We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Montgomery Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    AU$534 Average
    |||
    |||
    AU$0AU$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Montgomery area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 22 Rentals in Montgomery
    Sort by:
    Default
    The following rentals are within 25 kilometres of Montgomery.
    Earth Berm House at Terra Casa Retreat Center1 / 11
    (5)Very good
    Plattekill
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Gardiner
    5 Bedrooms, 5 Bathrooms, Sleeps 24 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Stony Mountain House1 / 43
    (3)Very good
    Pine Bush
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Mountain View Vacation Home Near Mohonk Preserv1 / 14
    (4)Excellent
    Gardiner
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Gardiner, New York 12525
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Cozy Apple House1 / 18
    (1)Excellent
    Gardiner
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 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...
    See all reviews
    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...
    View all property information
    Location Information
    Gardiner, New York 12525
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Keith's Classic Film Retreat1 / 12
    (2)Very good
    Newburgh
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Patio
    • Secure Parking
    • Hot Tub
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 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 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...
    See all reviews
    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
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Modern, Eclectic, Tranquil Mountain Retreat1 / 8
    (2)Excellent
    Gardiner
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • DVD Player
    • Grill
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
    See all reviews
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Cabin 90 minutes from NYC with Lake, Skiing, Hiking, Vineyards and more1 / 13
    (1)Excellent
    Wurtsboro
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 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...
    See all reviews
    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...
    View all property information
    Location Information
    Wurtsboro, Catskill Region 12790
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Marlboro
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Marlboro, New York 12542
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Beacon
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Beacon, New York 12508
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    Save time - get the best Montgomery rentals sent straight to your email!
    Get the List
    Caren House Bed and Breafast1 / 5
    (1)Excellent
    Monroe
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Porch
    • Shared Garden
    • 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...
    View all property information
    Location Information
    Monroe, New York 10950
    Private Room - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    50 Mins from  Manhattan River view1 / 19
    (4)Excellent
    Cornwall on Hudson
    5 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Mountain Views
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 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...
    See all reviews
    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...
    View all property information
    Location Information
    Cornwall on Hudson, Cornwall 12520
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 17
    Make Enquiry
    Pine Bush
    6 Bedrooms, 8 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Pine Bush, Catskill Region 12566
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 18
    Make Enquiry
    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
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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 9 August 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 4 May 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...
    See all reviews
    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...
    View all property information
    Location Information
    Monroe, New York 10926
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 25
    Make Enquiry
    Newburgh
    3 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Newburgh, New York 07666
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 3
    Make Enquiry
    Beacon Nook, escape from the big city1 / 33
    (2)Excellent
    Beacon
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Central Heating
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 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 22 July 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...
    See all reviews
    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...
    View all property information
    Location Information
    Beacon, New York 12508
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Cozy Lakefront Catskills Cabin w/Decks and Dock1 / 30
    (3)Very good
    Wurtsboro
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 October 2017
    The cabin was perfect, nearly all of the amenities are provided for you (toiletries, seasonings, coffee, etc..) the queen sized beds were very comfortable, and you will have...
    Reviewed 1 March 2017
    This cabin was nothing short of amazing, it was well stocked for us guys and honestly the most comfortable stay we have had in a LONG time. Kent (the owner) awesome and keeps...
    See all reviews
    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! This fantastic lakefront home features 3 bedrooms, 1 bathroom and enough sleeping...
    View all property information
    Location Information
    Wurtsboro, Catskill Region 12790
    Cabin Holiday Rental - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Pine Bush
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Terrace
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the ultimate Hudson Valley retreat when you stay at this 4-bedroom, 3-bathroom vacation rental house in Pine Bush! The property is situated on 6 private acres of land and boasts an extensive 3,500 square feet of living space, making it ideal for large families or groups of up to 10...
    View all property information
    Location Information
    Pine Bush, Catskill Region 12566
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Ellenville
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    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...
    View all property information
    Location Information
    Ellenville, Catskill Region 12435
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    Make Enquiry
    Base Camp - Dutch Colonial Estate
    Beacon
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Beacon, New York 12508
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Central Valley
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    View all property information
    Location Information
    Central Valley, New York 10917
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Monroe
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This vacation rental home in Monroe is perfect for a family getaway! With 4 bedrooms and 3 bathrooms, the space can sleep 14 meaning you can even invite a few friends along. The furnished deck looks over the spacious yard and is an excellent place to spend your time. Each room is warm and inviting...
    View all property information
    Location Information
    Monroe, New York 10950
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
    Make Enquiry
    List your property
    Owner log in