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Book Chester Bed & Breakfast

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Compare 9 B&B in Chester with updated reviews, rates, and availability.

Captain Stannard B&B Country Inn
Front of property
Captain Stannard B&B Country Inn
3.0 star property
9.6 out of 10, Exceptional, (177)
"We had a wonderful time. The place was so cute and the staff and owners were so helpful and nice. We only stayed 1 night but I wish we stayed longer. We will definitely be back."
The price is $199
$221 total
includes taxes & fees
Jun 20 - Jun 21
Captain Stannard B&B Country Inn
Inn at Harbor Hill Marina
Property grounds
Inn at Harbor Hill Marina
3.5 star property
9.2 out of 10, Wonderful, (1000)
"The best comp breakfast. "
The price is $249
$286 total
includes taxes & fees
Jun 20 - Jun 21
Inn at Harbor Hill Marina
The Scranton Seahorse Inn
Staircase
The Scranton Seahorse Inn
3.0 star property
9.0 out of 10, Wonderful, (218)
"The Seashore is a special INN. It is very quaint, inviting and comfortable. I’d return again."
The price is $237
$264 total
includes taxes & fees
Jun 26 - Jun 27
The Scranton Seahorse Inn
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The Homestead
Room, 1 King Bed, Patio, Ground Floor (7) | Egyptian cotton sheets, premium bedding, down comforters
The Homestead
3.0 star property
10.0 out of 10, Exceptional, (63)
"Excellent accommodations and Host. "
The price is $419
$465 total
includes taxes & fees
Jun 20 - Jun 21
The Homestead
The Bevin House Bed & Breakfast
Seasonal outdoor pool, pool umbrellas, sun loungers
The Bevin House Bed & Breakfast
3.5 star property
9.6 out of 10, Exceptional, (65)
"Avery amazing house and what a breakfast!"
The price is $236
$263 total
includes taxes & fees
Jun 20 - Jun 21
The Bevin House Bed & Breakfast
Westbrook Inn B&B
Terrace/patio
Westbrook Inn B&B
3.0 star property
10.0 out of 10, Exceptional, (136)
"Always an excellent stay! "
The price is $254
$282 total
includes taxes & fees
Jun 20 - Jun 21
Westbrook Inn B&B
James Pharmacy Bed & Breakfast
Garden
James Pharmacy Bed & Breakfast
4.0 star property
9.6 out of 10, Exceptional, (8)
"Near nice shops and restaurants "
The price is $412
$578 total
includes taxes & fees
Jun 26 - Jun 27
James Pharmacy Bed & Breakfast
Thimble Islands Bed & Breakfast
Property grounds
Thimble Islands Bed & Breakfast
3.5 star property
10.0 out of 10, Exceptional, (4)
"Property was first class inside and out. The view was breath taking The owners made us feel at home and did not want to leave ! Already thinking about next trip back."
Thimble Islands Bed & Breakfast
Arbor View House B&B
Exterior
Arbor View House B&B
3.5 star property
9.2 out of 10, Wonderful, (13)
"This house was old but beautiful and decorated nicely inside. "
Arbor View House B&B
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See all available properties in Chester
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.

Other property types in Chester

Private Guest House w/ Deck + Spectacular Views!
Property grounds
Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, (13)
"Great place. Great host"
Private Guest House w/ Deck + Spectacular Views!
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Indoor pool, a heated pool
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
10.0 out of 10, Exceptional, (14)
"The Villa was beautiful and immaculately clean. The host, Taylor, was very easy to communicate with. "
The price is $175
$324 total
includes taxes & fees
Jun 20 - Jun 21
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (113)
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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.

Chester B&B information

Number of reviews
880
Accommodation
9 B&B
Lowest Price
$199
Highest Price
$419

Frequently asked questions

Searching for B&Bs in Chester?
If you’re looking for something a little more offbeat than the traditional hotel experience, a bed and breakfast could be the perfect alternative for your vacation. While you’re enjoying your trip to Chester, Connecticut Valley Railroad State Park Trail and Cockaponset State Forest are perfect spots to get in some fresh air and greenery.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to interact with the owner, and tasty breakfasts, B&Bs provide a one-of-a-kind environment.
What are the top B&Bs in Chester?
Below are some well-liked B&Bs in the area: Captain Stannard B&B Country Inn: 11 rooms. 8.3 mi (13.4 km) from the heart of Chester.Inn at Harbor Hill Marina: 16 rooms. 16.2 mi (26.1 km) from the downtown core. Enjoy the free full breakfast and marina onsite. The Scranton Seahorse Inn: 7 rooms. Situated 10.3 mi (16.5 km) from the heart of Chester. Enjoy the free full breakfast and spa. The Homestead: 10 rooms. 10.9 mi (17.6 km) from the heart of downtown. Enjoy the deli and unique décor. Westbrook Inn B&B: 9 rooms. Located 8.3 mi (13.4 km) from the core of Chester. Enjoy the free full breakfast and designer toiletries.
What's the best time of year to book my B&B in Chester?
When you’re dreaming of a escape to Chester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Chester is 54 inches.
What is there to do in Chester?
Spend some time exploring Connecticut River and Connecticut Valley Railroad State Park Trail if you’re hoping to see some of the area’s natural features. You might put Chester Creek Marina and Norma Terris Theater on your list if you want to see more of the area.
How can I get to and around Chester?
You can plan your excursions in and around Chester ahead of time with these transportation options. Fly into New Haven, CT (HVN-Tweed - New Haven Regional), which is located 23.1 mi (37.2 km) away from the city center. Otherwise, look for flights into New London, CT (GON-Groton - New London), which is 23.1 mi (37.2 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.

Recent reviews of Chester hotels
Expedia verified reviews

Mohegan Sun

Mohegan Sun

5/5 Excellent
After wedding get away !!
"It was easvand convenient. The spa services were great ! Great stay!!"
A verified traveler stayed at Mohegan Sun
Posted 1 day ago
Mohegan Sun