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

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

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

Stephentown

฿7,511

฿18,581 total

includes taxes & fees

13 Oct - 14 Oct

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

A spacious living room with large windows, a fireplace, and a variety of seating options.

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

2. Vacation Village in the Berkshires

Williamstown

Pofen

฿2,694

฿3,377 total

includes taxes & fees

1 Nov - 2 Nov

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

A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

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

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

3. Jiminy Peak Mountain Resort

Hancock

Olga

฿4,496

฿5,022 total

includes taxes & fees

18 Oct - 19 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 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.

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

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

4. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

฿3,134

฿3,501 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 swimming pool with a surrounding deck, a stone wall, and a building in the background.

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.

5. The Yankee Inn

Lenox

Basil

฿3,554

฿3,970 total

includes taxes & fees

1 Nov - 2 Nov

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

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

6. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

฿3,819

฿4,266 total

includes taxes & fees

7 Nov - 8 Nov

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

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

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

A library with bookshelves, a television, and two armchairs.

7. Hotel On North

Pittsfield

Lawrence

฿4,496

฿5,022 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 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.

A spacious living room with a large sofa, a coffee table, and a fireplace.

8. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

฿4,288

฿4,789 total

includes taxes & fees

1 Nov - 2 Nov

A conference room with a whiteboard, tables, and chairs.

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.

9. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

฿3,521

฿3,933 total

includes taxes & fees

6 Nov - 7 Nov

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

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

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.

10. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

C. David

฿5,102

฿5,698 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

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

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

Pittsfield

Ginger

฿3,319

฿3,708 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

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

12. The Springs Motel

New Ashford

Elizabeth

฿3,584

฿3,931 total

includes taxes & fees

9 Nov - 10 Nov

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

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

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

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

13. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

฿4,212

฿4,704 total

includes taxes & fees

1 Nov - 2 Nov

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

A garden with wooden Adirondack chairs and a stone pathway.

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

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

14. Berkshire Mountain Lodge

Pittsfield

marilyn

฿2,874

฿3,960 total

includes taxes & fees

9 Nov - 10 Nov

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

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

A spacious living area with a fireplace, wooden beams, and a large window.

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

15. The Williams Inn

Williamstown

Soleil

฿6,812

฿7,609 total

includes taxes & fees

8 Nov - 9 Nov

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

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

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

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

16. Berkshire Inn

Pittsfield

Linda

฿2,883

฿3,221 total

includes taxes & fees

19 Oct - 20 Oct

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 gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

17. Howard Johnson by Wyndham Lenox

Lenox

Mark

฿2,649

฿2,959 total

includes taxes & fees

18 Oct - 19 Oct

A hotel with a covered entrance, stone facade, and arched windows.

A spacious living area with a blue sofa, yellow armchair, and a coffee table. A staircase leads to an upper level with a balcony.

A hotel room with a bed, a desk, a sofa, a round table, and a large window with curtains.

A spacious living room with a stone fireplace, large windows, and modern furniture.

18. Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

Sean

฿3,677

฿4,081 total

includes taxes & fees

10 Nov - 11 Nov

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A modern hotel building with the name "Hotel Downtown" on the facade.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

19. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Tara

฿3,997

฿4,464 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.

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

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

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

20. Berkshires Untold

Lenox

Madhavi R

฿4,365

฿4,876 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

Vacation Village in the Berkshires

10/10 Excellent

"This is my go-to accommodation to visit Williams College in Williamstown."

Country Inn & Suites by Radisson, Downtown Albany New York

8/10 Good

"clean room air conditioning"

Berkshire Mountain Lodge

10/10 Excellent

"Comfortable and cozy suite, large living room/dining area, kitchen and large bedroom, will stay again"

Hampton Inn & Suites Albany-Downtown

8/10 Good

"Convenient"

Berkshires Untold

8/10 Good

"First this is a gorgeous property, the outdoor areas are wonderful, with comfy furniture, flowers and fire pits. The main area is an intimate restaurant and bar, with a seating area with books and plants. We enjoyed drinks and dinner there and it was excellent, particularly with the sunset and fire pit to begin our evening, Absolutely lovely! Upon checking in, we were assigned a “premium” room, which sounded great, however it turned out to be on the second floor, at the end of a very long outside corridor, parking and lobby quite distant. They have no elevator. We did lug our bags and a cooler to the room, which was lovely, but we knew we would be much more comfortable on the first floor closer to the lobby, as we are somewhat older. We asked to be moved, and we accommodated, found the room the same, but lacking the coffee service and luggage rack. We were brought a luggage rack, and complimentary coffee was available in the lobby in the morning, but it seemed odd that those would be considered premium in such a nice place. The star of the place is the beautiful outdoor space, and restaurant, we just loved that!"

