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Massachusetts Vacation Rental w/ Deck & Grill

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Cummington Vacation Rental | 4BR | 3BA | 2,900 Sq Ft | Steps Required to Access
Dining Area | Ample Natural Lighting
Spacious Yard Area | Fire Pit w/ Seating
Living Room | Free WiFi | Smart TV | Wood-Burning Stove
Living area

Reviews

9.4 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 8269.4 sq m

Popular amenities

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

Rooms & beds

4 bedrooms (sleeps 8)

Additional Sleeping (Loft)

1 Double Sofa Bed

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Double Bed

3 bathrooms

Full Bathroom

Full Bathroom

Full Bathroom

Spaces

Deck or patio
Kitchen
Separate dining area
Garden

About this property

Massachusetts Vacation Rental w/ Deck & Grill

Your next rejuvenating retreat awaits with a stay at this peaceful vacation rental nestled on 38 acres in Cummington, Massachusetts. This pet-friendly home comes equipped with 4 bedrooms, 3 bathrooms, a wraparound deck with a gas grill, a full kitchen, and ample entertainment space for the whole family. If you feel like venturing out, consider checking out the Bridge of Flowers or visiting the Berkshire Botanical Garden, then head back home for drinks shared with loved ones around the fire pit.

-- THE PROPERTY --

MassTaxConnect ID: C0412433450 | Pet Friendly w/ Fee | 38-Acre Property | Near Windsor State Forest

Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Full Bed | Loft: Twin Daybed

INDOOR LIVING: Wood-burning stove, Smart TVs, jetted tub, dining table, exercise bike, yoga mats, board games, Bose sound system
KITCHEN: Coffee maker & grinder, cooking utensils, dishware & flatware, dishwasher, hot water pot, microwave, spices, toaster, wine glasses
OUTDOOR LIVING: Deck, gas grill, fire pit w/ seating, dining area, hiking trails, on-site creek
GENERAL: Free WiFi, keyless entry, central heating, complimentary toiletries, hair dryer, hangers, in-unit laundry machines, laundry detergent, iron/board, linens/towels, trash bags/paper towels
FAQ: Steps required to access, pet fee (paid pre-trip), 2 exterior security cameras (facing out), hot tub not available for use, no A/C
PARKING: Driveway (5 vehicles)

-- THE LOCATION --

OPT OUTSIDE: Snowshoeing, hiking, bird watching; Westfield River (across street), Wahconah Falls State Park (11 miles), Natural Bridge State Park (15 miles), Zoar Outdoor Adventure Resort (16 miles), Bridge of Flowers (25 miles), Berkshire Botanical Garden (32 miles)
HIT THE SLOPES: Berkshire East Mountain Resort (16 miles), Bousquet Mountain Ski Area (23 miles)
NEARBY TOWNS: Adams (9 miles), Charlemont (16 miles), Pittsfield (19 miles), Shelburne Falls (25 miles), Berkshire (32 miles)
AIRPORTS: Bradley International Airport (56 miles), Albany International Airport (57 miles)

-- 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 --

- No smoking
- Pet friendly w/ $100 fee (+ fees & taxes, 1 pet max)
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: The property does not have air conditioning
- NOTE: The property requires stairs to access
- NOTE: The hot tub is nonfunctional and is not available for guest use
- NOTE: Your safety matters. This property features 2 exterior security cameras: camera 1 is a Ring Doorbell device located at the front entrance facing the driveway, and camera 2 is located in a tree near the driveway and is facing the driveway. The cameras are outward facing and do not look into interior spaces. Camera 1 records video and sound when activated by motion, while camera 2 only records video when activated by motion

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
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
A maximum of 1 pet is 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 and a first aid kit
Property Registration Number C0412433450

About the area

Windsor

Windsor is home to this holiday home. North Adams Center and Veterans Memorial Shopping Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Wahconah Falls State Park and Mount Greylock State Reservation. Berkshire Scenic Railway Museum and Thunderbolt Mountain Coaster are also worth visiting. Take the opportunity to explore the area for outdoor excitement like hiking/biking trails.
View more Holiday homes in WindsorOpens in a new window
Map
Cummington, MA

