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Chester Family & Kid Friendly Rentals

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    Don't let other travelers get your favorite Chester area vacation rental. You're so close to securing your perfect getaway. Book today.
    16 Matching Rentals in the Chester AreaView all 17 rentals
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    The following rentals are within 10 miles of Chester.
    Weekly Summer Beach Rental1 / 17
    (4)Excellent
    Old Lyme
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Cozy Artist decorated Cottage, walk to beach, pets Ok,  exceptional environment1 / 17
    (1)Very good
    Old Saybrook
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Old Saybrook
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Cornfield Point Beachfront Small Cottage1 / 8
    (4)Excellent
    Old Saybrook
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2018
    Cottage was cozy & clean and the beach was right there! Beautiful sunsets and good times. Nick & Andrew we’re very accommodating. Thank you!
    Reviewed July 2, 2018
    Great vacation for my husband and I with my daughter’s family. We were met by a family member when we arrived about 3:15. Everything was shown to us in detail. All our...
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    About this property
    A 2 Room, Small Cottage overlooking the Cornfield Point Private Beach on the Long Island Sound. INCLUDES: A fully stocked kitchen with microwave, coffeemaker, and toaster. A dinette table for four, A full-size custom futon sleeper sofa, a one half bath, with attached outdoor private hot and cold...
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    Location Information
    Old Saybrook, Connecticut 06475
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Perfect Getaway! Walk to the Beach or Relax on the Patio overlooking the Properties Dock by the River! Close to Area Attractions such as Goodspeed Opera House, Gillette's Castle, Towns of Mystic, Essex and New Haven Near Vineyards, Mohegan Sun & Foxwoods Casinos, Antiquing, Parks, Museums, Art...
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    Westbrook, Connecticut 06498
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Deep River
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
    • Housekeeping Included
    • Cable/satellite TV
    • Washer
    • Sauna
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Peace Barn is a cozy retreat close to art and culture and parks. You’ll love my place because of the outdoor space and the comfy beds. My place is good for families, couples, and furry friends. The Peace Barn sits on 15 acres of private land which can be used for group retreats, film making,...
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    Deep River, Connecticut 06417
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Clinton
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Waterfront
    • Patio
    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched along a luxurious peninsula jutting into the Long Island Sound, the Obstreperous Octopus sinks its tentacles into the sand and represents the finest in CT WATERFRONT real estate. Undergoing a complete renovation, the Octopus boasts 4 bedrooms, 2.5 bathrooms and an open concept chef's...
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    Clinton, Connecticut 06413
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Charming 6 Bedroom Oceanfront Cottage By The Sea1 / 37
    (2)Very good
    Clinton
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2018
    We were looking for a Connecticut place on the water, spacious and unpretentious. We found it. Mairzy Doats cottage had just the right charm, overlooking the beach and surf...
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    About this property
    **COTTAGE BY THE SEA** Six bedroom cottage for rent on a PRIME SHORELINE location at Clinton Beach (91 Shore Road, 'Mairzy Doats Cottage'), Clinton, CT. **9 ROOM, WATERFRONT Cottage, situated on a LARGE, PRIVATE BEACH only steps away from the ocean! Charm, Character, & Cleanliness! The cottage is...
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    Location Information
    Clinton, Connecticut 06413
    Rental Home - 6 Bedrooms, 2 Bathrooms, Sleeps 10
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    Old Lyme
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Ocean Views
    • Cable/satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I challenge you to find a cottage that provides more than our Pail and Shovel Inn at Old Colony Beach in Old Lyme, Connecticut! Known as - pail and shovel inn - all in one word online, we offer the following: Beds in 3 bedfrooms - King-size Bed (1) - Trundle (two twins) (2) - Twin/Single Bed...
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    Location Information
    Old Lyme, Connecticut 06371
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Old Saybrook
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic Old Saybrook has been a desired destination for family and friends for over 130 years, and our spacious villas are the perfect place to treat yourself to some quality time with the ones you love. Our villas are equipped with all of the necessities you will need during your stay; two...
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    Location Information
    Old Saybrook, Connecticut 06475
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Lyme
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Grill
    • Air Conditioning
    • Private Yard
    • DVD Player
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flat Rock Farm offers visitors a sophisticated home in the pastoral town of Lyme, CT, an easy two hour drive from NYC or Boston. Whether your objective is a family vacation, gathering of friends, or romantic escape, Flat Rock Farm offers visitors the perfect getaway. Set on an historic property,...
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    Location Information
    Lyme, Connecticut 06371
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A 3 bedroom, 1 1/2 bath home overlooking the Cornfield Point Private Beach on the Long Island Sound. FIRST FLOOR: A fully stocked kitchen with microwave and coffee maker. A dining area and formal dining room. A one half bath. A bedroom with two twin beds. Laundry Room also available. There is a...
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    Location Information
    Old Saybrook, Connecticut 06475
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Save $500 off September CT Lake Front  Victorian Mansion Truly Memorable1 / 21
    (3)Very good
    East Haddam
    7 Bedrooms, 4 Bathrooms, Sleeps 24 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Waterfront
    • Washer
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal Connecticut location on Beautiful Crystal Clear Bashan Lake. Victorian Mansion with magnificent water views. Perfect setting for family vacations, and family reunions!! Taking reservations thru Dec. 2018. Just 1 3/4 hours from New York or Newport RI or 2 hrs. from Boston! Canoe, kayak,...
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    Location Information
    East Haddam, Connecticut 06423
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 24
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    Old Lyme
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Copper Beech Guest House is conveniently located 2 hours from Boston and NYC. 30 minutes to the Casinos, 25 minutes to Mystic, 10 minutes to Essex and Old Saybrook and 1/2 mile from Historic Lyme Street in Old Lyme. The Beaches are just a 2 minute drive away. The River is less than 1/2 mile...
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    Location Information
    Old Lyme, Connecticut 06371
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Patio
    • Housekeeping Included
    • DVD Player
    • Shared Yard
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rates Are Based on A 7 Night Minimum Stay for 2 Guests Located in the Quaint, Historic, Shoreline Town of Westbrook, CT Lies this Unique 2 Bedroom Cottage! Escape from It All ~ Walk to the Beach or Stroll Down to the Dock on the Property's Riverfront. The Cottage is 1/2 mile from Town Center &...
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    Location Information
    Westbrook, Connecticut 06498
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Old Saybrook
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean front property the only one in the area that has a huge yard and beach. 4-bedrooms, beautiful sunroom, fireplace, gazebo. Old Saybrook is a quiet beach town that's very family friendly. It's also known for it's many great dining options. In addition to the beach right in front of the house,...
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    Location Information
    Old Saybrook, Connecticut 06475
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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