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Vacation Homes in Chester

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

10.0 out of 10, Exceptional, (103)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.4 out of 10, Exceptional, (14)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (67)
"The house is perfectly located. Quiet area but close to downtown Madison and Guilford and so much the CT shoreline has to offer. "
New Madison beach house - Ocean front- Great views- booking Summer 2025

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (14)
"the host was really great about getting back to us when we had a question or problem . his home was comfortable and artistic. the location was also easy to get to and the neighborhood was quiet and comvenient to all your needs."
Ranch style living at its best with country garden & patio!

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (68)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Iconic Bow House, an Oasis in the Heart of the Niantic Bay Marina

10.0 out of 10, Exceptional, (5)
"This home was amazing! We stayed here for most of the week so we could participate in USCGA graduation activities. The home had everything we could possibly need (including a diffuser for my curly-haired daughter). The labels in the kitchen made it super easy to find and put things away. We enjoyed chatting at the fire pit and warming up in the hot tub after a very chilly graduation day. Would absolutely stay here again."
Iconic Bow House, an Oasis in the Heart of the Niantic Bay Marina

2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

10.0 out of 10, Exceptional, (38)
"Lynne is very responsive and her property is lovely. We were pleased with our stay. "
2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

Close to Mystic, Stonington, Westerly. Room for everyone. 3 mins to Ocean Beach.

9.8 out of 10, Exceptional, (40)
"The house was clean and cute. The owners had very clear instructions in their house book as well as local recommendations. When I had a question, the owners were very responsive by text. Beds were comfortable and the shower had good water pressure. The house is near a school and we enjoyed the playground. It is also about 1 mile to Ocean Beach and parking passes were provided. We enjoyed a cruise and visiting Mystic which both were easy to get to from the house. We also enjoyed the quirky...
Close to Mystic, Stonington, Westerly. Room for everyone. 3 mins to Ocean Beach.

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!

Charming beach home, complete with pool & cozy guest house!

9.8 out of 10, Exceptional, (35)
"Very clean and comfy house. The guest cottage was a nice surprise! Walking distance to Beach and restaurants.We were during the recent heat wave and spent a lot of time in the pool.Would return again if in the area."
Charming beach home, complete with pool & cozy guest house!

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (15)
"Clean"
The price is AED 868
AED 2,339 total
includes taxes & fees
28 Oct - 29 Oct
Thames River Retreat · CT College+Casinos+USCGA

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

2.0 star property
10.0 out of 10, Exceptional, (7)
"We enjoyed our time in Westbrook! Hosts were more than accomodating and helpful throughout our stay - thank you! House is cute, the perfect size for a small group, and in a good location (walking distance to many shops and restaurants). Private beach access is easy to get to (beach area is small, but it worked!)"
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

The Beach House - Old Lyme

10.0 out of 10, Exceptional, (19)
"Exquisite botanical garden!"
The Beach House - Old Lyme

Amazing Lakefront Property

9.8 out of 10, Exceptional, (26)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property

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

10.0 out of 10, Exceptional, (48)
"Absolutely, beautiful and great hostess"
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC W/ 6 QUEENS 1 FULL BED

9.8 out of 10, Exceptional, (28)
"I rented this property for my daughter and friends after her prom! Neighbors were great and perfect location for shopping and restaurants. Rooms were spacious and it was a perfect weekend for them. "
PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC W/ 6 QUEENS 1 FULL BED

Luxury, New, Quiet - King Beds, 5 minutes to Mohegan Sun

10.0 out of 10, Exceptional, (4)
"Very clean and comfortable "
The price is AED 736
AED 1,784 total
includes taxes & fees
29 Oct - 30 Oct
Luxury, New, Quiet - King Beds, 5 minutes to Mohegan Sun

Storybook Cottage

10.0 out of 10, Exceptional, (2)
"Charming antique property full of character with private backyard, minutes to everything in Old Saybrook. Note- bedrooms half bath are upstairs along with lovely family room, full bath with shower is down. Property was clean and comfortable. We enjoyed our stay!"
Storybook Cottage

Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

9.6 out of 10, Exceptional, (48)
"We loved being next door to Ocean Beach."
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

9.8 out of 10, Exceptional, (6)
"This was the perfect house for our family’s long weekend getaway to coastal New England. The house was beautiful and spotless, and came with everything you might need and more. We loved the griddle, the hot tub and my son loved the game room. Would definitely stay again!"
Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.
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