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Middletown Vacation Rentals

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    All 26 Rentals in Middletown
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    The following rentals are within 20 miles of Middletown.
    The Appalachian Mountain Creek Vernon NJ 1 bedrm1 / 30
    (20)Excellent
    Vernon, NJ
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    #2 Updated Ski On Ski Off, 4 Season Resort1 / 26
    (3)Excellent
    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    The Appalachian Largest 1 BR luxury Condo/Hotel.1 / 25
    (5)Very good
    Vernon, NJ
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Luxury 2 Bedroom Bi-level Vernon Condo1 / 13
    (1)Excellent
    Vernon, NJ
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 16, 2018
    Located at the base of the mountain. Literally across the street. Everything nearby, from grocery store, gas station, restaurants, horseback riding right outside the complex...
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    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...
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    Vernon, New Jersey 07462
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cabin 90 minutes from NYC with Lake, Skiing, Hiking, Vineyards and more1 / 13
    (1)Excellent
    Wurtsboro
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 6, 2018
    The House was charming and property was comforting. The House was a little secluded, tucked into the woods a little bit. There were plenty of resting or relaxing sitting areas...
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    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...
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    Wurtsboro, Catskill Region 12790
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stony Mountain House1 / 43
    (2)Excellent
    Pine Bush
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • DVD Player
    • Mountain Views
    • Housekeeping Included
    • Washer
    • Grill
    • Terrace
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 9, 2017
    Perfect home for our group of 15. Excellent Decor. Comfy beds. Beautiful kitchen. Very clean. We came out here from Wisconsin to tour the headquarters and Branch offices of...
    Reviewed March 2, 2017
    We really enjoyed our stay! We were a big group and the house accommodated us very comfortable. House is big, super clean and roomy. Kitchen is well equipped! The owner Michelle...
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    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...
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    Pine Bush, Catskill Region 12566
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    Lakehouse with Stunning Views 1 hour from NYC!!1 / 32
    (2)Very good
    Greenwood Lake
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    • Waterfront
    • Mountain Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 1, 2017
    I want to start off saying this is a neatly kept, large and roomy home. It is worth booking, because it is on nice waterfront property, and is close to Warwick, which is a cute...
    Reviewed January 30, 2017
    Our party of 12 had a great time. The house is clean and fully stocked with everything you will need. There are amazing views from the living room and many of the bedrooms. The...
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    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...
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    Location Information
    Greenwood Lake, New York 10925
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Port Jervis
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Private Yard
    • Secure Parking
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private 100 meters River access w fishing, swimming, boating or rafts...hiking trails, outdoor lounging w firepits ++++ 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...
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    Location Information
    Port Jervis, New York 12771
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 7
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    Caren House Bed and Breafast1 / 5
    (1)Excellent
    Monroe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Porch
    • Shared Yard
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Monroe, New York 10950
    Private Room - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pine Bush
    6 Bedrooms, 8 Bathrooms, Sleeps 18 Quick View
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    • Cable/satellite TV
    • Grill
    • Secure Parking
    • Patio
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Pine Bush, Catskill Region 12566
    Rental Home - 6 Bedrooms, 8 Bathrooms, Sleeps 18
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    Orchard Hill Estate: Retreat, Reunions, Near West Point,Close to NYC, Hot tub,1 / 54
    (4)Excellent
    Monroe
    7 Bedrooms, 5 Bathrooms, Sleeps 25 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Mountain Views
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 2018
    Abbe, Jeff & Shana were wonderful hosts! We held a family reunion at their property with 28 overnight guests + 2 toddlers and had a fabulous time. All three members of this...
    Reviewed May 3, 2018
    We stay at Orchard Hill Estates and were able to have our entire wedding at the home from start to finish. The property is very well kept, clean and spacious. The owners are...
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    About this property
    Orchard Hill Estate is a gem with breathtaking views of spectacular sunrises and sunsets. There is plenty of space, allowing you to relax in style with your friends and family for the holidays or a getaway. Excellent for company and corporate retreats.Events and weddings can be held for an...
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    Location Information
    Monroe, New York 10926
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 25
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    Warwick
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Private Yard
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book now for summer fun! The Cottage at Millpond Falls is an idyllic getaway, perfect for couples, writers, artists, or honeymooners. Relax in this restored cottage overlooking a beautiful waterfall in a private setting. Fall asleep or meditate to the sound of rushing water. Close to Appalachian...
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    Location Information
    Warwick, New York 10990
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly Renovated LUXURY 3 Bedroom 2 Bath Ski condo in Vernon NJ with stunning mountain views! The condo has a luxurious rustic vibe with new cabinets, hardwood floors, beautiful furnishings and modern amenities (Wifi, 50' TV with Smart Apps). The Ultimate stay for groups, families and couples -...
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    Location Information
    Vernon, New Jersey 07462
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Vernon, NJ
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Washer
    • Mountain Views
    • Shared Indoor Pool
    • Sauna
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Location Information
    Vernon, New Jersey 07462
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Ellenville
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Porch
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Ellenville, Catskill Region 12435
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 6
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    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
    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...
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    Monticello, Catskill Region 12701
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Greenwood Lake
    5 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Waterfront
    • Washer
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Greenwood Lake, New York 10925
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 15
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    Port Jervis
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Central Heating
    • Terrace
    • Washer
    • Patio
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Port Jervis, New York 12771
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Housekeeping Included
    • Central Heating
    • Patio
    • Sauna
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Vernon, New Jersey 07462
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Delaware Riverfront Cottage1 / 5
    (2)Excellent
    Matamoras, PA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Waterfront
    • Outdoor Dining Area
    • Cable/satellite TV
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Matamoras, Pocono Mountains Region 18336
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Forestburgh
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Outdoor Dining Area
    • Cable/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,...
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    Forestburgh, Catskill Region 12777
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Kiamesha Lake
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Yard
    • Patio
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two leveled house is airy and plenty natural light access. Newly renovated and spacious. It is in a quiet community with front parking lot for two cars. There are modern stainless steel appliances and stereo sound system with celling speakers. There is a private backyard with swing and a...
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    Location Information
    Kiamesha Lake, New York 12751
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Vernon, NJ
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Children's Pool
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***I don't use auto booking only because I advertise on many other sites and I need to make sure I dont double book* Load up the golf clubs, put the skis on the This beautifully appointed condo features over 1,250 square feet of living space making you feel right at home. The living area with high...
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    Vernon, New Jersey 07462
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Vernon, NJ
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Vernon, New Jersey 07461
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Vernon, NJ
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Parking
    • Grill
    • Cable/satellite TV
    • Housekeeping Included
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paradise is closer than you think. Travel to another world which isn't a world a-way (about 1 hour from NYC) and enjoy all the beauty of a private mountain / lake community. Only 10 minutes from Mountain Creek Ski Resort and Water Park, 5 minutes from Hidden Valley Ski Resort, and 3 minutes from a...
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    Location Information
    Vernon, New Jersey 07422
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Central Valley
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tracing back to the 1770s American Revolution era, with additions built in 1849 and continual renovations since, our home is filled with a historic ambiance and classic interior designs. The guest rooms have elegant wallpapers, rustic wood floors, and traditional fireplaces that bring you back in...
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    Location Information
    Central Valley, New York 10917
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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