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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Chester bed & breakfast

A living room with a stone fireplace, grey sofas, and a coffee table.

1. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (286 reviews)
"An excellent choice for our brief stay in Old Saybrook. Clean, comfortable and very well maintained."
United States
Siegfried
The price is AED 668
AED 742 total
includes taxes & fees
15 Nov - 16 Nov
The Captain Stannard
A patio with Adirondack chairs, a fire pit, and a view of a lake.

2. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (206 reviews)
"This place is always the best love the rooms. The staff is excellent place is so clean always feel so comfortable here."
United States
Diane
The price is AED 762
AED 846 total
includes taxes & fees
18 Nov - 19 Nov
Westbrook Inn B&B
View from property

3. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.4 out of 10, Exceptional, (253 reviews)
"A lovely stay at a classic New England B & B. Perfect location for a visit to Madison."
United States
Tracy
The price is AED 863
AED 957 total
includes taxes & fees
16 Nov - 17 Nov
The Scranton Seahorse Inn
A two-story house with a porch, multiple windows, and a well-maintained lawn.

4. Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.8 out of 10, Exceptional, (1,000 reviews)
"Breakfast off a menu and cooked to order was a lovely surprise!"
United States
Lillian
The price is AED 584
AED 672 total
includes taxes & fees
1 Dec - 2 Dec
Inn at Harbor Hill Marina
A beach with houses in the background and a rainbow in the sky.

5. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (114 reviews)
"Beautiful and unique inn with great staff."
United States
Anita C
The price is AED 783
AED 870 total
includes taxes & fees
23 Nov - 24 Nov
The Homestead
A library with bookshelves, a chandelier, a desk, and a chair.

6. The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (92 reviews)
"Heaven on earth !!"
United States
NATANYA
The price is AED 871
AED 967 total
includes taxes & fees
16 Nov - 17 Nov
The Bevin House Bed & Breakfast
A bedroom with a bed, a grey sofa, two bedside tables with lamps, a small trash bin, and a rug.

7. The Williams Center --King-bed room-New London/Mystic area

The Williams Center --King-bed room-New London/Mystic area
3.0 star property
New London
9.8 out of 10, Exceptional, (75 reviews)
"Great place!"
United States
Bruce
The price is AED 396
AED 455 total
includes taxes & fees
15 Nov - 16 Nov
The Williams Center --King-bed room-New London/Mystic area
A bedroom with a bed, a grey sofa, two bedside tables with lamps, a small trash bin, and a rug.

8. Clean and cozy, King bed, private bathroom, ample parking, free internet

Clean and cozy, King bed, private bathroom, ample parking, free internet
New London
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, very helpful!"
United States
Kevin G.
The price is AED 441
AED 551 total
includes taxes & fees
15 Nov - 16 Nov
Clean and cozy, King bed, private bathroom, ample parking, free internet
A bedroom with a bed, two bedside tables with lamps, a door, and a window.

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

Clean master bedroom with King & 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 397
AED 500 total
includes taxes & fees
15 Nov - 16 Nov
Clean master bedroom with King & private bath, 2 blocks from Rt 95, Free Wi-Fi
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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Learn more about Chester

Charming galleries and local shops line Main Street, where you'll find handcrafted jewelry and Connecticut River Valley artwork. Catch a performance at the Goodspeed Opera House in East Haddam or kayak Chester Creek when summer temperatures rise.

See all hotels in Chester
A calm lake surrounded by vibrant autumn foliage.

Top reviews in Chester

A living room with a stone fireplace, grey sofas, and a coffee table.
The Captain Stannard

The Captain Stannard

The Captain Stannard
Westbrook Center

10/10 Excellent

The Captain Stannard house is a true gem in Westbrook. There are many restaurants, shops, parks, and beaches close by. The property has a private yard and a large rear porch for relaxation. My room was impeccably clean and spacious for being the smallest one in the house. Dianne was incredibly sweet and went out of her way to help all the guests.
United States
Julie
Reviewed May 27, 2024
The Captain Stannard

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?

Here are some well-liked B&Bs in the surrounding area: Inn at Harbor Hill Marina: 16 rooms. 16.2 mi (26.1 km) from the downtown core. Enjoy the free full breakfast and marina onsite. The Homestead: 10 rooms. Situated 10.9 mi (17.6 km) from the heart of Chester. Enjoy the deli and unique décor. The Captain Stannard: 11 rooms. 8.4 mi (13.5 km) from the heart of downtown. Enjoy the private yard and unique décor. The Bevin House Bed & Breakfast: 5 rooms. Located 12.1 mi (19.4 km) from the core of Chester. 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?

When you want to explore some things to do in town, Connecticut River and Chester Creek Marina are some notable sights to visit. You might put Norma Terris Theater and Connecticut Valley Railroad State Park Trail 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.

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