Montgomery Holiday Rentals, New York: Private House Rentals

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Our top choices for Montgomery hotels

A Holiday Inn Express & Suites building with a covered entrance, stone facade, and a parking area with a bench.

A reception area with a modern design, featuring a large abstract wall art, a seating area with a bench, and a potted plant.

A hotel room with a bed, a desk, a sofa, a coffee machine, and a microwave.

A hotel dining area with orange chairs and tables, a coffee station, and a wooden door.

1. Holiday Inn Express & Suites Montgomery by IHG

Montgomery

Darwin

2.768.304 ₫

3.270.060 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a porch, a front door, and a small garden area with potted plants.

A grand hallway with a wooden staircase, a patterned carpet, and a dining area with chairs and a table.

A cozy living room with a sofa, armchair, and a table with a vase. A chandelier hangs from the ceiling, and there are framed pictures on the walls.

A sign for The Borland House, a bed and breakfast offering breakfast and brunch.

2. Borland House Inn

Montgomery

Ruth

2.811.510 ₫

3.420.795 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A neatly made bed with white linens, flanked by two bedside tables with lamps, and two framed paintings on the wall above.

A hotel lobby with a brown leather sofa, a small table with a lamp, a reception desk, and a television on the wall.

A kitchen with a coffee machine, a trash bin, and a sign for 'Florida's Growers' Pride'.

A multi-story hotel with a flat roof, a parking lot, and a covered entrance area.

3. Super 8 by Wyndham Montgomery Maybrook

Montgomery

Ahmed

1.986.970 ₫

2.347.108 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A kitchen with a stainless steel sink, wooden cabinets, a granite countertop, and a coffee maker.

A living room with a fireplace, a ceiling fan, a flat-screen TV, and a coffee table.

4. Tin Brook Bed & Breakfast

Walden

Michael

3.557.400 ₫

4.024.648 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A spacious hotel lobby with a high ceiling, wooden beams, a large mural, and a seating area with a sofa and chairs.

A living room with a sectional sofa, a wooden coffee table, a dining table with chairs, and a wall clock.

An outdoor patio area with tables and chairs, colorful umbrellas, and a building with stone and concrete exterior.

A building with a green awning, stone facade, and a parking lot with marked spaces.

5. Harvest Inn

Pine Bush

Stacey

5.097.043 ₫

5.766.093 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.

A hotel room with two beds, a desk, a TV, and a chair.

A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

A vending machine area with two beverage dispensers and a snack shelf stocked with various products.

6. La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

Carlos

2.924.830 ₫

3.454.954 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel lobby with a reception desk, bar area, and a television displaying news.

A hotel room with a kitchenette, a living area with a sofa and a TV, and a large window with curtains.

A snack display area with various packaged snacks and a sign indicating 'TREATS'.

A hotel reception desk with a large 'happy.' poster on the wall, a counter with a computer, and a display of brochures.

7. Hampton Inn & Suites Newburgh Stewart Airport

Newburgh

Manus

3.716.513 ₫

4.390.131 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A Courtyard Marriott hotel with a covered entrance, outdoor seating area, and multiple balconies.

A modern hotel room with a flat-screen TV, a desk with drawers, a comfortable sofa, a bed, and a large window with curtains.

An outdoor patio area with wicker furniture and a stone wall.

A modern living room with a sectional sofa, two armchairs, a coffee table, and a TV.

8. Courtyard by Marriott Newburgh Stewart Airport

Newburgh

Trevor

4.243.008 ₫

5.012.183 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a desk, a chair, a desk lamp, a wall-mounted TV, and a window with curtains.

A modern hotel lobby with seating areas, a bar, and a television screen.

A covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.

A hotel entrance with stone pillars, a covered walkway, and a bench.

9. Sleep Inn & Suites Monroe - Woodbury

Monroe

Ian

2.871.016 ₫

3.247.837 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A breakfast area with a counter displaying hard-boiled eggs, a bowl of green apples, and various pastries.

A modern reception area with a curved wooden counter, seating area with colorful cushions, and pendant lighting.

A modern lounge area with seating, tables, and hanging chairs.

A modern hotel with a prominent 'tru by Hilton' sign, a covered entrance, and a well-lit facade.

10. Tru by Hilton Middletown

Middletown

Rebecca

2.100.289 ₫

2.480.966 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

A Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.

A modern restaurant with a long counter, wooden chairs, and pendant lighting.

11. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Aeron

3.337.488 ₫

4.109.282 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

A multi-story hotel with a prominent entrance, stone pillars, and a well-maintained lawn.

