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.

Monticello Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
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
    $304 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travelers get your favorite Monticello area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 21 Rentals in Monticello
    Sort by:
    Default
    Cabin By Lake in Bethel (Smallwood) 5 Minutes from Bethel Woods - Woodstock site1 / 12
    (3)Very good
    Monticello
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    The Jacky in Smallwood New York Home of the Original Woodstock1 / 10
    (1)Excellent
    Monticello
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Contemporary Lake House Getaway - 5 Acres - Lake Front  / Pool / Activities!1 / 24
    (4)Excellent
    Monticello
    4 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Catskills Lake House on Swinging Bridge Reservoir1 / 23
    (35)Excellent
    Monticello
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • DVD Player
    • Satellite TV
    • Central Heating
    • Washer
    • Grill
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Monticello, Catskill Region 12701
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    Monticello
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Patio
    • Balcony
    • Terrace
    • DVD Player
    • Grill
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CONTEMPORARY SPRAWLING LAKEFRONT HOME ON SWINGING BRIDGE RESERVIOR, THE LARGEST MOTOR BOAT LAKE IN SULLIVAN COUNTY. UNOBSTRUCTED VIEWS WITH FLOOR TO CEILING WINDOWS. 5 ACRES. HOT TUB. IN-GROUND HEATED POOL. ATV'S. JET SKIES. POOL TABLE. FUN ACTIVITIES FOR EVERYONE! Amazing for both winter and...
    View all property information
    Location Information
    Monticello, Catskill Region 12701
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Inquiry
    The following rentals are within 10 miles of Monticello.
    Liberty
    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    House was as advertised - spacious and bright, lots of room. The highlight though is the 165 acres - quiet, private and scenic.
    See all reviews
    About this property
    Lovely modern 6 bedroom home, with stunning 60 mile views just 2 hrs from Manhattan, 30 min from Bethel Woods, 5 min from golf, stroll in your own 165 acre private forest. Complete privacy BBQ, 1000 sq ft deck, fire pit, lake, trails, forest, view The space Wonderful property with tremendous...
    View all property information
    Location Information
    Liberty, New York 12754
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 16
    Make Inquiry
    Lakefront 3BR Catskills Cabin w/Decks and Dock!1 / 30
    (2)Average
    Wurtsboro
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Patio
    • Internet Access
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 28, 2017
    This cabin was nothing short of amazing, it was well stocked for us guys and honestly the most comfortable stay we have had in a LONG time. Kent (the owner) awesome and keeps...
    See all reviews
    About this property
    If you're in need of a peaceful lakefront retreat, look no further than this lovely Catskills vacation rental cabin, ideally situated on the pastoral shores of Yankee Lake in a quiet, family-oriented lake community! This fantastic lakefront home features 3 bedrooms, 1 bathroom and enough sleeping...
    View all property information
    Location Information
    Wurtsboro, Catskill Region 12790
    Cabin - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    Smallwood
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a relaxing getaway in the heart of the Catskills!!! Situated in the picturesque private lake community of smallwood in Bethel NY (home of the original Woodstock) During your stay take in all that the beautiful mountain and lake scenery has to offer in the Summer, Fall, Winter or Spring!...
    View all property information
    Location Information
    Smallwood, New York 12778
    Cabin - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Make Inquiry
    Smallwood
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Private Yard
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Lake Front Lodge! Just renovated! Minutes away from Bethel Woods Performing Arts Center ( Home of the original 1969 Woodstock) Enjoy a relaxing getaway in the heart of the Catskills!!! Situated on the picturesque and peaceful private Mountain Lake of Smallwood in Bethel NY. Close to all...
    View all property information
    Location Information
    Smallwood, New York 12701
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Inquiry
    White Lake
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Sauna
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is about 5 mins away from Bethelwoods Performing Arts Center, where the original Woodstock Concert took place. The house is fully furnished with all amenities necessary, just bring in your suitcase. The house has a fireplace, fire-pit and a fire-cage on the extra large deck overlooking a...
    View all property information
    Location Information
    White Lake, New York 12783
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    GREAT VACATION HOUSE IN UPSTATE NY1 / 47
    (2)Excellent
    Hurleyville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Wi-Fi
    • Parking
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2015
    This is an Amazing place to stay. The house is beautiful and well kept by the care taker George. The owner Michael is a great guy! Me and my family are having a great time here...
    See all reviews
    About this property
    Enjoy life from a better view. Unforgettable property with 25 acres private land, lrge swimming pond, nice detailing with unobstructed views from every single window of home. Long driveway through beautiful landscaped property leads to immaculate elevated home, surrounded by old trees,...
    View all property information
    Location Information
    Hurleyville, New York 12747
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    White Lake
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Central Heating
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely home is located in the private Beechwood Community of White Lake, not to be confused with Beechwoods at Villa Roma. It features lovely rear views to dense woods with lots of wildlife stopping by daily! It is just up the hill from beautiful, sparkling spring-fed White Lake and comes with...
