Stephentown Hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Stephentown hotels

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

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is P12,098
P34,171 total
includes taxes & fees
May 25 - May 26
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is P6,728
P7,515 total
includes taxes & fees
May 26 - May 27
The Yankee Inn

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,003 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is P6,782
P7,576 total
includes taxes & fees
May 21 - May 22
Best Western Plus Berkshire Hills Inn & Suites

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (455 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is P7,098
P7,787 total
includes taxes & fees
May 19 - May 20
Shaker Mill Inn

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (905 reviews)
"Facilities were excellent. Staff was very helpful and very efficient & courteous in taking care of any concerns I had."
United States
Barbara J
The price is P4,888
P5,761 total
includes taxes & fees
May 31 - Jun 1
Cozy Corner Motel

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (97 reviews)
"We enjoyed our stay. Staff was nice and the motel is set between several different towns to explore. We plan to stay again soon!"
United States
Shakeila
The price is P6,492
P7,122 total
includes taxes & fees
May 19 - May 20
The Springs Motel

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (94 reviews)
"Comfy, cozy, quiet stay in this lovely property full of character! Thank you, hard-working staff."
United States
Leslieann H
The price is P6,944
P7,708 total
includes taxes & fees
May 19 - May 20
Gregory House Country Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (950 reviews)
"Great stay!"
United States
Aditya
The price is P7,707
P8,609 total
includes taxes & fees
May 25 - May 26
Berkshires Untold

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (938 reviews)
"Clean and great job staffing "
United States
Pedro
The price is P5,414
P7,427 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is P7,839
P8,756 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Villager Motel

The Villager Motel
2.0 star property
Williamstown
8.8 out of 10, Excellent, (785 reviews)
"The room was comfortable and clean, I will stay there again"
United States
Monica
The price is P4,876
P5,446 total
includes taxes & fees
May 19 - May 20
The Villager Motel

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
"Great value"
United States
Ralph
The price is P4,876
P5,447 total
includes taxes & fees
May 19 - May 20
Howard Johnson by Wyndham Lenox

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very Good, (2 reviews)
"After a little snafu with check-in (we had completed the form in advance and never received the room number text), we were able to get checked in with the virtual front desk. The inn was clean and well appointed and centrally located. The common areas felt inviting and useful for both the adults and kids. We would stay again."
United States
Samantha
The price is P7,080
P7,908 total
includes taxes & fees
May 19 - May 20
Hideaway Inn Lenox

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (606 reviews)
"Very clean and comfortable room and grounds, pleasant and helpful hosts, relaxing setting. Highly recommended."
United States
David J.
The price is P6,728
P7,515 total
includes taxes & fees
May 20 - May 21
Maple Terrace Motel

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is P10,647
P11,893 total
includes taxes & fees
May 19 - May 20
The Revival House

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
"Avoid this place."
United States
Carole
The price is P5,864
P6,550 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (855 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is P4,937
P5,515 total
includes taxes & fees
May 25 - May 26
Berkshire Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"Great location "
United States
Edith
The price is P6,891
P7,698 total
includes taxes & fees
Jun 15 - Jun 16
Quality Inn Lee - Lenox South

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is P10,308
P11,514 total
includes taxes & fees
May 25 - May 26
Element by Marriott Lenox Berkshires

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (1,002 reviews)
"A nice stay at an affordable price. "
United States
Brian
The price is P4,984
P5,567 total
includes taxes & fees
May 21 - May 22
Willows Motel Williamstown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Stephentown attractions

Top Stephentown Hotel Reviews

More cheap stays in Stephentown

Find out more about Stephentown

Top reasons to visit Stephentown

  • Adventurous Skiing: Stephentown is a haven for ski enthusiasts, offering thrilling ski slopes and picturesque fields for an unforgettable winter experience.
  • Scenic Golfing: Enjoy a delightful day at the local golf club, set against the backdrop of beautiful landscapes, perfect for golf lovers.
  • Charming Accommodations: Choose from a variety of lodging options, from cosy resorts to unique agritourism stays, catering to all preferences.
  • Family-Friendly Attractions: Explore serene reserves and majestic mountains, ideal for families seeking outdoor adventures.
  • Romantic Getaways: With its scenic beauty, Stephentown provides a perfect setting for a romantic escape.

