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Vacation Homes in Chester

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (6)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
$460 nightly
The price is $520
Aug 7 - Aug 8
Total includes taxes and fees
Thames River Retreat · CT College+Casinos+USCGA

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (136)
"Perfect location for a get-away! Beautiful location on the water. The cottage was cozy & had everything we needed. Very clean. Lots to do in the area. Host was very nice We had a great time and will absolutely be back! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

6.0 out of 10, (4)
"Really convenient location breakfast was good. Rooms were clean."
$107 nightly
The price is $121
Aug 7 - Aug 8
Total includes taxes and fees
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

Shoreline Oasis

8.8 out of 10, Excellent, (5)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
$230 nightly
The price is $261
Aug 7 - Aug 8
Total includes taxes and fees
Shoreline Oasis

Perfect beach house getaway within walking distance to the beach

8.8 out of 10, Excellent, (8)
"Great weekend getaway - close to the beaches and towns. Lovely little house with firepit and very quiet neighborhood."
Perfect beach house getaway within walking distance to the beach

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (13)
"Very comfortable rockers and Adirondack chairs make it easy to relax and enjoy the lake view. Our bed was comfortable, and Nile supplied all we needed with linens and soaps. We appreciated all the space and large dining table. Lake is beautiful. Very enjoyable stay. Exceptional communication with our host. "
Grammy's Lake House w/ Private Waterfront Access

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

4.8 out of 10, (3)
"Overall, my girlfriends and I had a good stay at this accommodation. Transparently, there were some hiccups in communication between the property manager and I in the week leading up to our trip that were not clearly stated in the home's description prior to us booking our stay, however, I felt that they were able to address my concerns and came up with solutions that felt satisfactory to my group and I. The property manager was overall understanding and receptive to my feedback through our...
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (47)
"Home was very comfortable and a great location. The views were spectacular. Owner gave us great recommendations for restaurants and nearby attractions. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (20)
"We had a wonderful 2 day stay! We already knew the area……what a treat to stay so close to the beach in such a cozy cottage. Thank you!"
Oceanfront Beach House lay in bed and hear the waves, boats , birds

The Dollhouse is conveniently located. Mystic, Beaches, parks, casinos, shopping

10.0 out of 10, Exceptional, (17)
"Can’t say enough nice things about this property. Everything was beautiful and clean and attention was paid to every detail. We had to cut our stay short due to unforeseen circumstances, but we will definitely be back!"
The Dollhouse is conveniently located. Mystic, Beaches, parks, casinos, shopping

Historic New England home ,Reunions Beach pass

9.2 out of 10, Wonderful, (88)
"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."
$584 nightly
The price is $661
Sep 2 - Sep 3
Total includes taxes and fees
Historic New England home ,Reunions Beach pass

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
$571 nightly
The price is $646
Aug 13 - Aug 14
Total includes taxes and fees
adorable ranch in beach community

Charming 2-bedroom house in marvelous Montville with WiFi, AC

9.0 out of 10, Wonderful, (2)
"Perfect!"
Charming 2-bedroom house in marvelous Montville with WiFi, AC

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (92)
"We loved our time at White Gate. Very peaceful!"
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Groton Bay / Heated pool opens May 6th 2023!

8.8 out of 10, Excellent, (6)
"A bunch of friends stayed at this location for an overnight fishing trip. The house was clean, confidently located right off the highway, and close to everything we needed. Would definitely stay here again!"
$1,137 nightly
The price is $1,286
Aug 24 - Aug 25
Total includes taxes and fees
Groton Bay / Heated pool opens May 6th 2023!

The Beach Nest-Lux Cottage Steps to the Beach

9.8 out of 10, Exceptional, (6)
"Quick weekend stay as we needed to be in the area for a soccer tournament. The house was super clean and had everything we needed. Would definitely stay again. "
The Beach Nest-Lux Cottage Steps to the Beach

UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

10.0 out of 10, Exceptional, (63)
"We really enjoyed our stay at the property. The home was very clean, the beds were comfortable, and the location was convenient for all of our weekend activities."
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

The Beach House - Old Lyme

10.0 out of 10, Exceptional, (17)
"Exquisite botanical garden!"
The Beach House - Old Lyme

Gorgeous 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (74)
"We loved our stay at this beautiful cottage. The entire experience was very smooth, from pre-check in to getting there and even offers to help with anything we needed in our stayThe cottage is very cozy and well-cared for. The rooms are comfortable and the Internet fast. There is a lot to do in the area, with New Haven nearby and many good restaurants."
Gorgeous 4BR Beach House with Private Beach Access.

Spacious 5-bedroom house in charming New London, CT with WiFi & a Game Room.

8.8 out of 10, Excellent, (3)
"We had a great stay here! A great location and perfect for family time! A few things like fire pit etc would have added a lot of value! "
Spacious 5-bedroom house in charming New London, CT with WiFi & a Game Room.
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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Top Chester Hotel Reviews