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Pawling Holiday Homes

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    $373 Average
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    Don't let other travellers get your favourite Pawling area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Pawling
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    Pawling 1900 house near Darryl house,Thunder ridge1 / 73
    (11)Excellent
    Pawling
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Private Lakefront & Pool DeeLuxGlamping. NYC Getaway1 / 31
    (1)Excellent
    Pawling
    2 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    The following rentals are within 25 kilometres of Pawling.
    20'x40' inground private pool just for you&house with 4bedrooms1 / 24
    (4)Excellent
    New Milford, CT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    New Preston, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Internet Access
    • Washer
    • Satellite TV
    • Central Heating
    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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    Location Information
    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lanesville
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Hot Tub
    • Grill
    • Housekeeping Included
    • Central Heating
    • Mountain Views
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This single-family detached home, definitely have everything you need for a memorable vacation in Catskills, NY Originally built in the early 1900’s by a family with 25 kids (not kidding you), we know because most of the family members still live in the neighborhood and comes by once in awhile to...
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    Lanesville, New York 12450
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Wingdale
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Mountain Views
    • Washer
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all in this vacation home on private lake and nature preserve nestled in the foothills of the Berkshires. Perched on a peninsula on the shores of Lake Weil (viewable via Google map), this stunning 4-bedroom contemporary home offers exclusive use of your own 30-acre lake. Pack a...
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    Wingdale, New York 12594
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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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
    • 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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    Location Information
    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Danbury, CT
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Patio
    • DVD Player
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exceptional Waterfront Vacation Home! Located on Connecticut's largest man-made lake, Lake Candlewood. A perfect location for those day trips into NYC either by car or train! Picturesque perennial gardens, stunning lake views & an enticing lakefront w/sand beach, dock & more! A Gracious foyer...
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    Location Information
    Danbury, Connecticut 06811
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    LaGrangeville
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    Amenities & Details
    • Washer
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded on a knoll of Norway Spruce, atop eight acres, Frank Lloyd Wright associate Aaron Resnick's Mid-Century Modern (MCM) design is a classic example of organic Usonian architecture. This Usonian home features a completely private setting with a pool. The home is located in the heart of the...
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    Location Information
    LaGrangeville, New York 12540
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 3
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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
    • 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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    Location Information
    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Location Information
    Sherman, Connecticut 06784
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Brewster
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • DVD Player
    • Patio
    • Washer
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My precious cottage is located in a wonderful private lake community. The cottage has the perfect deck to enjoy morning sunshine and a terrific covered deck to enjoy the evening sunset. The living room have a cathedral ceiling and plenty of windows, the morning light streams in to brighten every...
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    Location Information
    Brewster, New York 10509
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Verbank
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • 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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    Location Information
    Verbank, New York 12585
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    New Milford, CT
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1840 completely renovated country house with lots of room, convenience and quietness. 4,000 sq. ft. furnished with many antiques. A most unique country kitchen, formal dining room, eat-in kitchen, library, living room, den, five bedrooms (some have 'Sleep Number' mattresses), and 5 and a half...
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    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Carmel
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Patio
    • Washer
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded lakefront cottage w/ private dock on China Pond in the Sedgewood Club One hour drive from Upper Westside. Enjoy swimming and fishing in pristine spring fed waters (no motorboats). Private golf course (no tee times) and clay tennis courts available on Club premises. Charming Adirondack...
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    Location Information
    Carmel, New York 10512
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    • 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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    Location Information
    Holmes, New York 12531
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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