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Vacation Rentals in Middletown, NY and nearby

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    Middletown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    The following rentals are within 20 miles of Middletown, New York.

    1 / 27
    5 of 5 stars (11) Excellent
    Vernon, NJ
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 19
    5 of 5 stars (4) Excellent
    Vernon, NJ
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 19
    5 of 5 stars (2) Excellent
    Monticello
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Air Conditioning
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful log cabin private setting, sit on large porch sipping your morning coffee. Warm up to a roaring fire on chilly nights. Beautiful drive up from the city (1.5 hours from Manhattan GWB) enjoy the changing foliage that fall brings to the Catskills. Or summer hikes or swimming in nearby... View all property information
    Location Information
    Monticello, Catskill Region 12701
    Highland Lakes, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Child-friendly
    • ?
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    • x
    About this property
    Enjoy the lakeside getaway of your dreams in this spacious 3-bed, 2-bath A-frame cabin with its very own private dock. Ski at Mountain Creek or Hidden Valley, hop into your personal kayaks, or venture out into the great outdoors for amazing hiking! This Highland Lakes cabin is simply the ideal... View all property information
    Location Information
    Highland Lakes, New Jersey 07422
    Vernon, NJ
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Mountain Views
    • Shared Indoor Pool
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    The Winter Ski Season is finally here!!! This is a year round resort offering;. Skiing, Golf, Horseback Riding, Minerals Spa, The Water park and more......Book Now!!!!! Fully furnished Condominium in Great Gorge Village Mountain Creek Resort The first floor consists of a Living room, Dining Room,... View all property information
    Location Information
    Vernon, New Jersey 07462
    1 / 26
    4.5 of 5 stars (3) Very good
    Vernon, NJ
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Children's Pool
    • Hot Tub
    • Skiing: Property Is...
    • Wi-Fi
    • Satellite TV
    • Mountain Views
    • Air Conditioning
    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    1 BR luxury condo, come with a cozy electric fireplace, fully equipped kitchenette,dininng room area for 6 and 2 LCD TVs, free cable, free internet, wifi, dishwasher,Mini-fridge, 2 burner cooktop, microwave, central AC. Granite countertops, and all feature private balconies overlooking the... View all property information
    Location Information
    Vernon, New Jersey 07462
    4 of 5 stars Reviewed May 21, 2015
    My wife's family lives in the area and we've gotten to the point where there are too many of us to fit under one roof. We typically stayed at a motel or B&B in the area but now...
    5 of 5 stars Reviewed February 1, 2015
    I thank Derrick for how amazing the place looked when we arrived. I was in Killington,VT last week and Mt. Creek was such better condition for skiing and room was so much nicer...
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    1 / 12
    5 of 5 stars (41) Excellent
    Ellenville
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Emerald Forest Bungalows is an enchanted locatin tucked away in Ellenville, NY. The White Pine is our brand new Chalet style Cabin. This unit was designed to blend perfectly with our forested landscape (we have just under 75 acres to frolic in). Ellenville is just a 2 hour drive north of... View all property information
    Location Information
    Ellenville, Catskill Region 12428
    5 of 5 stars Reviewed May 24, 2016
    The place is really nice, Mike the owner is the man, really easy to deal with. Great places in the area are the Mohonk preserve and minneswaska state park. Mike will give you...
    5 of 5 stars Reviewed August 27, 2015
    My wife were in the area to see our duaghter and found Emerald Forest to be very nice with an excellent host. Wish we could have spent more time at the Bungalow than we did, but...
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    Greenwood Lake
    5 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    • Waterfront
    • Washer
    • Hot Tub
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Tara House is a lakefront home that offers quality accommodations, lakefront property that is handicapped accessible and perfect for your family reunion, college reunion or any other get together for up to 15 people. The Tara House is one hour from NYC, 15 minutes from Woodbury commons, 30 minutes... View all property information
    Location Information
    Greenwood Lake, New York 10925
    Wurtsboro
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
    • ?
