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
$98 nightly
The price is $110 total per night from Nov 11 to Nov 12
$110 total
Nov 11 - Nov 12
Total with 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! (784 reviews)
Outstanding team, interesting rooms, nicely appointed and very clean. There was a little street noise (our room faced the road) but only in the morning. The adjacent restaurant was disappointing—-has aspirations but didn’t deliver, unfortunately. But I would definitely stay at this hotel again.
Reviewed on Oct 21, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
$335 nightly
The price is $374 total per night from Nov 9 to Nov 10
$374 total
Nov 9 - Nov 10
Total with 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 ...
9.2/10 Wonderful! (83 reviews)
My husband and I thoroughly enjoyed our stay at the Stockbridge Inn. Diane, the owner, greeted us warmly and escorted us to our room. Our accommodations were comfortable, warm and spacious and quiet enough for us to have a good night sleep. Diane was very helpful in recommending other accommodations ...
Reviewed on Oct 12, 2025
Hotel Northampton
36 King Street, Northampton, MA
Fully refundableReserve now, pay when you stay
$999 nightly
The price is $1,116 total per night from Oct 27 to Oct 28
$1,116 total
Oct 27 - Oct 28
Total with 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)
Best place around, I would definitely recommend to anyone.
Reviewed on Oct 20, 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $132 total per night from Nov 2 to Nov 3
$132 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool ...
9/10 Wonderful! (1,018 reviews)
Fresh breakfast menu, clean and great location.
Reviewed on Oct 23, 2025
Wagon Wheel Inn
484 Pittsfield Rd, PO Box 808, Lenox, MA
$69 nightly
The price is $77 total per night from Oct 27 to Oct 28
$77 total
Oct 27 - Oct 28
Total with 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! (636 reviews)
Beautiful area. Close to Mt. Greylock, Octobrr Mountain and Pleasant Valley Audubon.
Reviewed on Oct 17, 2025
1896 House Country Inn & Motels
910 Cold Spring Road, Williamstown, MA
$107 nightly
The price is $120 total per night from Oct 27 to Oct 28
$120 total
Oct 27 - Oct 28
Total with 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 (364 reviews)
Vintage feel!
Reviewed on Oct 20, 2025
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
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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More 4 star hotels in Western Massachusetts
33 Main
33 Main Street, Lenox, MA
$445 nightly
The price is $498 total per night from Nov 23 to Nov 24
$498 total
Nov 23 - Nov 24
Total with taxes and fees
9.8/10 Exceptional! (73 reviews)
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 | 1,486 hotels |
|---|---|
Lowest Price | $77 |
Highest Price | $1,116 |
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 |
Popular Luxury Stays in Western Massachusetts
Recent Western Massachusetts Hotel Reviews By Fellow Wanderers
Vacation Village in the Berkshires
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"This is a condo with all the amenities of home, excellent check in and professional service from the staff. This is the second time we have been here and plan on returning next year. "
A verified traveler stayed at Vacation Village in the Berkshires
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