Comfort Inn Glenmont - Albany South

8/10 Good

"Good location and great for one night stopover"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"The hotel is an older building but is clean and well maintained. The view of the lake was nice. Breakfast was just ok. Bed was very comfortable. Michelle was very helpful. My only disappointment was that the kayaks were not complimentary. It cost $30 an hour for each kayak."

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"The room was incredible. Just need to be a little friendly at the arrival."

Hilton Albany

8/10 Good

"The room was great, the staff very helpful. But due to scheduling we just checked in, went to bed, woke up very early and left using the hotel shuttle."

More cheap stays in Stephentown

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,082

฿2,326 total

13 Oct - 14 Oct

includes taxes & fees

5.4/10 (923 reviews)

Comfort Inn Glenmont - Albany South

37 Route 9W Glenmont NY

฿3,045

฿3,486 total

1 Nov - 2 Nov

includes taxes & fees

7.8/10 Good! (1,007 reviews)

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY

฿3,392

฿3,883 total

1 Nov - 2 Nov

includes taxes & fees

8.2/10 Very good! (1,150 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿3,554

฿3,970 total

1 Nov - 2 Nov

includes taxes & fees

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

฿3,677

฿4,081 total

10 Nov - 11 Nov

includes taxes & fees

8.8/10 Excellent! (1,004 reviews)

Hampton Inn & Suites Albany-Downtown

25 Chapel St Albany NY

฿3,819

฿4,373 total

18 Oct - 19 Oct

includes taxes & fees

8.8/10 Excellent! (1,057 reviews)

Frequently asked questions

Where is the best place to stay in Stephentown?

Located 5.3 mi (8.6 km) from the heart of Stephentown, Vacation Village in the Berkshires is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Country Inn & Suites by Radisson, Downtown Albany New York and Hampton Inn & Suites Albany-Downtown. See all available top hotels, or vacation rentals in Stephentown.

If I need to cancel my hotel reservation in Stephentown, will I receive a refund?

Yes! Most room reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of check in. If you have a non-refundable reservation, you might be able to cancel it and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Stephentown.

What's the best dog-friendly place to stay in Stephentown?

Berkshire Mountain House is a top dog-friendly B&B, and offers a rooftop terrace along with free WiFi for its human guests. See more pet-friendly hotel accommodations in Stephentown.

What are some accommodation options with pools in Stephentown?

Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge and Comfort Inn Glenmont - Albany South are a couple of other choices that offer an on-site pool. View all hotels with pools in Stephentown.

How is it to stay in Stephentown?

Visitors can enjoy all that Stephentown has to offer, including the ski areas and restaurants. In Stephentown, there are 18 hotels and other accommodation options to choose from. Find out more about Stephentown.

What should I see while I'm in Stephentown?

A couple of favourite places to visit are Zema's Nursery and Taconic Ridge State Forest. You'll also find Jiminy Peak Mountain Resort and Hancock Shaker Village in the area. Take a look at what more there is to see and do in Expedia's Stephentown guide.

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 ฿2,326

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. Best Western Plus Berkshire Hills Inn & Suites

5. The Yankee Inn

6. Hampton Inn & Suites Berkshires-Lenox

7. Hotel On North

8. Hilton Garden Inn Lenox Pittsfield

9. Holiday Inn & Suites Pittsfield-Berkshires by IHG

10. Fairfield Inn & Suites by Marriott Williamstown

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

12. The Springs Motel

13. Courtyard by Marriott Lenox Berkshires

14. Berkshire Mountain Lodge

15. The Williams Inn

16. Berkshire Inn

17. Howard Johnson by Wyndham Lenox

18. Comfort Inn & Suites East Greenbush - Albany

19. Hotel Downstreet, an Ascend Collection Hotel

20. Berkshires Untold

Stay near popular Stephentown attractions

Zema's Nursery

Top Stephentown Hotel Reviews

Vacation Village in the Berkshires

Country Inn & Suites by Radisson, Downtown Albany New York

Berkshire Mountain Lodge

Hampton Inn & Suites Albany-Downtown

Berkshires Untold

Comfort Inn Glenmont - Albany South

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Holiday Inn Club Vacations Oak 'n Spruce Resort

Hilton Albany

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

Frequently asked questions

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