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31 Aug - 1 Sep
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1 Sep - 2 Sep
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Our top choices for Stephentown hotels

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

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Stephentown
AED 823
AED 2,035 total
includes taxes & fees
1 Sep - 2 Sep
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

2. Huttopia Berkshires

Huttopia Berkshires
Williamstown
United States
GEORGINA
AED 357
AED 399 total
includes taxes & fees
8 Sep - 9 Sep
Huttopia Berkshires

3. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
United States
Jacqueline
AED 502
AED 561 total
includes taxes & fees
1 Sep - 2 Sep
Jiminy Peak Mountain Resort

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
United States
Alex
AED 355
AED 437 total
includes taxes & fees
1 Sep - 2 Sep
Vacation Village in the Berkshires

5. Berkshire Valley Inn

Berkshire Valley Inn
Williamstown
United States
Charlene
AED 612
AED 683 total
includes taxes & fees
7 Sep - 8 Sep
Berkshire Valley Inn

6. The Springs Motel

The Springs Motel
New Ashford
United States
Elizabeth
AED 438
AED 481 total
includes taxes & fees
13 Sep - 14 Sep
The Springs Motel

7. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
United States
Jermaine
AED 422
AED 471 total
includes taxes & fees
20 Sep - 21 Sep
Best Western Plus Berkshire Hills Inn & Suites

8. Gregory House Country Inn

Gregory House Country Inn
Averill Park
United States
Brian
AED 413
AED 459 total
includes taxes & fees
1 Sep - 2 Sep
Gregory House Country Inn

9. Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham
United States
Erdem
AED 511
AED 572 total
includes taxes & fees
1 Sep - 2 Sep
Inn at Silver Maple Farm

10. Hotel On North

Hotel On North
Pittsfield
United States
Drew
AED 657
AED 734 total
includes taxes & fees
7 Sep - 8 Sep
Hotel On North

11. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Debra
AED 433
AED 484 total
includes taxes & fees
7 Sep - 8 Sep
Holiday Inn & Suites Pittsfield-Berkshires by IHG

12. Berkshire Inn

Berkshire Inn
Pittsfield
United States
Adriana
AED 316
AED 353 total
includes taxes & fees
1 Sep - 2 Sep
Berkshire Inn

13. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
AED 364
AED 406 total
includes taxes & fees
1 Sep - 2 Sep
The Central Downtown Inn & Suites

14. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
AED 212
AED 237 total
includes taxes & fees
1 Oct - 2 Oct
FairBridge Inn Express

15. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Robert
AED 295
AED 412 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge

16. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
AED 544
AED 608 total
includes taxes & fees
13 Sep - 14 Sep
Hilton Garden Inn Lenox Pittsfield

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Steve
AED 433
AED 484 total
includes taxes & fees
8 Sep - 9 Sep
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

18. The Yankee Inn

The Yankee Inn
Lenox
United States
Karen
AED 318
AED 355 total
includes taxes & fees
28 Sep - 29 Sep
The Yankee Inn

19. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
Sheila
AED 290
AED 324 total
includes taxes & fees
1 Sep - 2 Sep
Howard Johnson by Wyndham Lenox

20. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Nancy
AED 453
AED 506 total
includes taxes & fees
13 Sep - 14 Sep
Hampton Inn & Suites Berkshires-Lenox
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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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"Best buy in the area during the high season. Spacious room and great location. Only negative is that property is a bit dated but recent renovations have been made."
Karen 3-night trip
Posted 2 hours ago
Berkshire Mountain Lodge
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

10/10 Excellent
"The Hyatt was beyond my expectations. Staff were friendly we ate dinner at the bar. Food was exceptional and the drinks were good as well. Would highly recommend and stay again if in the area."
LaNequa 1-night trip
Posted 5 hours ago
Hyatt Place Albany/Downtown
Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Great for families"
DANIEL 3-night trip
Posted 7 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Nice to have a kitchenette to cook in"
Jacqueline 1-night trip
Posted 10 hours ago
Jiminy Peak Mountain Resort
Berkshires Untold

