Stephentown Holiday Rentals, New York: Private House Rentals

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Our top choices for Stephentown hotels

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

A spacious kitchen with a large island, built-in appliances, and a laundry area.

A dining area with a wooden table and chairs, a large wooden cabinet, and a kitchen in the background.

A modern living room with a fireplace, white cabinetry, a large flat-screen TV, and a cozy seating area with patterned cushions.

1. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

5.815.936 ₫

14.388.210 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

2. Vacation Village in the Berkshires

Williamstown

Jacob

2.240.245 ₫

2.787.289 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A resort with multiple buildings, a parking area, and a mountainous backdrop.

A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

A wooden cabin with a porch and steps leading to a door, surrounded by snow.

3. Jiminy Peak Mountain Resort

Hancock

Karen

3.868.636 ₫

4.321.267 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A wooden cabin with a covered deck, a fire pit, and string lights.

A cozy room with a wood-burning stove, two wooden chairs, a small table, and a window overlooking a snowy landscape.

A swimming pool with a wooden deck, lounge chairs, and umbrellas.

4. Huttopia Berkshires

Williamstown

Dandara

1.962.879 ₫

2.192.536 ₫ total

includes taxes & fees

6 Oct - 7 Oct

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

5. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Joe

2.428.050 ₫

2.712.132 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

6. The Yankee Inn

Lenox

William

2.753.244 ₫

3.075.374 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A building entrance with a large planter with purple flowers and a small tree.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

7. Hotel On North

Pittsfield

Drew

2.902.594 ₫

3.242.198 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

A motel with a parking lot, a swimming pool, and outdoor seating.

A residential street with a paved road, a lamp post, and flowering trees.

A fenced outdoor area with a pool, lounge chairs, and umbrellas.

8. Berkshire Inn

Pittsfield

Kristina

2.232.644 ₫

2.493.864 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A patio area with outdoor furniture, a fire pit, and potted plants.

A hotel room with a large bed, a desk, a chair, and a view of the outdoors.

A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

A poolside area with lounge chairs, umbrellas, and a swimming pool.

9. The Springs Motel

New Ashford

Elizabeth

2.951.296 ₫

3.237.572 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A spacious lobby with a fireplace, seating area, and a bar.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A garden with wooden Adirondack chairs and a stone pathway.

10. Berkshire Mountain Lodge

Pittsfield

Jay

2.066.717 ₫

2.888.559 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

11. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

3.045.711 ₫

3.402.060 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

12. Howard Johnson by Wyndham Lenox

Lenox

COLLEEN

2.051.156 ₫

2.291.141 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A fire feature with a metal frame and a brick wall in the background.

A Fairfield Inn & Suites by Marriott hotel with a brick facade, large windows, and a covered outdoor seating area.

A modern restaurant with a long counter, multiple seating areas, and pendant lighting.

A modern living room with a fireplace, comfortable seating, a flat-screen TV, and a stone accent wall.

13. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

4.318.332 ₫

4.823.576 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

A bar area with wooden beams, red chairs, and a long wooden table.

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

14. The Williams Inn

Williamstown

Soleil

4.850.644 ₫

5.418.170 ₫ total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A snack bar with shelves of snacks and a refrigerated display.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A modern cafe with a counter, seating area, and large windows.

15. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Susan

2.571.426 ₫

2.872.284 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

A cozy library with bookshelves, a fireplace, and comfortable seating.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

16. Berkshires Untold

Lenox

Madhavi R

3.419.529 ₫

3.819.614 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A covered outdoor area with stone pillars and a view of a road and green hills.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

17. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

3.262.594 ₫

3.644.317 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

A hotel patio with outdoor seating and a fire pit.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

18. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

3.321.555 ₫

3.710.126 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

A compact living space with a kitchenette, a dining area, and a sofa.

A modern apartment with a living room, kitchenette, and dining area.

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

19. The Central Downtown Inn & Suites

Pittsfield

Rena

2.570.436 ₫

2.871.099 ₫ total

includes taxes & fees

7 Oct - 8 Oct

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

A wooden interior with a table, chair, and a view of a red barn through an open door.

