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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, (428 reviews)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
$101 nightly
The price is $115
Mar 15 - Mar 16
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, (503 reviews)
"Clean facilities, beautiful aesthetic, attentive staff, quiet area, tasty breakfast."
United States
Scarlett
$179 nightly
The price is $200
Mar 4 - Mar 5
Total with taxes and fees
Old Mill Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (293 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
$139 nightly
The price is $155
Mar 14 - Mar 15
Total with taxes and fees
Lakehouse Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
$190 nightly
The price is $212
Mar 3 - Mar 4
Total with taxes and fees
Chambery Inn

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
$251 nightly
The price is $280
Mar 13 - Mar 14
Total with taxes and fees
The Inn at Stockbridge

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
$329 nightly
The price is $367
Mar 3 - Mar 4
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
$469 nightly
The price is $524
Mar 5 - Mar 6
Total with taxes and fees
33 Main

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)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
$335 nightly
The price is $374
Mar 16 - Mar 17
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
$253 nightly
The price is $290
Mar 3 - Mar 4
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
$327 nightly
The price is $374
Mar 3 - Mar 4
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$253 nightly
The price is $290
Mar 3 - Mar 4
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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
$238 nightly
The price is $252
Mar 12 - Mar 13
Total with taxes and fees
Harbour House Inn

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
$346 nightly
The price is $395
Mar 3 - Mar 4
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$365 nightly
The price is $418
Mar 3 - Mar 4
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
$452 nightly
The price is $516
Mar 3 - Mar 4
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
$487 nightly
The price is $544
Mar 3 - Mar 4
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
$543 nightly
The price is $621
Mar 3 - Mar 4
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
$543 nightly
The price is $621
Mar 3 - Mar 4
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,002 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
$137 nightly
The price is $154
Mar 3 - Mar 4
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

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
$153 nightly
The price is $174
Mar 3 - Mar 4
Total with taxes and fees
Brook Farm 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

Find out more about Chester

Chester B&B information

Number of reviews
3,238
Accommodation
32 B&B
Lowest Price
$115
Highest Price
$621

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 $115 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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