The Berkshires Luxury Vacations 2026

Photo by Photo courtesy of Berkshire Visitors Bureau

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Top Luxury vacation packages in The Berkshires

Price found within the past 48 hours. Click for updated prices.

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

$896

per person

Nov 26 - Nov 29

found 15 hours ago

Roundtrip flight included

San Juan (SJU) to Albany (ALB)

9.2/10 Wonderful! (118 reviews)

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3 Night Luxury vacations in The Berkshires

Price found within the past 48 hours. Click for updated prices.

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

$896

per person

Nov 26 - Nov 29

found 15 hours ago

Roundtrip flight included

San Juan (SJU) to Albany (ALB)

9.2/10 Wonderful! (118 reviews)

Don't see what you're looking for?

See all available trips from Columbus to The Berkshires

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4 Night Luxury vacations in The Berkshires

Price found within the past 48 hours. Click for updated prices.

Vacation Village in the Berkshires

$457

per person

Nov 10 - Nov 14

found 10 hours ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

8.8/10 Excellent! (2,687 reviews)

Very spacious and clean room , at an affordable price vast of amenities surrounded by nature

Reviewed on Oct 6, 2026

Hotel On North

$524

per person

Nov 10 - Nov 14

found 10 hours ago

Roundtrip flight included

Dallas (DFW) to Albany (ALB)

9.6/10 Exceptional! (929 reviews)

Beautiful boutique hotel. We will be back!

Reviewed on Oct 5, 2026

Chambery Inn

$1,147

per person

Nov 22 - Nov 26

found 12 hours ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

9.6/10 Exceptional! (388 reviews)

This is a charming little inn. We enjoyed a cozy suite with a fireplace and a hot tub. The bed was very comfortable and the doorside delivery of hot coffee and a continental breakfast in a cute picnic basket was a nice touch. Although the room was at the basement level (with small windows at the top of the ceiling), the fireplace added nice ambiance. The bathroom soaps and shampoo were a bit basic, but absolutely serviceable. And while we never met the innkeepers, they had left the keys and a useful packet of information for us when we arrived. This was a nice location for our two day stay to experience music at Tanglewood. I would stay here again.

Reviewed on Sep 15, 2026

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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 $457. 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

26 Glendale Road, RR 183 Stockbridge MA

46 min drive from Jiminy Peak Mountain Resort

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 Orchards Hotel

222 Adams Rd Williamstown MA

25 min drive from Jiminy Peak Mountain Resort

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, ...

Lantern House Motel

256 Stockbridge Road Great Barrington MA

58 min drive from Jiminy Peak Mountain Resort

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

See all 1,096 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.