Photo by Elizabeth Massa Peroulakis

Book Chester Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

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

Check prices for these dates

Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7
In one month
Dec 19 - Dec 21
In two months
Jan 16 - Jan 18

B&B in Chester

Room (Louis XIV) | 2 bedrooms, individually decorated, individually furnished
Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast

3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (421)
"Simple yet delicious and well executed breakfast. Perfectly cooked eggs. "
United States
Donna
$112 nightly
The price is $127
Nov 19 - Nov 20
Total with taxes and fees
Naomi's Inn Bed & Breakfast
Room, River View (The Williamsburg Suite) | Private kitchen | Coffee/tea maker, cleaning supplies, paper towels
Old Mill Inn

Old Mill Inn

3.0 star property
Hatfield
9.4 out of 10, Exceptional, (499)
"Loved our stay! "
United States
Jay
$219 nightly
The price is $245
Nov 20 - Nov 21
Total with taxes and fees
Old Mill Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
$190 nightly
The price is $212
Nov 19 - Nov 20
Total with taxes and fees
Chambery Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
United States
Roberta
$181 nightly
The price is $202
Nov 20 - Nov 21
Total with taxes and fees
Lakehouse Inn
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
$150 nightly
The price is $168
Nov 21 - Nov 22
Total with taxes and fees
Whistler's Inn Bed & Breakfast
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
$263 nightly
The price is $294
Nov 20 - Nov 21
Total with taxes and fees
The Inn at Stockbridge
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$441 nightly
The price is $493
Dec 3 - Dec 4
Total with taxes and fees
33 Main
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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

Lenox
$239 nightly
The price is $306
Nov 19 - Nov 20
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
$369 nightly
The price is $412
Nov 21 - Nov 22
Total with taxes and fees
Devonfield Inn B&B
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
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."
United States
Elizabeth
$219 nightly
The price is $219
Dec 1 - Dec 2
Total with taxes and fees
Tanglewood Suites
Business center
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)
"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
$414 nightly
The price is $462
Dec 2 - Dec 3
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"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!! "
United States
Lorie
$249 nightly
The price is $264
Dec 1 - Dec 2
Total with taxes and fees
Harbour House Inn
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
$239 nightly
The price is $306
Nov 21 - Nov 22
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.

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

Lenox
$256 nightly
The price is $325
Nov 20 - Nov 21
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

Lenox
$274 nightly
The price is $345
Nov 20 - Nov 21
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
$294 nightly
The price is $368
Nov 19 - Nov 20
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
Fireplace
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
$376 nightly
The price is $459
Nov 23 - Nov 24
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Lenox
$410 nightly
The price is $497
Nov 20 - Nov 21
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Living area
Elegant suite with a king bed, fireplace, and kitchenette.

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

Lenox
$465 nightly
The price is $559
Nov 20 - Nov 21
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.
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
$468 nightly
The price is $562
Nov 19 - Nov 20
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Clean, cozy, workers are very attentive. The bar and activity center is a lot of fun. "
Paige 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about Chester

Chester B&B information

Number of reviews
2,317
Accommodation
32 B&B
Lowest Price
$127
Highest Price
$562

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 $127 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.

Explore a world of travel with Expedia