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Find a Bed and Breakfast in Chester from CA $123

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Check prices for these dates

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

Browse Select Chester B&B

Inn at Harbor Hill Marina
Relax in a serene outdoor space surrounded by lush greenery and beautifully manicured lawns.

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 CA $343
CA $394 total
includes taxes & fees
Sep 3 - Sep 4
Inn at Harbor Hill Marina
The Captain Stannard
Cozy up by the fireplace in this stylish living room, featuring a comfortable sofa, armchair, and decorative artwork.

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (237)
"Everything was fantastic, will stay again!"
The price is CA $244
CA $271 total
includes taxes & fees
Sep 3 - Sep 4
The Captain Stannard
The Homestead
Relax in a spacious room with a large bed, seating area, and cozy fireplace.

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
The Bevin House Bed & Breakfast
Relax in a serene poolside setting surrounded by lush greenery and shaded seating.

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 CA $319
CA $355 total
includes taxes & fees
Aug 20 - Aug 21
The Bevin House Bed & Breakfast
Westbrook Inn B&B
Relax in the serene outdoor patio area, surrounded by lush greenery and comfortable seating options.

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 CA $284
CA $315 total
includes taxes & fees
Sep 2 - Sep 3
Westbrook Inn B&B
James Pharmacy Bed & Breakfast
Relax in a classic room with a four-poster bed, flat-screen TV, and comfortable armchair.

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
James Pharmacy 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 CA $123
CA $169 total
includes taxes & fees
Aug 7 - Aug 8
Clean master bedroom with queen & private bath, 2 blocks from Rt 95, Free Wi-Fi
Higganum House B&B
Stroll through the serene grounds, surrounded by lush greenery and a well-manicured lawn.

Higganum House B&B

3.0 star property
Higganum House B&B
Thimble Islands Bed & Breakfast
Enjoy a romantic dinner for two on the balcony overlooking the water.

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
Enjoy a serene beach experience with calm seas and a picturesque view.

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
The Williams Center
Standard Single Room

The Williams Center

2.0 star property
The price is CA $127
CA $146 total
includes taxes & fees
Aug 7 - Aug 8
The Williams Center
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

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"Nice place to rest."
Kenneth 1-night trip
Posted 2 days ago
Quality Inn Old Saybrook - Westbrook