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Book Chester Bed & Breakfast

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    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 10 - Oct 12
In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30

B&B in Chester

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
$163 nightly
The price is $182
Oct 28 - Oct 29
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Naomi's Inn Bed & Breakfast
Room (Louis XIV) | 2 bedrooms, individually decorated, individually furnished

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (416)
"Great host and breakfast was excellent."
$115 nightly
The price is $130
Oct 6 - Oct 7
Total with taxes and fees
Naomi's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (493)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
$158 nightly
The price is $177
Nov 2 - Nov 3
Total with taxes and fees
Whistler's Inn Bed & Breakfast
Old Mill Inn
Room, River View (The Williamsburg Suite) | Private kitchen | Coffee/tea maker, cleaning supplies, paper towels

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (497)
"Loved our stay! "
$264 nightly
The price is $295
Oct 28 - Oct 29
Total with taxes and fees
Old Mill Inn
Daniel Stebbins House
Exterior

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (47)
"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
Oct 5 - Oct 6
Total with taxes and fees
Daniel Stebbins House
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
Tanglewood Suites
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
$250 nightly
The price is $279
Oct 6 - Oct 7
Total with taxes and fees
Chambery Inn
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
$179 nightly
The price is $200
Nov 1 - Nov 2
Total with taxes and fees
Brook Farm Inn
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (283)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
$175 nightly
The price is $196
Nov 2 - Nov 3
Total with taxes and fees
Lakehouse Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

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 "
$335 nightly
The price is $374
Oct 20 - Oct 21
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (52)
"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!! "
$247 nightly
The price is $262
Oct 30 - Oct 31
Total with taxes and fees
Harbour House Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
$379 nightly
The price is $423
Oct 5 - Oct 6
Total with taxes and fees
Devonfield Inn B&B
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
3 bedrooms, bed sheets

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

$232 nightly
The price is $299
Oct 28 - Oct 29
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (71)
"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! "
$449 nightly
The price is $502
Nov 2 - Nov 3
Total with taxes and fees
33 Main
Eastgate Inn B&B
Porch

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 Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
$388 nightly
The price is $434
Nov 2 - Nov 3
Total with taxes and fees
The Inn at Stockbridge
The Red Door B&B
Interior

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."
$270 nightly
The price is $302
Oct 27 - Oct 28
Total with taxes and fees
The Red Door B&B
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

$285 nightly
The price is $358
Oct 28 - Oct 29
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

$267 nightly
The price is $338
Oct 28 - Oct 29
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Fireplace

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

$458 nightly
The price is $551
Oct 9 - Oct 10
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
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

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"All that was needed is a Hot tub for these elderly bones and raise the temperature in the pool "
Frederick 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Springfield MA

Find out more about Chester

Find out more about Chester

Chester B&B information

Number of reviews
3,043
Accommodation
32 B&B
Lowest Price
$130
Highest Price
$551

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 $130 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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