    View all property information
    Location Information
    White Lake, New York 12786
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    Large Modern Cabin with Hot Tub Tucked in Woods1 / 15
    (4)Excellent
    Bethel
    5 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Internet Access
    • Satellite TV
    • Central Heating
    • Grill
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 12, 2017
    This house exceeded my expectations. I would definitely recommend and even plan another trip there in the future. The house has everything you need to cook and stay entertained.
    Reviewed August 9, 2016
    Exactly what our group of 12 look for when getting away from the city and want to enjoy a secluded and rejuvenating getaway. Enjoyed a large outdoor space featuring a huge deck...
    See all reviews
    About this property
    Our cabin was built to allow you to enjoy the best of Catskill living. Five minutes from Bethel Woods Performing Arts Center, 15 Minutes from skiing at Holiday Mountain, 15 minutes from swimming at Lake Superior, minutes from boating and fishing at White Lake and 15 minutes from golf and tennis at...
    View all property information
    Location Information
    Bethel, Catskill Region 12749
    Cabin - 5 Bedrooms, 5 Bathrooms, Sleeps 13
    Make Inquiry
    Bethel
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Washer
    • Outdoor Dining Area
    • Balcony
    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakefront Contemporary Home, Sleeps 10, walk to Bethel woods, Private lakefront and Dock. Game room, pinball, foosball, large screen TV, Cable, internet wifi, Kayaks, Peddle Boat, rowboat, fire pit, and more...
    View all property information
    Location Information
    Bethel, Catskill Region 12720
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Inquiry
    Beautiful Catskills Cabin1 / 23
    (2)Excellent
    Bethel
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2017
    We really enjoyed staying at Meghan's cabin house. It was very cute and cozy making it the perfect weekend getaway spot. If we are ever up that way again we'd definitely stay...
    See all reviews
    About this property
    Enjoy a relaxing getaway in the heart of the Catskills!!! Situated in the picturesque private lake community of smallwood in Bethel NY (home of the original Woodstock) During your stay take in all that the beautiful mountain and lake scenery has to offer in the Summer, Fall, or Spring! Just a...
    View all property information
    Location Information
    Bethel, Catskill Region 12778
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Make Inquiry
    Wurtsboro
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Clipper Cottage is the perfect Catskill Mountain getaway located on Yankee Lake, 90 minutes from NYC. This hip and trendy home is newly renovated, with a 300 sq ft porch and deck area. The property is gorgeous and merges indoor and outdoor living seamlessly. There is a long patio table for...
    View all property information
    Location Information
    Wurtsboro, Catskill Region 12790
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Rock Hill
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful lakefront home on private highly desired Wanaksink Lake. Home has three bedrooms, one full bath, living area and full kitchen. Home looks right out onto beautiful lake. Three kayaks and a dingy boat available for your enjoyment. Hiking, biking, fishing, swimming, ice fishing all right...
    View all property information
    Location Information
    Rock Hill, New York 12775
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Inquiry
    Smallwood
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello welcome to our Log sided Cabin-this is an original condition 1939 one owner cabin in excellent condition. wood all around you-Sun shines on our cabin from sunrise to sunset with Beautiful Hiking Trails-Pond-Swimming Lake- Antiquing-Restaurants-Farming-all within minutes drive. We are a family...
    View all property information
    Location Information
    Smallwood, New York 12786
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Liberty
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Central Heating
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect get away great appeal for every taste and leisure activity. Great location: Close to Bethel Woods, hunting locations; casino; mins from shopping, restaurants, hiking / biking trails, antique shops or spend time on the 6-acre grounds to hike, relax in Adirondack chairs, wade in creek!...
    View all property information
    Location Information
    Liberty, New York 12754
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Inquiry
    Forestburgh
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Satellite TV
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Woodsy Catskill Summer House in Merriewold. Merriewold is a private enclave of summer homes dating back to the late 1890's. The house was built in 1931 by John Moody, the financier. The house is in a mature pine forest, surrounded by ferns and mountain laurel. Merriewold is entirely private,...
    View all property information
    Location Information
    Forestburgh, Catskill Region 12777
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    Woodridge
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • Private Yard
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Available to non-smokers from May 3rd to Columbus Day (Except Memorial Day Weekend) .. A fully furnished 2 bedroom cottage complete with linens and kitchenware, TV, A/C ,. Lake, large pool and tennis court on the premises. NOT a bungalow colony. 90 miles from New York City, one mile from the...
    View all property information
    Location Information
    Woodridge, New York 12789
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Inquiry
    Monticello Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    52° 34°
    October
    41° 26°
    November
    31° 18°
    December
    25° 12°
    January

    Additional Monticello Info

    Go to map view
    • Local time: 02:42 AM (EDT)
    List your property
    Owner log in