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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

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, (1004)
"Beautiful and comfortable room with excellent shower and great breakfast. "
The price is AED 496
AED 571 total
includes taxes & fees
19 Mar - 20 Mar
Inn at Harbor Hill Marina
The Captain Stannard
Standard Room, 1 Bedroom, Private Bathroom | Free WiFi, bed sheets

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (215)
"Hosts extremely welcoming and friendly. Easy to come and go. Beautiful common rooms and comfortable, charming room. Very clean and nicely updated. "
The price is AED 492
AED 546 total
includes taxes & fees
19 Mar - 20 Mar
The Captain Stannard
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 905
AED 1,004 total
includes taxes & fees
25 Mar - 26 Mar
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, (146)
"Very nice owner. Very comfortable. Would definitely stay again. "
The price is AED 756
AED 840 total
includes taxes & fees
19 Mar - 20 Mar
Westbrook Inn B&B
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)
"Charming in every aspect. Highly recommend, Hosts are wonderful people."
The price is AED 930
AED 1,032 total
includes taxes & fees
31 Mar - 1 Apr
The Homestead
The Scranton Seahorse Inn
Staircase

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (236)
"Amazing and too short. Loveliest little B&B with one of the best breakfasts I've ever had. Incredibly clean with updated bathroom(s). So quiet, even though almost full. Will be going back, regularly!"
The price is AED 943
AED 1,047 total
includes taxes & fees
31 Mar - 1 Apr
The Scranton Seahorse Inn
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
James Pharmacy Bed & Breakfast
Garden

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 1,110
AED 1,673 total
includes taxes & fees
1 Apr - 2 Apr
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
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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Other property types in Chester

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
The price is AED 496
AED 570 total
includes taxes & fees
31 Mar - 1 Apr
Postcard Cabins Machimoodus
Waterfront House with picture-perfect views from all 3 levels.
Interior

Waterfront House with picture-perfect views from all 3 levels.

9.6 out of 10, Exceptional, (80)
"Enjoyed a long weekend here. Nice and clean, kitchen equipped with all upgraded utensils and pans, very comfy beds and plenty of space for all. Will definitely come back."
Waterfront House with picture-perfect views from all 3 levels.
Regency Inn & Suites
1 bedroom, iron/ironing board, WiFi, bed sheets

Regency Inn & Suites

The price is AED 279
AED 458 total
includes taxes & fees
19 Mar - 20 Mar
Regency Inn & Suites
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 B&B Country Inn: 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 Bevin House Bed & Breakfast: 5 rooms. 12.1 mi (19.4 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 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.