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Wingdale Holiday Homes

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    Don't let other travellers get your favourite Wingdale area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Wingdale
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    Wingdale
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    The following rentals are within 25 kilometres of Wingdale.
    20'x40' inground private pool just for you&house with 4bedrooms1 / 36
    (4)Excellent
    New Milford, CT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    LaGrangeville
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    Sherman, CT
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Mountain Views
    • Grill
    • Housekeeping Included
    • Waterfront
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private secure community with million dollar homes. Perfect weekend retreat. 90 minutes from NYC. This two bedroom cottage has all the necessary amenities. Includes access to two private beaches on Candlewood Lake and Green Pond. Just renovated with new wood floors, new appliances, new...
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    Sherman, Connecticut 06784
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Lake Bliss the Perfect Getaway1 / 20
    (9)Very good
    Holmes
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2016
    Review received! Just one more thing to do…We have received your review for Property #141424 Once you confirm it, we can work on getting it live! Read the review below; if...
    Reviewed 7 July 2016
    Great little getaway for the weekend. Really enjoyed the lake, the barbecue, and the canoes. There isn't much else to do, so a long vacation may not be the best idea. I think an...
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    About this property
    Fully furnished gorgeous home directly on beautiful Whaley Lake only 1-1½ hours from New York City. Two levels each with full kitchen and bath. Washer & dryer, wireless internet, plenty of parking. The units can be rented separately or together. Lower level with huge panoramic windows overlooking...
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    Holmes, New York 12531
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Verbank
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Former mother/daughter apartment. Close to attractions / activities: historical Hyde Park, Walkway Over The Hudson. 18 miles of biking/walking trails, the Culinary Institute and many fine eateries, Vassar and Marist colleges, farms, wineries and breweries, great music venues, the quaint towns of...
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    Verbank, New York 12585
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Kent, CT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Room with private bath, queen bed, antique furniture, air conditioning, and radiator heat. Shared living room, dining room, porch, and kitchen. On Main Street in town. Plenty of parking. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to...
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    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    New Milford, CT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our house has a soul. It is not like a fancy hotel but instead all elements of decor have some story to tell. The indoor is painted by an artist. We have grand piano which if you know how to play will make time together more fun. The pool is just amazing. Deep end has 8' and shallow 4.5'.We love it...
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    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rhubarb Hill, a Charming 1850's Farmhouse1 / 21
    (1)Excellent
    New Preston, CT
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2014
    We arrived all type A with many plans to hike and swim, ended up enjoying the comfort of the house, cooking, hanging out together. Switching from indoor seating for outdoor...
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    About this property
    Near Lake Waramaug $300 per night with a 3-night minimum $1800 per week. June $6,000 per month July $6,000 per month Aug $6,000 per month Memorial Day to Labor Day $14,000. During the winter months-mid-October-mid-March, I seek long term rentals. I only rent by the month during this...
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    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Kent, CT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Patio
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This former servant's quarters w/full bed has private bath with claw foot tub/shower. Original back staircase just outside the door which leads directly to the kitchen. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to ten people staying...
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    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kent, CT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully decorated room with private bath, queen bed, antique furniture and Cable TV. Shared living room, dining room, porch, and kitchen. On Main Street in town. Plenty of parking. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to ten...
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    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Private Lakefront & Pool DeeLuxGlamping. NYC Getaway1 / 31
    (1)Excellent
    Pawling
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2017
    Love the place. It was great for our family. Very spacious and clean. The place is also located in a great area so it was perfect. We will rent it again next year for our...
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    About this property
    You will have full access to this 2 bedroom camper that sleeps 8. We are located on a private/quiet road. This is not a camp ground. You will be the only family staying with us. We have a huge in ground salt water system pool that you will have full access to. We live here on the grounds, so the...
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    Location Information
    Pawling, New York 12564
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Roxbury, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Mountain Views
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best way to experience Roxbury Connecticut... A completely Private Apartment in Modern contemporary home located on Route 67 in Roxbury Connecticut. 2 Bedrooms, Full Kitchen, Full Bathroom, Living Room, Oversized Deck, Outdoor Grill, and 3+ Acres of Land with Outdoor Seating. Close to...
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    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Kent, CT
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Private Garden
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    First floor suite king bed, couch and desk. Sitting room with single bed, chairs, television and desk. Large bath with stall shower. Shared living room, dining room, porch and kitchen. Please enjoy all the common areas in the home. We do not live in the home and there may be a total of up to ten...
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    Location Information
    Kent, Connecticut 06757
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Kent, CT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Grill
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large master suite with private bath including claw foot tub and stall shower. Queen bed with sitting room area, window air conditioner. Shared living room, dining room, porch and kitchen. On Main Street in town. Please enjoy all the common areas in the home. We do not live in the home and there...
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    Location Information
    Kent, Connecticut 06757
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    New Fairfield, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor a piece of Connecticut paradise at this 3-bedroom, 2-bathroom New Fairfield vacation rental house! Suitable for up to 10 guests, this Hampton-style home featuring an outdoor kitchen and 4 levels of outdoor space provides travelers with an ideal location on Candlewood Isle, where you can enjoy...
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    Location Information
    New Fairfield, Connecticut 06812
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Warren, CT
    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Parking
    • Washer
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Note that this home can be rented in conjunction with VRBO listing 3921932ha (Evolve #256841) for discounted rates. Please inquire for additional info ** Seeking the perfect place to stay for your next peaceful getaway? Look no further than ‘Carriage House!’ Situated on the Lake Waramaug...
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    Warren, Connecticut 06777
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    New Preston, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Central Heating
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit the beautiful shores of Lake Waramaug in this charming 3-bedroom, 2-bathroom New Preston vacation rental cottage that comfortably sleeps 6. Relax and recharge on the brand new stone patio and spend your days by the water on the private lakefront area and 22 foot dock. With 1,300 square feet...
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    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenia
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Magnolia Cottage!! 44,000 Gallon in-ground saltwater pool. Covered Front Porch with wicker chairs. Gardens, Greenhouse, & Walking Trails. Side Patio with BBQ and Gas Fire Pit. Basic Stocked Fridge (milk, eggs, butter, jams, etc.). High thread-count cotton linens and towels. Two...
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    Amenia, New York 12501
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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