We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Wingdale Holiday Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    £213 Average
    |||
    |||
    £0£1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Wingdale area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Wingdale
    Sort by:
    Default
    Wingdale
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Wingdale
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Wingdale
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    The following rentals are within 25 kilometres of Wingdale.
    Pawling 1900 house near Darryl house,Thunder ridge1 / 73
    (11)Excellent
    Pawling
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Parking
    • Porch
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2017
    We had booked this home for a group of girl friend attending a show at Daryl's House. We all loved the house it was charming and quaint but also very comfortable, spotlessly...
    Reviewed 20 February 2017
    Great house! Cute town within walking distance. The house is so comfortable you may not want to go out! If we go back to Pawling, I'd definitely stay here again. I highly...
    See all reviews
    About this property
    Historic beauty built in 1900 in the heart of the village Town of Pawling only a 90 min metro north train ride from Manhattan and no need for a car you can walk to the house and to most things or take a local taxi if needed for places outside of the village. .. Short walk to Metro North train(2...
    View all property information
    Location Information
    Pawling, New York 12564
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    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
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2014
    This is a spacious 4 bedroom property. it is high above the local road and is surrounded by trees. Neighbours are a good distance away, so the loudest sounds are from the local...
    Reviewed 21 July 2014
    A spectacular week in a secluded spot and yet minutes from quaint New Milford Village. Pool is GREAT
    See all reviews
    About this property
    LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful!! very private country setting; four bedrooms, large family room with cathedral ceilings and grand piano. All amenities: cable TV, CD, DVD,VCR, internet and air conditioning. Deck--including a screen house; gas grill. 20x40 inground pool with...
    View all property information
    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Poughkeepsie
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located on the border of Poughkeepsie and the Historic Hyde Park, home to Franklin and Eleanor Roosevelt. The Culinary Institute of America is a five minute drive and has not only wonderful classes but also restaurants that are open to the public (get reservations!). Marist college is...
    View all property information
    Location Information
    Poughkeepsie, New York 12601
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Sherman, CT
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Sherman, Connecticut 06784
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Rhubarb Hill, a Charming 1850's Farmhouse1 / 21
    (1)Excellent
    New Preston, CT
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Satellite TV
    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 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...
    See all reviews
    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...
    View all property information
    Location Information
    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Poughkeepsie
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be welcome and comfortable for work or pleasure in my 1 bedroom apartment near Vassar College, Marist College and the Culinary Institute of America. The apartment sleeps 4. The rooms are spacious and professionally decorated. Full kitchen with all necessary cooking and eating equipment...
    View all property information
    Location Information
    Poughkeepsie, New York 12603
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Beautiful Family Farm in the Heart of Hunt Country, Millbrook NY1 / 8
    (2)Excellent
    Millbrook
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2015
    If you want a taste of the old with modern conveniences, this spacious farmhouse is for you. Ten of us stayed here comfortably. Don't expect good internet in all parts of the...
    Reviewed 10 September 2014
    The house is beautifully furnished, the grounds are lovely, we had a most wonderful stay. We swam in the pond which is a perfect temperature and has a small sandy 'beach...
    See all reviews
    About this property
    Idle Hour Farm is located in the heart of Hunt Country, Dutchess County NY. It is a peaceful place among rolling hills, horse farms and dairy farms. It is conveniently located 1 1/2 hours from NYC, 1 hour from the Catskill Mountains, 4 hours from the Adirondack Mountains. It is situated on 16...
    View all property information
    Location Information
    Millbrook, New York 12545
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    Save time - get the best Wingdale rentals sent straight to your email!
    Get the List
    New Milford, CT
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Garden
    • Wi-Fi
    • Satellite TV
    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...
    View all property information
    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    Lake Bliss the Perfect Getaway1 / 20
    (9)Very good
    Holmes
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 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 6 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...
    See all reviews
    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...
    View all property information
    Location Information
    Holmes, New York 12531
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Clinton Corners
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, beautifully appointed and very clean, 2 bedroom, 2 full bath cottage on 2.5 acres in Clinton Corners, Hudson Valley. Quiet and private yet 7 minutes to Omega Insititute for a swim or spa treatment. close to Rhinebeck, Milbrook, Red Hook, Stamfordville and Hyde Park. Sunroom office, great...
    View all property information
    Location Information
    Clinton Corners, New York 12514
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Clinton Corners
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sun filled 4 bed / 2 bath house in Clinton Corners on 3 acres with a lot of privacy. You'll enjoy grilling on the deck, relaxing in the private backyard, & swimming in the pool. ~15 minutes from downtown Rhinebeck. We recently purchased our home and won't be able to use it for a few weeks this...
    View all property information
    Location Information
    Clinton Corners, New York 12514
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Fishkill
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Patio
    • Parking
    • Air Conditioning
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1,700 square foot vacation rental home in Fishkill, New York is perfect for 10 guests looking to get away from it all and spend a relaxing vacation in this sleepy Hudson Valley village. The 3-bedroom, 2-bathroom home was originally built in 1928 for the president of Texaco. It goes without...
    View all property information
    Location Information
    Fishkill, New York 12524
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    LaGrangeville
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    LaGrangeville, New York 12540
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 3
    Make Enquiry
    Fishkill
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Parking
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay. ** Enjoy your visit to the Hudson Valley during your stay in this vacation rental studio apartment in Fishkill. The cozy studio is perfect for a romantic getaway and is within a...
    View all property information
    Location Information
    Fishkill, New York 12524
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    Pawling
    2 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will have full access to this 2 bedroom camper that sleeps 12. 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...
    View all property information
    Location Information
    Pawling, New York 12564
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 12
    Make Enquiry
    Amenia
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Internet Access
    • Air Conditioning
    • 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...
    View all property information
    Location Information
    Amenia, New York 12501
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Clinton Corners
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a historic property located on a scenic and historic country road in a designated "Ag district" in the town of Clinton Corners, NY. Large properties surround this home, and there is plenty of privacy. The home was converted from a horse and carriage barn in the 1920s and has antique post...
    View all property information
    Location Information
    Clinton Corners, New York 12514
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    New Preston, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Verbank
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Verbank, New York 12585
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Clinton Corners
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Porch
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pumpkin Lane, Clinton Corners, NY<BR>Large private home off Taconic Parkway on 20 acres of land. <BR>Available for summer months (June July August). <BR>$12k per month. Brokers welcome.<BR>Less than 90 minutes from New York City. 15 Minutes from Poughkeepsie and Rhinebeck townships.<BR>Outdoor...
    View all property information
    Location Information
    Clinton Corners, New York 12514
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Stormville
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Sauna
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Far View Farm is located on Stormville Mountain. This offers breath taking views of the Hudson Valley. This farmhouse goes back to the early 1800's but has everything to make it a private retreat from your busy life. It has 25 private acres with trails and no neighbors to be seen. Enjoy the views...
    View all property information
    Location Information
    Stormville, New York 12582
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Clinton Corners
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, gracious colonial on 5.2 acres surrounded by trees and lawns, with 40' heated in-ground pool, a pond and back deck. Enjoy the great room and open eat-in kitchen with 4 bedrooms, a jacuzzi in the master bathroom, 2.5 bathrooms and finished basement with in-home theater. Only 90 minutes...
    View all property information
    Location Information
    Clinton Corners, New York 12514
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    List your property
    Owner log in