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    • x
    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! With 3 bedrooms, 1 bathroom and enough sleeping arrangements for 6 guests to... View all property information
    Location Information
    Wurtsboro, Catskill Region 12790
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    Wurtsboro
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Family Friendly and/or Romantic Getaway home at the foot of the Catskills Mountains in the quaint village of Wurtsboro, 90 minutes from NYC. 3 bedroom property on 3 acres - private creek, giant trampoline, swing and slide set, hammock and lots and lots of space!! Ideally located near many... View all property information
    Location Information
    Wurtsboro, Catskill Region 12790
    Harriman
    6 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • x
    About this property
    Unique and historic 7,000 sq. ft. mansion, hand built by craftsmen in 1859.... ~ 1 year before Abraham Lincoln became president ~ 2 years before the start of the civil war ~ The same year that Dickens published "A Tale of Two Cities" and Darwin published "On the Origin of Species". Just a short... View all property information
    Location Information
    Harriman, New York 10926
    1 / 32
    5 of 5 stars (20) Excellent
    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Skiing: Property Is...
    • Sauna
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    • Mountain Views
    • Hot Tub
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Private country setting with great mountain views. On premises you have 1 indoor & 2 outdoor pools, golf course, minerals spa, indoor tennis, indoor basketball, racketball, game room, 2 jacuzies, steam room, sauna, indoor track, exercise room & gourmet restaurant. Close by you have horse back... View all property information
    Location Information
    Vernon, New Jersey 07462
    5 of 5 stars Reviewed 4 days ago
    Great stay , house was great . Communication with owner was very good , spa and pools awesome as usual
    5 of 5 stars Reviewed 2 weeks ago
    The condo was beautiful. Very clean and comfortable. Bruce the owner was easily available to answer questions.
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    1 / 5
    5 of 5 stars (2) Excellent
    Matamoras, PA
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Waterfront
    • Outdoor Dining Area
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    • x
    • x
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    • x
    About this property
    Very private 3+ acre property with two bedrooms, 1 bath and a 400 square foot Great Room. Wood covered walls, lots of windows, expensive leather furniture, unique art throughout, cable TV with ProLogic sound system, Wi-Fi. Two miles into town. There are many restaurants and stores and a brand new... View all property information
    Location Information
    Matamoras, Pocono Mountains Region 18336
    1 / 12
    4.5 of 5 stars (4) Very good
    Vernon, NJ
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    The Appalachian at Mountain Creek offers year round vacation excitement by owner at discount rates. Ski in, ski out or snowboard in winter. Other seasons use the nearby Water Park, Freeride Mountain Biking Park, golf at seven championship courses, horseback ride or use the exciting new Zip line.... View all property information
    Location Information
    Vernon, New Jersey 07462
    5 of 5 stars Reviewed May 6, 2014
    Bill was great to communicate with and was very responsive to my initial contact as well as follow up emails. Our trip was last minute and he went out of his way to help us. The...
    4 of 5 stars Reviewed March 1, 2012
    We went for a holiday ski weekend. Although the ski conditions are not good this year, we all had a great time. The condo was large, clean and comfortable. The lodge next door...
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    1 / 25
    Ellenville
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The deluxe lodge is located on our amenity filled resort and includes a private bedroom with a queen-sized bed. An 8' x 12' carpeted loft for kids with 3 pull-out single mattresses. A full kitchen and living room with a double-bed futon sofa, hardwood floors and a 8' x 12' screened in porch! There... View all property information
    Location Information
    Ellenville, Catskill Region 12435
    1 / 12
    4 of 5 stars (2) Very good
    Vernon, NJ
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Shhh! The secret is out, but not everyone knows it yet. There is finally an all year round resort that caters to the sports person providing skiing, snowboarding, mountain biking at Diablo Park, water park activities, and other fun such as golf at 7 championship courses, horseback riding and ice... View all property information
    Location Information
    Vernon, New Jersey 07462
    3 of 5 stars Reviewed March 7, 2015
    We had an amazing time on our trip. But we where staying very far up the mountain and of course is snowed three times while there. The first time we experianced the snow it was...
