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 wooden deck with a bench and umbrella, a door, and a window.

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

฿7,322

฿18,114 total

includes taxes & fees

29 Aug - 30 Aug

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.

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

2. Vacation Village in the Berkshires

Williamstown

Nyra

฿2,840

฿3,530 total

includes taxes & fees

31 Aug - 1 Sept

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

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

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

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

3. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Jermaine

฿3,752

฿4,191 total

includes taxes & fees

20 Sept - 21 Sept

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.

4. Jiminy Peak Mountain Resort

Hancock

Sandy

฿4,678

฿5,225 total

includes taxes & fees

30 Aug - 31 Aug

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

A multi-story hotel with a brick facade and a flat roof.

A pool area with a glass ceiling, multiple levels, and outdoor seating.

5. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Myrna

฿3,890

฿4,345 total

includes taxes & fees

24 Sept - 25 Sept

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

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

A spacious living area with a high ceiling, a staircase with a wooden railing, a large blue patterned rug, and a white sofa.

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

6. Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

Michael

฿3,942

฿4,376 total

includes taxes & fees

7 Sept - 8 Sept

A greenhouse with a transparent roof, a seating area with cushions, and a potted plant.

A living room with a fireplace, sofa, armchair, and a TV.

A dining table with plates of food, a coffee cup, and a plant.

A cozy library with wooden bookshelves, a reading area, and a fireplace.

7. Berkshire Valley Inn

Williamstown

฿5,443

฿6,079 total

includes taxes & fees

7 Sept - 8 Sept

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

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

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.

8. The Yankee Inn

Lenox

Karen

฿5,001

฿5,586 total

includes taxes & fees

13 Sept - 14 Sept

A dining table set for two with red plates, silverware, and a wine glass, viewed through a window overlooking a red building.

An outdoor seating area with tables and chairs covered in beige cloths, connected by a string of lights.

A cozy living room with a leather sofa, a wooden coffee table with a vase of flowers, and a staircase leading to an upper level.

A wooden sign for The Gregory House, County Inn and Restaurant, with a rustic design and a natural backdrop.

9. Gregory House Country Inn

Averill Park

Brian

฿3,677

฿4,082 total

includes taxes & fees

27 Aug - 28 Aug

A modern hotel lobby with a dining area, a reception desk, and a bar.

An outdoor seating area with blue sofas and a stone fire pit.

A snack and treat section with shelves stocked with various snacks and beverages, a microwave, and a refrigerator.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a tiled deck.

10. Hampton Inn & Suites Albany-East Greenbush

East Greenbush

Thomas

฿5,064

฿5,736 total

includes taxes & fees

20 Sept - 21 Sept

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

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

11. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

฿4,782

฿5,341 total

includes taxes & fees

13 Sept - 14 Sept

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

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

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

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

12. The Springs Motel

New Ashford

Shakeila

฿4,008

฿4,397 total

includes taxes & fees

31 Aug - 1 Sept

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

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

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

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

13. Hotel On North

Pittsfield

Drew

฿5,851

฿6,536 total

includes taxes & fees

7 Sept - 8 Sept

A modern living room with a fireplace, a large TV, and a seating area with a blue sofa and armchairs.

A reception area with a modern design, featuring a reception desk, two yellow armchairs, a blue abstract painting, and a wooden panel wall.

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

14. Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

Rensselaer

James

฿3,988

฿4,427 total

includes taxes & fees

6 Sept - 7 Sept

A modern living room with a fireplace, a dining area with chairs, and a kitchen in the background.

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

A banquet hall with round tables set for dining, surrounded by chairs.

A large, well-lit conference room with round tables and chairs, a flat-screen TV, and a wooden floor.

15. Country Inn & Suites by Radisson, Downtown Albany New York

Downtown Albany

Margaret

฿3,449

฿3,949 total

includes taxes & fees

30 Aug - 31 Aug

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.

16. Howard Johnson by Wyndham Lenox

Lenox

Sheila

฿2,582

฿2,884 total

includes taxes & fees

31 Aug - 1 Sept

A hotel lobby with leather armchairs, a blue sofa, a white coffee table, and a stone fireplace.

A modern living room with leather armchairs, a blue sofa, and a patterned ottoman.

A hotel reception area with a modern design, featuring a reception desk, a wall-mounted TV, and a shelf with snacks.

A Fairfield Inn & Suites Marriott hotel with a covered entrance, stone facade, and multiple floors.

