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Chesapeake Inn of Lenox

Property class: 3

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Photo gallery for Chesapeake Inn of Lenox

A house with a blue front door, a wreath above it, and two American flags on the roof. - Chesapeake Inn of Lenox (Lenox)
A dining area with a wooden table set for four, blue placemats, and a lamp. - Chesapeake Inn of Lenox (Lenox)
A swimming pool with a grassy area and lounge chairs. - Chesapeake Inn of Lenox (Lenox)
A table and four chairs in a grassy outdoor area. - Chesapeake Inn of Lenox (Lenox)
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall. - Chesapeake Inn of Lenox (Lenox)
Located close to Tanglewood Music Center and Frelinghuysen Morris House and Studio, Chesapeake Inn of Lenox provides free cooked-to-order breakfast, an adjacent golf course, and a terrace. Stay connected with free in-room WiFi, and guests can find other amenities such as a garden and dry cleaning/laundry services.

Reviews

7.4 out of 10
Good

Popular amenities

  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant

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Skip the crowds, keep the savings. AARP members save more after Labor Day. Book by Oct 7, 2026.

Room options

Available filters for rooms
Showing 2 of 2 rooms

View all photos for Double Room, Private Bathroom, Garden View

A bedroom with a bed, a nightstand, a dresser, a window with curtains, and a painting on the wall.

Double Room, Private Bathroom, Garden View

  • Garden view
  • 21 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Triple Room, Private Bathroom, Garden View

A bedroom with a bed, a window with curtains, a guitar, and a door.

Triple Room, Private Bathroom, Garden View

  • Garden view
  • 22 sq m
  • Sleeps 3
  • 1 Queen Bed and 1 Twin Bed

About the neighborhood

Located in Lenox, Chesapeake Inn of Lenox is next to a golf course and near the beach. Ventfort Hall Mansion and Gilded Age Museum and The Mount are notable landmarks, and if an activity is on the agenda, check out Wyndhurst Golf & Club. Tanglewood Music Center and Lenox Library are two other places to visit that come recommended. Spend some time exploring the area's activities, including skiing. Visit our Lenox travel guide
View more B&B in Lenox
Map
210 West Street, P.O. Box 1920, Lenox, MA, 01240

What's nearby

  • A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.
    Tanglewood Music Center
    5 min walk - 0.3 miles
  • A large white mansion surrounded by dense green trees and a clear blue sky with clouds.
    The Mount
    6 min drive - 3.1 miles
  • A calm river surrounded by autumn foliage.
    Norman Rockwell Museum
    13 min drive - 7.3 miles
  • Lenox Library
    3 min drive - 1.2 miles
  • Stockbridge Bowl
    3 min drive - 1.8 miles

Getting around

  • Pittsfield Intermodal Transportation Center
    15 min drive
  • Albany Intl. Airport (ALB)
    57 min drive

Restaurants

  • Antimony Brewing - Craft Brewery & Kitchen
    6 min drive
  • Tanglewood Cafe
    16 min walk
  • Lenox Coffee
    3 min drive
  • Bistro Zinc
    3 min drive
  • Firefly
    3 min drive

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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free area shuttle
  • Free self parking on site
  • Wheelchair-accessible parking available

Food and drink

  • Free cooked-to-order breakfast available daily
  • A restaurant

Things to do

  • Outdoor pool
  • Outdoor tennis court

Conveniences

  • 24-hour front desk
  • Free newspapers in lobby
  • Laundry facilities
  • Luggage storage

Guest services

  • Concierge services
  • Dry cleaning/laundry service
  • Housekeeping (daily)
  • Tour and ticket assistance

Business services

  • Business center
  • Meeting room

Outdoors

  • Barbecue grill
  • Garden
  • Picnic area
  • Terrace

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Wheelchair-accessible parking

