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Our top choices for West Stockbridge hotels

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is CA $217
CA $304 total
includes taxes & fees
Mar 9 - Mar 10
The Red Lion Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (864 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
The price is CA $137
CA $153 total
includes taxes & fees
Mar 2 - Mar 3
Berkshires Untold

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (864 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is CA $156
CA $205 total
includes taxes & fees
Mar 17 - Mar 18
Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (844 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is CA $147
CA $191 total
includes taxes & fees
Mar 10 - Mar 11
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,000 reviews)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is CA $134
CA $149 total
includes taxes & fees
Mar 19 - Mar 20
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is CA $183
CA $210 total
includes taxes & fees
Mar 26 - Mar 27
The Cornell Inn, Lenox & The Berkshires

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is CA $327
CA $383 total
includes taxes & fees
Mar 13 - Mar 14
The Inn at Stockbridge

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $423
CA $512 total
includes taxes & fees
Mar 13 - Mar 14
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
The price is CA $299
CA $334 total
includes taxes & fees
Feb 28 - Mar 1
Hampton Terrace Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (767 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is CA $208
CA $232 total
includes taxes & fees
Mar 30 - Mar 31
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (290 reviews)
"Super cute place and walking distance to a bunch of great shops and food! "
United States
Gina
The price is CA $133
CA $149 total
includes taxes & fees
Mar 4 - Mar 5
The Whitlock

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
Whistler's Inn Bed & Breakfast

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is CA $127
CA $142 total
includes taxes & fees
Mar 8 - Mar 9
The Yankee, Trademark Collection by Wyndham

The Ponds at Foxhollow

The Ponds at Foxhollow
3.0 star property
Lenox
8.6 out of 10, Excellent, (141 reviews)
"Great place"
United States
Lisa
The Ponds at Foxhollow

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1,000 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is CA $141
CA $157 total
includes taxes & fees
Mar 16 - Mar 17
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (554 reviews)
"Great friendly staff"
United States
Pablo
The price is CA $150
CA $168 total
includes taxes & fees
Mar 16 - Mar 17
The Little Lion

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is CA $131
CA $144 total
includes taxes & fees
Mar 2 - Mar 3
Shaker Mill Inn

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very good, (197 reviews)
"Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!"
United States
Miguel
The price is CA $244
CA $285 total
includes taxes & fees
Mar 3 - Mar 4
Gateways Inn & Restaurant

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (293 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is CA $191
CA $225 total
includes taxes & fees
Feb 28 - Mar 1
Lakehouse Inn
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.

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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

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Find out more about West Stockbridge

Top reasons to visit West Stockbridge

  • Vibrant Arts and Culture: Enjoy local theatre performances and music concerts that showcase the region’s artistic flair.
  • Scenic Outdoor Adventures: Explore national parks and nature preserves, perfect for hiking and connecting with nature.
  • Charming Downtown Area: Discover quaint shops and eateries in a picturesque setting that invites leisurely strolls.
  • Family-Friendly Activities: Engage in various activities suitable for all ages, ensuring fun for the entire family.
  • Cozy Accommodations: Choose from delightful bed and breakfasts and pet-friendly hotels for a comfortable stay.

Find great hotels near West Stockbridge

West Stockbridge offers a charming selection of accommodations, including cozy bed and breakfasts and inviting hotels, perfect for families and adventurers alike. With pet-friendly options and a focus on creating memorable experiences, you'll find the ideal spot to unwind after exploring the stunning Berkshires. Whether you're searching for the best hotels or a quaint retreat, West Stockbridge has something to cater to every traveller's needs.

