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Montgomery Holiday Homes

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    Don't let other travellers get your favourite Montgomery area holiday rental. You're so close to securing your perfect getaway. Book today.

    The following rentals are within 25 kilometres of Montgomery, New York.

    1 / 23
    4 of 5 bubbles (1) Very good
    Beacon
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 24
    5 of 5 bubbles (3) Excellent
    Cold Spring
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    1 / 21
    Beacon
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 13
    5 of 5 bubbles (5) Excellent
    Cold Spring
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
    • Washer
    • Mountain Views
    • Internet Access
    • DVD Player
    • Outdoor Dining Area
    • Parking
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This cozy 3 bedroom lakeside deck house is perfect for a small family (pet friendly!) to spend a weekend, a week or a whole month. Nestled in the woods near Cold Spring, NY on the Hudson River, an hour and 20 minutes from Manhattan, the property includes a small lake perfect for cool summer swims... View all property information
    Location Information
    Cold Spring, New York 10516
    5 of 5 bubbles Reviewed 2 December 2013
    My parents visit me every year in New York City and this year we wanted to get out of the city. I did some research and came upon this place and took a leap of faith, renting it...
    5 of 5 bubbles Reviewed 12 August 2013
    The house very appealing and well equipped and the owner is very pleasant, informative and easy to work with. There is glass all around to view the spectacular wooded surroundings...
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    1 / 7
    Beacon
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • DVD Player
    • Patio
    • Internet Access
    • Washer
    • Satellite TV
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    All the comforts of home smack dab in the middle of all the best that Beacon has to offer. This airy 1920s bungalow is 3 blocks from cafe's, antique shops, and great restaurants on Main St. There is a fireplace, large eat-in kitchen, 6 person dining table, brand new bathroom, great backyard and... View all property information
    Location Information
    Beacon, New York 12508
    1 / 43
    5 of 5 bubbles (1) Excellent
    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 12566
    5 of 5 bubbles Reviewed 2 March 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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    1 / 12
    4 of 5 bubbles (1) Very good
    Newburgh
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Patio
    • Waterfront
    • Grill
    • Balcony
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Newburgh, New York 12550
    4 of 5 bubbles Reviewed 14 July 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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    1 / 19
    5 of 5 bubbles (3) Excellent
    Cornwall on Hudson
    5 Bedrooms, 3 Bathrooms, Sleeps 17 | Quick View
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    • Mountain Views
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Washer
    • Patio
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    We are 60 minutes from Manhattan ..yet totally secluded . Heated in ground swimming pool <BR>Lots of historic things to see here . Also can rent kayaks to cruise the River<BR>20 Minutes from Woodbury Commoms world famous out let stores.<BR>Huge fire place and skiing near by. Walking distance... View all property information
    Location Information
    Cornwall on Hudson, Cornwall 12520
    1 / 13
    5 of 5 bubbles (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 12589
    5 of 5 bubbles 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 / 8
    5 of 5 bubbles (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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Gardiner, New York 12566
    5 of 5 bubbles Reviewed 21 April 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...
    5 of 5 bubbles Reviewed 23 October 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 laid...
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    1 / 23
    Pine Bush
    6 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Parking
    • Patio
    • Internet Access
    • DVD Player
    • Mountain Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This incredible, newly-built home is nestled on three sides by private old growth forest with a meadow on the southern side for maximum solar gain in winter. Large white oak trees hug the southern side providing natural cooling shade in summer. The radiant floor heat along with other energy... View all property information
    Location Information
    Pine Bush, Catskill Region 12566
    1 / 5
    5 of 5 bubbles (1) Excellent
    Monroe
    Private Room, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • DVD Player
    • Porch
    • Shared Garden
    • Parking
    • 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 10950
    1 / 10
    Beacon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Charming and cozy mini apartment with a private entrance, west end of Beacon. Steps from historic Main Street, shopping and Metro North train station. My place is good for couples, solo adventurers, and business travelers. Quiet residential neighborhood just off Main Street close to galleries,... View all property information
    Location Information
    Beacon, New York 12508
    1 / 90
    Monroe
    7 Bedrooms, 5 Bathrooms, Sleeps 27 | Quick View
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    • Patio
    • Washer
    • Mountain Views
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    • 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
    Monroe, New York 10926
    1 / 1
    Beacon
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Beacon, New York 12508
    1 / 14
    5 of 5 bubbles (4) Excellent
    Gardiner
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Air Conditioning
    • Mountain Views
    • Patio
    • Grill
    • Washer
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Spacious cozy home with Lg. kitchen,living room, 3 bedrooms, 2 bathrooms, In ground Pool, game room,Internet, 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 Beds View all property information
    Location Information
    Gardiner, New York 12525
    1 / 22
    Washingtonville
    3 Bedrooms, 4 Bathrooms, Sleeps 20 | Quick View
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    Amenities & Details
    • 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 10992
    1 / 11
    4.5 of 5 bubbles (5) Very good
    Plattekill
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Central Heating
    • Grill
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The house features picturesque forrest landscapes, warm lighting, wide plank wood floors, rustic hard wood beams, and modern kitchen. Venture on the grass roof of the earth sheltered house, as well as hike trails, snow shoe, XC ski and explore nature on the 150 acres of land we have :) Great space... View all property information
    Location Information
    Plattekill, New York 12589
    4 of 5 bubbles Reviewed 3 weeks ago
    My first contact with america! I was 1 month in Casa Terra, I shared a very interesting project with john and amber. A month that I spend quickly to feel at home. I shared jobs...
    4 of 5 bubbles Reviewed 4 weeks ago
    Staying as John + Ambers first long term guest along with another fellow volunteer, I believe was it was a good learning experience for everyone in many ways. There is a lot of...
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    1 / 5
    Wallkill
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    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 12589
    1 / 14
    Marlboro
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Satellite TV
    • Housekeeping...
    • Central Heating
    • Parking
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Marlboro, New York 12542
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    1 / 6
    New Windsor
    20 Bedrooms, 25 Bathrooms, Sleeps 50 | Quick View
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    • Private Garden
    • Secure Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Camp grounds, beautiful and serene. Can reserve groups of up to 210 campers. Private lake, retreats, hiking trails, archery, biking, fishing, rock wall climbing, zip line, canoeing, swimming, basketball, soccer, football, tennis, horse back riding, baseball, sand volleyball, meditation, arts &... View all property information
    Location Information
    New Windsor, New York 13865
    1 / 4
    Newburgh
    3 Bedrooms, 2 Bathrooms, Sleeps 3 | Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • 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... View all property information
    Location Information
    Newburgh, New York 07666