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B&B in Chester

The Ellery

3.5 star property
9.2 out of 10, Wonderful, (787)
"Wonderful breakfast and cute and cozy lobby "
$134 nightly
The price is $150
Aug 18 - Aug 19
Total includes taxes and fees
The Ellery

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Lovely place. Excellent staff, Wonderful breakfast."
$163 nightly
The price is $182
Sep 1 - Sep 2
Total includes taxes and fees
The Cornell Inn, Lenox & The Berkshires

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (406)
"We had a great stay and breakfast was delicious!"
$113 nightly
The price is $128
Aug 17 - Aug 18
Total includes taxes and fees
Naomi's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (480)
"Nice quaint out of the ordinary vacation experience. "
$182 nightly
The price is $203
Aug 14 - Aug 15
Total includes taxes and fees
Whistler's Inn Bed & Breakfast

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (488)
"The staff were very polite and accomodatin"
$235 nightly
The price is $262
Aug 19 - Aug 20
Total includes taxes and fees
Old Mill Inn

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (277)
"Great Views & Hospitality"
Lakehouse Inn

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (156)
"Wonderful cozy and warm feel. Property, location and service are all excellent."
$254 nightly
The price is $284
Sep 3 - Sep 4
Total includes taxes and fees
Brook Farm Inn

Tanglewood Suites

2.5 star property
7.4 out of 10, Good, (18)
"Made a Friday night reservation for their 2BR suite in August. When we arrived at the location listed on Expedia, we found ourselves in a residential neighborhood with no "Tanglewood Suites" in sight. I had emailed in advance for clarification on the location but didn't get a reply. We called the place and the proprietor said there was no record of a reservation and that she never rents for one night only. We were left high and dry with no reasonably priced play to stay in the area. "
$269 nightly
The price is $269
Aug 14 - Aug 15
Total includes taxes and fees
Tanglewood Suites

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
33 Main

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (46)
"The area is lovely and this building is full of history but they have managed to fit modern air-conditioning into this 226 year old building. "
$270 nightly
The price is $302
Aug 17 - Aug 18
Total includes taxes and fees
Daniel Stebbins House

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
$250 nightly
The price is $279
Aug 14 - Aug 15
Total includes taxes and fees
Chambery Inn

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!! "
$244 nightly
The price is $258
Sep 8 - Sep 9
Total includes taxes and fees
Harbour House Inn

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
$425 nightly
The price is $475
Aug 26 - Aug 27
Total includes taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
$309 nightly
The price is $345
Sep 1 - Sep 2
Total includes taxes and fees
Devonfield Inn B&B

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

$234 nightly
The price is $301
Sep 1 - Sep 2
Total includes taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (69)
"Dahlia is great. Excellent accommodation. We walked to Tanglewood "
Eastgate Inn B&B

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
The Red Door B&B

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

$465 nightly
The price is $559
Sep 1 - Sep 2
Total includes taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.

Chesapeake Inn of Lenox

3.0 star property
7.4 out of 10, Good, (8)
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"
Chesapeake Inn of Lenox
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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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 $128 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.