Find a Bed and Breakfast in Cherry Plain from CA $176

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Cherry Plain B&B

The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is CA $176
CA $250 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
The Trail in Adams - Berkshires’ Art Hotel
Cozy cabin with a spacious living area, featuring a glass-top table and comfortable seating, and a separate kitchen area with a refrigerator and microwave.

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (132)
"Stayed only one night Very cosy, quiet place "
The price is CA $258
CA $288 total
includes taxes & fees
Aug 11 - Aug 12
The Trail in Adams - Berkshires’ Art Hotel
Gardner Farm Inn
Stroll through the serene garden, surrounded by a variety of flowering plants and a large tree.

Gardner Farm Inn

3.5 star property
10.0 out of 10, Exceptional, (187)
"John is a most welcoming host! Always good to return to the Gardner Farm Inn. Beautiful outdoor garden and patio space and wonderful comfortable artistically decorated rooms. Highly recommend!"
The price is CA $199
CA $221 total
includes taxes & fees
Sep 8 - Sep 9
Gardner Farm Inn
Inn at Silver Maple Farm
Set amidst lush greenery, this multi-story property features distinct buildings with gabled and flat roofs.

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (91)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
The price is CA $288
CA $322 total
includes taxes & fees
Sep 2 - Sep 3
Inn at Silver Maple Farm
Olde Judge Mansion
Step into the historic charm of the Old Judge Mansion, a welcoming bed and breakfast with a traditional atmosphere.

Olde Judge Mansion

2.0 star property
8.8 out of 10, Excellent, (240)
"My two daughters and I enjoyed a wonderful stay at Olde Judge Mansion. Tina is an awesome proprietor who made us feel comfortable and prepared a good breakfast in the morning. This is a unique and memorable place to stay and is much more interesting than a chain hotel. We loved it!"
The price is CA $193
CA $215 total
includes taxes & fees
Sep 8 - Sep 9
Olde Judge Mansion
Harbour House Inn
Stunning traditional architecture with a central entrance and beautifully landscaped surroundings.

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is CA $325
CA $344 total
includes taxes & fees
Aug 21 - Aug 22
Harbour House Inn
Berkshire Mountain House
Enjoy meals in the kitchen with a dining table and chairs, microwave, toaster, and stove.

Berkshire Mountain House

3.0 star property
9.4 out of 10, Exceptional, (26)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House
Inn at Kenmore Hall
Guests can enjoy a peaceful atmosphere in this elegant space, featuring a console table with decorative items, a potted plant, and a framed photograph.

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"This is a beautiful property straight out of a magazine. Service was impeccable"
Inn at Kenmore Hall
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Cozy retreat with a dresser, comfortable bed, and a warm throw blanket.

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

The price is CA $285
CA $411 total
includes taxes & fees
Sep 1 - Sep 2
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Elegant suite with a king bed, fireplace, and kitchenette.
Relax in this stylish living room with a large coffee table, two sofas, and a fireplace.

Elegant suite with a king bed, fireplace, and kitchenette.

The price is CA $561
CA $760 total
includes taxes & fees
Sep 1 - Sep 2
Elegant suite with a king bed, fireplace, and kitchenette.
Historic Susan B. Anthony Room - Cozy & Charming Stay
Step outside to a serene outdoor space with a deck, Adirondack chairs, and a charming playhouse.

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is CA $351
CA $494 total
includes taxes & fees
Sep 1 - Sep 2
Historic Susan B. Anthony Room - Cozy & Charming Stay
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Relax in a stylish room with a comfortable bed, a small table, and a dresser, plus a large mirror and artwork on the wall.

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

The price is CA $450
CA $622 total
includes taxes & fees
Sep 1 - Sep 2
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Cozy Carriage House room with a double bed and private balcony
Cozy retreat with a neatly made bed, bedside table, and elegant mirror.

Cozy Carriage House room with a double bed and private balcony

The price is CA $329
CA $466 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Carriage House room with a double bed and private balcony
Experience Timeless Elegance in The Edith Wharton Room!
Cozy retreat with a large bed, dresser, desk, and TV.

Experience Timeless Elegance in The Edith Wharton Room!

The price is CA $285
CA $411 total
includes taxes & fees
Sep 1 - Sep 2
Experience Timeless Elegance in The Edith Wharton Room!
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Relax in a serene bedroom with a tufted headboard, desk, and dresser, perfect for work and rest.

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is CA $495
CA $677 total
includes taxes & fees
Sep 2 - Sep 3
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Relax in this stylish living room with a lofted area, sofa, coffee table, and floor lamp, offering a comfortable space to unwind.

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

The price is CA $561
CA $760 total
includes taxes & fees
Sep 1 - Sep 2
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Elegant Carriage House room with a queen bed and private patio.
Cozy retreat with a large bed, dresser, and table, set amidst classic floral wallpaper and a decorative ceiling.

Elegant Carriage House room with a queen bed and private patio.

The price is CA $307
CA $439 total
includes taxes & fees
Sep 3 - Sep 4
Elegant Carriage House room with a queen bed and private patio.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cherry Plain Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Reallt liked the property. Great location. Would suggest more comfortable chairs outside."
Susan 6-night trip
Posted 1 day ago
Berkshire Mountain Lodge