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Charming Chester Retreat- Near Village Center

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Exterior
Property grounds
Private kitchen
Living area
Room

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms1 bathroomSleeps 41100 sq ft

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Deck or patio
  • Free WiFi

Explore the area

View in a map
Chester, CT
  • Place, Connecticut Valley Railroad State Park Trail
    ‪10 min walk‬
  • Place, Norma Terris Theater
    ‪2 min drive‬
  • Place, Goodspeed Opera House
    ‪8 min drive‬
  • Airport, New Haven, CT (HVN-Tweed - New Haven Regional)
    ‪50 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Back Bedroom

1 Queen Bed

Front Bedroom

1 Queen Bed

1 bathroom

Large Bathroom

Bathtub · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Dining area

About this property

Charming Chester Retreat- Near Village Center

**Come for your Winter Escape** This thoughtfully designed and smartly decorated 2 bed, 1 bath unit is the perfect blend of style and comfort. The space has been completely re-designed and renovated, featuring a new modern kitchen, soaking tub and cozy wood-burning fireplace. The unit also features a rear deck that overlooks our mature maple trees and a sprawling front porch complete with his and hers rockers. Each bedroom has blackout blinds to ensure a restful night sleep. Great for 1-2 couples, small families or group of friends! Ask about our single roll-away bed and if you are traveling with a little one, please let us know. We have most things "baby" related and happy to provide. Some thing we offer include pack-n-play, changing station, use of jogger stroller, high-chair, age appropriate toys and other gear. **Lake access in the summer**

What sets this space apart from the rest is it's size, added amenities and location. The space boasts nearly 1,200 square feet of living space, contains a large, well-appointed kitchen (to cook real meals) and a full-size washer/dryer. It's a 15 minute walk to Chester Town Center and minutes to the highway, yet is set on a heavily wooded lot that allows for privacy. It's perfect for a weekend getaway, but also great for a weekly summer rental or a longer-term stay. Traveling nurses, actors, actresses and directors welcome! Ask for more details on weekly/monthly rates.

The rental space is the front portion of our house which is attached to the main house where my husband, daughter and I live. The two spaces share only one wall, which we have soundproofed. There are also two sets of doors that separate the units that remain locked at all times.

The unit is accessed via a smart lock key system and instructions are provided upon booking.

Small pets considered, additional deposit required. Message for details.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 3:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
Service animals allowed
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Smoking

Smoking is not permitted
Please do your dishes upon departure. Leaving them in drying rack is fine--
Request you remove shoes.
Accidents happen! If you spill or stain something, please let me know so I can take care of it prior to the nest guests arrival.

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Chester

Chester Center, a neighborhood in Chester, is home to this vacation home. Connecticut Valley Railroad State Park Trail and Connecticut Valley Railroad State Park are local landmarks, and some of the area's activities can be experienced at Chester Creek Marina and Essex Island Marina. Traveling with kids? Consider Essex Steam Train and Sweet Martha's. Kayaking and motor boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
View more Vacation Homes in ChesterOpens in a new window
Map
Chester, CT

What's nearby

  • Connecticut Valley Railroad State Park Trail - 10 min walk - 0.9 km
  • Norma Terris Theater - 2 min drive - 1.8 km
  • Goodspeed Opera House - 8 min drive - 9.5 km
  • Mohegan Sun Casino - 41 min drive - 59.8 km
  • Mohegan Sun Arena - 41 min drive - 59.8 km

Getting around

  • Old Saybrook Station - 16 min drive
  • New London, CT (GON-Groton - New London) - 37 min drive

Restaurants

  • ‪Brushmill by the Waterfall - ‬4 min drive
  • ‪High Nine Brewing - ‬17 min walk
  • ‪Cumberland Farms - ‬3 min drive
  • ‪Tropical Smoothie Cafe - ‬14 min drive
  • ‪Rusty Rail Tavern - ‬5 min drive

Frequently asked questions

Is Charming Chester Retreat- Near Village Center pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Charming Chester Retreat- Near Village Center?

As of May 3, 2026, prices found for a 1-night stay for 2 adults at Charming Chester Retreat- Near Village Center on May 6, 2026 start from $297, 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?

Onsite parking is available at the property.

What time is check-in at Charming Chester Retreat- Near Village Center?

