Middlefield Rentals USA Massachusetts Middlefield

1840's Whaling Captain's Farm Estate, 6-10 guests | House in Chester

10.0 (5 Reviews) |   Pet Friendly   4 Bedrooms  3 Bathrooms  10 Guests
Middlefield House | 1840's Whaling Captain's Farm Estate, 6-10 guests

4 Bedroom House in Middlefield, Chester

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.

1840's Whaling Captain's Farm Estate, 6-10 guests is located in Middlefield. 1840's Whaling Captain's Farm Estate, 6-10 guests provides accommodation, featuring Fireplace/Heating, Barbecue/Outdoor Cooking, Pet Friendly, among other amenities. This House features Fireplace/Heating, Barbecue/Outdoor Cooking, Pet Friendly, to make your stay a comfortable one.

1840's Whaling Captain's Farm Estate, 6-10 guests has 4 Bedrooms , 3 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Middlefield has interesting places to visit. If you want to learn more about the House in Middlefield, such as places to visit and things to do nearby, you can check below to learn more.

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Chester, 01011, USA

Amenities

Air Conditioner
Parking
Pet Friendly
Designated Smoking Area
TV
Balcony/Terrace
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Bathtub or shower
  • Shampoo
  • Toilet paper
  • 3 bathrooms
  • Hair dryer
  • Soap
  • Towels provided
Bedroom
  • Bed sheets provided
  • Sofa bed
  • 4 bedrooms
  • Dining table
  • Living room
  • Wood stove
  • Fireplace
  • Dining room
Kitchen
  • Paper towels
  • Refrigerator
  • Lobster/crab pot
  • Dishwasher
  • Blender
  • Oven
  • Coffee/tea maker
  • Microwave
  • Stovetop
Laundry
  • Laundry facilities
  • Washing machine and dryer
Parking
  • Onsite parking
Pet Friendly
  • Pet friendly
  • Welcoming dogs only
  • 2 total pets
Accessibility
  • No elevators
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 2 stairs to reach property
  • Tile flooring in public areas
  • Wheelchair-accessible path of travel
  • Designated smoking areas
  • Thin carpet in public areas
  • Area rugs in public areas
  • Hardwood flooring in public areas
Activities
  • Wildlife and game walks nearby
  • Hunting nearby
  • Birdwatching nearby
  • Hiking nearby
  • Kayak on site
  • Fishing nearby
  • Cycling nearby
  • Power boating nearby
  • Fitness center
  • Ecotours nearby
  • Hiking/biking trails nearby
Entertainment
  • Music library
  • Books
  • Stereo
  • Smart TV
  • Games
General
  • Unit size: 3300 sq ft (307 sq m)
  • English
  • Spanish
  • French
  • Near outlet shopping
  • Near a health or beauty spa
  • On the lake
  • In the mountains
  • Desk
  • Computer monitor
  • Printer
Guest Services
  • Stair gate
  • Children's games
  • Playground
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Firepit
  • Barbecue grill
  • Outdoor furniture
  • Patio
  • Garden
Security/Safety
  • Fire extinguisher
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • First aid kit

Policies

Check-in
Check-in time starts at 4:00 pm minimum check-in age: 30
Check-out
Check-out before 1:00 pm
Child Policy
Children are welcome. note from host: 2 fire ponds. patio without railing
Event Policy
Events allowed: family gatherings, birthday parties, weddings;maximum event attendees: 40;with prior approval and rate discussion.
Pet Policy
2 total pets pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking allowed: in designated areas
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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property note from host: with prior approval and rate discussion. parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 40 property registration number c0521279424 safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
License number: C0521279424

Reviews

Kristin L.
Jul 16, 2025 12:56:48 AM
Review Score:   10
Summary: 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.
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FAQ's

Is this Middlefield house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Middlefield house have a swimming pool?

No, this Middlefield house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Middlefield house?

Best-rates for the Middlefield house starts from $830 per night with includes Parking, Bedding/Linens, Entertainment, Internet, Fireplace/Heating, Barbecue/Outdoor Cooking, Pet Friendly, Balcony/Terrace, Sports/Activities, Kitchen, Laundry, Designated Smoking Area, TV, Wellness Facilities, Guest Services, Child Friendly, Air Conditioner with all other facilities. RBO matches every traveller with their perfect accommodation, whether you are travelling with a group, friends, family, or pets.

Is Middlefield house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Middlefield house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Middlefield house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Middlefield house?

Based on the information reported by the owner or manager, the Middlefield house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Middlefield house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Middlefield house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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