Entire home
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Photo gallery for Lakefront Berkshires Retreat w/ Deck, Dock & Boat!





Reviews
7.2 out of 10
Good
4 bedrooms2 bathroomsSleeps 102000 sq ft
Popular amenities
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 Twin 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 with $75 per stay fee (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
-- 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 with $75 per stay fee (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
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Stunning Lakefront Berkshire Rental, Lake Garfield: private dock, boats, more
Stunning Lakefront Berkshire Rental, Lake Garfield: private dock, boats, more
- Kitchen
- Washer
- Dryer
- Pet friendly
10.0 out of 10, Exceptional, (35 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
Children
Children allowed: ages 0-17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
Property Registration Number C0198611130
We should mention
A car is recommended for transportation to and from this property
About the neighborhood
Great Barrington
Located in Great Barrington, this vacation 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 motor boating nearby, or enjoy the great outdoors with hiking and hunting.

Great Barrington, MA
What's nearby
- Housatonic River - 6 min drive - 4.3 km
- Art et Industrie - 6 min drive - 4.0 km
- Monument Mountain Reservation - 7 min drive - 5.4 km
- Monument Mountain - 11 min drive - 10.0 km
- Norman Rockwell Museum - 11 min drive - 8.2 km
Getting around
Restaurants
- Cumberland Farms - 12 min drive
- McDonald's - 12 min drive
- Café Holli - 12 min drive
- Berkshire Mountain Bakery - 6 min drive
- Pizza House - 11 min drive
Frequently asked questions
Reviews
7.2
Good
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window6.4/10
Cleanliness
8.0/10
Amenities
6.0/10
Property conditions & facilities
9.2/10
Check-in
8.4/10
Communication
9.2/10
Location
7.6/10
Listing accuracy
Reviews
This review is from a guest who booked and stayed through a partner site and can't be verified.
Jul 29, 2025
4/10 Poor
Carol W.
Aug 8, 2025
Liked: Location
Disliked: Cleanliness, listing accuracy
Carol W.
Stayed 4 nights in Jul 2025
10/10 Excellent
Jeffrey K.
Aug 1, 2023
Liked: Check-in, communication, location, listing accuracy
Lake house in the Berkshires
Jeffrey K.
Stayed 7 nights in Jul 2023
10/10 Excellent
Matt C.
Feb 12, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Pleasant Stay and Great Location
Matt C.
Stayed 2 nights in Feb 2023
6/10 Okay
Alif F.
Oct 6, 2024
Liked: Check-in, listing accuracy
Disliked: Cleanliness
Family getaway
Alif F.
Stayed 2 nights in Sep 2024
10/10 Excellent
Colleen F.
Apr 23, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Fishing Spot
Colleen F.
Stayed 3 nights in Apr 2023
8/10 Good
Sarah C.
Sep 24, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Retreat with college friends
Sarah C.
Stayed 2 nights in Sep 2024
10/10 Excellent
Diane M.
Sep 11, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wondrful family get away
Diane M.
Stayed 7 nights in Aug 2023
8/10 Good
Alicia A.
Jan 4, 2025
Liked: Check-in, communication, location, listing accuracy
Christmas 2024
Alicia A.
Stayed 5 nights in Dec 2024
10/10 Excellent
John B.
Jun 24, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic lake house experience...
John B.
Stayed 2 nights in Jun 2019
4/10 Poor
A guest from Plymouth, CT G.
Aug 8, 2022
Liked: Location
Disliked: Cleanliness, communication
House needs attention
A guest from Plymouth, CT G.
Stayed 7 nights in Jul 2022
10/10 Excellent
Jason L.
Jan 30, 2023
Liked: Check-in, communication, location, listing accuracy
Guys fishing weekend
Jason L.
Stayed 3 nights in Jan 2023
8/10 Good
Katelyn
Nov 8, 2022
Liked: Cleanliness, amenities, communication
Katelyn
4/10 Poor
Tricia R.
Aug 15, 2019
Liked: Check-in, communication, location
Disliked: Cleanliness, listing accuracy
Plumbing couldn't hold 10 people
Tricia R.
Stayed 7 nights in Jul 2019
10/10 Excellent
mary g.
Jun 24, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful surroundings
mary g.
Stayed 3 nights in Jun 2022
2/10 Terrible
Margaret P.
Oct 20, 2023
Disliked: Cleanliness, check-in, communication, location, listing accuracy
No Review
Margaret P.
Stayed 7 nights in Oct 2023
2/10 Terrible
Brian C.
Sep 11, 2023
Liked: Check-in
Disliked: Cleanliness, communication, location, listing accuracy
Do not go here
Brian C.
Stayed 3 nights in Sep 2023
2/10 Terrible
Karen H.
Jun 14, 2021
Liked: Communication
Disliked: Cleanliness, listing accuracy
Should not be listed as a rental property
Karen H.
Stayed 3 nights in Jun 2021
2/10 Terrible
Logan A.
May 22, 2023
Liked: Check-in, location
Disliked: Cleanliness, communication, listing accuracy
Should be condemned.
Logan A.
Stayed 2 nights in May 2023
2/10 Terrible
Jared P.
Dec 17, 2022
Liked: Check-in, location
Disliked: Cleanliness, communication, listing accuracy
Worst vacation experience ever!
Jared P.
Stayed 5 nights in Aug 2022
4/10 Poor
Wendy M.
Aug 30, 2023
Liked: Check-in, location
Disliked: Cleanliness, listing accuracy
Dirty and unsafe
Wendy M.
Stayed 4 nights in Aug 2023
4/10 Poor
Michael Z.
Feb 8, 2026
Liked: Check-in, communication, location
Disliked: Cleanliness, listing accuracy
Michael Z.
Stayed 3 nights in Jan 2026
10/10 Excellent
Aidan W.
Sep 8, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Aidan W.
Stayed 3 nights in Aug 2025
10/10 Excellent
Joanna L.
Nov 22, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Weekend Trip!
Joanna L.
Stayed 3 nights in Nov 2022
10/10 Excellent
Darby I.
Sep 16, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing property
Darby I.
Stayed 3 nights in Sep 2022
About the host
Hosted by Evolve
Languages:
English, French, German, Spanish
Tell us how we can improve our siteShare feedback




























