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Holiday Rentals and Apartments in Middletown, NY and nearby

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    1 / 13
    Middletown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    The following rentals are within 30 kilometres of Middletown, New York.

    1 / 19
    5 of 5 stars (5) Excellent
    Vernon, NJ
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 26
    4.5 of 5 stars (3) Very good
    Vernon, NJ
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 13
    Vernon, NJ
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Grill
    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 26
    Wurtsboro
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Balcony
    • Patio
    • Terrace
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Space Open floor plan designed by Hudson Valley architect is a warm, intimate space perfect for relaxing. Every room is filled with natural light accentuating the hardwood floors and natural wood beams. The most striking feature are the floor to ceiling two floor windows facing the lake. Even... View all property information
    Location Information
    Wurtsboro, Catskill Region
    1 / 11
    Vernon, NJ
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Air Conditioning
    • Hot Tub
    • Washer
    • Mountain Views
    • Shared Indoor Pool
    • Sauna
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 27
    5 of 5 stars (12) Excellent
    Vernon, NJ
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
    • Satellite TV
    • Private Outdoor...
    • Sauna
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to The Appalachian Hotel, a 4 season ski-in/ski-out luxury hotel on the mountain. When you rent by owner, you enjoy the same Suites as the Hotel with all amenities included for a much lower price. This 1 bedroom Suite (Additional Studios and One bedrooms are also available) sleeps 4 and... View all property information
    Location Information
    Vernon, New Jersey
    5 of 5 stars Reviewed 2 weeks ago
    Excellent rental. Owner Joe was very detailed on what to expect. Checking in and out an hour early and late makes a big difference in avoiding the hotel crowd and convenient since...
    4 of 5 stars Reviewed 21 October 2015
    My husband and I expected to be out in the middle of nowhere in Vernon, NJ. We were pleasantly surprised. Keep in mind, this is not a hotel so housekeeping is not an option...
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    1 / 24
    Monticello
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Central Heating
    • Patio
    • Balcony
    • Terrace
    • DVD Player
    • Grill
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    1 / 12
    5 of 5 stars (45) Excellent
    Ellenville
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Parking
    • Outdoor Dining Area
    • Internet Access
    • Porch
    • Grill
    • Central Heating
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed 6 days ago
    Loved the place looks exactly like the pictures, mike was very friendly and welcoming always checked on us to make sure everything was good, showed us things to do around...
    5 of 5 stars Reviewed 1 week ago
    We really enjoyed our short visit to Emerald bungalows. Beautiful & very relaxing. Mike ( the owner ) was great & he recommended some great restaurants in town. Thanks for a...
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    1 / 7
    Woodridge
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Private Garden
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
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    1 / 13
    5 of 5 stars (1) Excellent
    Wallkill
    Private Room, 3 Bathrooms, Sleeps 2 | Quick View
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    • Wi-Fi
    • Skiing: Property Is...
    • Air Conditioning
    • Housekeeping...
    • Patio
    • DVD Player
    • Mountain Views
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed 7 September 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 / 39
    Harriman
    6 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Grill
    • Patio
    • Satellite TV
    • Washer
    • Mountain Views
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    1 / 5
    5 of 5 stars (1) Excellent
    Monroe
    Private Room, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • DVD Player
    • Porch
    • Shared Garden
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    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    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
    • Satellite TV
    • Waterfront
    • Sauna
    • Mountain Views
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed 6 May 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 1 March 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 / 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
    • Satellite TV
    • Mountain Views
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    1 / 43
    Pine Bush
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    • DVD Player
    • Mountain Views
    • Housekeeping...
    • Washer
    • Grill
    • Terrace
    • Central Heating
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 12
    4 of 5 stars (2) Very good
    Vernon, NJ
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Satellite TV
    • Hot Tub
    • Balcony
    • Washer
    • Air Conditioning
    • Internet Access
    • Sauna
    Suitability
    • 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
    3 of 5 stars Reviewed 8 March 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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    1 / 22
    Washingtonville
    3 Bedrooms, 4 Bathrooms, Sleeps 20 | Quick View
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    • Mountain Views
    • Air Conditioning
    • Hot Tub
    • Grill
    • Internet Access
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 11
    Pine Bush
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Garden
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    1 / 22
    Port Jervis
    Private Room, 1 Bathroom, Sleeps 7 | Quick View
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    • DVD Player
    • Waterfront
    • Patio
    • Secure Parking
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Private 100 meters River access w fishing, swimming, boating or rafts...hiking trails, outdoor lounging w firepit, +++ Great for 1-2-3-4 ppl. Special rates for large groups. Contact us for more details... Cabin, camper, tent areas available too. Close to antiques shoppes, golf, great lil town w... View all property information
    Location Information
    Port Jervis, New York
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    1 / 6
    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
    • Smoking allowed
    • 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
    1 / 20
    Wurtsboro
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 8
    Forestburgh
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Outdoor Dining Area
    • Satellite TV
    • Washer
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 8
    Vernon, NJ
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
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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
    1 / 5
    Wallkill
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    1 / 30
    5 of 5 stars (21) Excellent
    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    • Mountain Views
    • Hot Tub
    • Satellite TV
    Suitability
    • 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, racquetball, game room, 2 jacuzies, steam room, sauna, indoor track, exercise room & gourmet restaurant. We are spa members to our... View all property information
    Location Information
    Vernon, New Jersey
    5 of 5 stars Reviewed 5 weeks ago
    Had a wonderful time. Place was immaculate. Everything ran smoothly. I look forward to many return trips.
    5 of 5 stars Reviewed 27 July 2016
    Great stay , house was great . Communication with owner was very good , spa and pools awesome as usual
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    1 / 19
    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Skiing: Property Is...
    • DVD Player
    • Housekeeping...
    • Central Heating
    • Patio
    • Sauna
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    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 32
    Greenwood Lake
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Hot Tub
    • Mountain Views
    • Waterfront
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Incredible lake house, rented every weekend for the past two years with rave reviews! Incl. outdoor hot tub, private beach for swimming, multiple decks and patios for hosting, canoe, kayak and paddleboard available for free use! All mod cons with 6 bedrooms and a bathroom on each floor! Book... View all property information
    Location Information
    Greenwood Lake, New York
    1 / 26
    5 of 5 stars (1) Excellent
    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Sauna
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    • 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
    5 of 5 stars Reviewed 1 week ago
    We Arrived at the unit on Friday evening after a long long drive...the minute we approached the unit we felt better. We followed the simple instructions given to us by Bruce , and...
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    1 / 25
    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
    1 / 25
    Johnson
    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Grill
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    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    1 / 20
    Port Jervis
    5 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Balcony
    • Central Heating
    • Terrace
    • Washer
    • Patio
    • Secure Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 26
    Otisville
    7 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • DVD Player
    • Porch
    • Satellite TV
    • Internet Access
    • Waterfront
    • Grill
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    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
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    Pine Bush
    6 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Patio
    • Internet Access
    • DVD Player
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
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    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