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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

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Great Barrington Vacation Rental | 4BR | 2BA | 2,000 Sq Ft | Stairs Required
Exterior | Private Deck w/ Gas Grill
Interior | Main Living Area | Fireplace | Pet Friendly w/ Fee (Dogs Only)
Living area
Living area

Reviews

7.2 out of 10
Good
4 bedrooms2 bathroomsSleeps 10185.8 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Outdoor space
  • Parking available

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 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

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Outdoor space
Parking available

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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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
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
Property Registration Number C0198611130

We should mention

A car is recommended for transport to and from this property

About the area

Great Barrington

Located in Great Barrington, this holiday home is on the waterfront. National Shrine of the Divine Mercy and Chesterwood 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 hiking and hunting.
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Map
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

  • Pittsfield Intermodal Transportation Center - 28 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 27 min drive

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

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 29 Mar 2026, prices found for a 1-night stay for 2 adults at Lakefront Berkshires Retreat w/ Deck, Dock & Boat! on 18 July 2026 start from AU$532, 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).

Reviews

7.2

Good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 19 out of 50 reviews
Rating 8 - Good. 9 out of 50 reviews
Rating 6 - Okay. 8 out of 50 reviews
Rating 4 - Poor. 8 out of 50 reviews
Rating 2 - Terrible. 6 out of 50 reviews

6.4/10

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

From a partner site

4/10 Poor

Carol

Great location, not great house

Lovely lakefront but the house situation was not acceptable
Verified

10/10 Excellent

Jeffrey K.

Liked: Check-in, communication, location, listing accuracy

Lake house in the Berkshires

Beautiful spot! Older but we’ll maintained property. Ideal for a three family get together for a relaxing vacation.
Stayed 7 nights in Jul 2023
Verified

4/10 Poor

Carol W.

Liked: Location
Disliked: Cleanliness, listing accuracy
Lovely lakefront, but the house was not comfortable. Many broken items (shower, door) dirty, very unpleasant smell downstairs in the bedrooms.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Matt C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pleasant Stay and Great Location

I stayed with a group of friends for a weekend while we skied nearby Ski Butternut mountain. The home was exactly as described and we had a very nice stay. It was warm upon entry (important after a day of skiing) and had everything we needed. The location, both on the pond and close to everything in Great Barrington, was great.
Stayed 2 nights in Feb 2023
Verified

10/10 Excellent

Colleen F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Fishing Spot

Enjoyed a few days “glamping” with my son and husband. The pond was beautiful and a great fishing spot. The owner was very responsive.
Stayed 3 nights in Apr 2023
Verified

6/10 Okay

Alif F.

Liked: Check-in, listing accuracy
Disliked: Cleanliness

Family getaway

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
Stayed 2 nights in Sep 2024
Verified

8/10 Good

Sarah C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Retreat with college friends

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.
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Diane M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wondrful family get away

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.
Stayed 7 nights in Aug 2023
Verified

8/10 Good

Alicia A.

Liked: Check-in, communication, location, listing accuracy

Christmas 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
Stayed 5 nights in Dec 2024
Verified

10/10 Excellent

John B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic lake house experience...

In excellent condition given its age and the interior in particular is immaculate and well maintained. The location is amazing, there are no signs of civilization anywhere in sight on the other side of the lake, so you have a sense of real solitude, a rarity considering you are within range of having pizza delivered. We loved it and will look here first for availability when next we travel to the Berkshires.
Stayed 2 nights in Jun 2019
Verified

4/10 Poor

A guest from Plymouth, CT G.

Liked: Location
Disliked: Cleanliness, communication

House needs attention

Great fishing and great location but house is falling apart.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Jason L.

Liked: Check-in, communication, location, listing accuracy

Guys fishing weekend

Beautiful setting, cool kind of old school rustic feel. Perfect for 6 guys away fishing for a nice break. I would bring the family here as well. Just don't expect modern, perfct interior. For the price, can't beat it! Easy of the highway location. The pictures and description were definitely accurate. Hope to go back soon!
Stayed 3 nights in Jan 2023
Verified

8/10 Good

Katelyn

Liked: Cleanliness, amenities, communication
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!
Verified

4/10 Poor

Tricia R.

Liked: Check-in, communication, location
Disliked: Cleanliness, listing accuracy

Plumbing couldn't hold 10 people

It is a lovely spot. If you are troubled by gunfire, there is a firing range across the street, so for about 15 minutes a day, there is some loud gunfire. And it is a small pond. For my family, by the time we got there in July, the water was low and swimming was not that appealing.
Stayed 7 nights in Jul 2019
Verified

10/10 Excellent

mary g.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful surroundings

The house is spacious. Beds comfortable, sheets and towels soft. I've never been to a rental with so many amenities. Bathrooms and kitchen well stocked. We spent almost all our time on the huge deck and around the fire pit. I do think older people and small children would have difficulty with all of the stairs inside and the steps to the dock. Some wood could be replaced, but it didn't impact our stay. We enjoyed the property so much we never went into town. Perhaps next time.
Stayed 3 nights in Jun 2022
Verified

2/10 Terrible

Margaret P.