Berkshires Untold

10/10 Excellent
"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."
Naomi 2-night trip
Posted 1 day ago
Berkshires Untold
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
Dorothy 1-night trip
Posted 2 days ago
The Red Lion Inn

More cheap stays in Stephentown

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
AED 212
AED 237 total
1 Oct - 2 Oct
includes taxes & fees
FairBridge Inn Express
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
AED 318
AED 355 total
28 Sep - 29 Sep
includes taxes & fees
The Yankee Inn
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

25 Chapel St Albany NY
AED 389
AED 445 total
6 Sep - 7 Sep
includes taxes & fees
Hampton Inn & Suites Albany-Downtown
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY
AED 403
AED 461 total
7 Sep - 8 Sep
includes taxes & fees
Country Inn & Suites by Radisson, Downtown Albany New York
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY
AED 418
AED 464 total
27 Sep - 28 Sep
includes taxes & fees
Comfort Inn & Suites East Greenbush - Albany
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
AED 433
AED 484 total
8 Sep - 9 Sep
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Stephentown

Top reasons to visit Stephentown

  • Outdoor Adventures: Stephentown is perfect for adventure seekers, offering skiing at local resorts and beautiful golf courses.
  • Natural Beauty: Explore stunning nature preserves and picturesque mountains that enhance your outdoor experience.
  • Family-Friendly Activities: The area provides a range of activities suitable for families, ensuring enjoyable experiences for all ages.
  • Diverse Accommodation Options: Choose from cozy resorts, agritourism stays, or romantic getaways tailored to your needs.
  • Cultural Exploration: Immerse yourself in local culture while enjoying a vibrant downtown atmosphere and nearby neighborhoods.

Find great hotels near Stephentown

Discover the charm of Stephentown, New York, with a variety of lodging options tailored to your vacation needs. Whether you're seeking a family-friendly resort, an adventurous agritourism experience, or a romantic getaway, you'll find the perfect hotel to suit your preferences. Explore top-rated accommodations, read insightful hotel reviews, and uncover the best hotels in the area for an unforgettable stay in the heart of the beautiful New York countryside.

  • The Yankee, Trademark Collection by Wyndham: Experience a blend of comfort and business-friendly amenities at The Yankee, Trademark Collection by Wyndham. Situated just 19.3km from Stephentown, this hotel caters to the discerning business traveler seeking a productive stay. Guests can enjoy spacious, well-equipped rooms featuring modern technology for seamless work experiences. The property also offers meeting spaces, high-speed internet access, and convenient business services, making it an ideal choice for corporate trips.
  • Holiday Inn & Suites Pittsfield-Berkshires by IHG: Embrace the spirit of adventure at the Holiday Inn & Suites Pittsfield-Berkshires by IHG, located 16.1km from Stephentown. This 3-star hotel is centered around winery and city-themed experiences, perfect for travelers looking to explore local vineyards and outdoor activities. Guests can indulge in a range of adventure sports such as skiing, horseback riding, and hiking, all easily accessible nearby. The hotel’s prime city-center location enhances the convenience for those wanting to experience local attractions and dining.
  • Berkshire Mountain Lodge: Nestled 19.3km from Stephentown, Berkshire Mountain Lodge offers a cozy retreat suited for both adventure seekers and business travelers. This 3-star lodge features a variety of recreational activities, including biking, ziplining, and kayaking, ensuring there’s something for everyone. Ideal for those balancing work and leisure, the lodge provides comfortable accommodations alongside essential business facilities. Guests appreciate the serene surroundings that invite relaxation after a day of exploration.

