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Chester Holiday Rentals

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    Don't let other travellers get your favourite Chester area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 17 Rentals in Chester
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    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Stay in The Heart of Chester Village, Convenient to Shoreline and Middletown1 / 18
    (5)Very good
    Chester
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    The following rentals are within 15 kilometres of Chester.
    Weekly Summer Beach Rental1 / 17
    (5)Excellent
    Old Lyme
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Cottage By The Sea... September Specials!!1 / 36
    (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 Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 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
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
    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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    Deep River, Connecticut 06417
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Old Lyme
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    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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    Old Lyme, Mystic Country 06371
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Old Lyme
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    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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    Old Lyme, Mystic Country 06371
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Lyme
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Grill
    • Air Conditioning
    • Private Garden
    • 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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    Lyme, Mystic Country 06371
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Wi-Fi
    • Patio
    • Housekeeping Included
    • DVD Player
    • Shared Garden
    • Private Garden
    • 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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    Westbrook, Connecticut 06498
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Steps to beach 4bd 2 bth Sleeps 141 / 19
    (1)Excellent
    Clinton
    3 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Parking
    • Patio
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2019
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 14
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    $500 off 2020 book by12/31/19 CT Victorian Lakefront Mansion Truly Memorable1 / 21
    (3)Very good
    East Haddam
    7 Bedrooms, 4 Bathrooms, Sleeps 22 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
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 22
    Quaint CT Shore Cottage - Ocean View1 / 11
    (1)Excellent
    Westbrook
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Parking
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2019
    I brought my two daughters for a stay, and we had a fabulous time. The cottage has three comfortable bedrooms and a large sitting area/ dining area. We walked three cottages...
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    About this property
    New England charm with modern amenities. Connecticut shore cottage with ocean views, sun porch, knotty-pine great room--and winterized for year-round living. Historic seashore style with vintage cottage details and modern updates. 50-yard walk to either a private or town beach. Close to nine area...
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    Location Information
    Westbrook, Connecticut 06498
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    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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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Old Saybrook
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Secure Parking
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unobstructed water views! Less than 1 mile to downtown. Golf, town beaches and many more amenities just minutes away. Private dock with tandem kayak and paddleboard, cornhole set, grill, firepit, outdoor shower. Top of the line kitchen appliances, billards room facing the water. Beautiful large...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Old Saybrook
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Patio
    • Washer
    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and enjoy the Connecticut sea breeze at this Saybrook Manor home where luxury and comfort combine for the perfect getaway! This 3-bedroom, 1-bath house is located in a quiet shoreline neighborhood within easy walking or biking distance of beaches, boating, dining, and shopping. With a full...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Essex
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brimming with small-town charm, Essex should be the next stop on your bucket list! This inviting 2-bedroom, 1.5-bathroom vacation rental is loaded with country charm as well as a fully equipped kitchen and outdoor living space, making it the perfect home base for your next coastal getaway. Spend...
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    Essex, Connecticut 06426
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Westbrook
    5 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leave your cares behind and let beach living set the agenda for your Westbrook retreat! This 3-bedroom, 2.5-bath vacation rental boasts numerous decks just 1 block from the marina and Pilot Point's stunning white-sand beach. After mornings boating, fishing and sunbathing, stop by Bill's Seafood...
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    Location Information
    Westbrook, Connecticut 06498
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 6
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