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Vacation Rentals in Chester, CT and nearby

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    The following rentals are within 10 miles of Chester, Connecticut.

    1 / 21
    4.5 of 5 stars (2) Very good
    Old Saybrook
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 22
    Haddam
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 59
    3 of 5 stars (4) Average
    Old Saybrook
    5 Bedrooms, 2 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Internet Access
    • Washer
    • Private Yard
    • Air Conditioning
    • Porch
    • Grill
    • Secure Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This unique property, located near the banks of the Oyster River, and conveniently on the Boston Post Road (US 1), was built in 1795 by Nathaniel Clark, a 4th generation descendant of Captain Nathaniel Clark, a famous local seaman. It was at a time when General William Hart built one of the... View all property information
    Location Information
    Old Saybrook, Connecticut 06475
    5 of 5 stars Reviewed December 7, 2014
    The night before we had had Guest from Yale, the window smashed and we did not know about this. The Guest arrived 4 hours early, so when they arrived, the home it was not ready...
    5 of 5 stars Reviewed March 12, 2014
    The weekend was perfect in every way. Little Roma celebrated her first birthday in style, surrounded by our dearest friends in a beautiful setting. We cooked lots of yummy food...
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    1 / 14
    4 of 5 stars (1) Very good
    East Haddam
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Sauna
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Duplex house at the Old Sindelar Farm. Everything was redone last year.Really clean. Enjoy the deck off the back or join us fireside. We have 3 beds, one queen with a memory foam mattress and two full size beds. All have 1800 count sheets so rest well. The kitchen is furnished with a blender and... View all property information
    Location Information
    East Haddam, Connecticut 06423
    4 of 5 stars Reviewed November 29, 2015
    We have 30 people that show up for Thanksgiving and they stay the whole weekend. I have a large lab that loves food and I had to find a place that would allow a dog because he...
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    Old Saybrook
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Porch
    • Patio
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Awesome Cottage! Great Owner! Absolutely loved this house and will definitely plan on staying here again! My husband is originally from Connecticut and his entire family still lives there. Traditionally we stay with family when we visit but I decided to rent a house this trip so we could entertain... View all property information
    Location Information
    Old Saybrook, Connecticut 06475
    1 / 32
    5 of 5 stars (1) Excellent
    Old Saybrook
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Amenities & Details
    • Porch
    • Grill
    • Satellite TV
    • Wi-Fi
    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Please contact us for Mid-week special Rates !!! Relax and enjoy the sea breezes at our home located in a quiet shoreline neighborhood setting with easy access to beaches, boating, restaurants, and shopping. Luxury and comfort combine for the perfect getaway. Enjoy a day in the sand at our... View all property information
    Location Information
    Old Saybrook, Connecticut 06475
    5 of 5 stars Reviewed March 13, 2013
    very clean, comfortable. Love this beach house, walking distance to the beach, kids love the beach, they catch crab. you will have loads of fun there...
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    1 / 59
    5 of 5 stars (1) Excellent
    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Waterfront
    • Satellite TV
    • Parking
    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Cornfield Point Waterfront Beach House is located in a quiet shoreline neighborhood setting. Kids can ride their bikes. Lovely large yard with great water-view for relaxing, picnics and outdoor family activities. Feel like at home with fully equipped kitchen and most amenities that you need.... View all property information
    Location Information
    Old Saybrook, Connecticut 06475
    5 of 5 stars Reviewed September 15, 2015
    The house was excellent, well-maintained. We had four adults and two young children. It had a private beach, rocky but access to a very sandy beach with beach passes only a 10th...
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    1 / 27
    Old Lyme
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Amenities & Details
    • Grill
    • Washer
    • DVD Player
    • Internet Access
    • Satellite TV
    • Parking
    • Porch
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Looking to rent a vacation beach house on the Connecticut shoreline? Here it is! Beautiful, private beach community. Short walk to a well kept beach. This cottage offers plenty of sleeping room with 4 bedrooms, screened porch, private back deck with new gas grill and fire pit in yard. Completely... View all property information
    Location Information
    Old Lyme, Connecticut 06371
    1 / 24
    5 of 5 stars (1) Excellent
    Old Lyme
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Porch
    • Satellite TV
    • Patio
    • Parking
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come and enjoy a relaxing vacation in Old Lyme, Connecticut. This freshly renovated furnished cottage located in a private beach community (Old Colony Beach) has enough room for family and friends and is ideally located at the entrance to the beach! Enjoy activities for adults and children all... View all property information
    Location Information
    Old Lyme, Connecticut 06371
    5 of 5 stars Reviewed September 16, 2015
    been renting here for 5 years and every year gets better! was looking for a vacation rental that was safe when my grandchildren were young. this is a gated community and the...
