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Holiday Rentals in Chester

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    ₹ 33,127 Average
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    ₹ 0₹ 75,000+
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    Don't let other travellers get your favourite Chester area holiday home. You're so close to securing your perfect getaway. Book today.
    All 11 Rentals in Chester
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    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The following rentals are within 15 kilometres of Chester.
    $500 off 2020 book by 4/15/20 CT Victorian Lakefront Mansion Truly Memorable1 / 21
    (3)Very good
    East Haddam
    7 Bedrooms, 4 Bathrooms, Sleeps 22 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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    Weekly Summer Beach Rental1 / 17
    (5)Excellent
    Old Lyme
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2019
    Wonderful home to escape to! Cute, Clean, and well furnished with everything you could need! No musty smell that sometimes occurs with beach homes and great little beach just a...
    Reviewed 13 July 2018
    We had a wonderful week at this home. It is incredibly spacious, clean and equipped with everything imaginable for a fun family beach vacation. The kitchen, in particular, is...
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    About this property
    Amazing remodel of this beachside, 4BR, 2Bath colonial. Two private beaches to choose from in this gated community. Dogs are welcome and a fenced area is provided! Plenty of room for 4 to 5 cars off street. The association includes access to basketball court, tennis courts, baseball diamond,...
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    Location Information
    Old Lyme, Mystic Country 06371
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Old Saybrook
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Air Conditioning
    Suitability
    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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    Location Information
    Old Saybrook, Connecticut 06475
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Deep River
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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
    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • 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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    Location Information
    Westbrook, Connecticut 06498
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Lyme
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Lyme, Mystic Country 06371
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Steps to beach 4bd 2 bth Sleeps 141 / 19
    (1)Excellent
    Clinton
    3 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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
    Old Saybrook
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Quaint CT Shore Cottage - Ocean View1 / 11
    (1)Excellent
    Westbrook
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Parking
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 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
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