Check-in begins at 3:00 PM.

What time is check-out at Charming Chester Retreat- Near Village Center?

Check-out is at 11:00 AM.

Where is Charming Chester Retreat- Near Village Center located?

This family-friendly Chester vacation home is located in Chester Center, within 1 mi (2 km) of Connecticut Valley Railroad State Park Trail and Norma Terris Theater. Connecticut River and Chester Creek Marina are also within 3 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 28 out of 28 reviews
Rating 8 - Good. 0 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Andrea D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
I booked this stay as a 40th birthday weekend for my husband, and it was everything we hoped for. The cottage was cozy and perfect for disconnecting, yet just a short drive to Main Street in charming Chester.We loved having two bedrooms with different mattress options (we preferred the firm), and the space balanced historic charm with bright, updated decor. The clawfoot tub was a highlight, and the attached setup still felt private with a locked door.Thank you for the wonderful hospitality!
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

stacy d.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great hosts, great communication. Perfect spot for our small family when we visit relatives in Connecticut!
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Emily R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean space, comfy beds, and one of those places that’s even nicer than the pictures.
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Austin G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very lovely retreat tucked away in Chester, CT. The guest home was stunning from the outside and inside. Very accommodating hosts as that stock the home with everything you need for your vacation.
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Steven S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a fantastic place to stay! We loved this place and everything about it. Charming, absolutely!!! Clean, wonderfully so!!! Perfect location for what we needed as well; we will gladly stay here again!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Ismenia A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic experience! The host was wonderful—very responsive and welcoming. The place was spotless and well-kept, and the location was perfect for everything we wanted to do. Highly recommend!
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Martin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend break

Perfect location for a weekend break. Short walk into Chester. Great amenities, nice decor. Would recommend this cottage.
Stayed 2 nights in Mar 2025
Verified

10/10 Excellent

Audra S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Super adorable cottage

The pictures truly don’t do the cottage justice. It truly is amazingly cute, clean and in the most perfectly tranquil area. Communication and friendliness with host A. Would stay here again and would highly recommend.
Stayed 9 nights in Jun 2025
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy
This Charming Chester Retreat was so comfortable we wanted to stay longer! Plenty of room, the kitchen and bathroom were nicely appointed and the decor was lovely. It is on a quiet tree lined street with lots of privacy. We stayed there to have our own space while visiting family and it was a great place to relax. Our favorite part was the wide covered porch with a couple rocking chairs, perfect for watching the leaves fall and hosting friends.Our hosts were friendly and very responsive. We will definitely stay here again.
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Danielle S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great short stay

My family were visiting Connecticut to see the steam train in Essex for Christmas and stayed at Bridget's cottage. It was lovely, clean, spacious and perfect for our 2 day stay. Bridget was a lovely host and so accommodating, especially with our children in tow. We would happily stay again!
Stayed 2 nights in Dec 2024
Verified

10/10 Excellent

stacy d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just lovely

We loved this stay! Everything was clean, labeled, and beautifully furnished. 5 stars isn't enough! This was a great place to stay.
Stayed 2 nights in Nov 2024
Verified

10/10 Excellent

Mara S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet and Beautiful

We enjoyed our stay. The house is beautiful and has all the amenities. Highly recommended.
Stayed 3 nights in Apr 2024
Verified

10/10 Excellent

Beatrice B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend in Chester

Very pretty and comfortable property! We particularly loved the light in the kitchen, and Bridget was amazing in communication. And so easy to get into downtown Chester--a quick walk!
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Andrea H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection

The cottage was beautiful! Our host was perfect. The little town of Chester was idyllic and friendly. I hope to stay there again soon!
Stayed 3 nights in Apr 2024
Verified

10/10 Excellent

Kaitlyn C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A quick getaway

We had a wonderful time! It was everything we needed and will definitely keep this in mind when we need another :)
Stayed 2 nights in Dec 2023
Verified

10/10 Excellent

joanne r.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winter

a quiet comfortable cozy wooded setting ...we relish the wonderful wood fire & soaker tub & comfortable furniture.
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

Alison R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Throughly Enjoyed Our Stay!

