Olivias Overlook - West Stockbridge, Massachusetts

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Our top choices for West Stockbridge hotels

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (461 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 547
AED 600 total
includes taxes & fees
23 Jun - 24 Jun
Shaker Mill Inn

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is AED 264
AED 290 total
includes taxes & fees
25 Jun - 26 Jun
Pleasant Valley Motel West Stockbridge

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is AED 467
AED 522 total
includes taxes & fees
23 Jun - 24 Jun
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, (1,000 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is AED 408
AED 456 total
includes taxes & fees
24 Jun - 25 Jun
Best Western Plus Berkshire Hills Inn & Suites

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (108 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is AED 525
AED 587 total
includes taxes & fees
29 Jun - 30 Jun
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (55 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is AED 564
AED 631 total
includes taxes & fees
22 Jun - 23 Jun
Wilder House Berkshires

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,010 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is AED 380
AED 425 total
includes taxes & fees
24 Jun - 25 Jun
Quality Inn Great Barrington

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (569 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is AED 323
AED 361 total
includes taxes & fees
22 Jun - 23 Jun
The Little Lion

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (873 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is AED 283
AED 316 total
includes taxes & fees
22 Jun - 23 Jun
Monument Mountain Motel

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (829 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is AED 208
AED 232 total
includes taxes & fees
5 Jul - 6 Jul
FairBridge Inn Express

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (472 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is AED 248
AED 278 total
includes taxes & fees
29 Jun - 30 Jun
Berkshire Travel Lodge

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
"Clean room and breakfast"
United States
Raphael
The price is AED 501
AED 724 total
includes taxes & fees
1 Jul - 2 Jul
The Red Lion Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (990 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is AED 606
AED 676 total
includes taxes & fees
6 Jul - 7 Jul
Berkshires Untold

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (424 reviews)
"Below average B&B"
United States
Larry
The price is AED 386
AED 444 total
includes taxes & fees
22 Jun - 23 Jun
Locust Tree Bed and Breakfast LLC

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (85 reviews)
"Excellent lodge, recommend."
United States
Jason
The price is AED 559
AED 626 total
includes taxes & fees
24 Jun - 25 Jun
Little Cat Lodge

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (228 reviews)
"It’s a wonderful place to rest for a while. it has all you need, everything it’s in good conditions also it’s near of many activities like hiking."
United States
Daniel
The price is AED 514
AED 576 total
includes taxes & fees
24 Jun - 25 Jun
the Alander

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,002 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is AED 511
AED 570 total
includes taxes & fees
23 Jun - 24 Jun
Quality Inn Lee - Lenox South

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (775 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is AED 547
AED 611 total
includes taxes & fees
24 Jun - 25 Jun
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (994 reviews)
"The staff was very helpful. It was very clean and the bed was comfortable. We would stay there again."
United States
Andrew
The price is AED 515
AED 658 total
includes taxes & fees
21 Jul - 22 Jul
Berkshire Mountain Lodge

Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (154 reviews)
"Great location, spacious rooms, comfortable and well decorated"
United States
Jack
The price is AED 433
AED 490 total
includes taxes & fees
30 Jun - 1 Jul
Howard Hotel
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Stay near popular West Stockbridge attractions

Learn more about West Stockbridge

The historic Turn Park Art Space showcases outdoor sculptures along winding paths overlooking the Housatonic River. Grab breakfast at Six Depot Roastery before browsing the charming shops and galleries along Main Street.

Olivias Overlook - West Stockbridge, Massachusetts

Top West Stockbridge Hotel Reviews

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Hotels in West Stockbridge with star-rating

Find out more about West Stockbridge

Top reasons to visit West Stockbridge

  • Charming Getaways: West Stockbridge offers a romantic escape with cozy accommodations, perfect for couples and families alike.
  • Cultural Attractions: Enjoy local theater performances, live music, and a rich historical heritage in the surrounding Berkshires.
  • Outdoor Activities: Explore nature preserves and national parks, ideal for hiking and enjoying the scenic beauty.
  • Community Vibe: Experience the warm hospitality and vibrant local scene, making it a delightful destination.
  • Convenient Location: A central gateway to nearby attractions, perfect for day trips and adventures.

Find great hotels near West Stockbridge

Explore the charming accommodations of West Stockbridge, where a variety of options await you, from cozy bed and breakfasts to inviting hotels. Perfect for families, adventure seekers, and pet owners alike, you'll find the ideal place to unwind after a day of exploration. Discover popular spots like the Stockbridge Inn and the Inn at Stockbridge, and read reviews to choose the best hotel for your unforgettable vacation experience.

