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The Oliver Wendell Holmes Guest Cottage   Holmesdale
The Oliver Wendell Holmes Guest Cottage   Holmesdale
Michael
Response rate: 100% • Response time: < 12h

The Oliver Wendell Holmes Guest Cottage Holmesdale

Pittsfield, Massachusetts, United StatesMap
Exceptional5.0(1)Booked once
Entire place
2 guests
1 Bedroom
1 Bathroom
2 beds
Gym nearby or in the propertyWi-FiPoolParking

The Reveal

CozyRelaxingCentral location

***Clothing optional pool**** Historic landmark, "Holmesdale" built on an entire hilltop in the Berkshire mountains in 1848 as the summer cottage of Poet Oliver Wendell Holmes Sr. set on 16 beautiful acres. This originally 22,000 acre homestead named "Canoe Meadows" was partially donated to Mass Audubon as a wildlife sanctuary

This mansion hosted poets & authors such as Longfellow, Melville, Sir Arthur Conan Doyle & Hawthorne

The two story guest cottage with original spiral staircase was originally Oliver Wendell Holmes Private billiard house for entertaining guests.

The cottage includes original hardwood floors, Mitsubishi split system with independent climate controlled central air and heating. Kitchen with exotic granite and high end appliances subzero, TV including streaming options. Serta iComfort mattress with luxurious 1000tc Egyptian cotton linens, Tufted leather chesterfield sofa bed, Trails, tennis, pool, reflecting pond, river frontage. Clothing optional when using pool

I have security camera(s) outside of my place

How the beds work

Bedroom1 King Size Bed

Little Luxuries

Gym nearby or in the property
Wi-Fi
Pool
Parking
Air conditioning
Kitchen
Heating
Dishwasher
TV
The Classics
Wi-Fi
Kitchen
Pool
Air conditioning
TV
Terrace
Essentials
Hair dryer
Dishwasher
Iron
Heating
Outdoor dining area
Parking
LGBTQ+ Favorites
Adult Only
Gym nearby or in the property
Spa salon nearby
My location
Countryside
Near lake
Near mountains
Fire protection
Smoke alarm
Carbon monoxide alarm
Fire extinguisher

Meet Your Proud Host

Michael5.0(1 review)
E-mail verifiedPhone verifiedID verified
Member sinceAug. 2019
Response rate100%
Response time< 12h
We enjoy hosting guests at our historic cottage. Love to make guests feel at home
View profile

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September 2026
SMTWTFS
October 2026
SMTWTFS

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Where It's All Happening

Pittsfield, Massachusetts, United StatesExact location disclosed after booking only.
LGBTQ+ Safety Score: Pittsfield
5out of 5Very safeRated by 1 local misterb&b members

Nearby Attractions

The property is very peaceful and the location couldn't be more convenient for shopping and restaurants nearby in Pittsfield, the country seat of the Berkshires and for quickly driving to nearby sights in Lenox, Stockbridge, and Lee to the south or Mt Greylock to the north. Tranquil location convenient to the theaters. Close to Tanglewood, Jacobs’ Pillow, Shakespeare and Co, Restaurants, cafés, shopping centers, museums, Private wooded property close to downtown Pittsfield on a private road. Canoe meadows conservation area is within walking distance for nature walks. Tanglewood music center is 10 minute drive as well as all that historic Lenox and the Berkshires has to offer.

House Rules & Conditions

Check-infrom 3pm to 10pm
Checkoutto 12pm
Host recommendations

Welcome to Holmesdale, we hope you enjoy your stay with us. We ask you please take time to go over our house manual. If you have any questions or concerns please feel free to contact us. 1. Upon arrival please call or message to inform us you have arrived, we will advise you how to proceed to the guest cottage with your personal one time stay entry code to begin your stay. 2. Please use the parking spots available on the left side of the main house by the cottage entrance gate 3. Sign and return the property liability waiver upon arrival. All guest are required to sign a waiver of liability upon arrival due to the on-site swimming pool and expansive 16 acre river front property. 4. WiFi username and password are posted on the wall next to the entry door. 5. Brochures of area shops, restaurants and activities are available in the cottage for your convenience. 6. The smart TV in the guest cottages has apps installed. To watch cable television please select the spectrum app from the menu . In addition for your convenience you may log in to any app of your choice installed with your own ******** log out when done ie (Amazon, Netflix, Hulu). 7. Air fresheners, stovetop and countertop cleaners are located under the kitchen sink. 8. Shampoo, conditioner and body wash are in the dispenser inside the shower. 9. Please be sure to close any gate after entering or leaving. 10. Please only wear tennis shoes on the tennis court. 11. Tennis rackets are available for guest use inside the gazebo located by the tennis court. We ask you please return them to the proper location when done using. 12. We ask you please supervise children at all time throughout your stay. Children are not to be left alone and unsupervised at the swimming pool, in the guest cottage or on the property at anytime. 13. Please do not flush anything but toilet paper. All feminine hygiene products must be discarded in proper waste receptacle. 14. Proper swimming attire/ clothing optional for pool use. Swimming pool hours are between 9 AM and 9 PM. 16. Please be sure stove is off before leaving the cottage. 17. We ask guests to keep the kitchen ceiling fan on while cooking and not fry fish of any kind for the courtesy of all future guest. 18. We ask you please keep doors and windows closed while using the air conditioning/heating systems. 19. Makeup, face creams, and tanning products will stain towels and bed linens. Please remove makeup using only the dark makeup towel provided. 20. Trash pick up is on Fridays. Because of local wildlife we ask you to please keep all garbage inside the until the end of your stay or contact your hosts If needed.

Extra per guest$50 per night after 2 guest(s)

$50 per night after 2 guest(s)

Minimum stay (nights)2 nights

2 nights

Cleaning fees$80 USD

$80 USD

Deposit$250 USD

$250 USD

Massachusetts certificate numberC0748295168

C0748295168

Cancellation Policy

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ReviewsExceptional5(1)

Reviews come from verified guests, are sorted chronologically and not subjected to prior monitoring.

Cleanliness5.0
Location5.0
Accurate description5.0
Check-in5.0
Value for money5.0

Our Community Has Spoken:

JosephStayed in August 2025
Reviewed on Aug. 12, 2025

Lovely spot to stay in the Berkshires. The pool was great and the hosts are very nice. There's a lot to do in the area and the cottage was very comfortable.

Response from Michael
Aug. 13, 2025

We enjoyed hosting you both. Visit next time you come to the Berkshires

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