Where to stay near Stephentown

Stephentown, New York, offers a delightful blend of adventure and relaxation, perfect for ski enthusiasts and families alike. Experience cozy getaways in the picturesque mountains or enjoy the vibrant downtown atmosphere. From romantic escapes to budget-friendly options, there's something for everyone. Explore nearby neighborhoods for stunning scenery and family-friendly activities, making your vacation an unforgettable experience in this charming region.

  • Pittsfield: Situated about 16.1km from Stephentown, Pittsfield is a vibrant city that offers a year-round adventure for outdoor enthusiasts. With its visitor numbers peaking from June to August, the city is a hub for skiing, hiking, and exploring nearby lakes and mountains. Notable attractions include ski resorts and fields that cater to both beginners and seasoned skiers. The city is also home to various monuments that reflect its rich history, making it an ideal destination for those seeking both excitement and cultural insights.
  • Hancock: Located 9.7km from Stephentown, Hancock is a charming city that attracts visitors primarily for its thrilling outdoor sports and skiing opportunities. The best time to visit is from March to April and during July, when the area bustles with travelers eager to experience its scenic ski resorts. Surrounded by stunning mountains and serene lakes, Hancock is perfect for adventurers and sports enthusiasts alike. Don't miss the chance to explore historic college campuses nearby, adding a touch of educational charm to your visit.
  • Lenox: About 24.1km from Stephentown, Lenox is a cultural gem that draws visitors with its romantic atmosphere and vibrant entertainment scene. The peak travel season from June to August offers a plethora of music concerts and theatrical performances, creating an engaging experience for art lovers. With beautiful lakes and mountains nearby, Lenox also serves as a picturesque backdrop for relaxation and exploration. The presence of notable places of worship adds to the city's diverse cultural fabric, making it a well-rounded destination for all travelers.

Things to do in and around Stephentown

Stephentown offers an exciting blend of outdoor adventures, making it perfect for a ski or sports vacation. Visitors can enjoy skiing at local ski resorts and explore various ski fields. Additionally, the area boasts a golf club for those looking to tee off amidst beautiful scenery. With its range of activities, Stephentown is an ideal destination for adventure seekers and sports enthusiasts alike.

Shopping

In Stephentown, you can explore Zema's Nursery for unique gifts. If you're up for a drive, Guido's Marketplace, 19.3km away, offers a vibrant public market experience. The Bookstore, located 24.1km from town, is perfect for finding literary treasures.

Recreation

Experience the Tanglewood Music Center for captivating concerts that uplift your spirit. Visit Skyline Country Club for a day of golfing in a beautiful outdoor setting. Unwind at Kennedy Park, where you can enjoy serene nature walks and peaceful relaxation amidst scenic views.

Adventure

At Jiminy Peak Mountain Resort, 8.0km from Stephentown, enjoy thrilling skiing and snowboarding with stunning mountain views. Bousquet Ski Area, 17.7km away, offers excellent slopes for all skill levels. Pineridge Cross Country Ski Center, located 16.1km from town, provides picturesque trails for cross-country skiing enthusiasts.

Nightlife

Experience the vibrant nightlife by visiting the Williamstown Theatre Festival for captivating performances, or enjoy a show at the Colonial Theater and Barrington Stage Company, both offering a blend of romance and culture just 16.1km from Stephentown.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Stephentown

To save money on your trip to Stephentown, plan to visit during the cheaper months of March or December to January, avoiding the peak summer and fall seasons. Booking accommodations for Monday can also help reduce costs compared to Saturday. Use Expedia to find budget-friendly hotels by sorting results by price and considering eco-certified options. Additionally, combining your hotel, flights, and activities into a package deal can lead to significant savings. Be on the lookout for discounts and last-minute deals to maximize your travel budget.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Stephentown are March and December to January, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Stephentown is Monday. The most expensive day to stay in Stephentown is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool is designed to help you find accommodations that fit your budget and preferred location, among other criteria. You can easily sort your results by price, allowing you to view the most affordable hotels first. Additionally, you have the option to narrow your search by hotel type—if you select the Eco-certified filter, you'll be presented with sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your Stephentown hotel reservation with your flights and activities through an Expedia package deal.