  • The Yankee, Trademark Collection by Wyndham: Located 11.3km from West Stockbridge, The Yankee offers a business-friendly atmosphere perfect for corporate travelers. Guests appreciate the well-appointed rooms equipped with modern amenities, including high-speed Wi-Fi and spacious work desks. The hotel features a business center, making it easy for guests to conduct meetings or prepare for presentations. With its convenient location, visitors can enjoy both local attractions and a productive stay.
  • Berkshire Mountain Lodge: Situated 12.9km from West Stockbridge, the Berkshire Mountain Lodge is a 3-star retreat designed for adventure seekers and business travelers alike. Guests can indulge in a variety of adventure sports, including hiking, biking, and ziplining nearby. The lodge also provides comfortable accommodations with a rustic charm, ideal for unwinding after a day of exploration. With recreational activities available onsite, it’s perfect for those looking to embrace the great outdoors while enjoying modern comforts.
  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Located 9.7km from West Stockbridge, this 3.5-star resort is the ideal family-friendly destination. Welcoming to LGBTQIA travelers, the resort boasts amenities tailored for children, including an onsite mini-golf course, arcade game room, and a playground. Spacious accommodations ensure a relaxing stay for families, while business travelers can also find suitable facilities, including meeting rooms. With its commitment to inclusivity and family fun, this resort is a top choice for a memorable vacation.

Where to stay near West Stockbridge

West Stockbridge, Massachusetts, offers a charming blend of romantic escapes and cultural adventures. Nestled in picturesque New England, this central location serves as a gateway to family-friendly attractions and serene landscapes. Travelers can enjoy the warm hospitality of the region while exploring nearby towns, indulging in local entertainment, and soaking in the scenic beauty. Whether you're on a budget or seeking a romantic getaway, West Stockbridge promises an unforgettable experience.

  • Lenox: Nestled about 8.0km from West Stockbridge, Lenox is a charming city known for its vibrant cultural scene and romantic ambiance. Visitors flock to Lenox for its entertainment offerings, which include music concerts, theater performances, and outdoor skiing experiences. The summer months, particularly June to August, see a peak in traveler arrivals, making it a lively time to explore. Notable attractions include serene lakes and picturesque mountains, ideal for both relaxation and adventure. Whether you're enjoying a concert at Tanglewood or exploring local art galleries, Lenox promises a delightful getaway.
  • Stockbridge: Located just 6.4km from West Stockbridge, Stockbridge is a historic town that captivates travelers with its romantic and cultural pursuits. The peak tourist season runs from July to September, offering an array of activities such as music concerts and theater events. With a rich history reflected in its charming streets and landmarks, including local monuments and serene lakes, Stockbridge is perfect for those seeking a blend of relaxation and entertainment. Enjoy a leisurely stroll through the Norman Rockwell Museum or take in the scenic beauty that inspired many artists.
  • Richmond: Situated a mere 4.8km from West Stockbridge, Richmond is an outdoor enthusiast's paradise. Known for its adventure and skiing experiences, the city attracts visitors looking to embrace the great outdoors, especially during the peak months of July to September. Enjoy exhilarating skiing at local ski fields or take in the breathtaking views of the surrounding mountains and lakes. Richmond's vibrant community events, including music concerts, offer a lively atmosphere for travelers seeking both excitement and relaxation in nature's embrace.

Things to do in and around West Stockbridge

West Stockbridge offers a charming escape perfect for romantic getaways and culture enthusiasts. Enjoy a variety of activities including local theater performances, live music concerts, and nearby ski fields. Ideal for a day trip, this quaint town invites you to explore its unique attractions and immerse yourself in the vibrant local scene, making it a delightful destination for entertainment and relaxation.

Shopping

In West Stockbridge, you can shop at Hoffman's Pottery for unique ceramics, Charles H. Baldwin & Sons for a variety of goods, and Ebenezer II Gifts and Antiques for charming antiques and gifts. If you're up for a drive, check out local boutiques in nearby towns for more options.

Recreation

Experience the vibrant atmosphere at Tanglewood Music Center, where you can enjoy live concerts amidst nature. For outdoor enthusiasts, Wyndhurst Golf & Club offers a challenging course surrounded by scenic landscapes. Unwind at Kennedy Park, a tranquil spot perfect for relaxation and wellness activities.

Adventure

Bousquet Ski Area offers thrilling winter sports and skiing vibes, located 11.3km from West Stockbridge. Experience the scenic beauty while gliding down the slopes. For a scenic hike, the Housatonic River Walk, 14.5km away, promises outdoor adventure amidst breathtaking views. Enjoy ziplining at Catamount Aerial Adventure Park, 19.3km distant.

Nightlife

In West Stockbridge, enjoy a vibrant nightlife filled with culture and romance at nearby theaters. Shakespeare and Company, just 6.4km away, offers captivating performances, while the Berkshire Theatre Festival, 8.0km out, adds to the entertainment. Don't miss the Mahaiwe Performing Arts Center, located 16.1km away, for a memorable experience.

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

Booking tips and Expedia advantages for West Stockbridge

To save money on your trip to West Stockbridge, plan your visit during the cheaper months of January, April, or November, and avoid weekends, particularly Saturdays. Enjoy free activities like the National Shrine of the Divine Mercy and Lake Buel. Use walking or a rental car for affordable transportation. Leverage Expedia to compare hotel rates, find deals, and consider booking packages that combine flights and accommodations. Look for eco-certified hotels to save while being environmentally friendly, and always filter for the best prices to maximize your savings.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in West Stockbridge are January, April and November, 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 West Stockbridge is Wednesday. The most expensive day to stay in West Stockbridge is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your choices based on your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in West Stockbridge with your flights and activities through an Expedia package deal.

