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Holiday Rentals in Madison

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    ₹ 17,456 Average
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    All 31 Rentals in Madison
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    Indian Summer and Leaf Peeper Cottage for rent on Connecticut Shoreline1 / 17
    (10)Excellent
    Madison
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Madison
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    The following rentals are within 25 kilometres of Madison.
    Old Saybrook
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Weekly Summer Beach Rental1 / 17
    (1)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 2 days ago
    this is a great house, super close to the beach, fully stocked, very spacious and clean! allowing pets is an added bonus, we definitely plan on returning
    Reviewed 18 July 2017
    Beautiful house and yard just a few houses from the beach. Cleanest place I have ever rented. No end to the hot water. Every thing you could possible need for a week at the...
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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, Connecticut 06371
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Ennis Cottage with private beach on Branford shore1 / 17
    (15)Excellent
    Branford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Cable/satellite TV
    • Patio
    • Grill
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2016
    Thank you Ron and Bernie for making our vacation an excellent one. The rental house was compact, but with everything we needed, at hand. At the end of our vacation we didn't...
    Reviewed 11 July 2016
    The cottage was everything we expected and more!! Ron and Bernie were the friendliest of people and we could tell that they wanted our vacation to be the best. They are very...
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    About this property
    This newly renovated one bedroom cottage is set in the midst of other cottages. With a private back garden, patio, beautiful flowers, and steps from a private neighborhood beach , the cottage is clean, and comfortable. For cool nights there is a gas fire, and an air conditioner in the bedroom...
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    Branford, Connecticut 06410
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Connecticut Retreat: a magical hide-away1 / 73
    (8)Excellent
    Chester
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Wi-Fi
    • Grill
    • Air Conditioning
    • DVD Player
    • Outdoor Dining Area
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2014
    The hosts were very easy going and combined with a clean, comfortable house in a lovely scenic location it made for a most enjoyable stay.
    Reviewed 12 July 2014
    We were in a bit of a lurch on a family getaway and needed a house due to our children (ages 3, 4 & 16) and not partial to hotels for the length of time we were there (10...
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    About this property
    The Connecticut Retreat was built by a pair of New Yorkers who wanted a 'spiritual and artist retreat' convenient to NYC but far from the fast-paced lifestyle of the City. The Retreat is situated on 10 wooded acres surrounded by 1000 acres of forest. Take a short walk through the woods to the...
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    Chester, Connecticut 06412
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Cornfield Point Beachfront Small Cottage1 / 8
    (2)Excellent
    Old Saybrook
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Old Lyme
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    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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    Old Lyme, Connecticut 06371
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Guilford
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Porch
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is located down a dirt road off of the beaten path. Enjoy an extraordinary country wooded vacation, holiday, getaway or reunion retreat for the two of you, the whole family, or up to 6-8 friends and family. Situated on 40 wooded acres of absolute privacy in the middle of 1100 acres of...
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    Guilford, Connecticut 06437
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Clinton
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Parking
    • Ocean Views
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private beach. Sleeps 10 people. Front of house has Long Island Sound Views and the back overlooks tranquil Marsh area. Large gourmet kitchen with Subzero refrigerator, two sinks, double wall oven, and microwave. Huge granite island for food prep and parties. Open concept living with kitchen...
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    Location Information
    Clinton, Connecticut 06413
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    9 ROOM WATERFRONT SUMMER COTTAGE (WITH 6 BEDROOMS) FOR RENT ON PRIVATE BEACH1 / 32
    (1)Average
    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
    About this property
    **COTTAGE BY THE SEA** Weekly cottage for rent on a PRIME SHORELINE location at Clinton Beach (91 Shore Road), Clinton, CT. **9 ROOM, WATERFRONT Cottage, situated on a LARGE, PRIVATE BEACH only steps away from the ocean! Charm, Character, & Cleanliness! The cottage is professionally cleaned after...
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    Clinton, Connecticut 06413
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
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    Westbrook
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Garden
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Old Saybrook
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Charming** Genuine New England Large Ppty-Weddings-Reunions w/large garden This is a five bedroom with a working fireplace, The home sleeps 14 people. Since 2007, this historic and one-of-a-kind property, has been offered successfully for family reunions, retreats, weddings, film shootings,...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    East Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Parking
    • Ocean Views
    • Grill
    • Waterfront
    • Balcony
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated direct beach front house on private beach, beautifully furnished and detailed. All the comforts of home and more! Fully equipped new 'vintage reproduction' kitchen, washing machine and dryer, towels linens, beach chairs, outdoor stove in enclosed screened in porch and cooking area...
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    East Haven, Connecticut 06512
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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 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
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    Charming Waterfront Beach Cottage-WOW! Sunsets1 / 45
    (4)Excellent
    Guilford
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Porch
    • Waterfront
    • Shared Garden
    • Grill
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2016
    The previous reviews are all pretty spot on. This is an incredibly charming, wonderful property that makes you feel like you're inhabiting a Wes Anderson movie. The location...
