Western Massachusetts Luxury Holidays

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All you need to know about luxury holidays in Western Massachusetts

What can I expect from a luxury Western Massachusetts holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Western Massachusetts?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Western Massachusetts holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Western Massachusetts?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Western Massachusetts starting at . Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Western Massachusetts?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Western Massachusetts spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Western Massachusetts?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Western Massachusetts?

You can wangle a top-notch luxury holiday in Western Massachusetts for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

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

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Western Massachusetts with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Western Massachusetts to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

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
Stay at this 4.5-star luxury B&B in Stockbridge. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Chesterwood ...
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer ..."

Reviewed on 27 Jul 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
Stay at this 3.5-star historic hotel in Northampton. Enjoy free Wi-Fi, free parking and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,000 reviews)
"Beautiful historic building, there was a wedding party the night we stayed but we were in a 5th floor room and heard nothing. Lots of fun dining options within a couple blocks."

Reviewed on 6 Jul 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
Stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Colonial Plaza and Linear Park are ...
"A little dated. Restaurant shut down for renovations, disappointing"

Reviewed on 9 Mar 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. Flight-inclusive packages are ATOL protected.