The Berkshires Luxury Vacations

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4 Night Luxury vacations in The Berkshires

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

$595
per person
Nov 9 - Nov 13
found 7 hours ago
Roundtrip flight included
Las Vegas (LAS) to Albany (ALB)
8.4/10 Very Good! (1,002 reviews)
This hotel has seen better days. The lobby has turned into what you would expect at a gas station or mini-mart. The entire building stinks of cleaners and disinfectants. To get some air in my room I found the window screen that had been pulled out, did my best to unbend it, and put it in the window for fresh air. The hallways and elevator are scratched up. The lobby has a rack of extremely overpriced junk food for sale (like a gas station), most of the bins empty and dirty. The carpet in the room was dirty and sticky on my bare feet. The sink didn’t drain. It was noisy at night from slamming doors. Apparently the management cares about their money, but not maintenance. I would not stay here again. If you want breakfast go into Pittsfield or head over to the Big Y supermarket. Do yourself a favor and spend more money on a better room elsewhere. This is not the hotel I remember.

Reviewed on Sep 27, 2026

Hotel On North

Hotel On North

$652
per person
Nov 9 - Nov 13
found 7 hours ago
Roundtrip flight included
Las Vegas (LAS) to Albany (ALB)
9.6/10 Exceptional! (923 reviews)
We enjoyed our stay. A unique property. This was a quick overnight to attend a show at tanglewood. Dined at the restaurant on the property, which was convenient and very good as well. Would visit again.

Reviewed on Sep 26, 2026

Vacation Village in the Berkshires

Vacation Village in the Berkshires

$599
per person
Nov 9 - Nov 13
found 7 hours ago
Roundtrip flight included
Las Vegas (LAS) to Albany (ALB)
8.8/10 Excellent! (2,668 reviews)
It was a well appointed suite with kitchen, dining area, living room with a fireplace and the bedroom and a nice quiet corner of the property. I did sit out on the balcony and watch the sun go down and I had the best night sleep. I’ve had in a long time I would definitely go back. I didn’t use any of the amenities that they charge extra for, but because I was traveling, it was nice to just have a quiet night in.

Reviewed on Sep 26, 2026

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All you need to know about luxury vacations in The Berkshires

What can I expect from a luxury The Berkshires vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury The Berkshires vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in The Berkshires?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap The Berkshires luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $595. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in The Berkshires?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in The Berkshires with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in The Berkshires?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in The Berkshires with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to The Berkshires with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury The Berkshires Hotels

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

26 Glendale Road, RR 183 Stockbridge MA
  • 12 min drive from Tanglewood Music Center
Spoil yourself with classy accommodations at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, where you'll enjoy amenities ...
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Orchards Hotel

The Orchards Hotel

222 Adams Rd Williamstown MA
  • 59 min drive from Tanglewood Music Center
Treat yourself to a luxury stay at The Orchards Hotel, where you can enjoy amenities like massage services, pillowtop beds, and more. The outdoor pool, restaurant, ...
The Orchards Hotel
Lantern House Motel

Lantern House Motel

256 Stockbridge Road Great Barrington MA
  • 24 min drive from Tanglewood Music Center
Lantern House Motel awaits for a deluxe vacation. Popular amenities include an outdoor pool and a garden.
8.2/10 Very Good! (455 reviews)
Avoid staying here if you can.
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ..."

Reviewed on Nov 22, 2021

Lantern House Motel
See all 1,092 properties in The Berkshires
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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