Photo by Annette Babek

Holiday Homes in Chester

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Featured Holiday Homes in Chester

Charming 2-bedroom townhome

2.0 star property
9.6 out of 10, Exceptional, (5)
"The home was beautiful and I would stay there again."
The price is AU$264
includes taxes & fees
24 Nov - 25 Nov
Charming 2-bedroom townhome

Waterfront Beach House

9.6 out of 10, Exceptional, (39)
"This was perfect for us. We had a family funeral and this was a nice retreat. We would stay again for sure. "
Waterfront Beach House

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

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

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

10.0 out of 10, Exceptional, (17)
"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

Historic Essex Home w/ Large Yard Near Downtown!

9.8 out of 10, Exceptional, (40)
"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."
Historic Essex Home w/ Large Yard Near Downtown!

Beach House

9.8 out of 10, Exceptional, (47)
"It's Christmas all year and we loved it! So so cozy. From my elderly mom to my toddler everyone was happy. Kids lived the playground and we loved how easy and comfortable the house was. Joe also left us delicious cookies from a local bakery. Thank you Joe!!! "
Beach House

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

9.4 out of 10, Exceptional, (33)
"Our second stay at the cottage. We spent a long weekend and the weather cooperated. The house is quite quirky, but has a really pleasant feel at home vibe. Beds were very comfortable. Kitchen could use some updates, but was sufficient. (still need a new can opener) The porch overlooking the Sound is magical. Nice neighborhood. If you have one...bring a golf cart! Lots of golf carts about. Host is always pleasant, communicating through Vrbo. We hope to return again. Thank you Khalig Family...
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

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

9.6 out of 10, Exceptional, (44)
"We loved being next door to Ocean Beach."
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

Amazing Lakefront Property

9.8 out of 10, Exceptional, (23)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property

Summer at the Haddam House

10.0 out of 10, Exceptional, (49)
"Hands down , Very nice property , highly recommend staying at this location . You won’t be let down . "
Summer at the Haddam House

NEW! Seaside Beach Haven with a private beach!

10.0 out of 10, Exceptional, (11)
"Good"
NEW! Seaside Beach Haven with a private beach!

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

10.0 out of 10, Exceptional, (2)
"Started with Kristine greeting us as we drove in. Was accommodating to our requests and was very quick to reply to our few messages. Clothes dryer is very small. Short walk to a great park and beach."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Vacation Starts Now! Pet friendly, beach fun 5 min away!

Vacation Starts Now! Pet friendly, beach fun 5 min away!

Minutes from Beaches | Large Spa - Home Theater

9.8 out of 10, Exceptional, (10)
"We enjoyed our stay. The amenities were great. The kitchen was well supplied for all our needs. Great large table for celebrating birthdays. The beds were very comfortable. The hot tub was a big hit with some of the family. The backyard seating area was perfect for visiting on a beautiful day. We highly recommend this clean,well kept comfortable property. A suggestion: at least one bedroom could use a mirror and a picture on the blank walls. A small bureau would be helpful as...
Minutes from Beaches | Large Spa - Home Theater

Guilford home -self check in, off-street parking

9.4 out of 10, Exceptional, (8)
"The property was nice, clean and comfortable. "
Guilford home -self check in, off-street parking

Charming year-round beach home in Indian Town, Old Saybrook

The price is AU$1,313
includes taxes & fees
1 Dec - 2 Dec
Charming year-round beach home in Indian Town, Old Saybrook

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

7.2 out of 10, Good, (7)
"Stayed here for a weekend at Mystic with my parents who are older. Lots of steps from the street so bear in mind. Claude was very kind when I called him with questions and the water and fruit on the kitchen table was a nice touch. Neighborhood is a bit loud from front bedroom but beds were oh so cozy and again, CLEAN CLEAN CLEAN!"
The price is AU$434
includes taxes & fees
26 Nov - 27 Nov
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

10.0 out of 10, Exceptional, (19)
"Lovely house. Perfect for a family getaway for children and adults. Nice number of sleeping options. Three full bathrooms a big plus. Great communal areas and a wonderful backyard. Short walk to the beach. Great time of year to enjoy being on the beach without all the crowds and summer heat. "
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (58)
"Great"
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
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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Other property types in Chester

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

10.0 out of 10, Exceptional, (28)
"The only ‘concern’ we had was that the heated pool wasn’t heated. Ice cold. Also, one other minor issue was that there were no coffee creamers supplied to the unit. Other than that, the stay was pretty good and room ess quiet and comfortable. "
The price is AU$532
includes taxes & fees
24 Nov - 25 Nov
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (23)
"We loved our trip. The cottage is beautifully done and the views incredible. We appreciated the hospitality extended by our host (and Nico the dog!) and enjoyed exploring the nearby woodland. Our kids are already asking if we can go back and visit again. "
Private Guest House w/ Deck + Spectacular Views!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.