20. Inn at Silver Maple Farm

East Chatham

Erdem

6.077.916 ₫

6.807.266 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Stephentown attractions

Zema's Nursery

Enjoy a stop at Zema's Nursery, an entertaining place to visit in Stephentown. Discover the mountain views in this quaint area or enjoy its ski slopes.

See properties

Top Stephentown Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Every single thing impressed us. The young woman working the check in desk was sweet, efficient and opened a beer for us with office supplies! Our HERO! Room was immaculate. Beds pillows and sheets so comfy. Great shower. We can’t WAIT to get back here."

Vacation Village in the Berkshires

10/10 Excellent

"Great place great price!"

The Yankee Inn

8/10 Good

"Room was nice but did not have the view I was hoping for. Another hotel property is mostly blocking views from Yankee Inn looking West; the direction rooms with balcony’s face. The location near"

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good

"Staff very pleasant and helpful. On site restaurant was good and reasonably priced. Room was large with a nice view. Breakfast, which is continental, seemed a bit skimpy. Plenty of parking and in a great central area with many restaurants."

Berkshires Untold

8/10 Good

"All was good for the price. Great location. Gentlemen at the bar and check-in was very pleasant and helpful. Dinner could have been better prepared."

Country Inn & Suites by Radisson, Downtown Albany New York

10/10 Excellent

"Nice place."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Most helpful staff, very clean and best breakfast around"

The Williams Inn

10/10 Excellent

"Great"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Wonderful resort"

More cheap stays in Stephentown

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.612.364 ₫

1.801.011 ₫ total

4 Oct - 5 Oct

includes taxes & fees

5.4/10 (911 reviews)

Comfort Inn Glenmont - Albany South

37 Route 9W Glenmont NY

2.216.102 ₫

2.537.437 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY

2.627.270 ₫

3.008.223 ₫ total

1 Nov - 2 Nov

includes taxes & fees

8.2/10 Very good! (1,112 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.753.244 ₫

3.075.374 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

2.958.439 ₫

3.283.868 ₫ total

2 Nov - 3 Nov

includes taxes & fees

8.8/10 Excellent! (1,003 reviews)

Hampton Inn & Suites Albany-Downtown

25 Chapel St Albany NY

3.067.647 ₫

3.512.456 ₫ total

11 Oct - 12 Oct

includes taxes & fees

Hotels in Stephentown with star rating

Frequently asked questions

What's the seasonal weather like in Stephentown?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stephentown are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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Book Hotels in Stephentown on Expedia.com

Find hotels in Stephentown, NY from 1.801.011 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Stephentown

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Stephentown hotels

1. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

2. Vacation Village in the Berkshires

3. Jiminy Peak Mountain Resort

4. Huttopia Berkshires

5. Best Western Plus Berkshire Hills Inn & Suites

6. The Yankee Inn

7. Hotel On North

8. Berkshire Inn

9. The Springs Motel

10. Berkshire Mountain Lodge

11. Hampton Inn & Suites Berkshires-Lenox

12. Howard Johnson by Wyndham Lenox

13. Fairfield Inn & Suites by Marriott Williamstown

14. The Williams Inn

15. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

16. Berkshires Untold

17. Courtyard by Marriott Lenox Berkshires

18. Hilton Garden Inn Lenox Pittsfield

19. The Central Downtown Inn & Suites

20. Inn at Silver Maple Farm

Stay near popular Stephentown attractions

Zema's Nursery

Top Stephentown Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Vacation Village in the Berkshires

The Yankee Inn

Hotel Downstreet, an Ascend Collection Hotel

Berkshires Untold

Country Inn & Suites by Radisson, Downtown Albany New York

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Williams Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

More cheap stays in Stephentown

FairBridge Inn Express

Comfort Inn Glenmont - Albany South

Country Inn & Suites by Radisson, Downtown Albany New York

The Yankee Inn

Comfort Inn & Suites East Greenbush - Albany

Hampton Inn & Suites Albany-Downtown

Hotels in Stephentown with star rating

Frequently asked questions

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