Leaf-Peeper Paradise in the Berkshires

Photo gallery for Leaf-Peeper Paradise in the Berkshires

A dining area with a wooden table, chairs, and a ceiling fan.
A staircase with a wooden handrail and a white wall with a light switch.
A kitchen with wooden cabinets, a black countertop, a window with a view, and a hanging bag.
A two-story house with a wrap-around porch, a fenced yard, and a driveway leading to the house.
A hallway leading to a bedroom with a dresser and a mirror on the wall.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Sledding nearby
    A rare find — snowy slopes for sledding are just minutes away.
  • Discover nearby landmarks
    Close to Housatonic River

Popular amenities

  • Dog-friendly
  • Air conditioning
  • Refrigerator
  • Internet
  • Washer
  • Onsite parking available

Explore the area

View in a map
Great Barrington, MA
  • Place, Housatonic River
    ‪2 min walk‬
  • Place, Monument Mountain Reservation
    ‪5 min walk‬
  • Place, Art et Industrie
    ‪2 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪48 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 Double Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Double Bed

Living Room 1

1 Double Sofa Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Bidet · Toilet · Shampoo · Hair dryer

Spaces

Porch or lanai
Kitchen
Separate dining area
Number of living rooms

Add dates for prices

Similar properties

View to house from private lake
Serene, Private Waterfront House --Perfect Summer Retreat!
Sherwood Forest
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
9.8 out of 10, Exceptional, (139 reviews)
Serene, Private Waterfront House --Perfect Summer Retreat!

About the neighborhood

Great Barrington

Located in Great Barrington, this vacation home is on a river. Chesterwood and Mahaiwe Performing Arts Center are local landmarks, and the area's natural beauty can be seen at Monument Mountain Reservation and Monument Mountain. Berkshire Botanical Garden and Hoffman's Pottery are also worth visiting. Enjoy the area's slopes with cross-country skiing and snowboarding, and don't miss out on the sledding and ice skating.
View more Vacation Homes in Great BarringtonOpens in a new window
Map
Great Barrington, MA

What's nearby

  • Housatonic River - 2 min walk - 0.2 km
  • Monument Mountain Reservation - 5 min walk - 0.5 km
  • Art et Industrie - 2 min drive - 1.5 km
  • Ski Butternut - 11 min drive - 11.3 km
  • Tanglewood Music Center - 20 min drive - 19.5 km

Getting around

  • Pittsfield Intermodal Transportation Center - 30 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 34 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Café Holli - ‬7 min drive
  • ‪Berkshire Mountain Bakery - ‬14 min walk
  • ‪Cumberland Farms - ‬7 min drive
  • ‪Marketplace Kitchen Table - ‬5 min drive

Frequently asked questions

Is Leaf-Peeper Paradise in the Berkshires pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at Leaf-Peeper Paradise in the Berkshires ?

As of Nov 10, 2026, prices found for a 1-night stay for 2 adults at Leaf-Peeper Paradise in the Berkshires on Jan 8, 2027 start from $250, 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?

Onsite parking is available at the property.

What time is check-in at Leaf-Peeper Paradise in the Berkshires ?

Check-in begins at 4:00 PM.

What time is check-out at Leaf-Peeper Paradise in the Berkshires ?

Check-out is at 11:00 AM.

Where is Leaf-Peeper Paradise in the Berkshires located?

Situated on a river, this vacation home is within 1 mi (2 km) of Monument Mountain Reservation and Art et Industrie. Housatonic River and Monument Mountain are also within 3 mi (5 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 22 out of 29 reviews
Rating 8 - Good. 6 out of 29 reviews
Rating 6 - Okay. 1 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

9.2/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, very quiet, all good!
Stayed 1 night in Oct 2026
Response from VrboOwner on Oct 6, 2026
Thank you Lucy!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, excellent communication, would gladly stay again or recommend to friends.
Stayed 1 night in Sep 2026
Response from VrboOwner on Sep 7, 2026
Thank you so much! 😺
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a wonderful stay! Excellent communication from the host and Studley was the purfect co-host. If you love cuddly cats and nature, book here!
Stayed 1 night in Sep 2026
Response from VrboOwner on Oct 12, 2026
Thank you so much for your kind words! Studley really is the best.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place...... wish the 1st floor had a half bath.... but besides that, it was great
Stayed 5 nights in Sep 2026
Response from VrboOwner on Sep 29, 2026
Thank you so much Kevin!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
What an interesting quirky old house! Marisa was great, very responsive. And the cat is so polite and snuggly - a perfect co-host. Our stay was short and we didn't use the kitchen much, but everything seemed to work fine. For a cat-lover, this is a wonderful rental!
Stayed 2 nights in Sep 2026
Response from VrboOwner on Sep 29, 2026
Thank you so much Hannah! 😺
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step.
Stayed 1 night in Jun 2026
Response from VrboOwner on Jun 13, 2026
Thank you so much! Studley really is the host with the most 😸
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)
Stayed 2 nights in Mar 2026
Response from VrboOwner on Apr 15, 2026
Thanks so much Colin! I can't wait to see the film.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome location. Host was very informative and responsive.
Stayed 1 night in Apr 2026
Response from VrboOwner on Apr 15, 2026
Thank you so much! Happy to host you 😊
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Close to a great bakery and near to a farm market and shopping mall.
Stayed 1 night in Oct 2025
Verified review

