Modern Cottage in the heart of the Berkshires with new exterior flex space!

Stockbridge, Massachusetts
$493 avg/night Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 2 nights

Min Stay

Drive down our private road to find an adorable and spacious cottage, nestled on four secluded wooded acres, with every modern amenity including central air conditioning, Internet TV and WIFI. Added for 2021 - Custom shed that serves as an office with direct ethernet connection OR for fabulous movie watching or yoga space. Stay plugged in or disconnect and enjoy the faint whooshing sound of the Housatonic River and the exquisite natural beauty around our property and in the Berkshires. Ourhome has three bedrooms plus a den with a pull-out couch. The three bedrooms are on the second floor. There is a spacious primary bedroom suite with a king bed and an attached, walk-out deck, private bathroom and a large walk-in closet that is big enough for a pack-in-play for the little one. The two other bedrooms have a queen bed and a full/double size bed with ample closet space and a full bath for those bedrooms to share. There is also a half bath on the main level. All of the mattresses are new and extremely high quality. On the first floor, there is a den with a full-sized pull-out couch which doubles as a peaceful reading room or a playroom for the kids. If you like to cook, enjoy the spacious open-concept kitchen. There is a lovely screened-in porch for al fresco dining and a covered porch to relax and unwind, which also has a gas grill. ADDED IN 2022 - 60 amp dedicated outlet in garage to charge your Electric Vehicle. And for added security there is a video doorbell installed on the front door.

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

Feature Features

  • SKI

    Close To Skiing
  • PETS

    Pet Friendly
  • BEACH

    Beach Sun Loungers Beach Towels
  • 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

    3 Bedrooms Bed Sheets Provided
  • GENERAL

    Recycling Unit Size: 1650 Sq Ft (153 Sq M)
  • KITCHEN

    Coffee Grinder Dishwasher Electric Kettle Microwave Oven Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Required Electric Car Charging Station On Site Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Firepit Garden Gas Grill Outdoor Furniture
  • BATHROOMS

    2.5 Bathrooms Bathtub Or Shower Hair Dryer Jetted Bathtub Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Office
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Cycling Nearby Fishing Nearby Fitness Center Golf Nearby Golfing On Site Hiking Nearby Kayaking Nearby Mountain Biking Nearby Mountain Climbing Nearby Tennis On Site Wildlife And Game Walks Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Books Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Children's Toys Travel Crib
  • LOCATION HIGHLIGHTS

    In A Rural Location Near A Health Or Beauty Spa Near A Hospital
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Jessica Z.

    Submitted Dec 31, 2025

    Stayed Dec 27, 2025

    Beautiful wooded property and cozy clean home.Great home base to ski at Butternut and shop/ restaurants in Stockbridge and Great Barrington.

  • Jane G.

    Submitted Dec 26, 2025

    Stayed Dec 24, 2025

    Everything was truly lovely. Comfortable, beautiful, well stocked, thoughtful - and provided great location and perfect in-home gathering spots.

  • greg m.

    Submitted Dec 2, 2025

    Stayed Nov 26, 2025

    My third time at this Berkshires charmer. Great secluded intimate home that provides comfort and warmth. Perfectly located a short drive to Lenox, Lee and a Great B.

  • Davette B.

    Submitted Oct 10, 2025

    Stayed Oct 3, 2025

    Great accomodations and fun run area for the dog. Kitchen is well stocked. Just as advertised and conveniently located.

  • David A.

    Submitted Aug 11, 2025

    Stayed Jun 19, 2025

    We had a wonderful stay at Valentine Lane again this summer! This is the second summer that we have stayed for several weeks. The house is incredibly comfortable and has everything we could need and the owner is always helpful and responsive, often replying within minutes if we had a question about anything. The house is particularly well set up for remote work because of the separate and well-finished shed. We love how dog friendly the house is - our large golden retriever really enjoyed the huge backyard. The house also features a beautiful sunroom that is perfect for both working and eating. We look forward to coming back again!

  • Maureen K.

    Submitted Jun 9, 2025

    Stayed Jun 6, 2025

    Such a peaceful, private property. We enjoyed sitting on the deck listening to the birds. The house was very clean. The beds were comfortable. Worked well for six adults. Plenty of spots to relax. We had everything we needed. Easy drive to both Great Barrington and Stockbridge. I recommend and would definitely stay again if in the area.

  • Suzy B.

    Submitted Mar 19, 2025

    Stayed Mar 14, 2025

    We had another wonderful weekend! The house is perfectly appointed, the home is clean and welcoming. The property is beautiful. Communication with our hosts was easy and we were able to arrange an early check-in. This is now our fourth time staying in this home and we cannot wait to return. An absolute gem.

  • Jennifer S.

    Submitted Feb 24, 2025

    Stayed Feb 18, 2025

    Perfect blend of privacy and accessibility. House was clean and comfortable and has everything a family would need for a great vacation. We all loved it

  • Jeffrey C.

    Submitted Feb 18, 2025

    Stayed Feb 14, 2025

    Great location in the heart of the Berkshires. The house is secluded (can’t see a single neighbor) yet just minutes from anything you want or need. Flexible space easily accommodated our family weekend (even when we were snowed in). Great communication with our host.

  • Joshua R.

    Submitted Oct 21, 2024

    Stayed Oct 18, 2024

    Our second stay in the property and we can't recommend it enough!

  • Alan F.

    Submitted Sep 1, 2024

    Stayed Aug 1, 2024

    We stayed for the entire month of August (for the fourth year in a row) and enjoyed every minute. Perfect house in every respect, and terrific hosts.

  • David A.

    Submitted Aug 3, 2024

    Stayed Jun 20, 2024

    My wife and I (and our large golden retriever!) spent a delightful month at Valentine Lane. The property is located just minutes from downtown Stockbridge on a beautiful piece of land down a long private driveway and has a giant backyard that both we and our dog adored. The house is spacious, very well-maintained, and stocked with everything we needed for a comfortable stay. We particularly loved the porch area and the “she shed” that made a great separate office (super helpful as we were both working remotely during the week). Alison the host is terrific — extremely responsive (often getting back to us within minutes) and full of useful information about the house and surrounding area. Overall we had such a wonderful stay and would highly recommend it!

  • Phillip B.

    Submitted Jun 19, 2024

    Stayed Jun 1, 2024

    Beautiful spot, great house, loved the she shed and yard. Would highly recommend.

  • Felicia S.

    Submitted May 27, 2024

    Stayed May 24, 2024

    Highly recommend! Great location, amazing property, good for families.

Your dates are Available!

Total

Includes taxes and fees
$493+
View details