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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Chester bed & breakfast

Property grounds
Inn at Harbor Hill Marina

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1,001 reviews)
"Everything was perfect, from the room to the staff. "
United States
Kathleen
The price is AED 584
AED 672 total
includes taxes & fees
14 Jan - 15 Jan
Inn at Harbor Hill Marina
IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (259 reviews)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
The Captain Stannard
Fireplace
Westbrook Inn B&B

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (178 reviews)
"Our stay was amazing! All the staff were so accommodating and kind. The inn has a rustic charm and was so festive for the holidays! Rooms are a good size, clean, and have everything you need. The breakfast was delicious and they even had free tea/coffee/cookies for all guests to enjoy :) "
United States
Chewon
The price is AED 718
AED 797 total
includes taxes & fees
1 Feb - 2 Feb
Westbrook Inn B&B
1 bedroom, free WiFi, bed sheets
Clean master bedroom with queen & private bath, 2 blocks from Rt 95, Free Wi-Fi

Clean master bedroom with queen & private bath, 2 blocks from Rt 95, Free Wi-Fi

Clean master bedroom with queen & private bath, 2 blocks from Rt 95, Free Wi-Fi
New London
8.0 out of 10, Very Good, (1 review)
"The host was nice, helpful and easy to communicate with. Our room had an assigned bathroom, it wasn’t in the room, but just down the hall. That worked fine for us. We needed a clean, reasonably priced place for an overnight stay on our road trip and this ticked all the boxes."
United States
Warren
The price is AED 327
AED 450 total
includes taxes & fees
14 Jan - 15 Jan
Clean master bedroom with queen & private bath, 2 blocks from Rt 95, Free Wi-Fi
Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio
The Homestead

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (91 reviews)
"Beautiful property- wonderful staff- clean, comfortable and relaxed feeling with a lovely breakfast 😄"
United States
Anthony
The price is AED 1,033
AED 1,147 total
includes taxes & fees
15 Jan - 16 Jan
The Homestead
Library
The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (83 reviews)
"Wonderful stay. Excellent staff that treats the guest like family and friends. "
United States
Liliana
The price is AED 868
AED 964 total
includes taxes & fees
15 Jan - 16 Jan
The Bevin House 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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Top Chester Hotel Reviews

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Perfect! Everything about here!"
Samantha 2-night trip
Posted 1 day ago
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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, you might want to explore the theater scene by catching a show at Norma Terris Theater.
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. 8.4 mi (13.5 km) from the downtown core. Enjoy the private yard and unique décor. The Bevin House Bed & Breakfast: 5 rooms. Situated 12.1 mi (19.4 km) from the heart of Chester. Enjoy the free full breakfast and designer toiletries. 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. 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?
When you want to explore some things to do in town, Connecticut River and Connecticut Valley Railroad State Park Trail are some notable sights to visit. 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.