Entire home

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

Holiday home in Stockbridge with kitchen and patio

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

Exterior
Property grounds
Exterior
Exterior
Exterior detail

Reviews

10 out of 10
Exceptional
5 bedrooms5 bathroomsSleeps 11339.1 sq m

Popular amenities

  • Dryer
  • Pet-friendly
  • Parking available
  • Washer
  • Kitchen
  • Outdoor space

Explore the area

View map
  • Place, Berkshire Botanical Garden
  • Place, Norman Rockwell Museum
  • Place, National Shrine of the Divine Mercy
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)

Rooms & beds

5 bedrooms (sleeps 11)

5 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden

About this property

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

*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.*

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.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Mountain view

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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
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

We should mention

This property does not have any lifts

About the area

Stockbridge

Stockbridge is home to this holiday home. Naumkeag Museum and National Shrine of the Divine Mercy are local landmarks, and travellers looking to shop may want to visit Lee Premium Outlets and Guido's Marketplace. Berkshire Botanical Garden and Hoffman's Pottery are also worth visiting.
Map
Stockbridge, MA

What's nearby

  • Berkshire Botanical Garden - 1 min drive - 1.5 km
  • Naumkeag Museum - 3 min drive - 2.9 km
  • Norman Rockwell Museum - 3 min drive - 3.2 km
  • National Shrine of the Divine Mercy - 4 min drive - 3.2 km
  • Tanglewood Music Center - 10 min drive - 8.9 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬13 min drive
  • ‪The Red Lion Inn - ‬5 min drive
  • ‪Stockbridge Coffee And Tea - ‬5 min drive
  • ‪Six Depot Roastery and Cafe - ‬7 min drive
  • ‪Pleasant and Main - ‬9 min drive

Frequently asked questions

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

Check-in begins at 4:00 PM.

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

Checkout is at 11:00 AM.

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

7.6/10

Cleanliness

8.0/10

Check-in

8.0/10

Communication

8.0/10

Location

8.0/10

Listing accuracy
Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

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

Candace S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Jul 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

Premier Host

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