Photo by Annette Babek

Search B&B in Chester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

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

Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1001)
"Beautiful property, loved the views, even in winter and especially waking up to snow. Patti, is wonderful, Melanie makes a great bfast. We will be back especially if my child gets into the nearby Academy."
The price is AED 447
AED 514 total
includes taxes & fees
23 Feb - 24 Feb
Inn at Harbor Hill Marina
The Scranton Seahorse Inn
Front of property

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (235)
"This was a one night stay. The property is an older house in the city center. We were here to help a friend celebrate a birthday. The B&B was very close to the party making it easy to come and go. The room was small but comfortable. The bed was very comfortable. Breakfast was fantastic. "
The price is AED 943
AED 1,047 total
includes taxes & fees
27 Feb - 28 Feb
The Scranton Seahorse Inn
The Homestead
Exterior

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (77)
"Charming in every aspect. Highly recommend, Hosts are wonderful people."
The price is AED 837
AED 929 total
includes taxes & fees
27 Feb - 28 Feb
The Homestead
Westbrook Inn B&B
Dock

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (144)
"The host was very friendly and helpful. The property was well maintained. It is quite and we enjoyed our stay. "
The price is AED 632
AED 701 total
includes taxes & fees
16 Feb - 17 Feb
Westbrook Inn B&B
The Captain Stannard B&B Country Inn
Exterior

The Captain Stannard B&B Country Inn

3.0 star property
9.6 out of 10, Exceptional, (214)
"We had a wonderful time and the owner was great. We had a fun time talking about history of both inn’s. Look forward to returning and doing more next time"
The price is AED 659
AED 732 total
includes taxes & fees
20 Feb - 21 Feb
The Captain Stannard B&B Country Inn
The Bevin House Bed & Breakfast
Exterior detail

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (70)
"Our room was beautiful, spacious and clean, with a wonderful bathroom. The innkeeper was friendly and very helpful and provided a delicious breakfast."
The price is AED 788
AED 875 total
includes taxes & fees
19 Feb - 20 Feb
The Bevin House Bed & Breakfast
Arbor View House B&B
Room

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
James Pharmacy Bed & Breakfast
Room

James Pharmacy Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (14)
"We loved staying in the historic pharmacy. We stayed in the Ann Petry room and it is well appointed, clean and charming. The property sits on the town's main street and is very walkable to shopping and dining. We look forward to our next stay. "
The price is AED 1,272
AED 1,852 total
includes taxes & fees
16 Feb - 17 Feb
James Pharmacy Bed & Breakfast
Thimble Islands Bed & Breakfast
Front of property

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
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chester

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (4)
"Loved how tranquil this site is. Was great to disconnect in nature. "
The price is AED 331
AED 380 total
includes taxes & fees
4 Mar - 5 Mar
Postcard Cabins Machimoodus
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises
Living area

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises

10.0 out of 10, Exceptional, (13)
"We were thoroughly pleased with our stay. This villa is homey, inviting and all of your needs and extra perks are covered.Kellie is a lovely host she answers all of your questions promptly. She and her husband love this property and it is reflective when you enter the villa.We will be back sooner than later."
The price is AED 496
AED 990 total
includes taxes & fees
25 Feb - 26 Feb
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Living area

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

10.0 out of 10, Exceptional, (31)
"The perfect place to relax and get ready for a night out after an amazing day at the spa. Wish we had more time to enjoy the fireplace and rhe balcony. Nice open space wirh plenty of room and very well equipped, comfortable. We loved it!"
The price is AED 643
AED 1,259 total
includes taxes & fees
17 Feb - 18 Feb
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
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.

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, Cockaponset State Forest and Connecticut Valley Railroad State Park Trail 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: Inn at Harbor Hill Marina: 16 rooms. 16.2 mi (26.1 km) from the heart of Chester. Enjoy the free full breakfast and marina onsite. The Scranton Seahorse Inn: 7 rooms. 10.3 mi (16.5 km) from the downtown core. Enjoy the free full breakfast and spa. The Homestead: 10 rooms. Situated 10.9 mi (17.6 km) from the heart of Chester. Enjoy the deli and unique décor. Westbrook Inn B&B: 9 rooms. 8.3 mi (13.4 km) from the heart of downtown. 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 Cockaponset State Forest and Connecticut River if you’re hoping to see some of the area’s natural features. You might put Norma Terris Theater and Connecticut Valley Railroad State Park Trail 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.