What's nearby

  • Wahconah Falls State Park - 18 min drive - 20.6 km
  • Susan B. Anthony Birthplace Museum - 19 min drive - 19.2 km
  • Mount Greylock State Reservation - 19 min drive - 18.8 km
  • Swift River - 21 min drive - 24.9 km
  • Massachusetts Museum of Contemporary Art - 28 min drive - 31.6 km

Getting around

  • Pittsfield Station - 28 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 40 min drive

Restaurants

  • ‪Pub 116 - ‬8 min drive
  • ‪Burkeshire Campfire - ‬22 min drive
  • ‪Swistak's - ‬15 min drive
  • ‪Lighthouse Natural Products - ‬8 min drive

Frequently asked questions

Is Massachusetts Vacation Rental w/ Deck & Grill pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Massachusetts Vacation Rental w/ Deck & Grill?

As of 28 Mar 2026, prices found for a 1-night stay for 2 adults at Massachusetts Vacation Rental w/ Deck & Grill on 6 July 2026 start from AU$675, 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 Massachusetts Vacation Rental w/ Deck & Grill?

On-site parking is available at the property.

What time is check-in at Massachusetts Vacation Rental w/ Deck & Grill?

Check-in begins at 4:00 PM.

What time is check-out at Massachusetts Vacation Rental w/ Deck & Grill?

Checkout is at 10:00 AM.

Where is Massachusetts Vacation Rental w/ Deck & Grill located?

Situated in Windsor, this holiday home is within 9 miles (15 km) of Susan B. Anthony Birthplace Museum, Tannery Falls and Swift River. Adams Theater and Berkshire Scenic Railway Museum are also within 12 miles (20 km).

Reviews

9.4

Exceptional

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. 20 out of 25 reviews
Rating 8 - Good. 2 out of 25 reviews
Rating 6 - Okay. 2 out of 25 reviews
Rating 4 - Poor. 1 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

9.0/10

Cleanliness

6.0/10

Amenities

8.0/10

Property conditions & facilities

10/10

Check-in

9.4/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Donna G.

Liked: Check-in, communication, location, listing accuracy
Place was exactly as described. I did leave my coat behind which was a bummer. Our family did enjoy the stay.
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Montgomery M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time. The location is beautiful and so is the property. However there is an infestation of paper wasps that should be addressed. They don't bite but they look scary!
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Gary B.

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

Great Cabin

Stayed with some work friends for a local outing. Great spot!
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Sid H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful setting. Very peaceful.
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Michele K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. House was very private and clean. Well stocked kitchen and other amenities. Would definitely recommend for quiet escape - plenty of space for larger group.
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Douglas N.

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

Great property!

Great spot for a ski weekend at Berkshire East.
Stayed 2 nights in Feb 2025
From a partner site

10/10 Excellent

Matt

Amazing property and service!

We found a truly quiet, mansion-like escape in a beautiful rural setting. The space is clean, private, and incredibly spacious. Everything felt high-end; the quality fixtures were clearly thoughtfully designed and came with excellent, helpful explanations. Highly recommended for anyone interested in hiking, cycling, or snow sports.
Verified

10/10 Excellent

Jesse D.

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

Lovely treehouse in the woods

Thanks for the comfortable and unique accommodation. Beautiful scenery and homey interior.
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Mairead M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at this property. It was such a unique home with plenty of room for our 7 adults. It was very well stocked and comfortable. One word to the wise, though. We stayed in the winter and it snowed while we were there. Our car isn’t great in the snow and this property has a very steep driveway. We couldn’t get all the way up to the house, but others in our group with SUVs could. The host did provide stone dust, which was a big help in getting 1/2 way up to a separate parking area. We will definitely look up this property to stay again.
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Garry W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Check in was easy good communication. House was clean, kitchen well equipped. Secluded location which is nice. Be sure to bring groceries and other provisions because there isn’t much around for shopping.
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Amit

Liked: Cleanliness, property conditions & facilities, communication
Very nice property.
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

Ashley H.

