Western Massachusetts Luxury Vacations

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Top Luxury vacation packages in Western Massachusetts

Price found within the past 48 hours. Click for updated prices.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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3 Night Luxury vacations in Western Massachusetts

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The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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See all available trips from Columbus to Western Massachusetts
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4 Night Luxury vacations in Western Massachusetts

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1896 House Country Inn & Motels
Inn on Boltwood
Quality Inn & Suites Northampton - Amherst
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See all available trips from Columbus to Western Massachusetts
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All you need to know about luxury vacations in Western Massachusetts

What can I expect from a luxury Western Massachusetts vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Western Massachusetts 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 Western Massachusetts?

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 Western Massachusetts 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 $668. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Western Massachusetts?

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 Western Massachusetts 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 Western Massachusetts?

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 Western Massachusetts 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 Western Massachusetts 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 Western Massachusetts 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

4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
  • 48 min drive from Six Flags New England
Spoil yourself with classy accommodations at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, where you'll enjoy amenities ...
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."

Reviewed on Nov 2, 2024

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

Hotel Northampton

3.5 out of 5
36 King Street, Northampton, MA
  • 47 min drive from Six Flags New England
Be treated to luxurious accommodations at Hotel Northampton, where you can enjoy amenities like designer toiletries, premium channels, and more. Notable amenities ...
9/10 Wonderful! (1,001 reviews)
"Nice overall"

Reviewed on Aug 20, 2025

Hotel Northampton
The Orchards Hotel

The Orchards Hotel

2.5 out of 5
222 Adams Rd, Williamstown, MA
  • 2 hours drive from Six Flags New England
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, ...
"A little dated. Restaurant shut down for renovations, disappointing"

Reviewed on Mar 9, 2020

The Orchards Hotel
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.