See all properties
Entire home

1840's Ship Captain's Farm Estate, 6-10 guests

Middlefield vacation home with kitchen

Choose dates to view prices

Photo gallery for 1840's Ship Captain's Farm Estate, 6-10 guests

Terrace/patio
Dining
Interior
Property grounds
Interior

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 103300 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Chester, MA

Room options

About the neighborhood

Middlefield

On lake.At this Middlefield vacation home, you'll be within 3 miles (5 km) of Glendale Falls and 6 miles (10 km) of Fox Den Wildlife Management Area. Skyline Trail is within 6 miles (10 km) and Kushi Institute is within 9 miles (15 km).
View more Vacation Homes in MiddlefieldOpens in a new window

Getting around

  • Pittsfield Station - 37 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 49 min drive

Restaurants

  • ‪Neon Newt - ‬23 min drive
  • ‪Chester Village Market - ‬17 min drive
  • ‪Liston's Bar & Grill - ‬20 min drive
  • ‪Carm’s Restaurant - Charlies Garage - ‬17 min drive
  • ‪The Goldenrod Country Inn - ‬23 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

1840's Ship Captain's Farm Estate, 6-10 guests

Step back in time. This thoughtfully restored, rustic yet elegant, property is surrounded by 72 acres of fields, brooks, and woodland, with all the amenities one could want, while maintaining the home's historic charm. If you are looking for “Restoration-Hardware-Perfect” this might not be the property for you…think historic, colonial, charm with a taste of modern style. This home is in a tranquil location perfect for an off the beaten path retreat or a friends and family get-away. You'll feel as though you've stepped back in time!

A lovely, 35 min drive to Tanglewood, Lenox & Lee , Jacob's Ladder (20), Stockbridge (45), Great Barrington, (55), Williamstown (60), and all that the Hilltowns offer - enjoy hiking, walking, swimming in waterfalls, or enjoy a day pass at Mirival Spa, lunch at the Red Lion Inn, some antiquing, The Clark Museum, Mass Mocha and innumerable gardens and historic home visits - or just lie in a hammock and read or paint while sitting on one of many patios.

We own another VRBO property in Greenport, Long Island with 55 (5) Star reviews.

Please note:
- We are 25min to a real grocery store
- We are 25 min to a hospital in Pittsfield. 40 to Westfield.
- All bedrooms are on the second floor as is the washing machine and dryer.
- 3 formal bedrooms w library pull out - sleeps 7-8 with additional sleeping on new air-mattresses.
- Half bath on the ground floor. 2 full bathrooms, and another half bathroom, upstairs.

Similar properties

House (5 Bedrooms) | Interior
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Lee
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
5.0 out of 5, Exceptional, 1 review
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area
  • Wood stove

Entertainment

  • Books
  • Games
  • Music library
  • Smart TV
  • Stereo

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Computer monitor
  • Desk
  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 2 steps to reach entrance
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • No elevator
  • Thin carpet in public areas
  • Tile flooring in public areas
  • Wheelchair-accessible path of travel
  • Designated smoking areas

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the mountains
  • Near a health/beauty spa
  • Near an outlet shopping mall
  • On a lake

Things to do

  • Gym
  • Kayak
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Unit size: 3,300 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 30

Check-out

Check-out before 1:00 PM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights, lock the doors, and return the keys
Please leave trash in the bins provided in the small sunroom and do not lock the door.
Failure to complete these may result in a negative review from the host.

Rules

The patio nor ponds have safety railings so you are responsible for supervising and maintaining a safe distance.
Weddings and larger events must be agreed upon as a separate fee and with additional guidelines and rules.
Any modifications to reservations must be made by renter by cancelling and rebooking or a 10% processing fee will be applied.

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 pets
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.
  • Note from host: 2 fire ponds. Patio without railing

Events

Events allowed: family gatherings, birthday parties, weddings
With prior approval and rate discussion.

Smoking

Smoking allowed: in designated areas

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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 40
Note from host: with prior approval and rate discussion.
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 40. Note from host: with prior approval and rate discussion. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property Registration Number C0521279424

Frequently asked questions

How close is 1840's Ship Captain's Farm Estate, 6-10 guests to the airport?

This vacation home is 24.7 mi (49-min drive) away from the Pittsfield, MA (PSF-Pittsfield Municipal) airport, the closest popular airport to the property.

Does 1840's Ship Captain's Farm Estate, 6-10 guests have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is 1840's Ship Captain's Farm Estate, 6-10 guests to the beach?

