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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sep - 7 Sep
In two months
3 Oct - 5 Oct

B&B in Chester

Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1003)
"Really cute bed and breakfast! Great location on the marina. The food was good and the people were very friendly. "
The price is AED 915
AED 1,052 total
includes taxes & fees
4 Sep - 5 Sep
Inn at Harbor Hill Marina
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (237)
"Everything was fantastic, will stay again!"
The Captain Stannard
The Homestead
Room, 1 King Bed, Patio, Ground Floor (7) | 1 bedroom, Egyptian cotton sheets, premium bedding, down comforters

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (82)
"Best breakfast. The little things that were provided (warm bathroom towels, comfortable bed, patio outside our room just for us to enjoy) added to our wonderful 3 day get away in Madison. Don't want to forget the freshly made popcorn in the evening we so enjoyed. "
The Homestead
James Pharmacy Bed & Breakfast
Miss Anna James Room | 1 bedroom, individually decorated, individually furnished

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
The price is AED 1,514
AED 2,121 total
includes taxes & fees
13 Aug - 14 Aug
James Pharmacy Bed & Breakfast
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (155)
"My granddaughter and I had a lovely stay."
The price is AED 1,136
AED 1,261 total
includes taxes & fees
18 Aug - 19 Aug
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, (77)
"Welcoming, fun, and absolutely stunning! A cuddly turkey didn’t hurt either. "
The price is AED 851
AED 944 total
includes taxes & fees
13 Aug - 14 Aug
The Bevin House Bed & Breakfast
Clean master bedroom with queen & private bath, 2 blocks from Rt 95, Free Wi-Fi
1 bedroom, free WiFi, bed sheets

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

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."
The price is AED 327
AED 450 total
includes taxes & fees
10 Aug - 11 Aug
Clean master bedroom with queen & private bath, 2 blocks from Rt 95, Free Wi-Fi
The Williams Center
Standard Single Room | Free WiFi

The Williams Center

2.0 star property
The price is AED 338
AED 389 total
includes taxes & fees
12 Aug - 13 Aug
The Williams Center
Higganum House B&B
Exterior

Higganum House B&B

3.0 star property
Higganum House B&B
Thimble Islands Bed & Breakfast
Porch

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
"A beautiful, quiet home in a stunning setting run by two extremely gracious hosts. Breakfast on both days was excellent."
Thimble Islands Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
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

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

10/10 Excellent
"It didn’t start out great but I called the hotel staff and they changed out room and made it right. Definitely a game changer for our stay. Thank you "
Jane 1-night trip
Posted 12 hours ago
Hyatt Place Uncasville - Casino 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. 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. Enjoy the private yard and unique décor. 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. 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.