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Chester Vacation 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.
    All 17 Rentals in Chester
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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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    Cornfield Point Beachfront Small Cottage1 / 8
    (4)Excellent
    Old Saybrook
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Clinton
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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. Check us out on line for the latest information--obstreperousoctopus dot com. Undergoing a complete renovation,...
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    Clinton, Connecticut 06413
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Deep River
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Housekeeping Included
    • Balcony
    • Air Conditioning
    • Washer
    • Grill
    • Sauna
    • DVD Player
    • Patio
    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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    Location Information
    Deep River, Connecticut 06417
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Charming 6 Bedroom Oceanfront Cottage By The Sea1 / 38
    (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, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make the most of your Old Lyme beach vacation when you stay at this newly remodeled 3-bedroom, 1-bathroom vacation rental cottage, just steps from the shores of the Atlantic Ocean. With sleeping accommodations for up to 6 traveling guests, this cottage is perfect for groups of families or friends...
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    Location Information
    Old Lyme, Connecticut 06371
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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    $500 off EARLY RESERVATION 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. 2020. 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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    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • 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
    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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    Steps to beach 4bd 2 bth Sleeps 121 / 19
    (1)Excellent
    Clinton
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Parking
    • Patio
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Private Yard
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    Even though it was March, our weekend getaway was wonderful. The beach was so close and the sunsets were beautiful. So convenient to town for restaurants and stores, and being...
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    About this property
    Amazing waterview property seen right from your front door which is 4 houses away. Steps to 2 private beaches and a 10 min walk to the town beach. Included to make your stay easier are Linens, towels, beach towels & chairs. Welcome to this 3 bedroom with a loft bedroom upstairs. Fully equipped...
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    Location Information
    Clinton, Connecticut 06413
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Old Lyme
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note this property is connected to the homeowners beach house with a completely separate entrance and unit ** Run away to the Connecticut coast and stay at this breezy 2-bedroom, 1-bathroom vacation rental apartment! Situated in the charming town of Old Lyme, this northeast gem offers...
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    Location Information
    Old Lyme, Connecticut 06371
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Old Saybrook
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Wi-Fi
    • Terrace
    • DVD Player
    • Balcony
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your New England getaway awaits you at this one-of-a-kind vacation rental home in Old Saybrook. The 'Nathanial Clarke House' has 5 bedrooms, 2 bathrooms, and provides accommodations for 14 guests. This beautifully decorated home boasts a wraparound porch, gorgeous gardens, and was featured on the...
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    Location Information
    Old Saybrook, Connecticut 06475
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    Old Saybrook
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to Old Saybrook when you stay at this charming 2-bedroom, 1-bathroom vacation rental cottage. Featuring accommodations for 6 guests, this home is perfect for families or close friends seeking a memorable getaway. This property is nestled in a quiet neighborhood where you can play yard games,...
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    Location Information
    Old Saybrook, Connecticut 06475
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Moodus
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your Connecticut getaway on a private lake beach during your stay at this 2-bedroom, 1-bathroom vacation rental cottage in Moodus! This cozy cottage is within walking distance to beautiful Moodus Reservoir and comfortably sleeps up to 5 guests. You can spend your days boating, swimming and...
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    Location Information
    Moodus, Connecticut 06469
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Clinton
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Clinton, Connecticut welcomes you to this lovely 3-bed, 1-bath vacation rental house that sleeps 6. Enjoy colorful sunsets or sunrises with a walk to one of the 2 private beaches, or take the provided bicycles for a spin 2 miles north to Clinton Town Beach near the New Harbor Marina. It will be...
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    Location Information
    Clinton, Connecticut 06413
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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