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Check prices for these dates

Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec

Featured B&B in Chester

Naomi's Inn Bed & Breakfast
Room (Louis XIV)

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (417)
"Great host and breakfast was excellent."
The price is AU$190
includes taxes & fees
20 Oct - 21 Oct
Naomi's Inn Bed & Breakfast
Old Mill Inn
Room, River View (The Williamsburg Suite) | Private kitchen

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (497)
"Loved our stay! "
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. "
The price is AU$460
includes taxes & fees
22 Oct - 23 Oct
Daniel Stebbins House
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (285)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
The price is AU$312
includes taxes & fees
13 Oct - 14 Oct
Lakehouse Inn
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!! "
The price is AU$411
includes taxes & fees
30 Oct - 31 Oct
Harbour House Inn
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, (1005)
"Very friendly staff. "
The price is AU$279
includes taxes & fees
6 Nov - 7 Nov
The Cornell Inn, Lenox & The Berkshires
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."
The Red Door B&B
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft)

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
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."
Chambery Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (495)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
The price is AU$246
includes taxes & fees
2 Nov - 3 Nov
Whistler's Inn Bed & Breakfast
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. "
The price is AU$670
includes taxes & fees
2 Nov - 3 Nov
The Inn at Stockbridge
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

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

4.5 star property
9.2 out of 10, Wonderful, (106)
"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. "
The price is AU$571
includes taxes & fees
27 Oct - 28 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (72)
"The Inn is beautiful. Decor and rooms are well appointed. Breakfast was delicious and served in beautiful rooms. The staff is friendly and welcoming. Our room was on the first floor, and although it was pretty, it was noisy in the morning (starting very early) as it was close to the kitchen/breakfast dining."
The price is AU$831
includes taxes & fees
5 Nov - 6 Nov
33 Main
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
3 bedrooms, bed sheets

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

The price is AU$467
includes taxes & fees
28 Oct - 29 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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."
Devonfield Inn B&B
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is AU$467
includes taxes & fees
28 Oct - 29 Oct
Experience Timeless Elegance in The Edith Wharton Room!
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets

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

The price is AU$509
includes taxes & fees
4 Nov - 5 Nov
Elegant Carriage House room with a queen bed and private patio.
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

The price is AU$542
includes taxes & fees
4 Nov - 5 Nov
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is AU$573
includes taxes & fees
5 Nov - 6 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Fireplace

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

The price is AU$716
includes taxes & fees
9 Nov - 10 Nov
Experience Timeless Elegance in The Niles Johnson Room 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

Blue - A Modern Hotel, Ascend Hotel Collection

Blue - A Modern Hotel, Ascend Hotel Collection

10/10 Excellent
"Very clean !"
Jay 1-night trip
Posted 4 days ago
Blue - A Modern Hotel, Ascend Hotel Collection

Find out more about Chester

Chester B&B information

Number of reviews
3,043
Accommodation
32 B&B
Lowest Price
AU$190
Highest Price
AU$831

Frequently asked questions

Searching for B&Bs in Chester?
If you're looking for something a little more offbeat than your standard hotel, a stay at a bed and breakfast could be the perfect alternative for your holiday. While you're enjoying your trip to Chester, you might want to explore the theatre scene by watching a show at Chester Town Hall.
Why would you choose B&Bs instead of traditional hotels?
Every B&B has its own unique feel — whether it's a garden for guests to admire or a beautiful breakfast room, the quaint details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Chester?
Below are some well-liked B&Bs in the area: The Cornell Inn, Lenox & The Berkshires: 16.6 mi (26.7 km) from the heart of Chester. Enjoy the free full breakfast and unique decor. Lakehouse Inn: 14 rooms. 14.8 mi (23.9 km) from the city centre. Enjoy the free full breakfast and snack bar/deli. Chambery Inn: 9 rooms. Situated 14.1 mi (22.7 km) from the heart of Chester. Enjoy the private garden and snack bar/deli. Brook Farm Inn: 15 rooms. Located 16.7 mi (26.8 km) from the core of Chester. Enjoy the free cooked breakfast and outdoor pool.
What's the best time of year to book my B&B in Chester?
When you're planning your escape to Chester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.
What is there to do in Chester?
If you want to see some popular attractions in Chester, you might enjoy a visit to Chester Town Hall. Glendale Falls and Pyramid Lake are also some sites to visit if you want to see more of the area.
How can I get to and around Chester?
Mapping out your trip in and around Chester is easy with these transportation options. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) away from the city centre. Otherwise, you can search for flights to Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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