The Berkshires Luxury Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Discover the most popular places to visit in The Berkshires
Massachusetts Museum of Contemporary Art
Mount Greylock
Top Luxury The Berkshires Hotels
"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...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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."
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG"It’s very outdated and shower curtain did not work and room had musty smell"
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires
"Lovely property, imaginative and we. Well-maintained. Food was very good but somewhat overpriced. Staffing was a bit scant. No cash on the property so it was difficult to change a bill and provide an accurate tip for housekeeping."
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...
How to find luxurious holiday packages in The Berkshires?
How to find a luxury holiday in The Berkshires?
Whether you fancy heading off on an unforgettable spa break or relaxing on an all-inclusive vacation, finding your perfect 2026 luxury escape The Berkshires couldn’t be easier. Use Expedia’s filters to find luxury escapes The Berkshires hotels and luxury holiday rentals with the amenities you need to make your holiday extra special.
How to book a luxury holiday in The Berkshires with Expedia?
Once you’ve identified your ideal luxury holiday The Berkshires you simply need to enter your travel dates to view your travel and accommodation options. You can select from luxury holiday rentals to luxury hotels. Use the filters to find luxury escapes The Berkshires deals around your selected dates and you could save money too.
Are luxury holidays in The Berkshires worth the cost?
Memories are priceless so splashing out on luxury getaways to The Berkshires in 2026 can be well worth the extra expense. That said, there are some great value luxury escapes The Berkshires deals available if you’re prepared to book a holiday out of season. Consider booking villas or luxury holiday homes in The Berkshires for a group or larger family holiday to keep costs down.
How do I choose the perfect luxury holiday package for The Berkshires?
Make sure you think carefully about what you want from your luxury holiday in The Berkshires before you book. If you’re taking the kids, click on the “family-friendly” filter to find hotels with facilities they’ll love—along with a pool bar and sauna for the adults to enjoy.
Where can I find excellent deals on luxury holidays in The Berkshires?
Luxury doesn’t have to cost the earth. If you’re looking for discount luxury escapes The Berkshires deals, then Expedia can help. Whether you’re after cost-effective luxury weekend getaways to The Berkshires or a longer trip with luxury hire car, use the filters to access some of the best deals available.
How to find luxury spa The Berkshires holiday packages?
Expedia can help you discover some of the most luxurious spa hotels to fit your budget, taste, and dates. You can compare prices and read reviews before deciding. It’s also often possible to get a luxury holiday The Berkshires with free cancellation too, so you can book with confidence.
How to discover last-minute luxury holiday deals to The Berkshires with Expedia.
While booking ahead is a good way to seal in some great value deals, it’s also possible to access top-notch last-minute luxury escapes to The Berkshires. Simply enter your dates to see what’s on offer, and if you can be flexible about flights and hotels, so much the better for your pocket.
How to find luxury pet-friendly The Berkshires holiday packages?
If you don’t want to leave your pet at home, no problem. It doesn’t mean you have to miss out on luxury facilities. Use the “pet-friendly” filter to find luxury escapes The Berkshires hotels that will welcome your furry friend.
How to find great luxury beach holiday packages in The Berkshires?
To discover some of the most luxurious beach lodgings available, tick the “all-inclusive” and “sea view” filters. You’ll be able to select from a big selection of luxury escape The Berkshires hotels and apartments with direct access to beaches.
Why book luxury holiday packages in The Berkshires with Expedia?
Expedia’s handy travel filters can help you search through a huge number of options and book a luxury escape The Berkshires you’ll never forget. From rooms with a view to resorts with top-rated golf courses, you can customise your vacation and find one that ticks all your boxes.