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Featured Cottages in Chester

Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, 12 reviews
"The guest house was cozy and well stocked. We had a great and relaxing stay. We didn't have great weather to enjoy it, but the deck and outdoor space were lovely, and the view was amazing. The host was very helpful and attentive."
Private Guest House w/ Deck + Spectacular Views!
Social Distancing Haven on Oxoboxo Lake. Direct Lakefront
9.6 out of 10, Exceptional, 66 reviews
"A perfect weekend getaway with a breath taking lake view! Peaceful & quite. Great location short drive to many places of interest. Very clean & comfortable accommodations and wonderful communication with the host of this property. If you are looking for a lake front escape this is the place! "
Social Distancing Haven on Oxoboxo Lake. Direct Lakefront
Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, 8 reviews
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
The price is AU$445
per night
29 June - 30 June
Shalom Cottage with private beach rights.
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Go Jump in the Lake!
10.0 out of 10, Exceptional, 127 reviews
"House was very clean, well equipped and had everything we needed to enjoy a relaxing getaway as a family. We enjoyed the firepit, covered porch and lakeside fun."
The price is AU$436
per night
12 June - 13 June
Go Jump in the Lake!
Luxury Cottage near Saybrook Point Marina- Dog Friendly!
9.4 out of 10, Exceptional, 30 reviews
"I was in the area for my niece's college graduation at Wesleyan University and loved the chance to explore this beautiful part of the country. Being so close to the water in Old Saybrook was amazing, and the house itself was both fresh and cozy. The hosts were very responsive, and the only issue (which they acknowledged in advance) was that a portion of the fence was missing, due to a recent storm. That said, they were up front and apologetic, knowing that I'd booked because my dogs were along....
The price is AU$778
per night
11 June - 12 June
Luxury Cottage near Saybrook Point Marina- Dog Friendly!
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, 81 reviews
"Beautiful house in a beautiful location! We hope to return soon!"
Waterfront Cottage in Branford
Beach Bungalow, large porch, 1/2 mile to the water.
The price is AU$646
per night
10 June - 11 June
Beach Bungalow, large porch, 1/2 mile to the water.
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, 8 reviews
"We were there for a family event in Glastonbury for just a couple of days, and so we didn't go to the lake. However, the cottage was perfect for our needs -- quiet, allowed for contemplation, and privacy that we needed. We hope to perhaps and experience the beautiful lake."
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
The Bay Cottage · Rocky Neck Park, Beach & Niantic
10.0 out of 10, Exceptional, 5 reviews
"I booked this for a sister weekend. It was perfect for what we needed. It appears that the house was built to be a summer getaway, so it is pretty basic and no frills and comes with all the creaks and quicks of an older house. The living room is perfect for hanging out and the four chairs make it easy to rearrange to suit your needs. The kitchen is nicely stocked with everything you would need to stay with a family and the dining room is spacious enough to easily accommodate everyone staying...
The price is AU$876
per night
19 June - 20 June
The Bay Cottage · Rocky Neck Park, Beach & Niantic
"Salt 'n' Lyme" - Walk to everything !
9.2 out of 10, Wonderful, 21 reviews
"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...
"Salt 'n' Lyme" - Walk to everything !
Waterfront! Charming 4BR Cabin on the Niantic River!
9.6 out of 10, Exceptional, 53 reviews
"Enjoyed the uniqueness of the house and location. Note: House and grounds are very nice but not easy to get around if you are elderly and have problems walking.We were in our late sixties/early seventies, not easy getting up to second floor. Low ceilings and doors difficult for 6 ft people. We love the antiques, pantry and great supplies."
Waterfront! Charming 4BR Cabin on the Niantic River!
Waterfront Cottage w/ Sunroom + Patio & Grill
6.8 out of 10, 3 reviews
"Relaxing and beautiful sunset views , Clean and floor plan one floor plan was perfect ! Spacious and so nice to relax on this vacation ! Close to everything we needed !"
Waterfront Cottage w/ Sunroom + Patio & Grill
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
10.0 out of 10, Exceptional, 56 reviews
"The cottage was quite wonderful with a large kitchen and comfy porched living-room. Scott was very quick regarding any communication. The only thing in the description that I would add is that " you'll need to bring your own towels and bed linens". It wasn't a problem, but our airplane carry-on bags only were already packed. We made our adjustments and ended up checking a bag, no worries. Just a thought. We thoroughly enjoyed its quiet and relaxing location."
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
Charming Old Lyme Cottage, Steps to Private Beach!
7.4 out of 10, Good, 3 reviews
"Very intimate cottage setting, lovely beach scenery, walking distance to the beach, feet away from hearing the crash of the waves. Short drive to grab whatever you have forgotten or need to enhance your stay in this tiny home. Great location to unplug, energize, and bond with your family. You can create the quality time you miss out on in the world today, you will not have the distractions of television, internet, or gaming."
Charming Old Lyme Cottage, Steps to Private Beach!
Beach access Cozy Cottage
10.0 out of 10, Exceptional, 3 reviews
"My friends and I had a great time staying at this adorable cottage! The beach is so close and the parking pass is a lifesaver! We also loved making a fire and relaxing in the backyard. There was plenty of room in the kitchen to cook while spending time together. Will definitely book again!"
Beach access Cozy Cottage
Resting on an 18 acre farm, this historic cottage is the retreat of your dreams
10.0 out of 10, Exceptional, 1 review
"Immaculate and cozy one bedroom cottage next to numerous trails at Devils Hopyard and protected lands right from the door step. Very quiet and rural if that is what you're looking for. Restaurants about 5-10 miles away. Looking to stay again maybe next year for our Anniversary or another special occasion. Am going to recommend to family that I know would love this spot."
The price is AU$391
per night
12 June - 13 June
Resting on an 18 acre farm, this historic cottage is the retreat of your dreams
Charming Westbrook Cottage, Steps to Private Beach
Charming Westbrook Cottage, Steps to Private Beach
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, 89 reviews
"Mel and her husband were awesome! Perfect beach home and location was perfect. House was immaculate! I will stay there again. I only needed to use the first floor and did not have to use the stairs. Very close to the beach. Thank you, Mel!"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Enchanted Waterfront Cottage
9.2 out of 10, Wonderful, 12 reviews
"Only draw back was how busy the street was. Everything else was wonderful. Neighbor were very friendly pointed us in the best direction to catch some fish. Loved watching the rowers go by each morning. The family of ducks was something to look forward to each day."
Enchanted Waterfront Cottage
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See all available properties in Chester
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.

