Winthrop Estate – An Elegant Home | Villa in Lenox

10.0 (2 Reviews) |   12 Bedrooms  10 Bathrooms  24 Guests
Lenox Villa | Winthrop Estate – An Elegant Home

12 Bedroom Villa in Lenox

Summary:
I’m Jamie, the proud steward of the timeless, beautiful Winthrop Estate, a restored 1920s mansion that blends historic charm with modern luxury. Perfect for groups, it features luxurious bedrooms, a chef’s kitchen, modern amenities & elegant gathering spaces– an ideal retreat for creating lasting memories.
Please note: By prior approval, we welcome special celebrations that include only resident guests, for up to 24. Events for more than 24 and outdoor amplified music are not permitted. Pre-wedding hair, makeup, photography, and special meals for resident guests are welcome.
The Space:
Thoughtfully renovated with modern touches, this jewel is set on 45 acres and offers the perfect blend of charm and convenience.
Location Highlights:
- Less than a mile from the center of Lenox, with its vibrant restaurants, cafes, bars, shops, and galleries.
- Within a mile of Kennedy Park, a 500-acre hardwood forest featuring:
- 15 miles of groomed trails for hiking, cross-country skiing, and picnics.
- A lookout point with breathtaking mountain vistas.
- Just 1.5 miles from Tanglewood’s front gate, making it an ideal, centrally located property.
Onsite Amenities:
- Grand Social Spaces:
- A purple-heartwood-paneled library.
- A plant-filled conservatory.
- Chef’s Kitchen:
- Fully equipped with a 10-burner Wolf stove and a suite of Wolf appliances.
- Outdoor Features:
- BBQ grill, fire pit, and stove.
- Whiffle ball and lawn croquet.
- Acres of hiking trails.
- Recreation & Workspaces:
- Game room with ping pong, foosball, Legos, and board games.
- Dedicated workstation with an external monitor and powered standing desk.
- EV charger compatible with all vehicle types
Accommodations:
- 7 main bedrooms comfortably accommodate 14 guests.
- 5 additional standard bedrooms with a shared bathroom can host 10 more guests.
- Total capacity: 24 guests.
- A dining room with seating for up to 24 people.
Please note: By prior approval, the Winthrop Estate welcomes special celebrations for up to 24 guests only. These are limited in scope and must follow our house rules. Large events, parties, and amplified music are not permitted. Pre-wedding preparation such as hair, makeup, photography, and curated meals for resident guests are always welcome.
Enjoy the perfect mix of historic elegance and modern comfort at the Winthrop Estate.
Other Things to Note:
To ensure a seamless and secure experience, all guests will be screened prior to check-in and asked to sign a house rules agreement.
Please keep in mind that the Winthrop Estate is nestled in the scenic countryside of Lenox. While we strive to maintain a clean and comfortable environment, the natural surroundings may include occasional encounters with flies and other wildlife. This is part of the charm of country living, and we appreciate your understanding.
We look forward to hosting you at the Winthrop Estate!
Interaction with Guests:
Once you have made your booking, we will give you our contact information and you can reach us before and during your stay. We are happy to share local information and house history.

Winthrop Estate – An Elegant Home is located in Lenox. Winthrop Estate – An Elegant Home provides accommodation, featuring Parking, Barbecue/Outdoor Cooking, Kitchen, among other amenities. This Villa features Parking, Barbecue/Outdoor Cooking, Kitchen, to make your stay a comfortable one.

Winthrop Estate – An Elegant Home has 12 Bedrooms , 10 Bathrooms, and max occupancy of 24 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 Villa because of the excellent services rendered by the owner or manager of this Villa, 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. Villa has a friendly neighborhood, and the Lenox has interesting places to visit. If you want to learn more about the Villa in Lenox, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

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

Policies

Check-in
Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out
Check-out before 11:00 am
Child Policy
Children are welcome.
Pet Policy
Pets not allowed

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 onsite parties or group events are strictly prohibited property registration number c0378281520 safety features at this property include a fire extinguisher and a first aid kit 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: C0378281520

Reviews

Jim T.
Sep 3, 2025 11:52:46 PM
Review Score:   10
Summary: Wonderful for our extended family gathering. Interesting opportunity to stay in a home from the Gilded Age, yet one equipped with all the modern conveniences. Jamie was an excellent and very responsive host, who provided great recommendations for local farmstands, kayaking, and bakery. Lots of spots for gathering in large groups, small groups and quiet time away from groups. The property had everything we needed (and then some). The yard was great for the 5-year and the rest of us to play lots of games (many provided with the property).
See All Reviews

FAQ's

Is this Lenox villa pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Lenox villa have a swimming pool?

No, this Lenox villa 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 Lenox villa?

Best-rates for the Lenox villa starts from $4,573 per night with includes Guest Services, Child Friendly, Balcony/Terrace, Wellness Facilities, Bedding/Linens, Fireplace/Heating, Internet, Air Conditioner, TV, Entertainment, Laundry, Security/Safety, Sports/Activities, Kitchen, Parking, Barbecue/Outdoor Cooking with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Lenox villa 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 villa Good or guests have recommended them suitable for families. As reported by the owner or manager, the villa has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Lenox villa wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Lenox villa 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 Lenox villa?

Based on the information reported by the owner or manager, the Lenox villa indicates 1 day stay policy at this villa. 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 Lenox villa?

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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