The Little Chestnut. A charming historic apartment in Downtown Chester
Nestled in the heart of the charming village of Chester, this cozy apartment sits above a beloved local bookstore, offering a unique small-town experience just steps from everything the village has to offer.
From the private entrance, you'll enter a mudroom before heading upstairs to the main living level. Here you'll find a bright living room, a fully equipped kitchen, a dining area, and a second bedroom featuring a trundle bed (two twin beds) perfect for children or additional guests.
One more flight of stairs leads to the peaceful third floor, where you'll find the primary bedroom with a comfortable queen bed and a full bathroom with a shower.
Thoughtfully equipped with heating, central air conditioning, high-speed Wi-Fi, and an in-unit washer, the apartment has everything you need for a comfortable stay.
Although located in the center of the village, this little hideaway feels surprisingly peaceful. Tucked behind the main street and bordered by a gentle brook, it offers the perfect blend of convenience and tranquility. Step outside and you're just moments from Chester's acclaimed restaurants, boutique shops, art galleries, and seasonal events. The beautifully maintained grounds feature colorful floral planters, and just across the brook you'll find a quaint park with a gazebo and picnic tables —the perfect spot to enjoy your morning coffee or unwind after a day of exploring.
Whether you're visiting for a weekend getaway, attending a local wedding, or discovering the Connecticut River Valley, this charming apartment is the perfect home base for experiencing all that Chester has to offer.
Last-minute getaway? Send us a message—we may be able to accommodate one-night stays based on availability.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
About the area
Chester
Located on a river, this apartment is in Chester Center, a neighbourhood in Chester. Chester Creek Marina and Essex Island Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Hammonasset Beach State Park and Connecticut Valley Railroad State Park Trail. Essex Steam Train and Connecticut Valley Railroad State Park are also worth visiting. Sailing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Connecticut Valley Railroad State Park Trail - 2 min drive - 1.5 km
Goodspeed Opera House - 8 min drive - 8.8 km
Mohegan Sun Casino - 42 min drive - 60.9 km
Mohegan Sun Arena - 42 min drive - 60.9 km
Getting around
Old Saybrook Station - 16 min drive
New London, CT (GON-Groton - New London) - 37 min drive
Restaurants
Brushmill by the Waterfall - 2 min drive
Cumberland Farms - 4 min drive
High Nine Brewing - 2 min drive
Rusty Rail Tavern - 5 min drive
Marker 37 - 4 min drive
Frequently asked questions
Is The Little Chestnut. A charming historic apartment in Downtown Chester pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at The Little Chestnut. A charming historic apartment in Downtown Chester?
As of 29 Jul, 2026, prices found for a 1-night stay for 2 adults at The Little Chestnut. A charming historic apartment in Downtown Chester on 26 Jan, 2027 start from S$714, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at The Little Chestnut. A charming historic apartment in Downtown Chester?
On-site parking is available at the property.
What time is check-in at The Little Chestnut. A charming historic apartment in Downtown Chester?
Check-in begins at 4:00 PM.
What time is check-out at The Little Chestnut. A charming historic apartment in Downtown Chester?
Checkout is at 11:00 AM.
Where is The Little Chestnut. A charming historic apartment in Downtown Chester located?
Located in Chester Center, this apartment building is within 2 miles (3 km) of Norma Terris Theater, Connecticut Valley Railroad State Park Trail and Chester Creek Marina. Gillette Castle State Park and Connecticut River are also within 2 miles (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This is an elegant little apartment in a charming little river town. The owner is completely on top of everything, it is a very easy check-in and access, the kitchen is terrific, there is ample parking space, and it is an easy walk to the center of town. Would stay here again in a moment! This has to be the nicest thing available in the area!
This property was such a nice place to stay! Its right above a little romantic bookshop which is a little added bonus. It is within walking distance of several boutiques, delcious restaurants, and a local brewery. Multiple hiking spots within short driving distance. The owner was also very helpful and kind. Loved our little getaway!
Can't say enough about the whole experience with this problem. The owner was super nice, walked me through the entry process. Was very responsive when I had questions about the property and local items. The Little Chestnut in Chester is an excellent jumping off spot for a lot of activities around the lower Connecticut River area. The town of Chester has a really nice vibe and could spend all the time there. The Little Chestnut is set up for about 4 people. The beds were super comfortable, and had extra blankets for this cool nights. The heater worked great and kept the cabin very warm. The electric fireplace was also very warm and gave an awesome atmosphere without the hassle of an actual fireplace. Hot water heater was plenty big for 3 adults to take a shower and not run out of hot water. The kitchen was fully stocked with cooking and eating utensils, however with so many great eating places we didn't do any cooking. When we stayed the little bookstore below was open and was a fun visit for the girls. If we could give more stars I certainly would.
Great location for a weekend. Shops and restaurants are awesome on main Street. It was also a quick drive to Old Saybrook.
Akash R.
Stayed 2 nights in Jul 2026
About the host
Hosted by Samantha Kerry
A native of France, i spent much of my youth in Africa and Spain before relocating to the United States. My husband and i are both of European roots but have lived most of our lives on the East coast of the United States. We now spend our time in Europe, Florida and Connecticut.
Why they chose this property
Chester is a Charming, friendly, artsy and musical place where it is nice to spend some relaxing quality time. Stay a weekend or stay a while and you will find out why.
What makes this property unique
Built around 1840, this charming village cottage has been part of Chester's story for generations. For many years it was a home to the beloved R.J. Vickers Herbery, a destination known for its beautiful gardens and handcrafted herbal goods. Today, the building continues its tradition of welcoming visitors as the home of Montgomery & Taggert Bookshop, Connecticut's first romance-themed bookstore, while the apartment above offers guests a peaceful retreat in the heart of one of New England's most picturesque villages.
Languages:
English, French, Italian, Spanish
Premier Host
They consistently provide great experiences for their guests