17. Fairfield Inn & Suites Albany East Greenbush

East Greenbush

Luis

฿3,862

฿4,287 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

18. Courtyard by Marriott Lenox Berkshires

Lenox

Laura

฿5,807

฿6,486 total

includes taxes & fees

7 Sept - 8 Sept

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

A wooden cabin with a porch and a small deck, surrounded by trees in a forest.

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

19. Huttopia Berkshires

Williamstown

GEORGINA

฿3,177

฿3,549 total

includes taxes & fees

8 Sept - 9 Sept

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

20. Berkshire Inn

Pittsfield

Adriana

฿2,942

฿3,286 total

includes taxes & fees

27 Aug - 28 Aug

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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

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Helpful staff, clean large suite with 2 beds and baths. Enjoyed the activity center and all it had to offer."

Country Inn & Suites by Radisson, Downtown Albany New York

10/10 Excellent

"VERY CLEAN AND LOTS OF FRESH TOWELS"

The Yankee Inn

10/10 Excellent

"Charming hotel with a wonderful breakfast and two lovely pools, plus a nature walk to a lake. The staff were great, really nice and helpful."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Nice place"

The Red Lion Inn

10/10 Excellent

"The room was very nice, super clean. Sitting on the porch is what we love most. Food was good, drinks a bit pricey..but when you're on vacation it hardly matters. The pool was nice, the hot tub too. A pleasant stay in a historic inn. It's the berkshires so its beautiful"

Berkshire Mountain Lodge

10/10 Excellent

"We were very happy with how large the rooms were and it felt like you were in an apartment great location and very clean excellent customer service at the front desk"

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"The experience and the comfort of the stay were appreciated."

Hilton Albany

10/10 Excellent

"Shuttle was on time and was great to have since the hotel is not close to the airport."

FairBridge Inn Express

10/10 Excellent

"It was very nice and everyone was extremely helpful"

More cheap stays in Stephentown

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,030

฿2,267 total

27 Aug - 28 Aug

includes taxes & fees

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY

฿3,449

฿3,949 total

30 Aug - 31 Aug

includes taxes & fees

8.2/10 Very good! (1,001 reviews)

Hampton Inn & Suites Albany-Downtown

25 Chapel St Albany NY

฿3,458

฿3,959 total

6 Sept - 7 Sept

includes taxes & fees

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

1055 South Street Pittsfield MA

฿3,890

฿4,345 total

24 Sept - 25 Sept

includes taxes & fees

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY

฿3,942

฿4,376 total

7 Sept - 8 Sept

includes taxes & fees

8.8/10 Excellent! (1,002 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿5,001

฿5,586 total

13 Sept - 14 Sept

includes taxes & fees

9.2/10 Wonderful! (1,022 reviews)

Frequently asked questions

Where is the best place to stay in Stephentown?

Located 19.5 mi (31.3 km) from the heart of Stephentown, Hilton Albany is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Vacation Village in the Berkshires and Country Inn & Suites by Radisson, Downtown Albany New York. 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?

Hilton Albany: Hotel, 4-minute walk from MVP Arena. Offers 2 restaurants, an indoor pool and complimentary wireless Internet access. Vacation Village in the Berkshires and The Yankee Inn 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 17 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 Pontoosuc Lake 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 ฿2,267

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. Best Western Plus Berkshire Hills Inn & Suites

4. Jiminy Peak Mountain Resort

5. Holiday Inn & Suites Pittsfield-Berkshires by IHG

6. Comfort Inn & Suites East Greenbush - Albany

7. Berkshire Valley Inn

8. The Yankee Inn

9. Gregory House Country Inn

10. Hampton Inn & Suites Albany-East Greenbush

11. Hilton Garden Inn Lenox Pittsfield

12. The Springs Motel

13. Hotel On North

14. Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

15. Country Inn & Suites by Radisson, Downtown Albany New York

16. Howard Johnson by Wyndham Lenox

17. Fairfield Inn & Suites Albany East Greenbush

18. Courtyard by Marriott Lenox Berkshires

19. Huttopia Berkshires

20. Berkshire Inn

Stay near popular Stephentown attractions

Zema's Nursery

Top Stephentown Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Country Inn & Suites by Radisson, Downtown Albany New York

The Yankee Inn

Hotel Downstreet, an Ascend Collection Hotel

The Red Lion Inn

Berkshire Mountain Lodge

Comfort Inn & Suites East Greenbush - Albany

Hilton Albany

FairBridge Inn Express

More cheap stays in Stephentown

FairBridge Inn Express

Country Inn & Suites by Radisson, Downtown Albany New York

Hampton Inn & Suites Albany-Downtown

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

Comfort Inn & Suites East Greenbush - Albany

The Yankee Inn

Frequently asked questions

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