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    1 / 18
    Old Lyme
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Porch
    • Central Heating
    • Grill
    • DVD Player
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    OLD LYME SHORES, BEACH ASSOCIATION. Adorable, fully furnished 3 bedroom, 1 ba. plus Hot/Cold outdoor shower house. Cottage sleeps 6-8. Minutes to private, sandy beach. Home offers large, enclosed front porch, complete with it's summer time wicker funiture. Cable TV,DVD and CD player. Bedrooms... View all property information
    Location Information
    Old Lyme, Connecticut 06371
    1 / 15
    5 of 5 stars (1) Excellent
    Haddam
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Satellite TV
    • Outdoor Dining Area
    • Parking
    • Patio
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Secluded behind a stand of tall pines, the Laurel Cottage has been restored and expanded to include a full kitchen, bathroom with double pedestal bathtub and a large subway tiled shower. A cozy double brass bed in the Great Room and a luxurious pull out queen size bed on the all season porch... View all property information
    Location Information
    Haddam, Connecticut 06438
    5 of 5 stars Reviewed August 20, 2015
    We were delighted with EVERYTHING about the Laurel Cottage (on the property of the Nehemiah Brainerd House B&B in Haddam)!! From the moment we arrived, the owners Maryan and...
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    1 / 17
    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Parking
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A newly renovated home at the end of a cul de sac which offers privacy in a quiet neighborhood. It is a lovely open concept house that has a large deck and patio with water views. There is a very large side yard perfect for family volleyball and baseball games. The kitchen is fully equipped. There... View all property information
    Location Information
    Old Saybrook, Connecticut 06475
    Old Lyme
    3 Bedrooms, 7 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • Satellite TV
    • Patio
    • Washer
    • Hot Tub
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This house is a great family vacation spot. It has fabulous views of the mouth of the CT River and Long Island Sound including the two lighthouses. You can swim and fish off the dock. WE leave canoes and kayaks for you to use. you can paddle easily to a great beach that is part of a nature preserve... View all property information
    Location Information
    Old Lyme, Connecticut 06371
    Old Saybrook
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Family friendly vacation home still available for summer weeks. 2 BR, 1 1/2 bath home in private beach association neighborhood. House and neighborhood are ideal for young families. Master BR with Queen bed, 2nd BR with bunk bed and full bed. Open living/dining. Spacious backyard with deck, grill... View all property information
    Location Information
    Old Saybrook, Connecticut 06475
    1 / 4
    4 of 5 stars (2) Very good
    Westbrook
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Indoor Pool
    • Hot Tub
    • Housekeeping...
    • Internet Access
    • Sauna
    • Waterfront
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    1 bedroom 1 bath condo sleeps four I king and 1 pullout couch. available august 26-Sept 2 2016. no other dates for the entire year available Max occupancy is 4 persons. Escape to Water's Edge Resort and Spa, Connecticut's premier beach resort for couples and families along the Connecticut... View all property information
    Location Information
    Westbrook, Connecticut 06498
    3 of 5 stars Reviewed October 28, 2015
    Property was very nice in a great location. Too many buildings and greenery for a decent view of the ocean from our condo. Customer service was minimal except for the valets who...
    5 of 5 stars Reviewed May 10, 2014
    This place is incredible! When you first pull up, you are greeted by lovely gardens and a typically elegant beach style hotel. The staff was courteous at check in and immediately...
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    Old Saybrook
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our home is located in a quiet, friendly beach neighborhood. In summer you have access to 2 private beaches on the LI Sound. Both are within blocks of the house and can be walked in about 5 minutes or driven in about 2 minutes. There is a marina, children's playground, gazebo and more. In the... View all property information
    Location Information
    Old Saybrook, Connecticut 06475
    Westbrook
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Housekeeping...
    • Patio
    • Balcony
    • Terrace
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    1 bedroom 1 bath condo sleeps four I king and 1 pullout couch. no other dates for the entire year available Max occupancy is 4 persons. Escape to Water's Edge Resort and Spa, Connecticut's premier beach resort for couples and families along the Connecticut Shoreline beach condominiums. Enjoy... View all property information
    Location Information
    Westbrook, Connecticut 06498