Smallwood Holiday Rentals, New York: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Smallwood

Pet friendly

Apartment

Pool

Cottage

Family friendly

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Smallwood hotels

A lobby with a sofa, two armchairs, a coffee table, a fireplace, a television, and a clock on the wall.

A hotel room with two beds, a desk, a television, and a window with curtains.

A motel with a central building and a covered parking area.

A restaurant interior with wooden tables and chairs, a stone wall, and a coffee station.

1. The Sullivan Inn

Monticello

1.843.765 ₫

2.083.453 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A modern kitchen area with a central island, various appliances, and a chalkboard wall with food-related drawings.

An indoor swimming pool with clear signage, including "NO LIFEGUARD ON DUTY" and "NO DIVING" warnings.

A Hampton Inn hotel with a modern facade, a clear entrance, and a welcoming gas station.

A hotel room with two beds, a nightstand with a lamp, a window with a view, and a carpeted floor.

2. Hampton Inn Monticello

Monticello

Yuta

3.968.893 ₫

4.484.850 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A modern living room with two sofas, a glass coffee table, and a painting of a horse.

A reception area with a marble counter, a wall-mounted artwork, and a ceiling with recessed lighting.

A large indoor swimming pool with a wooden deck and lounge chairs.

A hotel with a brick facade, a covered entrance, and a parking lot with cars.

3. Best Western Monticello

Monticello

Sonia

2.943.801 ₫

3.326.495 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A modern lobby with a curved sofa, a reception desk, and a flat-screen TV.

A spacious indoor area with multiple tables and chairs, a kitchen area with a counter, and a large window providing natural light.

A hotel room with two beds, a desk, a chair, and a large painting on the wall.

A banquet hall with round tables covered in white tablecloths and chairs, a carpeted floor, and a ceiling with recessed lighting.

4. Days Inn by Wyndham Liberty/Monticello

Liberty

Henry

2.578.937 ₫

2.914.198 ₫ total

includes taxes & fees

4 Oct - 5 Oct

An indoor water park with a large water slide, a pool area, and a glass ceiling structure.

A restaurant setting with a counter, a digital scale, and a person serving food.

A bar area with a central island, multiple bar stools, and a large screen displaying content.

A hotel with a pool area, outdoor seating, and a view of the sunset.

5. The Kartrite Resort & Indoor Waterpark

Monticello

Carla

4.197.094 ₫

6.591.150 ₫ total

includes taxes & fees

11 Sept - 12 Sept

A compact kitchenette with a microwave, refrigerator, and a small table with a TV and remote controls.

A pathway flanked by trimmed trees leading to a building with a stone facade and multiple windows.

A two-story house with a stone facade and a large window.

6. Kenoza Lake View Manor

Jeffersonville

Steven

3.215.568 ₫

3.742.766 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A spacious lobby with a stone fireplace, a flat-screen TV, and comfortable seating.

A hotel lobby with a reception desk, a patterned carpet, a stone wall, and a seating area with a checkered sofa and ottoman.

A lobby with a stone fireplace, two armchairs, a coffee table, and a dining area with tables and chairs.

A spacious bar area with a long counter, multiple seating options, and a stone fireplace.

7. Hampton Inn Matamoras/Milford

Matamoras

brian

2.733.233 ₫

2.979.224 ₫ total

includes taxes & fees

27 Sept - 28 Sept

An indoor swimming pool with clear water, tiled floor, and a few lounge chairs.

A modern restaurant interior with round tables and booths, pendant lighting, and a view of the street through large windows.

A modern bar area with a central island, bar stools, and overhead lighting.

8. Resorts World Catskills Casino

Monticello

David

3.870.351 ₫

5.021.798 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A covered outdoor area with a wooden deck and a view of a green landscape.

A neatly made bed with white linens, a wooden headboard, and two bedside lamps. A window with curtains is visible, and a small table with a chair is in the corner.

A cozy room with a wooden desk, a cushioned sofa, a flat-screen TV, and a window with curtains.

A wooden staircase with a cushioned bench at the bottom.

9. Inn at Tyler Hill

Tyler Hill

sandra

4.648.311 ₫

5.066.853 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A hotel room with two beds, a desk, a chair, a lamp, and artwork on the walls.

A two-story house with a gabled roof, a chimney, and an American flag.

A bathroom with a white sink, two faucets, a mirror, and a toilet.

A hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a nightstand.

10. Super 8 by Wyndham Monticello NY

Monticello

Nicole

2.076.894 ₫

2.346.891 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A fountain with water jets in the center, surrounded by a circular stone border. In the background, there is a building with a balcony and arched windows.

A water park with a water play structure and people enjoying the water.