Find the best attractions near West Stockbridge

West Stockbridge is perfect for romantic getaways and cultural explorations, offering a blend of historic homes, national parks, and nature preserves. Visitors can enjoy outdoor activities while immersing themselves in family-friendly experiences. Don't miss the chance to explore nearby Berkshires destinations and take a tour of Stockbridge for a deeper understanding of the region's rich heritage.

  • National Shrine of the Divine Mercy: Located 6.4km from West Stockbridge, this serene shrine offers a peaceful environment for reflection and prayer. With beautiful gardens and stunning architecture, visitors can immerse themselves in a spiritual experience surrounded by nature.
  • Norman Rockwell Museum: Also situated 6.4km away, this museum showcases the beloved works of iconic American illustrator Norman Rockwell. Explore a vast collection of art that captures everyday life and the essence of American culture, making it a must-visit for art enthusiasts.
  • The Mount: This historic house, located 6.4km from West Stockbridge, was the home of renowned author Edith Wharton. Visitors can stroll through the beautiful gardens and enjoy guided tours that delve into Wharton's literary legacy and the architectural beauty of the estate.

Best time to go to West Stockbridge

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1°C)Light RainMostly CloudyModerately LowSlightly Low
February24.6°F (-4.1°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageAverage
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnyModerately HighAverage
July70.3°F (21.3°C)Light RainMostly SunnyModerately HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnyAverageSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyModerately HighAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnyModerately LowSlightly Low
December29.5°F (-1.4°C)Light RainMostly CloudyModerately LowAverage

The nearest major airports for your trip to West Stockbridge

To visit West Stockbridge, Massachusetts, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is 72.4km away, with nearby hotels like DoubleTree by Hilton Hartford - Bradley Airport, 1.6km from the airport, and Simsbury 1820 House, 11.3km away. Albany, NY (ALB-Albany Intl.) is 57.9km distant, offering options such as Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from the airport. The closest airport is Pittsfield, MA (PSF-Pittsfield Municipal), just 11.3km away, with accommodations like The Central Downtown Inn & Suites, 3.2km from the airport, and Hampton Terrace Inn, 8.0km away.

Frequently asked questions

What's the best place to stay in West Stockbridge?
Shaker Mill Inn is one of the top choices for your stay based on our traveler data. This B&B offers free parking and a library. Pleasant Valley Motel West Stockbridge is another good choice for your visit. See all available top hotels, or vacation rentals in West Stockbridge.
What's the top vacation rental that West Stockbridge has to offer?
Cozy Riverside Berkshires Retreat: Visitors like this West Stockbridge vacation home rental. It is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and an electric kettle, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. See all vacation rentals in West Stockbridge.
If I need to cancel my hotel reservation in West Stockbridge, will I receive a refund?
Yes, you'll find most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in West Stockbridge.
Where can I learn more about changing or cancelling my trip to West Stockbridge?
For more information about rescheduling or cancelling your trip to West Stockbridge, go to https://www.expedia.com/service/.
What is the top LGBTQ-friendly accommodation in West Stockbridge?
Shaker Mill Inn is a top LGBTQ-friendly B&B that features free breakfast and free parking.
Where is the best place to stay close to Chesterwood?
Stockbridge Country Inn is one of the top choices for your stay based on our traveler data, and this 4.5-star B&B offers free breakfast and free parking. It's located just a short 0.4 mi (0.7 km) from Chesterwood. Other good choices within 5 miles include The Red Lion Inn and Tanglewood Suites.
What about the best place to stay close to Berkshire Botanical Garden?
One of the top choices for your stay is The Red Lion Inn, located 1.8 mi (2.9 km) from Berkshire Botanical Garden, and this 3.5-star hotel offers 3 restaurants and an outdoor pool. Tanglewood Suites and Stockbridge Country Inn are two other good choices within 5 miles.
What are some hotels with pools in West Stockbridge?
Berkshire Mountain Lodge: Provides free self parking, 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 onsite pool. View all hotels with pools in West Stockbridge.
What is the best accommodation for staying close to 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 is staying in West Stockbridge like?
Budget-minded travelers will find good deals in West Stockbridge, and many visitors are sure to appreciate the gardens and restaurants. Tourists can also enjoy so much more including its lake views. In West Stockbridge, there are 35 hotels and other accommodations to choose from. Find out more about West Stockbridge.
What is there to see in West Stockbridge?
Attractions like Charles H. Baldwin & Sons, Hotchkiss Mobile Studio, and Ebenezer II Gifts and Antiques are fun for kids of all ages. A couple of additional sights to add to your agenda are Stockbridge Bowl and Hoffman's Pottery. Check out what more to see and do in Expedia's West Stockbridge guide.
What's the weather like in West Stockbridge?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.