    Reviewed 20 September 2014
    If you are looking for an almost indescribably beautiful setting and a rustic, relaxing location, Seacliff is it. The view from the front screen porch and terrace is nothing...
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    About this property
    We love our cottage and you will too! 'Seacliff,' a classic turn of the century cedar shingled beach cottage, is located in the quiet Guilford, CT community of Mulberry Point. Direct water access for swimming, beachcombing, kayaking and fishing plus family-friendly association beach within a...
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    Guilford, Connecticut 06437
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Stay at The Old Sindelar Farm1 / 16
    (5)Very good
    East Haddam
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Sauna
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2017
    Picturesque, beautiful, and quiet! The house had everything that was needed for our group of girls, and the owners were wonderful and made us feel at home. Everything was clean...
    Reviewed 13 August 2016
    Doug & Doris are very friendly, they & their adult children work the small farm everyday. Doug greeted us and took my grandson on a tour to meet the calves, chickens and...
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    About this property
    Duplex house set on twelve rolling acres on The Old Sindelar Farm property. Many upgrades last year. House is fresh and clean. Enjoy the deck off the back for morning coffee or join us fireside at night. We have 3 beds, one queen with a memory foam mattress and two full size beds. All have 1800...
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    East Haddam, Connecticut 06423
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Walk to private beach from this two bedroom home1 / 17
    (5)Excellent
    Branford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Porch
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2017
    This home was just what we needed! The kitchen was well stocked with spices, some condiments and lots of dishes pots and pans. We were able to rent this home for less than a...
    Reviewed 8 September 2017
    Good location, great restaurants near by, enjoyed sitting at Owenego club.Teresa was very friendly & more than accommodating!!!!Thanks for making it possible for us to...
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    About this property
    This is a two bedroom house with a king size bed in the master bedroom and a full size in the guest bedroom. The bathroom has a jacuzzi tub and large shower. There is wi-if, cable to, a patio and all amenities. This property sleeps 4 and is PET FRIENDLY. The rental comes with private access to the...
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    Branford, Connecticut 06405
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Guilford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Scenic and classic NE Shoreline Town of Guilford : The area boasts some of the best fishing, kayaking, sight seeing, hiking nearby nature trails and the third largest antique home collection in the State of CT. There is the 5 acre Guilford Green with boutique shopping, fabulous restaurants, food &...
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    Guilford, Connecticut 06437
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    North Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled home with 4 bedrooms, 1.5 baths, family room, finished basement that can easily accommodate 8 people and is near everything. Just a quick commute to Yale, SCSU, Quinnipiac and University of New Haven, very close to the best restaurants in the greater New Haven area and within...
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    North Haven, Connecticut 06473
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    East Haven
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Grill
    • Patio
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hobbit House has been newly renovated and appointed to be cozy and comfortable with an antique flair. This property is beautiful inside and out. The beach use for this property is private and your rental of this property comes with everything you need to relax at the beach! This house has the...
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    East Haven, Connecticut 06512
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Old Saybrook
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    A lovely 3 bedroom, 2 bath home on a private cul de sac is just steps away from a private beach. It sleeps 6 comfortably. The home is fully equipped with linens, towels and all kitchen necessities. There is air conditioning and wifi. A wonderful spot to relax at the CT Shore. It is a short drive to...
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    Old Saybrook, Connecticut 06475
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Old Lyme
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
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    • Ocean Views
    • Cable/satellite TV
    • Private Garden
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Chester
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • Washer
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This striking 2.7 acre New England property blends historic design elements with modern amenities and is perched on a hillside overlooking the peaceful town of Chester, Connecticut. Its historic charm and vast amenities provide a unique backdrop unlike any other. The living room quickly becomes a...
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    Location Information
    Chester, Connecticut 06412
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Branford
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Secure Parking
    • Washer
    • Air Conditioning
    • Internet Access
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From generous picture windows enjoy views of Long Is. Sound and quaint Thimble Islands dotted with simple cottages and mansions. Large front room with a small kitchen hidden in a a 1930's armoire. A round dining table is lite from a 60' chandelier fit for a castle. Created by a professional...
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    Location Information
    Branford, Connecticut 06405
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    Old Saybrook
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    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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    East Haddam
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
    About this property
    The Sanctuary is a mind/body retreat and wellness center situated on a 40 acre, solar-powered land preserve with a walking labyrinth, permaculture gardens, beaver ponds, forest trails, an apiary, goats and chickens. We host yoga classes, meditation, sound healings, music, and various...
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    East Haddam, Connecticut 06423
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Branford
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
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    • Patio
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two acres of private New England charm over looking the Thimble Islands. Set atop a hill with a large rolling lawn perfect for all types of family lawn games.The vintage shingle stone home was built in 1932 for a wealthy Connecticut family. They created a sandy beach that rivals the size of the...
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    Location Information
    Branford, Connecticut 06405
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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