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Browse Select Chester Cottages

Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, 14 reviews
"Great place. Great host"
Private Guest House w/ Deck + Spectacular Views!
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 CA $281
CA $493 total
includes taxes & fees
Jun 23 - Jun 24
Go Jump in the Lake!
Charming Old Lyme Cottage, Steps to Private Beach!
7.6 out of 10, Good, 4 reviews
"The property was okay except washer & dryer were out of order and hot water wouldn't stay a steady temperature, also the toaster didn't work. But the major issue we had was with a schizophrenic man that lives next door who was intimidating us and was very angry, he even came right up in the front doorway when we were in the house. Talked to host about man having a key to the place and not feeling safe to spend a second night. Host knew all about man but would not refund our second night, so we...
Charming Old Lyme Cottage, Steps to Private Beach!
Beach Bungalow, large porch, 1/2 mile to the water.
The price is CA $313
CA $582 total
includes taxes & fees
Jul 2 - Jul 3
Beach Bungalow, large porch, 1/2 mile to the water.
"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 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
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
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!
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 CA $245
CA $397 total
includes taxes & fees
Jun 29 - Jun 30
Shalom Cottage with private beach rights.
Guilford Carriage House at Granite Lodge!
10.0 out of 10, Exceptional, 4 reviews
"Gorgeous cottage, spotless, tastefully decorated, thoughtful personal touches, many windows looking into private woods, comfortable bed with beautiful bedding!"
Guilford Carriage House at Granite Lodge!
The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, 9 reviews
"Robin was a great resource about the area. Her property was amazing the cottage was fantastic. Very comfortable and clean. We had a relaxing stay and a great time. We would love to go back again and again!"
The gardners Cottage 1 mile from long Island Sound - pet friendly
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
10.0 out of 10, Exceptional, 62 reviews
"This is our 2nd stay at Jaime’s quaint cottage. Spotlessly clean, well equipped and much enjoyed treats on arrival! We’ve already come back once and would not hesitate to do so in the future."
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Luxury Cottage walking distance to Saybrook Point Marina
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 CA $502
CA $826 total
includes taxes & fees
Jun 23 - Jun 24
Luxury Cottage walking distance to Saybrook Point Marina
Charming Deep River Vacation Rental on Star Lake!
10.0 out of 10, Exceptional, 1 review
"The cottage was very clean. The view of the lake and surroundings was beautiful and peaceful. It was about 10 minutes away from friends we were visiting in Ivoryton, so the location was perfect. I will keep it in mind for the next visit to CT."
Charming Deep River Vacation Rental on Star Lake!
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 CA $342
CA $441 total
includes taxes & fees
Jun 25 - Jun 26
Resting on an 18 acre farm, this historic cottage is the retreat of your dreams
Quaint Beach Cottage
Quaint Beach Cottage
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
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
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 CA $329
CA $682 total
includes taxes & fees
Jun 23 - Jun 24
The Bay Cottage · Rocky Neck Park, Beach & Niantic
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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, 14 reviews
"Great place. Great host"
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, 14 reviews
"The Villa was beautiful and immaculately clean. The host, Taylor, was very easy to communicate with. "
The price is CA $240
CA $443 total
includes taxes & fees
Jun 24 - Jun 25
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, 113 reviews
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
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.

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