  • The Yankee, Trademark Collection by Wyndham: The Yankee, Trademark Collection by Wyndham offers a professional atmosphere tailored for business travellers. Located 11.3km from West Stockbridge, this hotel provides a variety of business amenities, including a 24-hour business centre, multiple meeting rooms, and expansive conference spaces. With its focus on business needs, guests can expect efficient services and a conducive environment for work-related activities, making it an ideal choice for those looking to blend productivity with comfort.
  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: Just 9.7km from West Stockbridge, the Holiday Inn Club Vacations Oak n' Spruce Resort is a welcoming retreat for families and LGBTQIA travellers alike. With a 3.5-star rating, this resort features a variety of amenities that cater to guests of all ages, including a free crib service, an onsite mini-golf course, and an arcade game room. Business travellers will appreciate the inclusive business centre, while families can enjoy shared playground facilities. Its warm, inclusive atmosphere makes it a perfect getaway for diverse groups.
  • Best Western Plus Berkshire Hills Inn & Suites: Situated 11.3km from West Stockbridge, the Best Western Plus Berkshire Hills Inn & Suites is a pet-friendly haven for families and business travellers. This hotel offers essential business amenities such as a 24-hour business centre and meeting spaces, alongside family-friendly features like a games area and cribs (for a fee). With its accommodating pet policy, including a designated dog exercise area, guests can enjoy a stress-free stay with their furry companions, making it a versatile choice for all types of travellers.

Where to stay near West Stockbridge

West Stockbridge, Massachusetts, offers a delightful blend of culture and relaxation, perfect for both romantic getaways and family-friendly adventures. Explore the charming downtown area, where convenient spots abound, or venture into the picturesque Stockbridge region. Enjoy scenic views and a budget-friendly atmosphere, making your holiday truly memorable. Whether you're seeking entertainment or a peaceful retreat, West Stockbridge has something for every traveller.

  • Lenox: Located a mere 8.0km from West Stockbridge, Lenox is a vibrant city known for its seasonal appeal. The peak tourist months from June to August attract visitors seeking a blend of entertainment, romance, and family-friendly activities. Here, you'll find an array of experiences, from captivating music concerts and engaging theatre productions to thrilling ski adventures in winter. Nature lovers can also enjoy the nearby lake and mountain, making Lenox a perfect blend of culture and outdoor fun.
  • Stockbridge: Just 6.4km away from West Stockbridge, Stockbridge offers a rich cultural experience year-round, with visitor numbers peaking from July to September. This charming city is known for its romantic atmosphere and entertainment options, including music concerts and theatre performances. The local attractions, such as beautiful lakes and historical monuments, provide a picturesque backdrop for exploring the area. Don't miss the chance to visit the iconic shrine, adding a unique cultural touch to your itinerary.
  • Lee: Situated 9.7km from West Stockbridge, Lee is a delightful city that welcomes visitors with a blend of romance and family-friendly entertainment. The travel experience here is consistent throughout the year, with peaks during the summer months. Lee features a variety of activities, including theatre performances and music concerts, along with exciting ski fields in the winter. The stunning local landmarks, such as lakes, mountains, and monuments, promise an enriching experience that combines relaxation and exploration.

Things to do in and around West Stockbridge

West Stockbridge offers a delightful blend of entertainment, romance, and culture for your vacation. Enjoy local theatre performances, music concerts, and nearby ski fields. Don’t miss the local movie theatre for a cinematic experience, and consider visiting the golf club for a round of golf. This charming town promises a memorable getaway with its unique activities and attractions.

Shopping

In West Stockbridge, explore the charming Charles H. Baldwin & Sons, Ebenezer II Gifts and Antiques, and Hoffman's Pottery for unique gifts and souvenirs. If you're up for a drive, check out larger shopping centres nearby for even more options.

Recreation

Experience the vibrant atmosphere at Tanglewood Music Center, where captivating concerts elevate your spirit. Enjoy a round of golf amidst the serene landscapes at Wyndhurst Golf & Club, or unwind in the tranquil surroundings of Kennedy Park, perfect for relaxation and rejuvenation.

Adventure

Bousquet Ski Area, located 11.3km from West Stockbridge, offers exhilarating skiing experiences with a vibrant sports atmosphere. For hiking enthusiasts, the Housatonic River Walk, 14.5km away, showcases stunning scenery and outdoor adventure. Experience the thrill of ziplining at Catamount Aerial Adventure Park, situated 19.3km from town.

