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Montgomery Vacation Rentals

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    All 21 Rentals in Montgomery
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    The following rentals are within 15 miles of Montgomery.
    Earth Berm House at Terra Casa Retreat Center1 / 11
    (5)Very good
    Plattekill
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Gardiner
    5 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
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    Serene Vista Spa B and B of the Hudson Valley 21 / 13
    (2)Excellent
    Wallkill
    1 Bedroom, 3 Bathrooms, Sleeps 2 Quick View
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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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    Beacon
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Waterfront
    • Grill
    • Cable/satellite TV
    • Porch
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet dead end street leading to an abandoned bridge over Fishkill Creek, this idyllic brick period charmer has a quaint Mansard roof and dormered windows. Antique carriage lamps adorn the facade. Exposed wood beams and hardwood floors throughout. Exquisite attention to detail is what makes...
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    Location Information
    Beacon, New York 12508
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Mountain View Vacation Home Near Mohonk Preserv1 / 14
    (4)Excellent
    Gardiner
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious cozy home with Lg. kitchen,living room, 3 bedrooms, 2 bathrooms, In ground Pool, game room,Internet/WiFi, lg deck with view of Shawangunk mountain. 10 minute from Mohonk Mountain House and Town of New Paltz GOLF COURSE. 82 miles from NYC. (Pets not allowed) Beds: 2 Queen Beds, 2 Twin...
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    Gardiner, New York 12525
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    50 Mins from  Manhattan River view1 / 19
    (4)Excellent
    Cornwall on Hudson
    5 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
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    • Mountain Views
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 3, 2017
    We rented this for West Point Graduation and had 13 people staying at the house. Great layout made for plenty of room for all & places to gather. We couldn't have asked for...
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    About this property
    We are 60 minutes from Manhattan ..yet totally secluded . Heated in ground swimming pool Lots of historic things to see here . Also can rent kayaks to cruise the River 20 Minutes from Woodbury Commoms world famous out let stores. Huge fire place and skiing near by. Walking distance to places...
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    Cornwall on Hudson, Cornwall 12520
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 17
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    Marlboro
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large 3 bedroom first floor house located on top of a hill in a quiet neighborhood. Home owned by family for over 40 years. - Owner will rent for 7-120 days at 1st, after the renter will be able to renew the lease if they choose & if owner approves. The Space Looking to rent the first floor of a...
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    Location Information
    Marlboro, New York 12542
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Cozy Apple House1 / 18
    (1)Excellent
    Gardiner
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Yard
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2017
    House was so sweet and cozy. Decorated very cute!! Very clean I felt more than comfortable having my 9 month old son crawl all over the floors. The owner Rhonda was a great...
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    About this property
    Come stay at our quaint cottage in the shadow of the Shawangunk Mountains. A sweet alternative from the beach. There's so much to do: Hiking, Walking, Biking, Swimming, Apple Picking. Grab a tube and float down a cool lazy river or go for a hike and take in the amazing mountain air, not to...
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    Location Information
    Gardiner, New York 12525
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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    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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    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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    Modern, Eclectic, Tranquil Mountain Retreat1 / 8
    (2)Excellent
    Gardiner
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • DVD Player
    • Grill
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 2017
    Amazing house that felt like home the moment we stepped in the door!Such a cool house with 2 fab sound systems, some cool artwork, furniture and decorations. Lovely outside...
    Reviewed October 23, 2014
    We arrived on a Friday afternoon during peak foliage. The house is tucked away in the woods but close enough to hit all the important wineries in Hudson Valley. The house is...
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    About this property
    Beautiful, bright designer renovated house located 90 minutes from GW Bridge on a very quiet secluded dead-end road in the woods adjacent to state land. Designed with contemporary furniture with a queen size bed in each bedroom, the Minimalist inspired flowing 1st fl incorporates all the...
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    Location Information
    Gardiner, New York 12566
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ellenville
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • 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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    Keith's Classic Film Retreat1 / 12
    (2)Very good
    Newburgh
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Patio
    • Secure Parking
    • Hot Tub
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 4, 2017
    We stayed at Keith's place for two nights while visiting West Point. Beautiful home, lovingly decorated with antiques and in an Old Hollywood theme. Keith was very gracious. He...
    Reviewed July 14, 2016
    This place was beautifully decorated, and the bedroom was really nice and spacious with a great mattress. We only stayed one night for a wedding so didn't explore the area much...
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    About this property
    I am offering a 1912 lovely foursquare home overlooking historic Downing Park and pond ( private second floor with bedrooms and bath.... dinning room available). Home has most of it's original details. Home is filled with original artwork and Hollywood memorabilia. Newburgh is the second largest...
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    Newburgh, New York 12550
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Base Camp - Dutch Colonial Estate
    Beacon
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private getaway at the base of Mt. Beacon. Easy access to hiking trails and walking distance to downtown Beacon. Views of the Hudson Valley from the front exposure, and mountains to the rear. Large airy bedroom with a beautiful tiled bath. The Space The maid's wing of our brick Dutch colonial...
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    Location Information
    Beacon, New York 12508
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Beacon Nook, escape from the big city1 / 33
    (2)Excellent
    Beacon
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Central Heating
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2018
    We recently took our family on a quick getaway weekend to up Beacon, NY. The Beacon Nook had a little something special for everyone in the family. Spacious and comfortable...
    Reviewed July 22, 2018
    Beacon Nook is a lovely mix of brand new and original charm. It's very clean and spacious enough for our party of 8. Love the location, the shops, the river, the restaurants...
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    About this property
    Enjoy an entire house in Beacon- spacious and newly refurbished preserving the classic 1950s mid century style. The front porch is great for morning coffees and the backyard is fenced in. Walking to the Metro North train station and Main Street. Beacon offers so much to do - hiking through the...
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    Location Information
    Beacon, New York 12508
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Wallkill
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Location Information
    Wallkill, New York 12589
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Newburgh
    3 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It's a beautiful neat stable home, smoke free for a big family even children is able, must leave house the way we left it, neat and clean environment. You will be provided with free food as well, clean sheets, clean rest room, free pool area in the backyard with an indoor jacuzzi you will love it...
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    Location Information
    Newburgh, New York 07666
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 3
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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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