Find the best attractions near Stephentown

Stephentown, New York, is an ideal destination for adventure seekers and sports enthusiasts. Visitors can enjoy skiing and explore various attractions, including nature preserves, mountains, and local libraries. The area offers a rich blend of cultural experiences and outdoor activities, making it perfect for families and travelers looking to immerse themselves in the natural beauty and recreational opportunities available in and around Stephentown.

  • Williams College: Located 22.5km from Stephentown, Williams College is a renowned liberal arts institution with beautiful historic architecture and a vibrant campus culture. Explore its art museums, scenic landscapes, and attend events showcasing student talent.
  • Mount Greylock State Reservation Visitor Center: Just 14.5km away, this visitor center offers stunning views and access to outdoor activities like hiking and picnicking. It’s perfect for families and adventure seekers looking to explore Massachusetts' highest peak.
  • Hancock Shaker Village: Also 14.5km from Stephentown, this living museum showcases the unique culture and heritage of the Shaker community. Visitors can explore restored buildings, gardens, and learn about the Shaker way of life through engaging exhibits.

Best time to go to Stephentown

The best time to visit Stephentown is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January21.6°F (-5.8°C)Light RainMostly CloudySlightly LowSlightly Low
February23.5°F (-4.7°C)Light RainMostly CloudyAverageAverage
March31.3°F (-0.4°C)Light RainMostly CloudyAverageSlightly Low
April43.0°F (6.1°C)Light RainMostly CloudyAverageAverage
May55.2°F (12.9°C)Light RainMostly SunnyAverageAverage
June63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
July69.1°F (20.6°C)Light RainMostly SunnySlightly HighSlightly High
August67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
September60.3°F (15.7°C)Light RainMostly SunnyAverageAverage
October49.1°F (9.5°C)Light RainMostly SunnySlightly HighSlightly High
November36.9°F (2.7°C)Light RainMostly SunnySlightly LowAverage
December28.4°F (-2.0°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Stephentown

When planning your visit to Stephentown, New York, you have several airport options. Albany International Airport (ALB) is located 40.2km away, with nearby hotels such as the Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from the airport. Hartford's Bradley International Airport (BDL) is 90.1km away, offering the DoubleTree by Hilton Hartford - Bradley Airport just 1.6km from the terminal. Lastly, Pittsfield Municipal Airport (PSF) is the closest at 16.1km, with the Hampton Terrace Inn and The Stockbridge Country Inn nearby, providing convenient accommodation options for your trip.

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 traveler data. Two other choices for your trip to the area are Hilton Albany and Country Inn & Suites by Radisson, Downtown Albany New York. See all available top hotels, or vacation rentals in Stephentown.
What are some of the best vacation rentals in Stephentown?
Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room: This highly rated vacation home rental in Stephentown is located in a rural location and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 13 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a pool table and a hot tub. See all vacation rentals in Stephentown.
If I need to cancel my hotel reservation in Stephentown, will I receive a refund?
Yes! You'll find that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Stephentown.
Where can I learn more about changing or cancelling my trip to Stephentown?
For more details about changing or cancelling your trip to Stephentown, go to https://www.expedia.com/service/.
What's the best pet-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. Spacious 6-bedroom farmhouse in peaceful with additional barn/Stephentown withAC is another good option for a stay with your pet. See more pet-friendly hotel accommodations in Stephentown.
What are some accommodations 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. Hilton Albany and The Yankee Inn are a couple of other choices with an onsite pool. View all hotels with pools in Stephentown.
What is the best hotel near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What's it like staying 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 accommodations to choose from. Find out more about Stephentown.
What should I see while I'm in Stephentown?
A couple of favorite 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. Check out what more to see and do in Expedia's Stephentown guide.
What's the weather like in Stephentown?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Stephentown are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.