Nightlife

In West Stockbridge, Shakespeare and Company and the Berkshire Theatre Festival, both just 8.0km away, offer a charming blend of culture and romance. For a wider experience, the Mahaiwe Performing Arts Center, located 16.1km away, showcases captivating performances, perfect for family nights out.

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

Booking tips and Expedia advantages for West Stockbridge

West Stockbridge is an affordable vacation destination with free attractions like the National Shrine of the Divine Mercy and Lake Buel. To save on transportation, consider walking or using a car. January, April, and November are the cheapest months to visit, while Wednesdays offer the best hotel rates. Use Expedia to find budget-friendly accommodations, and consider package deals that combine hotels with flights and activities for additional savings. By planning your trip during off-peak times, you can enjoy West Stockbridge without breaking the bank.

  • 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: Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can easily arrange your results by price, starting with the most affordable hotels. Additionally, you have the option to refine your search by hotel type—by selecting the Eco-certified filter, for instance, you’ll discover sustainable and environmentally-friendly accommodations available for booking.
  • Consider bundling your trip: You can save money by combining your West Stockbridge hotel reservation with your flights and activities through an Expedia package.

Best time to go to West Stockbridge

The best time to visit West Stockbridge is dependant 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

If you're planning to visit West Stockbridge, Massachusetts, three major airports provide convenient access. Hartford, CT (BDL-Bradley Intl.) is approximately 72.4km away, with nearby hotel options such as the 4-star DoubleTree by Hilton Hartford - Bradley Airport, situated 1.6km from the airport. Albany, NY (ALB-Albany Intl.) is around 57.9km away, featuring 4-star accommodations like the Park Manor Hotel, 12.9km from the airport. The closest option is Pittsfield, MA (PSF-Pittsfield Municipal), located only 11.3km away; consider staying at the 4-star Lakehouse Inn, which is 11.3km from the airport. Each hotel offers accessible transportation services to their respective airports.

Frequently asked questions

What is the best area to stay in West Stockbridge?
The best area to stay in West Stockbridge is the village centre.

This area is the heart of West Stockbridge, known for its charming main street, Old Colony Road, lined with independent shops, art galleries, and acclaimed restaurants. It's very walkable, with many historic buildings and a picturesque river running through it, providing a quintessential New England village experience.

Couples looking for a relaxing getaway will find the village centre ideal. You can easily stroll between art studios, enjoy leisurely meals at farm-to-table restaurants, and browse unique boutiques. The overall ambience is peaceful and inviting, superb for unwinding.

For solo travellers seeking a quiet retreat with access to local culture, the village centre also offers a superb base.
What are the best hotels in West Stockbridge that travellers recommend?
Two highly recommended hotels in West Stockbridge that travellers consistently praise are the Shaker Mill Inn and the Pleasant Valley Motel West Stockbridge.

The Shaker Mill Inn has an exceptional review rating of 9.6. Guests have particularly enjoyed the nice food available. The inn offers comfortable amenities such as climate control for cooling, a fireplace, a balcony, a yard, a furnished patio, and a deck or patio.

Another great option is the Pleasant Valley Motel West Stockbridge. Guests frequently mention the comfortable and clean rooms, as well as its excellent and great location. The motel provides free self-parking and is conveniently located near a beach. Reviewers have also noted the good TV and great showers.
What are the best family hotels in West Stockbridge?
For a family-friendly hotel in West Stockbridge, consider the Shaker Mill Inn.

The Shaker Mill Inn, with an outstanding 9.6 rating, is much-loved by families. It offers useful amenities such as a sofa bed, a balcony or patio, a yard, and a fully equipped kitchen, providing plenty of space and convenience for families. Guests have also commented positively on the food. Find more child-friendly accommodations in West Stockbridge
What are the best spa hotels in West Stockbridge?
For a spa hotel in West Stockbridge, the Shaker Mill Inn is an excellent choice.

