Photo by Annette Babek

Search B&B in Chester

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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, (1000)
"It was very quaint very cozy .I will stay again great experience."
The price is AED 731
AED 841 total
includes taxes & fees
4 May - 5 May
Inn at Harbor Hill Marina
The Captain Stannard
LED TV

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (219)
"Wonderful welcome and impeccable property. We will plan to go again!"
The price is AED 723
AED 803 total
includes taxes & fees
5 May - 6 May
The Captain Stannard
The Scranton Seahorse Inn
Staircase

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (236)
"Great stay and will be back!"
The Scranton Seahorse Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (150)
"It is beautiful and comfortable. The breakfast was great. And the bed was extremely comfortable."
The price is AED 711
AED 789 total
includes taxes & fees
4 May - 5 May
Westbrook Inn B&B
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, (73)
"I really wanted to see the goats as silly as that sounds and had a great time doing it."
The price is AED 875
AED 971 total
includes taxes & fees
5 May - 6 May
The Bevin House Bed & Breakfast
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, (77)
"Wonderful rooms, exceptional staff, and convenient location"
The price is AED 1,136
AED 1,261 total
includes taxes & fees
15 May - 16 May
The Homestead
James Pharmacy Bed & Breakfast
Garden

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
The price is AED 1,110
AED 1,673 total
includes taxes & fees
5 May - 6 May
James Pharmacy Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (13)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
Thimble Islands Bed & Breakfast
Property grounds

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
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, (8)
"I love this place "
The price is AED 380
AED 585 total
includes taxes & fees
15 May - 16 May
Postcard Cabins Machimoodus
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access
Bar (on property)

Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

7.4 out of 10, Good, (3)
"Really convenient location breakfast was good. Rooms were clean."
The price is AED 300
AED 418 total
includes taxes & fees
4 May - 5 May
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access
Private Guest House w/ Deck + Spectacular Views!
Property grounds

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (25)
"We had a great time. Very nice location with lots to do withing 30 minutes. Did the casinos and mystic and do not miss out on Pauls Pasta restaurant."
Private Guest House w/ Deck + Spectacular Views!
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. If your ideal vacation to Chester includes spending lots of time outside, Connecticut Valley Railroad State Park Trail is a good spot to enjoy the scenery.
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 Captain Stannard: 11 rooms. 8.3 mi (13.4 km) from the downtown core. Westbrook Inn B&B: 9 rooms. Situated 8.3 mi (13.4 km) from the heart of Chester. Enjoy the free full breakfast and designer toiletries. The Scranton Seahorse Inn: 7 rooms. 10.3 mi (16.5 km) from the heart of downtown. Enjoy the free full breakfast and spa. James Pharmacy Bed & Breakfast: 3 rooms. Located 9.7 mi (15.7 km) from the core of Chester. Enjoy the local cuisine 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 Norma Terris Theater and Chester Creek Marina 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.