Stylish 5 bed/5 bath Hilltop Manor + Cottage - EV charger - Amazing location!!

Stockbridge, Massachusetts
$953 avg/night
Bed 5

Bed

Bath 5

Bath

Home Private Vacation Home

Property Type

Sleep 11

Max Sleeps

*This listing is for the 4-bedroom, 4-bath house. The 1-bedroom, 1-bath guest cottage with full kitchen is available for an additional $200/night.*

*Beyond the north side of the property lies the turnpike, so there is some road noise. We rarely notice it, especially inside the house, but we want to point this out to those who are sensitive to traffic noise.*

Room/bed breakdown:

Main House - Downstairs:
Room 1: 1 queen

Main House - Upstairs:
Room 2: 1 king
Room 3: 2 twins
Room 4: 2 twins + 1 twin mattress in loft

Guest Cottage (should you choose to add it on) - Upstairs:
Room 5: 1 queen

Just minutes to Tanglewood! This recently renovated historic homestead in Stockbridge has it all: a Revolutionary-era 4-bed, 4-bath Colonial home and 1-bed, 1-bath detached guesthouse that sit on a 9+ acre hill with an impressive view of Monument Mountain, a gentle-sloping lawn, abundant woods, and a gentle stream.

A spacious and luxurious retreat for family and friends, the main house offers multiple living spaces with an open kitchen and living room with wood-burning stove, library, billiard room, den/TV room with games and puzzles, and an attached greenhouse with a far infrared sauna that seats 5. An old house lover’s dream, it boasts ultra-wide-plank floors, three fireplaces, wrought iron rim locks, thumb latches, strap hinges, and heavy brass door knobs on hand-planed doors.

The guesthouse with full kitchen is an adorable wooden cottage that feels bright, open, and spacious with its double-high living room. The space was crafted out of a former barn by a local carpenter and has modern amenities alongside its rustic charm. While it is closely-sited to the main home, there is ample privacy with a separate parking spot, walkway, landscaping, and a private deck. It is the perfect place for hosting extended family and visitors, to be used as a writer’s sanctuary, or for a bridal suite. Everyone who steps inside adores it!

Come experience the best the Berkshires has to offer! Take a walk or a bike ride to the Berkshire Botanical Garden or Naumkeag - or drive a few minutes to downtown Stockbridge, Stockbridge Bowl, Norman Rockwell Museum, Tanglewood, downtown Lenox, West Stockbridge, and Great Barrington.

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

Feature Features

  • PETS

    2 Total (up To 50 Lbs Per Pet) Pet Friendly Welcoming Dogs Only
  • 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

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3650 Sq Ft (339 Sq M)
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Electric Car Charging Station On Site Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Garden Patio
  • BATHROOMS

    5 Bathrooms Hair Dryer Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English Spanish
  • ENTERTAINMENT

    Smart TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning Heating
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Upper Floors Accessible By Stairs Only

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

Map Map

School District Rates & Availability

Review Review

  • Harold R.

    Submitted Dec 28, 2025

    Stayed Dec 23, 2025

    The hosts Elis & Mickey were very friendly and helpful. They made it easy to check in and check out. The house was great!!! Very cozy & fun. If you are hosting a large group, this is the spot!! We enjoyed the large spaces, the kitchen, playing pool, using the sauna and escaping to the back carpenter's cottage.

  • Dave F.

    Submitted Dec 14, 2025

    Stayed Nov 26, 2025

    If you love older homes this one is super impressive. Tremendous character, very authentic. But, also very updated where you want it to be (Kitchen and bathrooms). Beautiful, large yard if you brought a dog or just want to stroll the grounds.

  • Maura L.

    Submitted Nov 17, 2025

    Stayed Nov 7, 2025

    The host was helpful & available for questionsBeautiful home close to center

  • Gabriella A.

    Submitted Nov 17, 2025

    Stayed Nov 14, 2025

    We had a great time at the house in Stockbridge. Very cosy by the fire and ver comfortable and spacious.

  • Candace S.

    Submitted Jul 27, 2025

    Stayed Jul 25, 2025

    My friends and I had a wonderful stay. The only issue was a lack of AC in an upstairs bedroom, but the owner responded with additional fans for our use and the issue was resolved. The property is wonderful! We loved hanging out in the large kitchen and the sitting room.The owners could not have been more accommodating.

  • Lauren Z.

    Submitted Feb 24, 2025

    Stayed Feb 15, 2025

    An amazing stay in a charming and elegant farmhouse. Close to all the southern Berkshire towns (Stockbridge, Great Barrington, Lenox) yet still maintains a removed, tranquil feel. Looking forward to returning soon!

  • Blythe B.

    Submitted Aug 15, 2023

    Stayed Aug 8, 2023

    Had a wonderful stay at this old farm! At the end of a secluded, wooded road, this quintessential New England farm house was loaded with charm. If you're looking for something modern, this is not for you. If you're looking for an original, authentic farmhouse you'll love this place. We're New Englanders so this old farm was right up our alley. All the creature comforts. No TV. Great communication and friendly owners.

  • Alyssa R.

    Submitted Jul 8, 2023

    Stayed Jun 30, 2023

    The location of this family friendly home was perfect for exploring all of the little towns the Berkshires has to offer. The kitchen was fabulous and well appointed. We loved hanging out in the living room and playing pool in the billiards room. There were so many spots outside for the family to hang out. The 2 year old in our group especially enjoyed the swing and trampoline.

Your dates are Available!

Total

Includes taxes and fees
$953+
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