More

  • 1 building
  • 2 floors
  • Built in 1845
  • Smoking not allowed

Room amenities

Bathroom

  • Free toiletries
  • Hair dryer (on request)
  • Private bathroom
  • Shower/bathtub combination
  • Towels provided

More

  • Air conditioning
  • Free daily newspapers
  • Iron/ironing board on request

Policies

Check-in

Check-in start time: noon; Check-in end time: midnight

Minimum check-in age: 18

Check-out

Check-out before 11:00 AM

Special check-in instructions

Front desk staff will greet guests on arrival at the property

Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

Pets stay free

Service animals are welcome, and are exempt from fees

Children and extra beds

Children younger than 12 are not allowed at this adults-only property; all guests 12 and older are welcome

Rollaway/extra beds are not available

Cribs (infant beds) are not available

Property payment types

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
Tax ID - C0009171520
This property accepts credit cards

We should mention

Guests under 12 years old are not permitted at this adults-only property

Frequently asked questions

Does Chesapeake Inn of Lenox have a pool?

Yes, this property has an outdoor pool.

Is Chesapeake Inn of Lenox pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Self parking is free at this property.

What time is check-in at Chesapeake Inn of Lenox?

Check-in start time: noon; Check-in end time: midnight.

What time is check-out at Chesapeake Inn of Lenox?

Check-out is at 11:00 AM.

Where is Chesapeake Inn of Lenox located?

Situated in Lenox, this golf bed & breakfast is within 1 mi (2 km) of Tanglewood Music Center, Frelinghuysen Morris House and Studio, and Lenox Library. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 3 mi (5 km).

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Reviews

Chesapeake Inn of Lenox Reviews

7.4

Good

7.2

Cleanliness

9.4

Location

9.6

Staff & service

7.0

Property conditions & facilities
Rating 10 - Excellent. 3 out of 8 reviews
Rating 8 - Good. 0 out of 8 reviews
Rating 6 - Okay. 4 out of 8 reviews
Rating 4 - Poor. 1 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

Reviews

Verified review

6/10 Okay

Verified traveler

Liked: Staff & service
Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive
Stayed 1 night in Oct 2019
Verified review

10/10 Excellent

Vincent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Location, location, location

John the Innkeeper is overly accommodating and offers terrific advice. The location couldn't be better and Lenox (downtown) is charming.
Stayed 2 nights in Aug 2019
Verified review

4/10 Poor

Anna

Liked: Staff & service
Disliked: Cleanliness, property conditions & facilities
The goodwill of the property owner does not outweigh the downsides of the property, unfortunately. The owner is kind, attentive, and very responsive. The bed had springs that you could feel (the owner did make an attempt to rectify this but it didn't happen in time for our stay). There is dirt in just about every corner of the house; the kitchen is not up to restaurant cleanliness standards. There is trash in the yard, broken pots near front door, and dirt on front porch (first impressions count). There is a continuing musty odor that is strong when you enter. Part of the upstairs bathroom sink is falling apart at the side. I feel bad for reporting this as the owner was so kind and thoughtful but I cannot justify giving this even 3 stars. It is close to Tanglewood however and the owner know the town very well. I would not stay here again.
Stayed 3 nights in Jun 2019
Verified review

6/10 Okay

Elizabeth

Liked: Staff & service
Disliked: Cleanliness, property conditions & facilities, room comfort
The host of the Inn couldn't be more nice and accommodating but the Inn and the rooms could really use a good dusting/cleaning and overall update. That being said, it is extremely well located to Tanglewood.
Stayed 1 night in Aug 2018
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Excellent service
Verified review

6/10 Okay

Verified traveler

Liked: Staff & service
Disliked: Room comfort

Clean and basic B & B close to Tanglewood grounds

Rooms are in a renovated older house. They are a little small, so the rooms themselves are not meant for lingering, although there is a living-room sized sitting room on the ground floor. The place is a little hard to find from the main road if you haven't been there before.
Verified review

6/10 Okay

Verified traveler

Stayed 1 night in Jul 2019
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Jul 2018