Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.
This peaceful Lenox hotel overlooks a picturesque lake where spectacular sunsets unfold daily. Enjoy Indian cuisine at Mint restaurant, complimentary breakfast, and free WiFi. Just 10 minutes from Tanglewood Music Center with convenient parking.
Immerse yourself in the Berkshires at this charming hotel just 5 minutes from Tanglewood Music Center. Enjoy hiking trails nearby, plus free WiFi and parking. A terrace, garden and helpful staff create a welcoming atmosphere for music lovers and nature enthusiasts alike.
Nestled in Lenox, this lodge offers easy access to Kennedy Park and Pleasant Valley Wilderness Sanctuary. The Club Room serves American cuisine, while the terrace provides a perfect spot to unwind after exploring local attractions.
Dive into the indoor pool at this Lenox hotel, just 10 minutes from Tanglewood Music Center. Enjoy a complimentary breakfast before exploring nearby attractions like Guido's Marketplace and Bousquet Ski Area. Free WiFi and parking complete your comfortable stay.
Escape to the heart of Pittsfield where this hotel offers an indoor pool and relaxing hot tub after exploring Tanglewood. Free breakfast, WiFi, and parking enhance your stay while nearby Guido's Marketplace awaits your discovery.
Dive into Berkshires charm at this centrally located Lenox motel, where you'll enjoy the refreshing outdoor pool and free parking. Near Guido's Marketplace and Bousquet Ski Area, with clean rooms and exceptionally helpful staff to enhance your stay.
Wake up to free breakfast at this cozy Berkshires inn where a garden terrace offers peaceful moments. The coffee shop/cafe and bar provide refreshments after exploring nearby attractions like The Bookstore and Lenox Library.
Embrace comfort at this Pittsfield retreat with an indoor pool and fitness center. Jae's Asian Fusion restaurant serves three daily meals, while rooms offer convenient refrigerators and microwaves. Guido's Marketplace and literary landmarks await nearby.
This peaceful Lee hotel offers free daily continental breakfast near local restaurants and shopping. Just minutes from Lee Library and Animagic Museum, guests praise the helpful staff. Enjoy convenient access to cultural attractions during your Berkshires stay.
Immerse yourself in the Berkshires at this centrally located hotel with an indoor pool and fitness center. Rooms feature microwaves and refrigerators, while the café and bar provide dining options. Free WiFi, parking, and proximity to Kennedy Park enhance your stay.
Embrace mountain charm at this Lenox hotel with free breakfast and parking. Take a refreshing dip in the indoor pool before heading to nearby Tanglewood or Kennedy Park. Grab a drink at the bar after exploring the scenic Berkshires.
Nestled in South Lee, this family-friendly retreat features 4 pools total - 2 indoor and 2 outdoor, including a seasonal option. Enjoy refreshments at the pool bar or coffee shop after exploring nearby Tanglewood Music Center and Berkshire attractions.
Unwind at this centrally located Pittsfield hotel with an indoor pool and health club. Just 15 minutes from Tanglewood Music Center and a quick 6-minute walk to transportation. Enjoy quiet rooms with microwaves, refrigerators, and a bar on-site.
Tucked into the Berkshires, this cozy B&B serves complimentary breakfast and provides free WiFi and parking. Explore nearby hiking trails, go kayaking, or visit local attractions like The Bookstore, all within easy reach of this charming retreat.
Tucked in Lenox, this charming hotel offers easy access to Tanglewood Music Center and local museums. Unwind by the seasonal pool or enjoy a cocktail at the bar after exploring nearby Ventfort Hall. Free WiFi and parking enhance your Berkshires getaway.
Immerse yourself in Lenox charm at this B&B featuring outdoor and poolside bars, just minutes from Shakespeare and Company. Enjoy complimentary breakfast, WiFi, and parking while the attentive staff ensures a memorable stay.