A hotel reception area with a wooden reception desk, multiple computer monitors, and a large chandelier.

A hotel lobby with round tables, cushioned chairs, a large pillar, and a projection screen displaying a movie.

11. Villa Roma Resort and Conference Center

Callicoon

DIANE

3.879.427 ₫

4.902.392 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A small, standalone structure with a pitched roof, possibly a gazebo or shelter, surrounded by well-maintained grass and plants. In the background, there is a sign for 'Scottish Inns' indicating the presence of a hotel nearby.

A hotel room with a large bed, two wall-mounted lights, and a decorative wall hanging.

A row of motel-style buildings with a central statue in a landscaped area.

12. Scottish Inns Milford

Milford

Kellie

2.593.200 ₫

2.826.588 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A bar area with a long counter, multiple stools, and a variety of bottles and glasses.

A hallway with a wooden floor, glass doors, and a sign for Annie's Lounge.

A spacious living area with a stone wall, wooden ceiling beams, and large windows offering a view of the outdoors.

An indoor swimming pool with clear reflections, lounge chairs, and large windows offering views of the outdoors.

13. Best Western Hunt's Landing Hotel Matamoras/Milford

Matamoras

GinaMarie

3.019.781 ₫

3.291.561 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A modern hotel room with a living area, a sofa, a coffee table, a TV, and a large window with a view.

A breakfast area with six round tables and chairs, a coffee station, and a view of greenery outside.

A multi-story building with a flat roof, multiple balconies, and a covered front porch.

14. Days Inn by Wyndham Wurtsboro

Wurtsboro

Danny

2.826.588 ₫

3.194.046 ₫ total

includes taxes & fees

17 Sept - 18 Sept

A modern lobby with a wooden accent wall, a seating area with sofas and ottomans, and a 'Museum Store' sign.

A person in a swimming pool with a tiled wall in the background.

A spacious indoor area with large windows and a high ceiling, suitable for group activities like yoga.

A covered patio area with stone pillars, wooden benches, and a view of a lake.

15. YO1 Longevity & Health Resorts, Catskills

Monticello

Rajvi

9.043.785 ₫

10.219.542 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A lakeside walkway with a wooden deck, surrounded by trees and a building with illuminated windows.

A restaurant with a long dining table, multiple chairs, and a high ceiling with hanging lights.

A modern building with a wooden walkway leading to a covered entrance.

A modern interior with a piano, bar area, and seating.

16. The Bradstan Boutique Hotel

Eldred

Susan

9.782.847 ₫

11.443.596 ₫ total

includes taxes & fees

15 Sept - 16 Sept

An indoor swimming pool with a central column, tiled floor, and a skylight above.

A spacious dining area with long tables and chairs, high ceilings with exposed beams, and hanging pendant lights.

An outdoor seating area with red chairs and tables, a fire pit, and a bar visible through the window.

An outdoor bar area with a stainless steel counter, bar stools, and a variety of bottles.

17. The Alder at Resorts World Catskills

Monticello

John

3.944.257 ₫

5.105.233 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A hotel room with two beds, a desk, a lamp, and a painting on the wall.

A two-story building with a 'Vacancy' sign and an 'Office' sign, featuring a front porch with steps and potted plants.

A reception area with patterned wallpaper, a wooden counter, a display of magazines, and a door with a view of the outside.

18. Rodeway Inn Milford - I-84

Milford

Jacqueline

2.314.431 ₫

2.522.730 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A rustic cabin with a stone foundation, surrounded by a well-maintained lawn and a variety of trees.

A rustic wooden interior with leather sofas, a round wooden coffee table, and a large window offering a view of a field.

A rustic interior with stone walls, wooden beams, and large windows offering a view of the outdoors.

A rustic lodge with a green roof, surrounded by tall pine trees and a well-maintained lawn.

19. Roscoe Mountain Club

Roscoe

Daniel

2.508.921 ₫

2.835.081 ₫ total

includes taxes & fees

29 Sept - 30 Sept

A spacious living room with a staircase, a dining area, and a decorative metal piece on the wall.

A single-story house with a front porch, a visible front door, and a small front yard with a concrete path leading to the door.

A bedroom with a bed, two bedside tables, a wall-mounted air conditioner, a framed picture, a door, and a patterned rug.

A dining room with a wooden table, six chairs, a chandelier, a grandfather clock, and a bookshelf.

20. Windsong Retreat 2

Bethel

Mark

7.235.028 ₫

9.201.192 ₫ total

includes taxes & fees

11 Sept - 12 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Smallwood Hotel Reviews

Callicoon Hills

10/10 Excellent

"My partner and I enjoyed the facilities so much so, that we’re thinking of getting married there."

