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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

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, (1000)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
The price is SAR 597
SAR 686 total
includes taxes & fees
15 Dec - 16 Dec
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, (258)
"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
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
United States
Rachel
The price is SAR 1,134
SAR 1,258 total
includes taxes & fees
16 Dec - 17 Dec
James Pharmacy Bed & Breakfast
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, (175)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is SAR 800
SAR 888 total
includes taxes & fees
17 Dec - 18 Dec
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)
"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 SAR 334
SAR 460 total
includes taxes & fees
14 Dec - 15 Dec
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, (89)
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
United States
Cynthia
The price is SAR 1,007
SAR 1,118 total
includes taxes & fees
17 Dec - 18 Dec
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, (81)
"The staff was super friendly and welcoming. The house was beautiful and the grounds full of things to explore. The breakfast was presently with panache and tasted great. We swam in the pool, ate at local restaurants, pet a turkey, and visited the local winery. I would highly recommend this establishment. "
United States
Juliette
The price is SAR 851
SAR 944 total
includes taxes & fees
12 Jan - 13 January 2026
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

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

10/10 Excellent
"Great choice if you need a stay local to Mohegan. Room was clean, basic but had everything we needed ( Executive King) for one night. Free shuttle and a nice free breakfast."
Roslyn 1-night trip
Posted 20 hours ago
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

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. 8.3 mi (13.4 km) from the downtown core. Enjoy the private yard and unique décor. 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. The Homestead: 10 rooms. Located 10.9 mi (17.6 km) from the core of Chester. Enjoy the deli and unique décor.
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 Norma Terris Theater are some notable sights to visit. You might put Connecticut Valley Railroad State Park Trail 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.