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Vacation Rentals in Middletown, NY and nearby

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    The following rentals are within 20 miles of Middletown, New York.

    1 / 19
    5 of 5 stars (2) Excellent
    Monticello
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 19
    5 of 5 stars (3) Excellent
    Vernon, NJ
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    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 / 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
    • Wheelchair access
    • Child-friendly
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    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 / 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
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    • Mountain Views
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    • Sauna
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    • Pet-friendly
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    • Child-friendly
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    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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    Wurtsboro
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Central Heating
    • DVD Player
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    • Child-friendly
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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
    1 / 26
    5 of 5 stars (1) Excellent
    Chester
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    65 mins from NYC, 5,500sq' cul-de-sac home on 5.5 quiet acres. Includes chef's kitchen, WiFi, sauna, pool table, theater room & laundry room. Cathedral ceilings, hardwood floors. Minutes to Woodbury Common, Renaissance Faire, Sugar Loaf, Storm King. -First floor has a mudroom/laundry room, chef's... View all property information
    Location Information
    Chester, New York 10918
    5 of 5 stars Reviewed 3 weeks ago
    beautiful, clean, bright, spacious house with well equipped kitchen (including pantry supplies); the huge porch was perfect for just relaxing, especially after shopping @ woodbury...
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    Pine Bush
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
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    • Private Outdoor...
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    • Pet-friendly
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    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
    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
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    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...
    5 of 5 stars Reviewed August 15, 2011
    We have stayed in this particular condo several times and have always loved it. This condo has the best location in the entire appalachian complex. It was the closest spot to...
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    Vernon, NJ
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Air Conditioning
    • Private Outdoor...
    • Mountain Views
    • Washer
    • Internet Access
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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
    1 / 32
    5 of 5 stars (17) Excellent
    Vernon, NJ
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Skiing: Property Is...
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    • Mountain Views
    • Hot Tub
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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 September 30, 2015
    Traveled with my husband and our children (5,12 and 14). Lots to do close by. Hubby is an avid mountain biker and the location of this place along one of their runs was perfect...
    5 of 5 stars Reviewed March 18, 2015
    I love the place. Love the pool. I'm definitly going back this summer. It's a little pricy but I really like it. I will recommended to other people.
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    1 / 26
    Otisville
    7 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
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    • Porch
    • Satellite TV
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    • Waterfront
    • Grill
    • Central Heating
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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 / 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
    • Wheelchair access
    • Child-friendly
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    About this property
    The Lake home is located in Monticello New York on Swinging Bridge Lake in the Catskills NY, 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... View all property information
    Location Information
    Monticello, Catskill Region 12701
    Johnson
    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Parking
    • Outdoor Dining Area
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
    • 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
    1 / 27
    5 of 5 stars (11) Excellent
    Vernon, NJ
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • Private Outdoor...
    • DVD Player
    • Sauna
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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 07462
    4 of 5 stars Reviewed October 20, 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...
    5 of 5 stars Reviewed July 1, 2015
    Beautiful and very clean will be and I plan on staying here again next year, the pools are fantastic and the view is amazing.
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    Wurtsboro
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Patio
    • Internet Access
    • Hot Tub
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
    • 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
    Monticello
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Grill
    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Paddle Boards, Kayaks, Fire Pit, BBQ, Hammock and a Big Pier... We Have it All!! Welcome to Heller High Water, a five bedroom, two and a half bathroom water front property retreat located on the nine mile Swinging Bridge Lake in Monticello New York. The house is seven miles from the Village of... View all property information
    Location Information
    Monticello, Catskill Region 12701
    1 / 24
    Washingtonville
    3 Bedrooms, 3 Bathrooms, Sleeps 20 | Quick View
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    • Mountain Views
    • Air Conditioning
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    • Internet Access
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
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    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 / 24
    Pine Bush
    6 Bedrooms, 8 Bathrooms, Sleeps 16 | Quick View
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    • Satellite TV
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    • Pet-friendly
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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 12566
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    1 / 12
    5 of 5 stars (40) Excellent
    Ellenville
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
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    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 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...
    5 of 5 stars Reviewed February 18, 2015
    The remote location of the chalet and property were exactly what we were seeking for a long weekend escape from Manhattan, yet it was very conveniently located for exploring...
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    1 / 8
    4 of 5 stars (1) Very good
    Ellenville
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
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    About this property
    Cozy 2 bedroom 1 bath cottage, sleeps 6, is available for summer rental. Beautiful wooded property leading to your private beach. Swim, fish or boat in a pristine 100 acre lake. The house is fully furnished, enclosed porch and a deck with lakeviews. Lots of hiking trails nearby. Ideal for... View all property information
    Location Information
    Ellenville, Catskill Region 12428
    4 of 5 stars Reviewed June 1, 2011
    Quite and secluded cottage on a lake. Great place to get away. Small private lake. Quick and easy transaction.
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    1 / 5
    5 of 5 stars (1) Excellent
    Monroe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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
    5 of 5 stars Reviewed May 27, 2012
    Whenever I visit my sister I love staying at the Caren House. Joan and Carmen are extremely friendly and hospitable. We would not ever ask for or expect a warmer or more...
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    Harriman
    6 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Pet-friendly
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    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 / 5
    5 of 5 stars (2) Excellent
    Matamoras, PA
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    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
    5 of 5 stars Reviewed June 7, 2012
    The cottage is a great escape from the city. It is quiet, peaceful, and has a great zen feeling. I've personally spent many nights Bbq'ing and enjoying the amenities of the...
    5 of 5 stars Reviewed June 5, 2012
    Hal is a great person to deal with, He will do his best to make sure any renter is happy with their stay. The cabin is on private property where we were able to have all the...
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    1 / 8
    5 of 5 stars (1) Excellent
    Greenwood Lake
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    About this property
    Year round playground 1 hour from New York City. Waterfront property with a dock for your boat or jet ski and you can cast your reel right from the yard for the many varieties of fish in Greenwood Lake. Great room with comfortable couches and dining table for six as well as a grand fireplace with... View all property information
    Location Information
    Greenwood Lake, New York 10925
    5 of 5 stars Reviewed 3 weeks ago
    We recently stayed here for a weekend in family and friends. It's overall a big space. Bedrooms are not huge , but with so much outside space and large living/dinning room , we...
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    1 / 13
    5 of 5 stars (1) Excellent
    Wallkill
    1 Bedroom, 3 Bathrooms, Sleeps 2 | Quick View
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    About this property
    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. Spa B&B of the... 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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    Forestburgh
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Outdoor Dining Area
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    • Pet-friendly
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    • Child-friendly
    • x
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    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