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Our top choices for Chester bed & breakfast

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (424 reviews)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
$102 nightly
The price is $116
Jan 19 - Jan 20
Total with taxes and fees
Naomi's Inn Bed & Breakfast

Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (501 reviews)
"Loved our stay! "
United States
Jay
$199 nightly
The price is $223
Jan 29 - Jan 30
Total with taxes and fees
Old Mill Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
$139 nightly
The price is $155
Jan 18 - Jan 19
Total with taxes and fees
Lakehouse Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
$190 nightly
The price is $212
Jan 19 - Jan 20
Total with taxes and fees
Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
$339 nightly
The price is $379
Jan 19 - Jan 20
Total with taxes and fees
Devonfield Inn B&B

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$384 nightly
The price is $429
Jan 18 - Jan 19
Total with taxes and fees
33 Main

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$291 nightly
The price is $333
Feb 1 - Feb 2
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$335 nightly
The price is $374
Feb 15 - Feb 16
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$291 nightly
The price is $333
Feb 1 - Feb 2
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$308 nightly
The price is $352
Feb 1 - Feb 2
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
$326 nightly
The price is $373
Feb 1 - Feb 2
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
$206 nightly
The price is $218
Jan 21 - Jan 22
Total with taxes and fees
Harbour House Inn

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$346 nightly
The price is $395
Feb 1 - Feb 2
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay

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

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
$432 nightly
The price is $494
Feb 1 - Feb 2
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$470 nightly
The price is $525
Feb 1 - Feb 2
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

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

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
$524 nightly
The price is $599
Feb 1 - Feb 2
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$524 nightly
The price is $599
Feb 1 - Feb 2
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
$174 nightly
The price is $198
Jan 16 - Jan 17
Total with taxes and fees
Brook Farm Inn

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
$161 nightly
The price is $179
Feb 1 - Feb 2
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
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.
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Top Chester Hotel Reviews

Find out more about Chester

Chester B&B information

Number of reviews
2,625
Accommodation
32 B&B
Lowest Price
$116
Highest Price
$599

Frequently asked questions

What is the nightly rate for a B&B in Chester?
Prices for B&Bs in Chester often vary, but you can find a great deal from $116 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Chester?
The best time to book a B&B in Chester is during the summer months, particularly from June to August. This vibrant season attracts visitors eager to enjoy the picturesque lakes, hiking trails, and outdoor activities that Chester has to offer. With warm weather and long daylight hours, it's an ideal time for families and adventure seekers to explore the natural beauty of the area.

July stands out as the peak month, bringing a lively atmosphere filled with community events, festivals, and a bustling local scene. Travelers can partake in activities such as kayaking on Lake Almanor or hiking in the nearby Lassen National Forest, all while basking in pleasant temperatures that typically range from the mid-60s to high 80s Fahrenheit.

If you're looking for a more budget-friendly option, consider visiting in September. This transitional month allows you to enjoy milder weather and fewer crowds, making it great for a peaceful getaway. You can still experience the stunning scenery, with early fall colors beginning to emerge, creating an enchanting backdrop for outdoor adventures.
What is the difference between a Chester B&B and a hotel?
Every Chester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chester B&Bs.

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