The Kartrite Resort & Indoor Waterpark

10/10 Excellent

"Súper limpio, el personal muy amable y atento.10/10"

Days Inn by Wyndham Wurtsboro

8/10 Good

"m"

Days Inn by Wyndham Liberty/Monticello

8/10 Good

"Convenient location for our trip. Quiet. Clean room, comfortable beds. Was startled by need for "deposit" as the room was already paid for. Was not aware of deposit until checking in. Side entry way door had worn curled outside carpet which could be a tripping hazzard to guests. Was nice enough that I would stay there again."

Inn at Tyler Hill

10/10 Excellent

"Beautiful quiet setting. Stayed in the Barn in the Beach Boys suite. It was beautiful, spacious, well-kept and very comfortable. Bed was great. AC, wifi and bathroom were terrific. Would definitely stay there again if I am in the areas."

Kenoza Lake View Manor

8/10 Good

"Loved the eclectic decor. Great to stay in a place with Catskills character. Took a while for the hot water to get to the third floor. Peaceful, quiet atmosphere."

Best Western Monticello

8/10 Good

"AC not working"

Villa Roma Resort and Conference Center

10/10 Excellent

"Peaceful. Refreshing resort."

YO1 Longevity & Health Resorts, Catskills

8/10 Good

"We tried to drop off our luggage (not check in) before going out to play golf, but they wanted to charge us $75 to leave our bags. Also, the outdoor spaces were okay, but there were massive amounts of bird droppings in some outdoor areas. Other than those complaints, we had a great time."

More cheap stays in Smallwood

Days Inn by Wyndham Liberty/Monticello

52 Sullivan Ave Liberty NY

2.578.937 ₫

2.914.198 ₫ total

4 Oct - 5 Oct

includes taxes & fees

6.8/10 (1,001 reviews)

Hampton Inn Matamoras/Milford

122 Westfall Town Dr Matamoras PA

2.733.233 ₫

2.979.224 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Days Inn by Wyndham Wurtsboro

21 Perron Dr Wurtsboro NY

2.826.588 ₫

3.194.046 ₫ total

17 Sept - 18 Sept

includes taxes & fees

7.6/10 Good! (662 reviews)

Best Western Monticello

16 Raceway Rd Monticello NY

2.943.801 ₫

3.326.495 ₫ total

1 Oct - 2 Oct

includes taxes & fees

8.2/10 Very good! (1,000 reviews)

Hampton Inn Monticello

29 Golden Ridge Road Monticello NY

3.968.893 ₫

4.484.850 ₫ total

7 Oct - 8 Oct

includes taxes & fees

The Alder at Resorts World Catskills

750 Resorts World Drive Monticello NY

3.944.257 ₫

5.105.233 ₫ total

20 Sept - 21 Sept

includes taxes & fees

Hotels in Smallwood with star rating

Frequently asked questions

What's the seasonal weather like in Smallwood?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Smallwood are January, February, December and March, with each month seeing an average of 24 cm of snowfall.

Explore a world of travel with Expedia

Book Hotels in Smallwood on Expedia.com

Find hotels in Smallwood, NY from 2.346.891 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Smallwood

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Smallwood hotels

1. The Sullivan Inn

2. Hampton Inn Monticello

3. Best Western Monticello

4. Days Inn by Wyndham Liberty/Monticello

5. The Kartrite Resort & Indoor Waterpark

6. Kenoza Lake View Manor

7. Hampton Inn Matamoras/Milford

8. Resorts World Catskills Casino

9. Inn at Tyler Hill

10. Super 8 by Wyndham Monticello NY

11. Villa Roma Resort and Conference Center

12. Scottish Inns Milford

13. Best Western Hunt's Landing Hotel Matamoras/Milford

14. Days Inn by Wyndham Wurtsboro

15. YO1 Longevity & Health Resorts, Catskills

16. The Bradstan Boutique Hotel

17. The Alder at Resorts World Catskills

18. Rodeway Inn Milford - I-84

19. Roscoe Mountain Club

20. Windsong Retreat 2

Top Smallwood Hotel Reviews

Callicoon Hills

The Kartrite Resort & Indoor Waterpark

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Liberty/Monticello

Inn at Tyler Hill

Kenoza Lake View Manor

Best Western Monticello

Villa Roma Resort and Conference Center

YO1 Longevity & Health Resorts, Catskills

More cheap stays in Smallwood

Days Inn by Wyndham Liberty/Monticello

Hampton Inn Matamoras/Milford

Days Inn by Wyndham Wurtsboro

Best Western Monticello

Hampton Inn Monticello

The Alder at Resorts World Catskills

Hotels in Smallwood with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app