Disliked: Cleanliness, check-in, communication, location, listing accuracy

No Review

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!!!
Stayed 7 nights in Oct 2023
Verified

2/10 Terrible

Brian C.

Liked: Check-in
Disliked: Cleanliness, communication, location, listing accuracy

Do not go here

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.
Stayed 3 nights in Sep 2023
Verified

2/10 Terrible

Karen H.

Liked: Communication
Disliked: Cleanliness, listing accuracy

Should not be listed as a rental property

Nothing positive to say about this property. We could not even unlock the main front door as the handle was about to fall out. We ended up going through the basement door every day. The place was dirty. By this I mean, stained showers, toilets which barely flushed, we had pet hair between the sheets of one bed, the basement ceiling tiles are water stained, one bedroom smelled moldy and the windows were filthy with dead bugs and cob webs. The electrical was scary with extension cords and I couldn’t dry my hair without popping a circuit breaker. This property should be pulled from any rental site until it gets a major renovation. The nightly rental amount is way overpriced. We left a day early as we couldn’t stand being there anymore.
Stayed 3 nights in Jun 2021
Verified

2/10 Terrible

Logan A.

Liked: Check-in, location
Disliked: Cleanliness, communication, listing accuracy

Should be condemned.

The listing pictures are very misleading. This house is in a beautiful spot, but the house itself is in really rough shape. It rained while we were there and water was running down the walls and ceiling. There is severe water damage everywhere because of this. On top of that there is black mold throughout the house and we had to cut our stay short because of the air quality. The back deck is on the brink of collapse and the dock was underwater and rotting. Some of the doors and windows wouldn’t seal so we also had a bug issue. Additionally there were some soft spots in the floor (probably from water damage) where someone heavy enough could easily break through. We planned this weekend 8 months in advance and our trip was ruined by the condition of this house. I would not recommend renting this house.
Stayed 2 nights in May 2023
Verified

2/10 Terrible

Jared P.

Liked: Check-in, location
Disliked: Cleanliness, communication, listing accuracy

Worst vacation experience ever!

Extremely dirty and dangerous. Booked it for a week to spend doing lake activities at end of summer. Dock is sinking, dock furniture rotted, stairs to water need new railing. Inside house was so dirty. Cobwebs. Musty smell in all rooms. Stained showers. Washer was broken with standing water in it with no notice ahead of time. We left after 18 hours when we booked 5 days. Wasted our one family get away for the summer! Filed grievance and property management company was easy to work with and after seeing the pictures and video they requested gave me immediate refund before we even left the property. However, we are still out hundreds on the VRBO service fee. After filing insurance claim with VRBO I still have not heard back for 3 months. All around this has been so bad it will be a long time before i consider using a rental like this.
Stayed 5 nights in Aug 2022
Verified

4/10 Poor

Wendy M.

Liked: Check-in, location
Disliked: Cleanliness, listing accuracy

Dirty and unsafe

The house was very dirty and unsafe. The electrical outlets are over taxed. The back screen door doesn’t close all the way so the bugs get in. There is a hole in the front screen door as well so it was hard to ventilate the house. The house smells damp and is covered up with air fresheners. The wall behind the fireplace leaks when it rains and so does the bathroom wall. They said it was small drips, but this was puddles. The glasses were dirty and had to be washed. Cobwebs everywhere. Outdoor table and chairs were dirty and rusty with holes in the metal trim. I can’t even get into the condition of the dock and steps leading down to it. . Life preservers we’re all moldy so we didn’t want to use them. We are pretty easy going and I thought the past renters were over exaggerating, but unfortunately they were not. We didn’t bother calling the housekeeper back because we didn’t want to lose a day of our vacation for someone to properly clean the house. I understand construction type work takes time to schedule, but cleaning the house should be very straight forward especially since there have been so many complaints about it being dirty. The only positive things I can say is that the location is great and there was plenty of sundries if you forgot something.
Stayed 4 nights in Aug 2023
Verified

4/10 Poor

Michael Z.

Liked: Check-in, communication, location
Disliked: Cleanliness, listing accuracy
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.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Aidan W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great spot for a weekend getaway to the lake!
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Joanna L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Weekend Trip!

Booked this as a weekend trip for my friends from college and I, the perfect meeting point from NYC and Boston. This house was clean and cozy and close to all the places we wanted to go in the Berkshires. Beautiful view with a quaint cabin vibe to escape city life. Hosts were so great and thoughtful, thank you for having us!
Stayed 3 nights in Nov 2022
Verified

10/10 Excellent

Darby I.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property

We absolutely love this property, it is incredible the views are beautiful. It. Was a perfect size and so tranquil. The only thing I would say that needs to be done is the railing near the dock needs to be fixed as it is loose, and the dock itself could use some upgrading seeing how it is old and has some parts curved in. Otherwise this whole place is amazing and incredible. We loved it here, and enjoyed the peacefulness.
Stayed 3 nights in Sep 2022

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