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

Great property

There’s a backup generator if you lose power!! Great log cabin feel and plenty of space.
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

stephen s.

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

What a spot

This place was spectacular. Definitely suggest staying here if you're looking in the area. Everything was spotless.
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Bernadette C.

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

Charming House - great memories

Our family enjoyed our stay in this unique and charming home. Very comfortable, lots of amenities, beautiful location. Would highly recommend!
Stayed 5 nights in Oct 2023
Verified

10/10 Excellent

Hope B.

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

Absolutely amazing!

I loved this house so much and can not wait to return!
Stayed 2 nights in Jan 2024
Verified

8/10 Good

Donna C.

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

Treehouse

Property was very spacious and comfortable.
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

JESSE S.

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

Loved it!

We really enjoyed our stay here. The house was well appointed and very clean. The instructions were clear and the listing was accurate. We loved hiking around the property and playing outside. Very comfortable beds and a cozy house! Would definitely come back!
Stayed 5 nights in Dec 2023
Verified

8/10 Good

kathleen e.

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

Magnificent

The photos do not do justice to this stunning home and property. Incredibly well- appointed and comfortable, from the kitchen with everything you could need to the comfortable beds. But the best part is the property. We heard nothing but silence and saw real darkness at night, with the exception of one rather annoying security light in the driveway.This is an exceptional place and we felt fortunate to be able to stay here!
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

David N.

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

Treehouse Treasure

A stunning multi level log cabin structure with a huge covered deck at tree top level. The house was immaculate with every last detail attended to. It sits on a secluded road bordering the state forest. We loved our time here, felt right at home and found the property to be just as advertised !
Stayed 2 nights in Jul 2023
Verified

10/10 Excellent

Cherie K.

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

Cozy, peaceful and rustic

This "tree house " was an amazing find! It was perfect for our family and friends to gather together for our daughter's college graduation weekend! We brought with us all that we would need but everything you could think of was there and available and a store was only 10 minutes away if needed. To sit out on the gorgeous deck and hear the stream was so peaceful and we will definitely return again to enjoy it when it's a less chaotic weekend for us!
Stayed 4 nights in May 2024
Verified

6/10 Okay

Andriana P.

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

Ok

Location was good. House was spacious with amenities. Bathrooms can definitely use some upgrading, along with the heating of the house. House was also pretty dirty when we arrived and definitely would’ve appreciated it if the house was clean prior to our arrival especially traveling with a one year old. Overall an ok stay.
Stayed 4 nights in Jan 2025
Verified

10/10 Excellent

Mario W.

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

Wonderful private getaway

Amazing place!! Perfect for a peaceful getaway with friends family, or loved ones. The home is nestled in the trees, and it is absolutely peaceful. You can only hear the wind blow through the trees and the babbling brook nearby. All amenities are there. Nothing was needed. The deck is awesome, and there’s a huge firepit on the property. Tons of rooms beds, and blankets. Kitchen is fully equipped. Nothing needed.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Robert T.

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

Exactly as advertised

What you see in the pics is what you get. Nice, large, comfortable cabin/house in a secluded area. Almost too secluded to be honest, three out of the four parties had difficulties finding the location (phone service is spotty at best in the area.) About a half hour from Sherbourne Falls/Charlemont (assuming you don’t get lost-gps had us take some crazy back roads) and rafting area. All in all thoroughly enjoyed our stay here. Highly recommend!!
Stayed 2 nights in Aug 2023
From a partner site

6/10 Okay

Dale

Needs TLC

Views are amazing. We were surprised that the weeds were so high outside that we needed to navigate through them to get inside. Also restricted our ability to enjoy the yard and paths. The master bath shower did not work, big disappointment! I called the contact to let them know and all she said was, "ok", but didn't do anything to correct it. Need to get rid of spider webs inside, could have been cleaner. Front bedroom needs a shade to block out the morning sun. On the positive side, kitchen is well equipped and the furniture comfy.
Stayed 3 nights in Aug 2024
Verified

4/10 Poor

Elizabeth B.

Stayed 2 nights in Oct 2025

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