Entire home

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

Lakefront vacation home with kitchen and patio

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Room options

About the neighborhood

Middlefield

This vacation home is located 1.9 mi (3.1 km) from Glendale Falls and within a 10-minute drive of Fox Den Wildlife Management Area. The vacation home includes a kitchen, a fireplace, and a patio.
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What's nearby

  • Glendale Falls - 10 min drive - 1.9 miles
  • Fox Den Wildlife Management Area - 11 min drive - 2.4 miles
  • Skyline Trail - 16 min drive - 4.2 miles
  • Chester Town Hall - 26 min drive - 8.0 miles
  • Jacob's Pillow - 41 min drive - 17.4 miles

Getting around

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

Restaurants

  • ‪Neon Newt - ‬23 min drive
  • ‪Liston's Bar & Grill - ‬20 min drive
  • ‪Carm’s Restaurant - Charlies Garage - ‬17 min drive
  • ‪Route 8 Pub - ‬23 min drive
  • ‪Chester Village Market - ‬17 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 Whaling Captain's Farm Estate, 6-10 guests

Jump back to an idyllic time when all you hear and see is nature all around. 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 old Colonial, family home - with the texture and lived in feeling that adds to its charm. This home is in a tranquil location perfect for a friends or family retreat. 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.

There is something for everyone here at Sunday Farm. 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.

For 5 guests or less, please reach out for discount.
The vacation home is air-conditioned and features a kitchen, 3 bathrooms, and a patio. There's space to spread out with 4 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a fireplace, and a sofa bed.

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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

  • This property welcomes pets
  • Dogs only
  • 2 total pets
  • Service animals exempt from fees

Children and extra beds

  • 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
  • Check-in: 4:00 PM
  • Check-out: 1:00 PM
  • Minimum check-in age: 30
Property Registration Number C0521279424

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • 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.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • There are no elevators.

Frequently asked questions

What's there to see near this vacation home?

This vacation home is located in Middlefield, close to Chester Town Hall, Skyline Trail, and Iroquis Waterfront. You'll also find Glendale Falls and Fox Den Wildlife Management Area within a short drive.

Is there parking available at this vacation home?

No, this vacation home doesn't offer parking.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Is 1840's Whaling Captain's Farm Estate, 6-10 guests a good place to stay for couples?

Amenities that appeal to couples at this lakeside vacation home include a fireplace, a kitchen, and a smart TV.

Does 1840's Whaling Captain's Farm Estate, 6-10 guests have a hot tub?

No, this vacation home doesn't have a spa tub.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

Although dogs can't stay for free, they are welcome at this vacation home.

Are there connecting rooms at this vacation home?

No, there aren't connecting rooms at this vacation home.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Pittsfield, MA (PSF-Pittsfield Municipal), which is 24.7 mi away (49 minutes by car). Another top airport is Westfield, MA (BAF-Barnes Municipal), which is located 29.2 mi away (49-minute drive).

Are there rooms with balconies at 1840's Whaling Captain's Farm Estate, 6-10 guests?

Yes, every accommodation at 1840's Whaling Captain's Farm Estate, 6-10 guests comes with a deck with some featuring mountain views.

Reviews

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

10

Exceptional

10/10

Cleanliness
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

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