Find great hotels near Stephentown

Stephentown, New York, offers a delightful array of accommodation options, from charming resorts to unique agritourism properties. Whether you're seeking a family-friendly retreat, a romantic getaway, or an adventurous escape, you'll find hotels that cater to your every need. With various reviews and recommendations available, you can easily discover the best hotels in the area, ensuring a memorable stay in this picturesque destination.

  • The Yankee, Trademark Collection by Wyndham: Offering a sophisticated atmosphere tailored for business travellers, The Yankee is an ideal choice for those seeking a productive stay. Located 19.3km away from Stephentown, this hotel features modern amenities, including high-speed internet and well-equipped meeting spaces. Guests can unwind in comfortable rooms designed for relaxation after a long day of work. The hotel’s business-centric facilities ensure seamless connectivity and convenience for corporate guests.
  • Best Western Plus Berkshire Hills Inn & Suites: Situated 14.5km from Stephentown, this family-friendly hotel welcomes guests of all types, including pets. Best Western Plus Berkshire Hills Inn & Suites is perfect for those looking for a blend of comfort and convenience during their stay. The property features amenities for children, such as games and cribs, making it suitable for family vacations. The pet-friendly policy and dedicated dog exercise area cater to four-legged companions, ensuring a warm, inclusive environment for all guests.
  • Hampton Inn & Suites Berkshires-Lenox: A welcoming haven for LGBTQIA travellers, the Hampton Inn & Suites Berkshires-Lenox is 19.3km away from Stephentown and offers a unique blend of comfort and inclusivity. This hotel features pet-friendly policies, ensuring that your furry friends are welcome, along with amenities like food and water bowls. With modern accommodations and a strong commitment to guest satisfaction, it’s an excellent choice for those looking to balance business and leisure in a supportive environment.

Where to stay near Stephentown

Stephentown, New York, offers a delightful mix of ski adventures and romantic getaways, making it a perfect destination for family-friendly vacations. Nestled in the scenic mountains, this charming locale provides a cosy retreat with easy access to downtown attractions. Explore the surrounding areas for budget-friendly options and enjoy the picturesque scenery, ensuring a memorable holiday experience filled with warmth and adventure.

  • Pittsfield: Nestled approximately 16.1km from Stephentown, Pittsfield is a vibrant city that attracts visitors year-round, particularly from June to August. This destination is renowned for its adventure and outdoor experiences, making it a fantastic spot for skiing enthusiasts. With ski resorts and fields close at hand, you can immerse yourself in exhilarating winter sports. In addition, the city is surrounded by stunning natural landmarks such as lakes and mountains, offering picturesque views and recreational opportunities. Whether you're hitting the slopes or enjoying the scenic landscape, Pittsfield promises a memorable travel experience.
  • Hancock: Located 9.7km from Stephentown, Hancock is a charming city that beckons adventure seekers and sports enthusiasts alike. Peak visitor arrivals occur in March to April and July, making it an ideal time to explore the area's ski resorts and fields. The stunning mountains and serene lakes add to Hancock's allure, providing a perfect backdrop for outdoor activities. History buffs will also appreciate the presence of a historic college university nearby, enhancing the cultural experience. Hancock is where adventure and history come together, making it a delightful stop on your vacation.
  • Lenox: Situated 24.1km from Stephentown, Lenox is a cultural gem that thrives from June to August, drawing visitors who seek entertainment and romantic experiences. Known for its vibrant music concerts and theatrical performances, Lenox offers a rich cultural tapestry that captivates the senses. Visitors can also enjoy the natural beauty of nearby lakes and mountains, perfect for a leisurely day spent in nature. Additionally, the town's places of worship add a serene touch to the overall experience. Lenox is a destination where culture and nature intertwine, making it a must-visit during your holiday.

Things to do in and around Stephentown

Stephentown is an ideal destination for ski enthusiasts and adventure seekers alike. Visitors can enjoy a variety of activities, including skiing at the local ski resort and exploring the picturesque ski fields. Additionally, golf enthusiasts will find a golf club nearby, offering a perfect blend of sports and leisure amidst the beautiful surroundings. Whether you're hitting the slopes or teeing off, Stephentown promises an exciting holiday experience.

