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Chesapeake Inn of Lenox

Traveler (3)
Room & Suite (9)
Dining (2)


The Chesapeake Inn of Lenox features: Four guestrooms with full, private, ceramic tiled baths; Three guestrooms with queen-sized beds; One guestroom with a queen-sized bed; and a twin-sized, custom built murphy bed; Central air-conditioning in the guest rooms; Free WI-FI HOTSPOT: High-speed, wireless, internet access; a 75 foot, in-ground, heated, lap pool. We pride ourselves on the personal services provided to our guests. For example, your full "Whatever You Want and Whenever You Want" breakfast will include your personal selections. Snacks are provided throughout the day and evening. During the summer season, fresh cut flowers are in each room, and every room has 2 windows with flowered window boxes. You are encouraged to use the grounds and barbecue. On Saturday evenings, we offer a complimentary BBQ during the summer season. It is only 1/4 mile from the Chesapeake Inn to Tanglewood's East Gate. This is an easy stroll for most people. It is 1 mile to the center of Lenox. It is less than 1 mile to Kripalu.
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Property amenities
Free High Speed Internet (WiFi)
Breakfast included
Free parking
Breakfast Available
Business Center with Internet Access
Laundry Service
Meeting rooms
Non-smoking hotel
Public Wifi
Shuttle Bus Service
Wheelchair access
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Room features
Air conditioning
Non-smoking rooms
Good to know
Hotel links
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Hotel virtual tour
3Room tips
Traveler rating
  • 13
  • 4
  • 1
  • 2
  • 3
Time of year
Traveler type
  • Filter
  • English
Popular mentions
The host was very accommodating and eager to help. So nice to not have to fit into a defined breakfast schedule. One morning we didn't eat until 11:00, and on the day of departure day we ate at 06:30.
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Could not be a more convenient place to stay when attending an event at Tanglewood, where one entrance is practically across the street. John was a kind, thoughtful host, and let us check in a bit early so we could make the performance. Lovely house, clean room, and incredibly
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Response from ChesapeakeInn, Owner at Chesapeake Inn of Lenox
Responded Sep 5, 2018
Thank-you, Theresa, for the kind words. It is very gratifying when our efforts to provide a fond memory are recognized. We'll be sure to forward the Tanglewood 2019 schedule as soon as it is announced. Happy Holidays!
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John is a very nice man but his place is “past due” as they say. It does smell musty so if you have allergies you do not want to stay here. It is perfectly located for Tanglewood so if shabby and not even remotely chic is ok with you it would work. I did honestly worry about
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Nice, short walk to Tanglewood. A lovely room, thoughtful and knowledgable host, custom ordered breakfast all made our visit extra pleasant. Loved the private bathroom! I would strongly recommend! Thank you, John!
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Response from ChesapeakeInn, Owner at Chesapeake Inn of Lenox
Responded Jul 23, 2018
Thank-you, Ann Marie. We're very glad that you have a fond memory.
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The Inn is very conveniently located to Tanglewood which attracted us. Thanks for all of hospitality to the Innkeeper John who was very personable and shared with us special knowledge of Tanglewood. The room was comfortable and pleasant with a working WiFi and John prepares
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Response from ChesapeakeInn, Owner at Chesapeake Inn of Lenox
Responded Jul 23, 2018
Thank-you very much, Antonina. Your thoughts are definitely appreciated. Hopefully you'll allow us to serve you in the future.
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Album Categories
All photosTravelerRoom & SuiteDining Pool & BeachFamily and Play Areas
One of the mirrors in the Inn.
This is from the room that made me feel the sickest!
This is just a small sample of the dust and mold in this hotel.
Photo provided by managementChesapeake Inn of Lenox
queen-sized bed + twin-sized murhy bed, central air-conditioning, 2 windows with flower boxes
Photo provided by managementChesapeake Inn of Lenox
queen-sized bed, central air-conditioning, 2 windows with flower boxes
"The front bedroom second floor is perfect, private and we could "people watch" everyone going to and from Tanglewood!"
"Each of the rooms are different. When you call John, he can describe each one for you."
"John can let you know which rooms are bigger, more private, etc. Just ask. :-)"
$222 - $446 (Based on Average Rates for a Standard Room)
United StatesMassachusettsBerkshiresLenox
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