8/10 Good

Liked: Check-in, communication, location
pictures were accurate. kitchen, dining room, and living room were good sized. tv/wifi was great. beds were small. only one socket in the bedroom, and it was damaged so only one plug worked. windows were very old. studley the cat was a charmer, and the host was exceptionally responsive and communicative. the price was low, but I'd probably spend more elsewhere next time
Stayed 1 night in Sep 2026
Response from VrboOwner on Sep 16, 2026
Thank you for your kind words Peter. I'm happy Studley was a charming host and you found the home to be as advertised. My apologies for the outlet. There was a second outlet in that bedroom, as well as an extension cord. I've had the issue with the outlet mentioned fixed! All the best.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing cosy property. The berkshires are beautiful and Marisa was a great host. Thank you for having us!
Stayed 2 nights in Nov 2025
Response from VrboOwner on Nov 26, 2025
Thank you Karla!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly.
Stayed 3 nights in Jan 2026
Response from VrboOwner on Mar 5, 2026
Thank you Jennifer! I was happy to host you and even happier you enjoyed your stay.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved our time here. It was a very cozy set up for a snowy week away, with a pellet stove, an ample amount of puzzles stocked in the house, and the surprise perk of Studley, a 12 year old cuddle machine of a cat who lives here and provided great company. The host was very responsive to all of my messages, and had the driveway promptly plowed in the inclimate weather
Stayed 6 nights in Feb 2026
Response from VrboOwner on Mar 5, 2026
Hannah, thank you so much for the kind review! I'm so happy you found the house cozy and that you loved Studley so much. He's a king for sure and the host with the most.
Verified review

10/10 Excellent

Everything was spotless and spot on based on the pictures and the description. What s
Stayed 3 nights in Dec 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location with nice space to hangout as a group - appreciated the music and games options. Comfortable space. Host was very responsive and checked in with us. Small bathroom for 4 people but nice big windows throughout the house for good light and great views. Everything was clean and ready for us when we arrived. .
Stayed 1 night in Oct 2025
Response from VrboOwner on Oct 27, 2025
thank you so much for all the positive feedback Rachel - I'm so happy you and your friends had a nice time! :)
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
Marisa's place was cozy and well-decorated. We enjoyed staying there for New Years and it was a good distance to the local downtowns while being quietly tucked away by the river.It was unclear to our party that the outdoor cats on the property lived within the rental unit until we received our check-in message. Mentioning this in case anyone is in a similar situation!The rooms were slightly less clean than we would have liked, with dust and hair in the corners, but overall it was well-stocked and served our purposes!
Stayed 2 nights in Dec 2025
Response from VrboOwner on Jan 6, 2026
Hi Sophia — thanks for your review and the feedback. The listing does mention that cats are on the property, but I’ll follow up with my team about being extra thorough in the harder-to-reach areas. And by my team, I mean me.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had the best time at Marisa's place. It was a charming and comfortable home, and, for our purposes, was an excellent location as we were on a bit of a tour to visit a few different towns where famous American authors lived. Near the house, we found good food -- Prairie Whale and Xicohtencatl Restaurant were our faves -- and my favorite dirty Chai ever at Cafe Holli. We also enjoyed Get Lit Bookstore and Wine Bar. The house was fantastic, the town lovely, but the real star of the show was Studley, the cat. He was truly the host, welcoming us back every time we returned in the rental car, walking us in, and hopping up into one lap after another up for a lounge -- he was truly the friendliest animal ever. Even the allergic one of us loved him! Overall, this stay was excellent. Marisa is a kind and easy host who responds quickly and is super helpful! I want to get back up there soon for more adventures and would certainly stay here again! :)
Stayed 3 nights in May 2026
Response from VrboOwner on Jun 22, 2026
Thank you so much! This review made me so happy and I love when guests love Studley. He really is such a special guy. 😸
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small) bathroom are on the second floor. The toilet sits low (below knee level) but a high step in is needed for the claw foot tub/shower. We stayed in mid Sept with highs in mid 70s and lows in the 50’s so it was reasonably comfortable even without AC by leaving windows open at night and using the fans provided during the day.
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very pleasant stay. We would love to come back.
Stayed 1 night in Jul 2026
Response from VrboOwner on Aug 7, 2026
Thank you! We'd be happy to have you.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
— ‘Whiskers on the Water’ lived up to its poetic name! The ‘whiskers’ were in the form of Studley, the friendliest feline we’ve ever encountered, while the ‘water’ was the picturesque Housatonic, just a stone’s throw from the front porch. Enjoyed a comfortable stay surrounded by elegant woodwork and myriad happy houseplants. Found our host Marisa to be friendly, helpful, and extremely responsive. Convenient location, and Studley’s cuddles and enthusiastic purring were an extra treat. We’ll be back! . . . .
Stayed 5 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our time here! The location was also a highlight, we went to the bakery down the street each morning. I really appreciated Marisa's fast communication and resident cat Studley's friendliness, both were amazing hosts! Thank you for having us!
Stayed 2 nights in Jul 2026
Response from VrboOwner on Jul 20, 2026
Thank you so much! The bakery and Studley really are such a great. 😸
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We thoroughly enjoyed our stay. The house was very comfortable and convenient. We loved Studley, the resident cat - such a sweetheart.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay in South Barrington Its proximity to the river made for a lovely morning run. Studley is super cute and snuggled up with us to enjoy an evening movie. Many thanks to our host for sharing her home.
Stayed 1 night in Jun 2026
Response from VrboOwner on Jun 28, 2026
Thank you so much! I'm happy you enjoyed your stay. 😸
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Stayed 1 night in Jul 2026
Response from VrboOwner on Jul 27, 2026
Thank you!
Tell us how we can improve our siteShare feedback