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    Vernon, NJ
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • Mountain Views
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    • Pet-friendly
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    • x
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    • x
    About this property
    Welcome to pure slope-side luxury just 47 miles from Manhattan! Black Creek Sanctuary is Mountain Creek's only gated neighborhood, and it's a quick stroll from the base of the ski mountain. This modern & cozy two bedroom bi-level unit comes with a gas fireplace, high-speed internet, Wi-Fi, fully... View all property information
    Location Information
    Vernon, New Jersey 07462
    1 / 24
    Pine Bush
    6 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    • x
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    • x
    About this property
    This incredible, newly-built home is nestled on three sides by private old growth forest with a meadow on the southern side for maximum solar gain in winter. Large white oak trees hug the southern side providing natural cooling shade in summer. The radiant floor heat along with other energy... View all property information
    Location Information
    Pine Bush, Catskill Region 12566
    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
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    • Pet-friendly
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    • x
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    • x
    About this property
    Our 3 BR/2 Bath condo has it all. Steam shower, 6 ft soaking tub with rain faucet shower head. Travertine marble bathroom and vanity with dual sinks. Stainless steel appliances, granite counter tops and 6 burner stove adorn this chef's kitchen. Upper and lower level living areas include reclining... View all property information
    Location Information
    Vernon, New Jersey 07462
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    1 / 22
    Washingtonville
    3 Bedrooms, 4 Bathrooms, Sleeps 20 | Quick View
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    • Mountain Views
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    • Pet-friendly
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    • x
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    • x
    About this property
    The perfect vacation home nestled in storybook woods just 60 miles from New York City. Find yourself surrounded by luxury within and lush greenery without. Spacious yet cozy, fully-furnished rooms are ideal for relaxation: TV and home entertainment system, kitchen with breakfast area, formal... View all property information
    Location Information
    Washingtonville, New York 10992
    1 / 13
    5 of 5 stars (1) Excellent
    Wallkill
    Private Room, 3 Bathrooms, Sleeps 2 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Serene Vista Spa B&B of the Hudson Valley is a boutique vacation destination that combines everything you expect from an upscale bed and breakfast, clean airy rooms, lovely living areas, and delicious breakfasts with the opportunity to benefit from spa treatments at the in-house Miracles Day Spa.... View all property information
    Location Information
    Wallkill, New York 12589
    5 of 5 stars Reviewed September 7, 2015
    We had such a wonderful relaxing time at the spab&b and are already looking forward to returning. Upon arrival, after taking in the spectacular view, we used the spa services and...
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    1 / 26
    Otisville
    7 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    This 7 bedroom 1920s Farmhouse style home has a dream wrap around, screened in porch which is 100 feet from the lake. Art deco wall sconces, a wood beam salon ceiling, and an open face wood stove set against an old stone fireplace add character to this rustic,charming old fashioned 1920s home. The... View all property information
    Location Information
    Otisville, New York 10963
    1 / 5
    5 of 5 stars (1) Excellent
    Monroe
    Private Room, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Caren House Bed and Breakfast is located 3 miles from Woodbury Commons Premium Outlets in Harriman, NY. We provide transportation to and from the Commons. We are also close to West Point Military Academy, a Jack Nicklaus Golf Course, the Applachian Trail, wineries, Orange County Choppers. We are... View all property information
    Location Information
    Monroe, New York 10950
    Johnson
    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    Come escape the hustle and bustle of city life at this secluded Wawayanda vacation rental home. Nestled on 62 private acres, surrounded by woods dappled in sunlight and beautiful nature, this property offers plenty of peace and quiet and will serve as a tranquil setting for your next retreat to New... View all property information
    Location Information
    Johnson, New York 10940
    Forestburgh
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    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
    Pine Bush
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Your home away from home is beautifully decorated with all of the comforts you will need for your visit to the Hudson Valley area. Sit back and prepare to relax in leather sofas next to the fire place or perhaps enjoy a nibble at our bar. Bring your sleds and let the kids enjoy our large yard in... View all property information
    Location Information
    Pine Bush, Catskill Region 12566
    Vernon, NJ
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    Come experience the best of New Jersey's Skylands region by staying at this lovely Vernon vacation rental townhome. Whether you’re in the mood for a relaxing getaway or a vacation filled with endless outdoor activities, you’ll find this townhome to be exactly what you desire at the end of the day!... View all property information
    Location Information
    Vernon, New Jersey 07462
    Port Jervis
    5 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Built in 1815 this lovingly renovated house is your home away from home Oldest house in the area this house is perfect for families that want to get away from the city and relax. Wood burning stove, big eat in kitchen, separate playroom and living room. 5 bedrooms to choose from: one double... View all property information
    Location Information
    Port Jervis, New York 12771
    Monticello
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
    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
    Wallkill
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • ?