Shopping

For a delightful shopping experience in Stephentown, visit Zema's Nursery for unique plants and gifts. If you're up for a drive, Guido's Marketplace offers a vibrant public market atmosphere 19.3km away, while Colonial Plaza, 24.1km away, features a variety of family-friendly shops.

Recreation

Tanglewood Music Center offers a vibrant atmosphere with captivating concerts, perfect for music enthusiasts. Shatford Memorial Park provides a tranquil setting for relaxation and leisure activities, ideal for unwinding. Skyline Country Club invites you to enjoy a day of golfing amidst stunning outdoor scenery, catering to sports lovers.

Adventure

Experience the thrill of skiing at Jiminy Peak Mountain Resort, located 8.0km from Stephentown, offering fantastic slopes and vibrant ski culture. For a unique adventure, visit the Berkshire Retreat Center, 16.1km away, where excitement awaits. Finally, explore the Williamstown Trailhead, 25.7km from Stephentown, for breathtaking outdoor adventures.

Nightlife

In Stephentown, the Mountain Coaster and Alpine Super Slide provide exhilarating amusement rides just 8.0km away, perfect for thrill-seekers. For a touch of culture, the Williamstown Theatre Festival, 16.1km away, offers romantic and entertaining performances, creating a vibrant atmosphere for a memorable night out.

*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 on your trip to Stephentown, consider visiting during the cheaper months of March or December to January, and aim for a stay on a Monday when prices are lowest. Utilise Expedia to find eco-friendly accommodations and sort by price for the best deals. Combining your hotel with flights and activities in an Expedia package can yield additional savings. Don't forget to look for last-minute offers and group discounts to maximise your budget while enjoying the area’s free activities.

  • 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: Utilise Expedia’s search wizard to tailor your preferences, including your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Stephentown hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Stephentown

Stephentown offers a delightful blend of skiing, adventure, and sports, making it an ideal destination for those seeking outdoor fun and cultural experiences. Notable attractions include serene reserves, majestic mountains, and a charming library, catering to families and outdoor enthusiasts alike. Whether you’re looking for a thrilling adventure or a peaceful retreat, Stephentown promises memorable moments for every visitor.

  • Taconic Lake: Located 20.9km from Stephentown, Taconic Lake offers a picturesque setting perfect for romantic getaways. Enjoy its sandy beach, scenic views, and a range of outdoor activities, making it an ideal spot for relaxation and adventure alike.
  • Williams College: Situated 22.5km away, this historic institution is renowned for its rich cultural heritage. Stroll through its beautiful campus, admire the stunning architecture, and immerse yourself in the vibrant arts scene that the college fosters.
  • Cherry Plain State Park: Just 6.4km from Stephentown, this national park boasts breathtaking scenery and diverse outdoor activities. Explore its hiking trails, picnic areas, and enjoy an adventurous day surrounded by nature’s beauty.

Best time to go to Stephentown

The best time to visit Stephentown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Stephentown falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Stephentown falls in January, 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 can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is positioned 90.1km away, with nearby hotels including the 4-star Simsbury 1820 House, located 11.3km from the airport, and the Marriott Hartford Downtown, 19.3km away. Albany, NY (ALB-Albany Intl.) is 40.2km distant, with excellent accommodation options like The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both 12.9km from the airport. Finally, Pittsfield, MA (PSF-Pittsfield Municipal) is just 16.1km away, offering hotels such as The Central Downtown Inn & Suites, 3.2km from the airport.

Frequently asked questions

Where is the best place to stay in Stephentown?
Located 11.8 mi (19.1 km) from the heart of Stephentown, Berkshire Mountain Lodge is a top choice for your stay based on our traveler data. Two other choices for your trip to the area are Comfort Inn Glenmont - Albany South and Berkshires Untold. 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! 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.
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. See more pet-friendly hotel accommodations in Stephentown.
What are some accommodations with pools in Stephentown?
Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. Comfort Inn Glenmont - Albany South and Vacation Village in the Berkshires are a couple of other choices with an onsite pool. View all hotels with pools in Stephentown.
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 17 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 Cherry Plain State Park and Jiminy Peak Mountain Resort 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.

Explore a world of travel with Expedia