This vacation home is 10.5 mi (28-min drive) from Iroquis Waterfront.

Does 1840's Ship Captain's Farm Estate, 6-10 guests offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at 1840's Ship Captain's Farm Estate, 6-10 guests?

No, there is no casino at this vacation home.

What time is check-in at 1840's Ship Captain's Farm Estate, 6-10 guests?

Check-in begins at 4:00 PM.

Is there free parking at 1840's Ship Captain's Farm Estate, 6-10 guests?

Free parking is not available at this vacation home.

Does 1840's Ship Captain's Farm Estate, 6-10 guests have a pool?

This vacation home does not have a pool.

Does 1840's Ship Captain's Farm Estate, 6-10 guests have a spa?

There are no spa services available at this vacation home.

How close is 1840's Ship Captain's Farm Estate, 6-10 guests to downtown Middlefield?

This vacation home is 1.3 mi away from Middlefield.

1840's Ship Captain's Farm Estate, 6-10 guests Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 5 out of 5 reviews
Rating 8 - Good. 0 out of 5 reviews
Rating 6 - Okay. 0 out of 5 reviews
Rating 4 - Poor. 0 out of 5 reviews
Rating 2 - Terrible. 0 out of 5 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Sarah K.

Liked: Cleanliness
The house and property are even better in person! We spent a lovely 10 days with the dog and baby getting lost in the outdoor maze and soaking up the sunshine from the patios, screen porch, and sunroom. Couldn’t think of a better place for some much needed family time. And Marcia went above and beyond to ensure our stay was magical, including leaving us farm fresh eggs and some lovely wine to enjoy.
Stayed 10 nights in Aug 2025

10/10 Excellent

Kristin L.

Liked: Cleanliness
We had an absolutely unforgettable stay at this stunning property! From the moment we booked, our host’s communication was exceptional — responsive, thoughtful, and genuinely committed to making our visit smooth and special. She went above and beyond, checking in with personalized recommendations and thoughtful touches that made all the difference.The home itself is gorgeous — rich with history and character, yet beautifully maintained. We’re still marveling at its charm! And the yard… what a dream! Our dogs had the time of their lives exploring the lush, expansive grounds — it was a perfect oasis for both humans and pups alike.We left feeling relaxed, cared for, and already looking forward to next year. Highly recommend this property if you're seeking a peaceful getaway with outstanding hospitality.
Stayed 4 nights in Jul 2025

10/10 Excellent

Michele K., Dallas TX

Liked: Cleanliness

Gorgeous Massachusetts getaway

The description of this property is spot on. It is stunningly gorgeous and we never tired of being on the patio, in the grass or exploring the many rooms of this authentic farmhouse. We loved how the original details are preserved, while having updated bathrooms and appliances. We had a group of 8-10 family/friends per night and then a family party with 20 people on the patio. The kitchen/sunroom/deck/patio made for easy circulating and serving food. Evenings on the patio with the party lights and a fire were truly special. We enjoyed every single minute. We also took lengthy walks/runs 4-8 miles (and bike rides) around the area. It is so scenic and we only saw a handful of cars, even on the paved roads.The owner was immediately responsive to questions, but we didn't have many. We pretty much used everything in the house--all the kitchen appliances, washer/dryer, etc--everything was easy. The pantry and kitchen were beyond amply stocked--this made our lives a lot easier because the area is remote with no shopping to speak of; we drove in with groceries.We really appreciated the delivery of farmfresh eggs our first morning--they were delicious.We would definitely return!
Stayed 4 nights in May 2025

10/10 Excellent

Kevina B.

Liked: Cleanliness

Berkshires at its best

Such a beautiful home and property. We had a great time exploring during the day and spending time together at night. Sunsets over the pond are particularly lovely and the screened in porch and sitting around a fire in the chiminea outside are the perfect spots for a cocktail. We look forward to our next visit!
Stayed 2 nights in Apr 2025

10/10 Excellent

Tim K.

Liked: Cleanliness

Tranquil getaway!

Wow, what a spot, the house and surrounding grounds are beautiful, accurately represented in the pics. It was so nice having coffee looking at the amazing view in the mornings and a fire in the wood stove while making dinner in the evenings. Even though we were off the radar, we went into Lenox for brunch and antique hunting.The house is well furnished, kitchen fully stocked, very comfy mattress/sheets and great water pressure. Marcia was very helpful and quick to respond! Will definitely stay again, thanks Marcia!
Stayed 2 nights in Apr 2025