The house couldn't be cuter, and was fully stocked with all essentials we needed during our trip. We instantly felt right at home. Bridget was extremely responsive and helpful when asked about the area, or if we were in need of anything extra :) We would highly recommend and plan on returning down the line!
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Amy O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Truly a retreat

This accommodation exceeded all my expectations. It is blissfully quiet and wonderfully comfortable. Couldn’t be cleaner and had every kitchen item, towel and bedding we needed. The hosts were so welcoming and helpful, while maintaining the privacy of the rental space. I look forward to staying again.
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Amy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely girls weekend away

We had a girls weekend with several of us traveling from out of state. This really is a fantastic stay in Chester. It was clean and little thoughtful touches everywhere. We had a little issue with wifi, host was super responsive and fixed it right away.
Stayed 1 night in Aug 2023
Verified

10/10 Excellent

Chris R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Karens birthday weekend

Very pleased with house it’s a real GEM!!!!!! Very clean unique and clean!!!! We had a very fun relaxing weekend away and Chester is a lot of fun.
Stayed 2 nights in Aug 2023
Verified

10/10 Excellent

Lynn M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Retreat

Exceptional! The property was very comfortable, and felt like home. It was spotless, well equipped, quiet, private....the host thought of everything. We will return without question!
Stayed 5 nights in Sep 2023
Verified

10/10 Excellent

Charles C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Time in Chester

What a beautiful place. Everything was immaculate. The furnishings were especially nice and the linens were also. Kitchen was well stocked with everything anyone would need for any type of cooking. The setting was down a pretty country lane. Bridget was very accommodating and easy to communicate with. We will definitely be back.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Lorenzo S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

This property was everything I needed it to be. IT was very clean with comfortable beds and a spacious bathroom. Quiet location in a sleepy little town. Very private. Didn't see or hear another soul. There's a small market conveniently located at the end of the street you can walk to. Great communication with owner. Overall an amazing experience.
Stayed 3 nights in Nov 2023
Verified

10/10 Excellent

Frank L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chester treasure!!

Wonderful and inviting home. Chester is a wonderful little cozy New England town with great restaurants and outstanding brewery serving up everything from hard seltzer to double IPAs and sours, all brewed on site. The home was perfectly located equidistant from a heater village and marina/river. Home was exceptionally clean and comfortable. Bridget (property mgr)was amazing to work with. Will definitely visit it again for holidays.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Christina M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect in every way

I cannot say enough great things about the experience we had in the Chester Retreat. It has a magical, tucked away quality; perfectly appointed, everything has been thought through so no need to search, everything has already been thought of. It was so comfortable, friendly and charming, we didn't want to leave! (this is the honest truth). Bridget was the most gracious hostess oozing authenticity and care for our comfort and enjoyment. Go! You won't regret it.
Stayed 2 nights in May 2024

About the host

Hosted by Bridget Chase

Host profile image
Hello! I'm Bridget. I live with my husband Ryan and daughter Nora in Chester, CT. We bought our house in Sept 2017 and spent a full year renovating it and creating a rental space. We love to host our friends and family, but have now opened our home to host others, looking to provide a unique and affordable stay in Connecticut's River Valley. We love this area and think you will too! Ryan and I love to travel and almost exclusively use Airbnb and VRBO when visiting other cities. We love that these platforms give us unique options and the opportunity to connect with others. When we're not traveling, we're most likely hiking, biking or doing something else that's active. Or cooking. We love to cook (and eat). Exploring areas through food is one of our favorite things. Have you ever done a food tour? No? Get on that-- it's one of the best things ever. Every major city has them. You're welcome. Please reach out if you have any questions-- we'd love to hear from you.

Why they chose this property

One of the best parts of our Airbnb is the location. It's set on a heavily wooded lot that is over 2 acres. When you're here you feel miles away from everything, yet you're minutes from the town center, the highway and all major conveniences. Chester itself is centrally located in the Connecticut River Valley area that is quaint and rich with history. There is plenty to do whether you're coming for a week or weekend!

What makes this property unique

The Charming Chester Retreat is a very comfortable 2 bedroom, 1 bath space that is nearly 1,200 square feet. It feels like a real home. The kitchen is fully equipped and there is a full-size washer and dryer, which makes the space great for both short and longer-term guests. There is also plenty of outdoor space including a huge front porch with his and her rockers, back deck with bistro set and string lights and a spiral staircase that leads to a roof deck.

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