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
$149 nightly
The price is $166 total per night from May 3 to May 4
$166 total
May 3 - May 4
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 ...
9.6/10 Exceptional! (846 reviews)
My wife and I both enjoyed our stay. The decor and atmosphere are very nice. The room was spacious. And the facilities were fun—I enjoyed the sitting area on the second floor with all the books, games, and puzzles.
Reviewed on Apr 27, 2026
Hotel Northampton
36 King Street Northampton MA
$165 nightly
The price is $184 total per night from May 25 to May 26
$184 total
May 25 - May 26
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 ...
9.2/10 Wonderful! (1,001 reviews)
Very Friendly and welcoming staff. Even the area was very relaxing especially being next to the Main Street. Beds are super comfortable. Highly recommend. Everything is within walking distance.
Reviewed on Apr 24, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
$103 nightly
The price is $115 total per night from May 3 to May 4
$115 total
May 3 - May 4
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. ...
9.2/10 Wonderful! (1,000 reviews)
Rooms where really clean, staff was great very helpful and generous. Breakfast was good, small selection but a good ones. Tub was nice n hit. Plenty clean towels
Reviewed on Apr 27, 2026
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.
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
Wagon Wheel Inn
484 Pittsfield Rd Lenox MA
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! (641 reviews)
We've been in worse, but not by much. It kept the wind out of our hair and the shower had plenty of hot water. That's about it
Reviewed on Oct 26, 2025
1896 House Country Inn & Motels
910 Cold Spring Road Williamstown MA
$112 nightly
The price is $125 total per night from Jun 2 to Jun 3
$125 total
Jun 2 - Jun 3
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, ...
6.6/10 (450 reviews)
Older strip type motel. That said room was clean and bed was comfortable. It was good for a couple of days that I stayed. No breakfast available at motel though they did give me a discount coupon to bar/resturant next door.
Reviewed on Apr 4, 2026
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 May 17 to May 18
$374 total
May 17 - May 18
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 ...
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 ...
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More 4 star hotels in Western Massachusetts
Hampton Terrace Inn
91 Walker Street Lenox MA
$296 nightly
The price is $331 total per night from May 4 to May 5
$331 total
May 4 - May 5
Total with taxes and fees
9/10 Wonderful! (44 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 | 1,549 hotels |
|---|---|
Lowest Price | $115 |
Highest Price | $398 |
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 Inn |
Popular Luxury Stays in Western Massachusetts
Recent Western Massachusetts Hotel Reviews By Fellow Wanderers
Vacation Village in the Berkshires
5 out of 5
Posted 13 hours ago
Travelocity Verified Review
"Everything was great!"
A verified traveler stayed at Vacation Village in the Berkshires
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