Entire home

Stylish 5 bed/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood

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Exterior
Property grounds
Exterior
Exterior
Exterior detail

Reviews

10 out of 10
Exceptional
5 bedrooms5 bathroomsSleeps 11

Popular amenities

  • Dryer
  • Washer
  • Pet-friendly
  • Air conditioning

Explore the area

Map
Stockbridge, MA
  • Berkshire Botanical Garden
    ‪16 min walk‬
  • Norman Rockwell Museum
    ‪5 min drive‬
  • National Shrine of the Divine Mercy
    ‪5 min drive‬
  • Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪18 min drive‬

Rooms & beds

5 bedrooms (sleeps 11)

5 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Spaces

About this property

Stylish 5 bed/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood

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.

Property manager

Property Manager/Owner

Languages

English, Spanish

Add dates for prices

Amenities

Washer
Dryer
Pet-friendly
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 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: dogs less than 23 kg per pet (limit 2 pets total)
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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

About the area

Stockbridge

Stockbridge is home to this holiday home. The area's natural beauty can be seen at Fairfield Brook WMA and Pleasant Valley Wilderness Sanctuary, while Tanglewood Music Center and Norman Rockwell Museum are cultural highlights. Berkshire Botanical Garden and Hoffman's Pottery are also worth visiting.
Map
Stockbridge, MA

What's nearby

  • Berkshire Botanical Garden - 16 min walk - 1.4 km
  • Naumkeag Museum - 4 min drive - 2.5 km
  • Norman Rockwell Museum - 5 min drive - 2.8 km
  • National Shrine of the Divine Mercy - 5 min drive - 2.6 km
  • Tanglewood Music Center - 9 min drive - 7.6 km

Getting around

  • Pittsfield Intermodal Transportation Center - 24 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 18 min drive

Restaurants

  • ‪McDonald's - ‬13 min drive
  • ‪Pleasant and Main - ‬9 min drive
  • ‪Vivaldi's Pizzeria - ‬12 min drive
  • ‪51 Park Restaurant & Tavern - ‬12 min drive
  • ‪Stockbridge Coffee & Tea - ‬5 min drive

Frequently asked questions

Is Stylish 5 bed/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

What time is check-in at Stylish 5 bed/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood?

Check-in begins at 4:00 PM.

What time is check-out at Stylish 5 bed/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood?

Checkout is at 11:00 AM.

Where is Stylish 5 bed/5 bath Hilltop Manor + Cottage - Amazing location!! 4mi Tanglewood located?

Situated in Stockbridge, this holiday home is within 2 miles (3 km) of Berkshire Botanical Garden, Naumkeag Museum and Housatonic River. National Shrine of the Divine Mercy and Norman Rockwell Museum are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

6.8/10

Cleanliness

7.4/10

Check-in

7.4/10

Communication

7.4/10

Location

7.4/10

Listing accuracy

Reviews

10/10 Excellent

Lauren Z.

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

Lovely Antique Home in the Berkshires

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!
Stayed 7 nights in Feb 2025

10/10 Excellent

Alyssa R.

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

Great stay!

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.
Stayed 7 nights in Jun 2023

10/10 Excellent

Blythe B.

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

Great house, great location!

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.
Stayed 6 nights in Aug 2023

About the host

Hosted by Property Manager/Owner

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Languages:

English, Spanish