Explore 77 Luxury Hotels in Western Massachusetts

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Best Luxury Hotels in Western Massachusetts

Hotel On North

297 North Street, Pittsfield, MA

Fully refundableReserve now, pay when you stay

$189 nightly

$211 total

Aug 12 - Aug 13

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's ...

9.4/10 Exceptional! (744 reviews)

Beautiful, perfect hotel

"Wow, I loved this hotel! The room was amazing, the beds were great. Great service, great people. Beautiful design. I would definitely stay here again."

Reviewed on Jul 5, 2025

Hotel Northampton

36 King Street, Northampton, MA

Fully refundableReserve now, pay when you stay

$166 nightly

$185 total

Jul 28 - Jul 29

Total includes taxes and fees

This historic hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour ...

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 Jul 6, 2025

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

Fully refundableReserve now, pay when you stay

$127 nightly

$141 total

Jul 27 - Jul 28

Total includes taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...

9/10 Wonderful! (1,000 reviews)

"Loved the Yankee Inn!"

Reviewed on Jul 14, 2025

Wagon Wheel Inn

484 Pittsfield Rd, PO Box 808, Lenox, MA

$69 nightly

$77 total

Jul 21 - Jul 22

Total includes taxes and fees

A hot tub is featured at this motel, along with free self parking. WiFi in public areas is free. Express check-out is also provided.

7/10 Good! (611 reviews)

"Convenient location for my trip"

Reviewed on Jul 6, 2025

1896 House Country Inn & Motels

910 Cold Spring Road, Williamstown, MA

$99 nightly

$111 total

Jul 27 - Jul 28

Total includes taxes and fees

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, ...

6.4/10 (343 reviews)

"The hotel is in 2 parts on opposite sides of the road. It's difficult to find in the dark. Even the GPS was confusing."

Reviewed on Jul 14, 2025

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

26 Glendale Road, RR 183, Stockbridge, MA

$421 nightly

$470 total

Aug 20 - Aug 21

Total includes taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...

"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 Jul 27, 2024

The Orchards Hotel

222 Adams Rd, Williamstown, MA

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal ...

"A little dated. Restaurant shut down for renovations, disappointing"

Reviewed on Mar 9, 2020

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Lantern House Motel

256 Stockbridge Road, Great Barrington, MA

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden and a picnic area are also provided.

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

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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.

More 4 star hotels in Western Massachusetts

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

26 Glendale Road, RR 183, Stockbridge, MA

$421 nightly

$470 total

Aug 20 - Aug 21

Total includes taxes and fees

Western Massachusetts Luxury Hotels

Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the Western Massachusetts luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in Western Massachusetts to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.

We want you to enjoy your next vacation in style and the top luxury resorts in Western Massachusetts will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Western Massachusetts, and plan your next opulent escape.

Western Massachusetts hotels essential information

Accommodation	1,482 hotels
Lowest Price	$77
Highest Price	$470
Popular hotels	The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, Hotel Northampton, The Orchards Hotel, Lantern House Motel, Wagon Wheel Inn, Hotel On North, 1896 House Country Inn & Motels, The Yankee, Trademark Collection by Wyndham