Other property types in Chester

Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, 12 reviews
"The guest house was cozy and well stocked. We had a great and relaxing stay. We didn't have great weather to enjoy it, but the deck and outdoor space were lovely, and the view was amazing. The host was very helpful and attentive."
Private Guest House w/ Deck + Spectacular Views!
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
10.0 out of 10, Exceptional, 13 reviews
"We just returned and loved our time at the villa! We chose to stay here for 2 nights of concerts at Mohegan sun and could not have been happier! The property is clean, comfortable and has everythign you could need. The snacks and water were a welcomed treat! Taylor was so accomodating and we hope to return one day!"
The price is AU$495
per night
10 June - 11 June
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, 112 reviews
"We were looking for a nice relaxing weekend getaway from NYC and happened to find this listing. The check in process was easy, and the owners were lovely! We'd absolutely book again."
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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.

Chester Cottages information

Number of reviews
539
Accommodation
104 Cottages
Lowest Price
AU$391
Highest Price
AU$876

Frequently asked questions

How much do cottages in Chester cost?
Expect to pay between AU$391 and AU$876 per night for cottages in Chester. Whatever your budget, an awesome stay is just a few clicks away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Chester?
Enjoy reconnecting with nature in one of the 104 cottages waiting for you in Chester. To help you select an ideal place, use our handy filter tool to search for amenities or perks you prefer.
What is there to do in Chester near my cottage?
You’ll find loads of impressive things that’ll fill up your itinerary in Chester. Discover attractions like Goodspeed Opera House, Devils Hopyard State Park and Chamard Vineyards. Chatfield Hollow State Park, Connecticut River Museum and East Haddam Historical Society and Museum also lure many visitors.

Recent Reviews in Chester
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