A spacious hotel lobby with a large dining table, comfortable seating, and ceiling fans.

A spacious living area with a curved sofa, a fireplace, and a modern chandelier.

12. Homewood Suites Stewart Airport

New Windsor

Tonia

3.936.425 ₫

4.649.903 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.

A modern restaurant with a central island, multiple tables, and chairs.

A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.

A conference room with multiple tables and chairs, a projector screen, and a green accent wall.

13. Home2 Suites by Hilton Middletown

Middletown

Carl

4.156.337 ₫

5.000.226 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A landscaped outdoor area with a fire feature, seating, and a pathway.

A modern bar area with a curved counter, bar stools, and a television screen.

A modern hotel lobby with a seating area, large windows, and a television screen.

A Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.

14. Courtyard by Marriott Middletown Goshen

Middletown

Kim

2.616.953 ₫

3.091.276 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel with a central entrance pavilion, a flag, and a landscaped garden.

A boat ride with passengers holding binoculars, surrounded by water and themed structures.

A modern dining area with blue upholstered chairs and a wooden table. There is a kitchen area visible through an open doorway.

A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.

15. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

WARREN

2.871.792 ₫

3.535.893 ₫ total

includes taxes & fees

10 Nov - 11 Nov

A Red Roof Inn & Suites building with a two-story structure, a balcony, and an American flag.

A hotel room with two beds, a desk, a chair, a television, and a door.

A hotel room with a desk, two chairs, a printer, and a sign indicating free Wi-Fi in all rooms.

An indoor swimming pool with a tiled floor, surrounded by lounge chairs and a high, sloped ceiling.

16. Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

New Windsor

Guilande

2.304.936 ₫

2.722.251 ₫ total

includes taxes & fees

25 Oct - 26 Oct

An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.

A spacious lobby with modern seating, a stone accent wall, and large windows offering views.

An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.

A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.

17. Residence Inn by Marriott Middletown Goshen

Middletown

jubert cruz

4.863.936 ₫

5.745.525 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

A hotel room with a sofa, a television on a wooden stand, a bed, and a view of the hallway.

A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

A gym with exercise equipment, treadmills, and weight machines.

18. Hampton Inn by Hilton Middletown

Middletown

Myung

2.177.129 ₫

2.571.734 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

A modern lobby with a brown sofa, yellow armchairs, a patterned carpet, and a decorative plant centerpiece.

A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

A Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.

19. Sleep Inn & Suites Middletown - Goshen

Middletown

Mark

2.616.953 ₫

3.091.276 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a green sofa, a small table, a bed with a headboard, a desk with a lamp, and a framed picture on the wall.

A rack of black hexagonal dumbbells with visible weight markings, arranged on a metal stand in a gym setting.

A restaurant with multiple tables and chairs, a kitchen area, and a microwave.

A spacious living area with sofas, a fireplace, and artwork on the walls.

20. Quality Inn & Suites Fishkill South near I-84

Fishkill

William

2.707.246 ₫

3.130.254 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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Stay near popular Montgomery attractions

Orange County Arboretum

8.0/10 (6 reviews)

This tranquil 35-acre botanical haven features themed gardens, water features, and a 9/11 Memorial. Stroll through seasonal displays while enjoying the meticulously curated collection of trees and flowering plants.

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City Winery Hudson Valley

This historic mill transforms into a vibrant winery, restaurant, and music venue along the Wallkill River. Enjoy award-winning wines with seasonal cuisine while overlooking riverfront views during performances.

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Thomas Bull Memorial Park

6.8/10 (5 reviews)

This 719-acre recreational haven features a championship golf course, arboretum, and equestrian facilities. Explore themed gardens or time your visit for the enchanting winter "Holiday Lights in Bloom" display.

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Orange County Tennis Center

This public tennis facility features six clay courts in a welcoming community setting. Enjoy casual matches or join local clinics during spring through fall when the outdoor courts shine.

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Learn more about Montgomery

Stroll through charming streets lined with historic buildings, soaking in the small-town atmosphere of this Hudson Valley gem. Explore nearby wineries and parks, or catch a show at the City Winery for a perfect blend of culture and nature.

See all hotels in Montgomery

A suspension bridge over a calm river with reflections, surrounded by hills and a clear sky.

Top Montgomery Hotel Reviews

Holiday Inn Express & Suites Montgomery by IHG

10/10 Excellent

"Good stay"

Comfort Suites Fishkill near Interstate 84

10/10 Excellent

"Location, cleanliness and quiet"

Overlook Lodge at Bear Mountain

10/10 Excellent

"Very nice place to stay. Very beautiful"

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent

"Newer property, well kept and very clean."

