Jul 29, 2025

    Stayed Jul 24, 2025

    Lovely lakefront but the house situation was not acceptable

  • Alicia A.

    Submitted Jan 4, 2025

    Stayed Dec 22, 2024

    The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind

  • Alif F.

    Submitted Oct 6, 2024

    Stayed Sep 27, 2024

    We went as a family to get away from the city life for the weekend. We have no complaints except that it could’ve been a bit cleaner in the sense that there were many cobwebs. Nonetheless we rlly enjoyed our weekend in Great Barrington

  • Sarah C.

    Submitted Sep 24, 2024

    Stayed Sep 20, 2024

    We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries.

  • Margaret P.

    Submitted Oct 20, 2023

    Stayed Oct 13, 2023

    I don’t want to publish review, but I really think the owners should let people know that two of thee bedrooms are in the basement and one has no windows. Also a big issue is the firing range next door. Gunshots every day and a poor dead bird on deck. Afraid to go outside!!!

  • Brian C.

    Submitted Sep 11, 2023

    Stayed Sep 8, 2023

    If you really and I mean really like a get-away spot that has a musty smell, mold, cobwebs and a roof that leaks then this is the place for you. The pictures do not accurately reflect the home or the lake. The home is dark, the bath tubs are filthy. The place was booked for 6 adults and we were provided towels for four. There were no kitchen towels. The path to the dock appears to be dangerous and the dock is not sturdy. The lake is over grown and stagnant.

  • Diane M.

    Submitted Sep 11, 2023

    Stayed Aug 19, 2023

    This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home.

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Total

Includes taxes and fees
$381+
View details