Photo by Annette Babek

Holiday Homes in Chester

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Featured Holiday Homes in Chester

Waterford Dollhouse
Fridge, microwave, oven, stovetop

Waterford Dollhouse

10.0 out of 10, Exceptional, (2)
"Owners went Above and beyond!!"
Waterford Dollhouse
Historical New England coastal holiday home-2 min. from Ocean Beach
Interior

Historical New England coastal holiday home-2 min. from Ocean Beach

10.0 out of 10, Exceptional, (33)
"The host was incredibly kind and accommodating. We particularly enjoyed the beach pass, as we drove ~3 min to the beautiful water in the morning. The amenities were absolutely gorgeous and beyond functional. Plenty of bathrooms, showers, sinks, sitting areas, etc. for our party. We had a wonderful stay!"
Historical New England coastal holiday home-2 min. from Ocean Beach
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Outdoor pool

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

10.0 out of 10, Exceptional, (84)
"This was such a central location for my East coast family to meet up. Perfect lodging for folks coming from lots of different areas and spatial needs. We had a lovely time going to the farm stand and made a beautiful meal from the produce we picked up. Thanks for an amazing stay! "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Charming cottage by the sea
On the beach, sun-loungers, beach towels

Charming cottage by the sea

9.8 out of 10, Exceptional, (8)
"Me, my husband and family members that stayed with us very much enjoyed the calmness and the beauty of the property. The view is amazing. It's very convenient that we can just take out the kayak right there to enjoy the out door activity! "
Charming cottage by the sea
#29 - Modern 5 Bedroom/2 Bath
Fridge, microwave, oven, stovetop

#29 - Modern 5 Bedroom/2 Bath

10.0 out of 10, Exceptional, (2)
"We enjoyed staying at this house while in town for a family wedding. The house was clean and recently renovated. Beds were comfortable and linens and towels were provided. Be aware there are no young child items. We brought our own baby gate for the stairs and plastic cups and dishwater. Plenty of nice cooking tools in the kitchen. Overall we enjoyed our stay."
The price is AU$918
includes taxes & fees
20 Dec - 21 Dec
#29 - Modern 5 Bedroom/2 Bath
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, sun-loungers, beach towels

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
Waterfront Beach House
Terrace/patio

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
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College
Aerial 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
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Fridge, microwave, oven, stovetop

Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

10.0 out of 10, Exceptional, (31)
"Heather’s home was the perfect stay for my son and daughter-in-law and my 2 granddaughters. Her home is sparkling clean and beautifully decorated with a relaxed beach theme. My grandchildren were so to stay there, that they asked when they could come back and stay again. "
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Historic Essex Home w/ Large Yard Near Downtown!
TV

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!
Enjoy a taste of New England in Historic Guilford Ct
Beach nearby

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (9)
"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."
Enjoy a taste of New England in Historic Guilford Ct
Ranch style living at its best with country garden & patio!
Exterior

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

9.8 out of 10, Exceptional, (7)
"We had a great time at this home and it is really fabulously decorated. Reggie called us right back when we had a question. "
Ranch style living at its best with country garden & patio!
Waterford Manitock Spring Water Residence with handicap accessible home
Outdoor dining

Waterford Manitock Spring Water Residence with handicap accessible home

10.0 out of 10, Exceptional, (3)
"Traveled to New London to visit my son at the US Coast Guard Academy. The House was very clean and spacious inside. Mike the owner was extremely helpful and willing to address any issues if there were any. It was only about 12 mins to the academy and about 3mins to downtown. I would stay there again if I ever come back into town. "
Waterford Manitock Spring Water Residence with handicap accessible home
NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly
Interior

NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly

10.0 out of 10, Exceptional, (1)
"Great home and nice activities with kids."
The price is AU$644
includes taxes & fees
27 Nov - 28 Nov
NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly
Luxe Lake House in Connecticut
Fridge, microwave, oven, stovetop

Luxe Lake House in Connecticut

The price is AU$1,445
includes taxes & fees
11 Dec - 12 Dec
Luxe Lake House in Connecticut
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!
Outdoor dining

Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We had an absolute fantastic time staying at this place. My son was got married at the Beech Tree Cottages (also was the perfect wedding venue) in Madison, Ct. about 15 minutes from the house which worked out perfectly for staying here. From start to finish, everything exceeded our expectations. The communication with Chase was smooth and prompt, making the booking process hassle free. Upon our arrival we were greeted with a welcome gift. The space was clean, modern and beautifully...
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Pool

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>
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Dining

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (25)
"We spent the weekend at the shore to celebrater my wife's 70th Birthday. The accommodations were fabulous and everyone enjoyed the home, the view and the location. Thank you to our host Laura."
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
On the beach, beach towels

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
Beautiful 4BR Beach House with Private Beach Access.
Beach nearby, beach towels

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.
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
Indoor pool, a heated pool

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$533
includes taxes & fees
1 Dec - 2 Dec
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Private Guest House w/ Deck + Spectacular Views!
Property grounds

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!
Miscellaneous

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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