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

8/10 Good

"very basic no frills imn he room except soap nd shampoo , a container for ice but no glasses. one desk chair only in a room wih two bed for tr wo guests"

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent

"Guest room was designed well. Very clean. Comfortable bed. Great shower, strong pressure, like a massage. Breakfast was excellent , fresh and hot. Will be back"

The Thayer Hotel at West Point

10/10 Excellent

"Incredible staff. Great location. Attention to guests superlative.West Point tours were fantastic. Only complaint was that it is extremely pricey. Which is understandable considering where we stayed. We ate there for 2 dinners, one lunch, and 1 breakfast. Meals are expensive but were great except for a breakfast that was stone-cold for $24 each."

Super 8 by Wyndham Montgomery Maybrook

8/10 Good

"Room was clean. Hotel is out dated."

Studio 6 Extended Stay Fishkill Westage Center NY

10/10 Excellent

"Wonderful staff"

More cheap stays in Montgomery

Ramada by Wyndham Newburgh/West Point

1289 Route 300 Newburgh NY

1.629.936 ₫

1.925.361 ₫ total

13 Oct - 14 Oct

includes taxes & fees

4.8/10 (1,004 reviews)

Holiday Inn Express Poughkeepsie by IHG

2750 South Road Poughkeepsie NY

2.250.864 ₫

2.613.817 ₫ total

8 Nov - 9 Nov

includes taxes & fees

8.6/10 Excellent! (1,008 reviews)

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

915 Union Ave New Windsor NY

2.304.936 ₫

2.722.251 ₫ total

25 Oct - 26 Oct

includes taxes & fees

Quality Inn Poughkeepsie

536 Haight Ave, Building A Poughkeepsie NY

2.397.041 ₫

2.783.564 ₫ total

1 Nov - 2 Nov

includes taxes & fees

7.6/10 Good! (602 reviews)

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

2.616.953 ₫

3.091.276 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

3.003.739 ₫

3.548.167 ₫ total

3 Nov - 4 Nov

includes taxes & fees

8.4/10 Very good! (1,005 reviews)

Hotels in Montgomery with star rating

Frequently asked questions

What's the weather like in Montgomery?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Montgomery are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

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Book Hotels in Montgomery on Expedia.com

Find hotels in Montgomery, NY from 1.925.361 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Montgomery

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Montgomery hotels

1. Holiday Inn Express & Suites Montgomery by IHG

2. Borland House Inn

3. Super 8 by Wyndham Montgomery Maybrook

4. Tin Brook Bed & Breakfast

5. Harvest Inn

6. La Quinta Inn & Suites by Wyndham Middletown-Goshen

7. Hampton Inn & Suites Newburgh Stewart Airport

8. Courtyard by Marriott Newburgh Stewart Airport

9. Sleep Inn & Suites Monroe - Woodbury

10. Tru by Hilton Middletown

11. Fairfield Inn & Suites by Marriott Goshen Middletown

12. Homewood Suites Stewart Airport

13. Home2 Suites by Hilton Middletown

14. Courtyard by Marriott Middletown Goshen

15. Holiday Inn Express Hotel & Suites Chester by IHG

16. Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

17. Residence Inn by Marriott Middletown Goshen

18. Hampton Inn by Hilton Middletown

19. Sleep Inn & Suites Middletown - Goshen

20. Quality Inn & Suites Fishkill South near I-84

Stay near popular Montgomery attractions

Orange County Arboretum

City Winery Hudson Valley

Thomas Bull Memorial Park

Orange County Tennis Center

Learn more about Montgomery

Top Montgomery Hotel Reviews

Holiday Inn Express & Suites Montgomery by IHG

Comfort Suites Fishkill near Interstate 84

Overlook Lodge at Bear Mountain

Sleep Inn & Suites Monroe - Woodbury

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Hyatt Place Poughkeepsie / Hudson Valley

The Thayer Hotel at West Point

Super 8 by Wyndham Montgomery Maybrook

Studio 6 Extended Stay Fishkill Westage Center NY

More cheap stays in Montgomery

Ramada by Wyndham Newburgh/West Point

Holiday Inn Express Poughkeepsie by IHG

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Quality Inn Poughkeepsie

Sleep Inn & Suites Middletown - Goshen

Overlook Lodge at Bear Mountain

Hotels in Montgomery with star rating

Frequently asked questions

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