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    • x
    About this property
    Serene Vista Spa B&B of the Hudson Valley is a boutique vacation destination that combines everything you expect from an upscale bed and breakfast, clean airy rooms, lovely living areas, and delicious breakfasts with the opportunity to benefit from spa treatments at the in-house Miracles Day Spa.... View all property information
    Location Information
    Wallkill, New York 12589
    Pine Bush
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • ?
    • ?
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    • x
    About this property
    A lovely stone residence, set on 37 acres of picture-perfect old oak trees and meadows, quiet and private, yet close enough to all Hudson Valley recreational and cultural attractions and historic sites. A perfect hideaway for nature lovers, hikers, artists and other folks simply seeking rest and... View all property information
    Location Information
    Pine Bush, Catskill Region 12566
    Vernon, NJ
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    You and your family can enjoy this retreat that can be used all summer long this trailer has two bedrooms, one bedroom has four bunk beds, central air conditioning. It also has and enclosed deck that is fully furnished. You and your family can enjoy all the amenities of recreation and have a great... View all property information
    Location Information
    Vernon, New Jersey 07461
    Sussex, NJ
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    1 Hour from George Washington Bridge For rent is a 2 bedroom, 1 bath, eat in kitchen & living room with deck Comes with Gas grill, kitchen stove, microwave, coffee maker, George Foreman grill, toaster over, blender and 2 window air conditioners. There is also a hammock and a large fire pit in the... View all property information
    Location Information
    Sussex, New Jersey 07461
    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Sauna
    • Housekeeping...
    • Satellite TV
    • Balcony
    • Shared Indoor Pool
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This is the ski on ski off condo you have been waiting for. You just walk down the steps, on to our deck and on to Mountain Creek's ski mountain. Perfect location for all skiers, boarders, bikers and hikers who want a slope side, scenic location. We are renovating with all new... View all property information
    Location Information
    Vernon, New Jersey 07462
    Vernon, NJ
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Washer
    • Balcony
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Hot Tub
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Let this 2-bedroom, 2-bathroom condo, which comfortably accommodates 4 guests, be the home base for your phenomenal vacation in Vernon Township. Enjoy all the amazing things there are to do at Mountain Creek Resort, including excellent skiing and hiking! Settled right next to a tranquil river,... View all property information
    Location Information
    Vernon, New Jersey 07462
    1 / 24
    Forestburgh
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Patio
    • DVD Player
    • Internet Access
    • Satellite TV
    • Washer
    • Central Heating
    • Waterfront
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Great all year round stay-cation! Private sanctuary with neighbors only visible from afar. A secluded lake with only 6 houses, this is the perfect getaway from NYC - only 90mins drive from George Washington Bridge or Lincoln Tunnel, and commute accessible: by bus to Monticello or by train to Port... View all property information
    Location Information
    Forestburgh, Catskill Region
    1 / 10
    Monticello
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The home is located in Monticello New York on Swinging Bridge Lake in the Catskills, just 10 miles from the Monticello Gambling Casino and Bethel Woods Center for the Arts. It is located adjacent to an eagle preserve as close to the water as you can get! This lake-house features a multilevel cedar... View all property information
    Location Information
    Monticello, Catskill Region 12701
    Monticello
    Private Room, 2 Bathrooms, Sleeps 1 | Quick View
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    • Wi-Fi
    • Grill
    • Private Yard
    • Air Conditioning
    • Secure Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    note::: this listing is for renting a private bedroom and bath: its a house share like a bed and breakfast style, if your looking to rent entire home, i have a separate listing on here listing #2577636 Beautiful log cabin private setting, sit on large porch sipping your morning coffee or a... View all property information
    Location Information
    Monticello, Catskill Region 12701