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.

Holiday Rentals in Pawling

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
    €308 Average
    €0€1,000+
    Suitability
    More filters
    All 28 Rentals in Pawling
    Sort by:
    Default
    Don't let other travellers get your favourite Pawling area holiday rental. You're so close to securing your perfect getaway. Book today.
    Pawling
    5 of 5 bubbles
    10 Reviews
    3 BedroomsSleeps 6Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    The following rentals are within 30 kilometers of Pawling.
    Poughkeepsie
    3 BedroomsSleeps 7Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    New Milford, CT
    5 of 5 bubbles
    4 Reviews
    4 BedroomsSleeps 8Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Wingdale
    4 BedroomsSleeps 11Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Wingdale, New York 12594
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
    Make Enquiry
    Clinton Corners
    4 BedroomsSleeps 6Quick 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
    Clinton Corners
    2 BedroomsSleeps 8Quick 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
    Millbrook
    5 of 5 bubbles
    2 Reviews
    5 BedroomsSleeps 10Quick 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
    Excellent of 5 bubbles
    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...
    Excellent of 5 bubbles
    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
    North Salem
    1 BedroomSleeps 5Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Grill
    • Balcony
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gracious and well appointed Coach House has been beautifully renovated. The Light and Airy Two Floor cottage is situated on the property of an historic home, and offers a Pool, mature gardens, riding and hiking trails. It's near excellent fishing spots. Dine al fresco on your private patio!...
    View all property information
    Location Information
    North Salem, Westchester County 10560
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    Make Enquiry
    New Milford, CT
    5 BedroomsSleeps 10Quick 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
    Beacon
    3 BedroomsSleeps 7Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Internet Access
    • Washer
    • Satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All the comforts of home smack dab in the middle of all the best that Beacon has to offer. This airy 1920s bungalow is 3 blocks from cafe's, antique shops, and great restaurants on Main St. There is a fireplace, large eat-in kitchen, 6 person dining table, brand new bathroom, great backyard and...
    View all property information
    Location Information
    Beacon, New York 12508
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Ridgefield, CT
    8 BedroomsSleeps 12Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Wi-Fi
    • Satellite TV
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The legendary Sunset Hall has captivated the hearts of its keepers since built for ambassador James Stokes in 1912 at Ridgefield's highest point to afford 50 mile views of the NY skyline and panoramic vistas of Round Pond from the widow walk perch. This regal Georgian has delighted subsequent...
    View all property information
    Location Information
    Ridgefield, Connecticut 06877
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 12
    Make Enquiry
    Holmes
    4.5 of 5 bubbles
    9 Reviews
    3 BedroomsSleeps 10Quick 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
    Excellent of 5 bubbles
    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...
    Very good of 5 bubbles
    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
    Beacon
    4 of 5 bubbles
    1 Review
    2 BedroomsSleeps 6Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Patio
    • Air Conditioning
    • Grill
    • Porch
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PLEASE NOTE: I DO NOT RENT FOR FOR 1 NIGHT. THERE IS A 2 NIGHT MINIMUM. Continue reading further down in this box for 5***** Reviews. Here's a sample: "More like a boutique hotel." "This house is a dream come true." "Great owner, great location!" This home in beautiful Hudson Valley is a...
    View all property information
    Location Information
    Beacon, New York 12508
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    New Preston, CT
    5 of 5 bubbles
    1 Review
    3 BedroomsSleeps 6Quick 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
    Excellent of 5 bubbles
    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
    Beacon
    3 BedroomsSleeps 7Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Private Garden
    • Wi-Fi
    • Secure Parking
    • Terrace
    • Patio
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 3 bedroom Victorian home in trendy Beacon, NY. Walk to shops, restaurants, bars, etc. Two full bathrooms, one outdoor 26-jet jacuzzi, sleeps 4, full (new) kitchen, French Provincial antiques, hardwood floors. Across from Memorial Park, walk to town to shop & eat, Mt. Beacon, and train...
    View all property information
    Location Information
    Beacon, New York 12508
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Clinton Corners
    4 BedroomsSleeps 6Quick 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
    Carmel
    2 BedroomsSleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Carmel, New York 10512
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Base Camp - Dutch Colonial Estate
    Beacon
    1 BedroomSleeps 2Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private getaway at the base of Mt. Beacon. Easy access to hiking trails and walking distance to downtown Beacon. Views of the Hudson Valley from the front exposure, and mountains to the rear. Large airy bedroom with a beautiful tiled bath. The Space The maid's wing of our brick Dutch colonial...
    View all property information
    Location Information
    Beacon, New York 12508
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Newtown, CT
    3 BedroomsSleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Housekeeping Included
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A historic and charming three bedroom, two bath saltbox farmhouse on the grounds of the beautiful and private McLaughlin Vineyards. The house is conveniently located in Northern Fairfield County, about four miles from I-84 and only 90 minutes from mid-town Manhattan. With a large expansive front...
    View all property information
    Location Information
    Newtown, Connecticut 06482
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Sherman, CT
    2 BedroomsSleeps 5Quick 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
    New Preston, CT
    3 BedroomsSleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Central Heating
    • Internet Access
    • Waterfront
    • Porch
    • 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 with room for up to 8. Relax and recharge on the brand new stone patio and spend your days by the water on the private lakefront area and dock. With 1,300...
    View all property information
    Location Information
    New Preston, Connecticut 06777
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Clinton Corners
    4 BedroomsSleeps 6Quick 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
    Beacon
    1 BedroomSleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming and cozy mini apartment with a private entrance, west end of Beacon. Steps from historic Main Street, shopping and Metro North train station. My place is good for couples, solo adventurers, and business travelers. Quiet residential neighborhood just off Main Street close to galleries,...
    View all property information
    Location Information
    Beacon, New York 12508
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Warren, CT
    7 BedroomsSleeps 14Quick View
    other traveller has booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Patio
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that this property can be rented in conjunction with VRBO listing 3921932ha (Evolve #256841) for discounted rates. Please inquire for additional information ** If you’re searching for the perfect place to stay for your next family gathering, “Carriage House” is just the spot for...
    View all property information
    Location Information
    Warren, Connecticut 06777
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
    Make Enquiry
    Washington, CT
    4 BedroomsSleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Street is a mint condition 4 bedroom home with a heated pool, wonderful flat private quiet yard with a swing set far back from the street. The home is in Washington, the most desirable historic rural town in Litchfield County with wonderful restaurants, land preserves, private schools,...
    View all property information
    Location Information
    Washington, Connecticut 06793
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Roxbury, CT
    2 BedroomsSleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Amenia
    3 BedroomsSleeps 6Quick 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
    5 BedroomsSleeps 10Quick 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
    List your property
    Owner log in