This inn, with an impressive 9.6 rating, offers a relaxing experience with massage services available. Guests can also enjoy the outdoors with amenities such as a balcony, yard, furnished patio, and deck or patio. Many rooms also feature a kitchen, providing added convenience. Guests have also commented on the nice food.

Overall, the Shaker Mill Inn is a highly-rated option for those seeking a spa experience in West Stockbridge. See all spa hotels in West Stockbridge
What hotels in West Stockbridge offer free breakfast?
For a hotel in West Stockbridge that offers free breakfast, the Shaker Mill Inn is an excellent choice.

This highly-rated hotel, with a superb 9.6 review score, provides a complimentary breakfast to start your day. Guests frequently mention the nice food. Many rooms also feature a balcony or patio, and some include a kitchen for added convenience. The hotel is very close to Ebenezer II Gifts and Antiques, just 0.1 km away. Find more hotels with free breakfast in West Stockbridge
What are the top pet-friendly hotels in West Stockbridge?
For top pet-friendly accommodation in West Stockbridge, the Shaker Mill Inn is an excellent choice.

The Shaker Mill Inn, with an outstanding 9.6 rating, warmly welcomes pets and provides amenities such as a yard, a furnished patio, a deck, or a patio, and a kitchen, ensuring a comfortable stay for both you and your furry companion. Guests have also praised the food here as being very nice. See more pet-friendly hotels in West Stockbridge
What are the best budget hotels in West Stockbridge?
For excellent budget hotels in West Stockbridge, consider the Shaker Mill Inn and Pleasant Valley Motel West Stockbridge.

The Shaker Mill Inn, with an outstanding 9.6 rating, offers a variety of amenities including free toiletries, free parking, and complimentary breakfast. Guests appreciate the outdoor spaces such as a balcony, yard, furnished patio, and deck or patio. It is conveniently located just 0.1 km from Ebenezer II Gifts and Antiques.

Another great option is the Pleasant Valley Motel West Stockbridge. This motel provides free parking, free WiFi, and free internet access. Guests have frequently commented on the comfortable and clean rooms, the excellent location, and the great showers. It is also near a beach and just 1.1 km from Ebenezer II Gifts and Antiques. View all budget hotels in West Stockbridge
What are the most romantic hotels in West Stockbridge for couples?
For couples seeking a romantic stay in West Stockbridge, the Shaker Mill Inn is an excellent choice.

This highly-rated inn, with an impressive 9.6 review score, offers a wonderful experience for couples. Guests frequently appreciate the private hot tubs available, great for a relaxing evening. Many rooms also feature balconies, providing a lovely space to unwind together. The inn provides a nice setting with its yard, furnished patio, and deck or patio areas, and some accommodations even include a kitchen for added convenience. See all romantic hotels in West Stockbridge
When is the best time to go to West Stockbridge?
The best time to visit West Stockbridge is during the autumn months, specifically from late September through October, when the foliage is at its peak.

This period offers stunning natural beauty as the Berkshire Hills transform into a vibrant canvas of reds, oranges, and yellows. The crisp, cool air is ideal for outdoor activities like hiking and exploring the local farm stands, which are abundant with seasonal produce. It's also a time when many local art galleries and studios, such as those found along Main Street, are fully open and showcasing new works.

Summer, from June to August, is also a very popular time to visit. The weather is warm and pleasant, great for enjoying the numerous outdoor concerts and theatre performances at nearby venues. Many visitors come to enjoy the area's natural landscapes, with opportunities for swimming in local lakes or cycling along quiet country roads.

For those seeking a quieter experience with fewer crowds and potentially lower prices, late spring (May to early June) or early autumn (early September) can be a good option.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in West Stockbridge.
How can I save on a West Stockbridge hotel booking with Expedia?
Members always get our best prices. Find our best West Stockbridge hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a West Stockbridge hotel?
Prices for hotels in West Stockbridge often vary, but you can find a great deal from CA $88 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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