The Berkshires Holidays
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Discover the most popular places to visit in The Berkshires
Massachusetts Museum of Contemporary Art
Mount Greylock
The Berkshires Hotel Deals
"This was our fourth year in a row staying at the Inn. They have a new sitting area outside with a gas fire pit, very nice. The pool is always very well maintained. We like to stay in the older section room away from the main building, the beds are comfortable and the room is basic but clean and nice. The breakfast is as good as any other hotel brand that offers breakfast. The shopping center is right next door within walking distance, with a few places to eat. It’s a great location also to get...
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel"My first time and I will go back."
"NA"
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce Resort"I thought the property was great for families because it did have the option of a basketball court, a tennis court and a volleyball court. There was also an indoor pool and an outdoor pool. My room was not comfortable at all. I took a two bedroom suite and the mattresses were terrible. It was very difficult to sleep comfortably. The tennis court was always in use. I would suggest they build more tennis courts and outdoor play space. The indoor pools and hot tubs were great. I would only suggest...
"Property is tired. Carpeting needs to be replaced. Room furniture needs to be replaced/TVs updated. Staff was very accomodating, helpfull, energetic."
Vacation Village in the Berkshires
Vacation Village in the BerkshiresFrequently Asked Questions
How much does a The Berkshires holiday package cost?
We make it simple to travel somewhere new, with The Berkshires packages starting from as little as . You'll have the flexibility to bundle your favourite airlines, hotels and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?
How do I get a cheap travel package to The Berkshires?
Just imagine all the thrilling things you could do in The Berkshires with extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and extras into a The Berkshires holiday package. You have plenty of choice when you book with Expedia too. In fact, you can pick from more than 550 airlines and 1,000,000 properties around the world. Whether you're holidaying with the family or embarking on a solo adventure, exploring The Berkshires is better with a package.
What are the top hotels in The Berkshires?
Hampton Inn Boston - Logan Airport and Boston Park Plaza know how to make their guests feel welcome in Great Barrington. If you also plan to explore Hancock, have a look at Hilton Boston Logan Airport and Sheraton Boston, a Marriott Hotel. Both are top picks with travellers.
How far in advance should I book my The Berkshires holiday?
Travellers are normally able to browse international flights on Expedia up to a year in advance of departure. Booking last minute? With a stroke of luck, it's still possible to purchase a cheaper ticket only weeks before your flight.
What does an Expedia The Berkshires travel package include?
Flights, hotels and a cool car for all your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings stack up. When it comes to organising your The Berkshires trip, you're in charge!
What should I know before booking a The Berkshires travel package?
Booking all the parts of your trip together is a simple way to save. Combine car rentals, airfares and hotels into a tidy little package. But hotels aren't your only option. Expedia has all kinds of properties, including holiday rentals such as beachside villas and serviced residences. You've got loads of choices!
Can I choose my airline with a The Berkshires Expedia holiday package?
Yes — that's one of the best things about an Expedia package. You're the boss! We have access to more than 550 airline partners across the globe, so you have options galore when putting together your The Berkshires escape.
If I'm not able to travel, can I cancel my The Berkshires holiday package?
Don't stress if you're rethinking your The Berkshires holiday package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We totally understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.
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Things to do near The Berkshires
The Berkshires offers a delightful blend of outdoor activities and scenic beauty, making it perfect for adventure seekers and those looking to relax. Popular activities include skiing at various resorts, vineyard trips, and family-friendly adventures. Visitors can enjoy leisurely strolls through picturesque landscapes and explore numerous hiking trails, ensuring an unforgettable experience in this charming region of Massachusetts.
Shopping
The Berkshires offers a delightful shopping experience. At Lee Premium Outlets, just 16.1km away, you can find a variety of brands. The Berkshire Mountain Country Store, located 17.7km from The Berkshires, features unique gifts, while The Bookstore, 24.1km away, is perfect for literary finds.
Recreation
At Jacob's Pillow, immerse yourself in the world of dance amidst a vibrant cultural atmosphere. Goose Pond Reservation offers serene trails and tranquil waters, perfect for relaxation and rejuvenation. Meanwhile, the Mahaiwe Performing Arts Center provides an enchanting venue for family-friendly performances and romantic evenings.
Adventure
At Ski Butternut, located 14.5km from The Berkshires, enjoy thrilling slopes and vibrant ski culture. Otis Ridge, a mere 4.8km away, offers excellent skiing experiences. For a scenic adventure, hike the Housatonic River Walk, situated 17.7km from The Berkshires, surrounded by breathtaking landscapes.
Nightlife
The nightlife in The Berkshires offers a charming mix of sophistication and local flair. Enjoy live music at the historic Mahaiwe Performing Arts Center or unwind with cocktails at The Red Lion Inn. For a lively atmosphere, visit the dance floor at Club Helsinki, where vibrant performances abound.
Find the best attractions near The Berkshires
The Berkshires, a picturesque region in Massachusetts, is ideal for outdoor enthusiasts and adventure seekers. Visitors can explore historic houses, serene lakes, and nature reserves that offer a blend of culture and adventure. Notable attractions include the Berkshire Museum and the scenic Berkshire Hills, providing ample opportunities for relaxation and exploration amidst stunning landscapes.
- McLennan Reservation: Located 6.4km from The Berkshires, this serene preserve offers breathtaking scenery and a tranquil environment for nature lovers. Enjoy picturesque trails that wind through lush landscapes, making it ideal for leisurely walks and birdwatching.
- Chesterwood: Situated 20.9km away, Chesterwood is the historic home and studio of sculptor Daniel Chester French. This site immerses visitors in rich cultural heritage, with beautifully maintained gardens and exhibitions showcasing French's iconic works, including the Lincoln Memorial.
- National Shrine of the Divine Mercy: Just 19.3km from The Berkshires, this serene shrine serves as a place of reflection and spiritual solace. Visitors can admire stunning architecture, peaceful grounds, and participate in various religious activities, making it a culturally enriching experience.
Best time to go to The Berkshires
The best time to visit The Berkshires 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.
Tips to save on your trip to The Berkshires
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to The Berkshires.
- Consider traveling to The Berkshires during the low season (March to April and November) for more affordable options.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.