This Lee motel offers a playful mini golf course on-site and free continental breakfast to start your day. Located near Greenock Country Club and Lee Premium Outlets, guests praise the helpful staff. Enjoy complimentary WiFi and parking during your stay.
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.
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.
Tanglewood Music Center is 1.3 mi (2 km) from central Lenox, why not stop by during your stay. If you enjoy the show and want to see another, Shakespeare and Company and Berkshire Theatre Festival are both not far.
If museums are on your list of things to see in Lenox, then you might want to head to The Mount. If you want to see more of the museums in Lenox, Ventfort Hall Mansion and Gilded Age Museum isn't far either.
You might want to practice your swing at Wyndhurst Golf & Club, a golf course located 1.3 mi (2.1 km) from central Lenox. If Wyndhurst Golf & Club doesn't quite scratch your golfing itch, Greenock Country Club is also nearby.
Shakespeare and Company is 0.6 mi (0.9 km) from central Lenox, why not stop by during your stay. If you enjoy the show and want to see another, Tanglewood Music Center and Berkshire Theatre Festival are both not far.
If visiting museums in Lenox are on your list, you might want to check out the upcoming exhibitions at Ventfort Hall Mansion and Gilded Age Museum. If you want to see more of the museums in Lenox, Berkshire Scenic Railway Museum isn't far either.
Travelers who enjoy the great outdoors might want to go to Kennedy Park, located 1.6 mi (2.6 km) from central Lenox.
Want to stretch your legs some more? Head to The Mount and Pleasant Valley Wilderness Sanctuary, both nearby.
Tucked into the Berkshires, this cultural haven revolves around Tanglewood, where the Boston Symphony Orchestra performs summer concerts under the stars. The Mount offers a glimpse into Edith Wharton's creative world, with gardens as meticulously crafted as her prose. Shakespeare & Company brings the Bard to life in intimate performances that make complex soliloquies feel like overheard conversations. Pleasant Valley Wildlife Sanctuary's hiking trails reveal why creative souls found inspiration here. Kennedy Park's trails accommodate both casual walkers and serious hikers. Ventfort Hall Mansion provides a window into Gilded Age excess, when industrial barons built 'cottages' with dozens of rooms and European craftsmanship.
The history behind the inn was great. Doug one of the owners could not have been any more hospitable. He made sure to go above and beyond throughout our entire stay. Our room was comfortably sized and the fireplace was a great perk to have at night. Breakfast and treats were delicious. We will be back!
Very clean room the staff were very pleasant. The breakfast was pretty decent. The only issue we had was parking that didn’t seem to be enough spots for the hotel when we came back from a concert at Tanglewood. Every spot at the hotel was taken. Luckily somebody left otherwise the place was great.
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
Great B&B with everything you need especially for a quick getaway to vist Stockbridge & Great Barrington Massachusetts.
The new owners have added new touches to this Inn and the pride of ownership shows.
Highly recommended 👌
The building is like going back in time -- the separate boys and girls stairways, the chalkboards in the rooms and historical pictures on the walls.
Breakfast was so well done, selections and presentation were wonderful. Room was extremely comfortable, especially the seating area for watching tv. Lots of nice restaurants and shops within walking distance.
High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free.
There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
It was very conveniently located to the activities we were doing on our mini-vacation. There were a couple of issues that developed during our stay, but the staff did an excellent job of dealing with the issues.
I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...
Hot tub in the cottage was wonderful. The provided guide was very comprehensive and we appreciated all the amenities available in the main and carriage house.
If you're looking for the flexibility to change your plans to Lenox, most hotels offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where should I consider staying in Lenox if I'm looking for a reasonably priced accommodation?
Where can I stay in Lenox if I want a vacation home instead of a hotel?
If you're looking for a good alternative to a hotel, look over our selection of 43 vacation homes. In addition, there are 15 apartments and 12 condos.
What will the weather in Lenox be like during my vacation?
July and August are typically the warmest months in Lenox when the average temp is 66°F. January and February are the coldest months when the average temperature is 27°F. October and July are the months with the most rain.
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