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 Dec 14 to Dec 15
$166 total
Dec 14 - Dec 15
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! (805 reviews)
Spacious rooms. Attentive staff. Free parking behind the hotel.
Reviewed on Dec 5, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
$414 nightly
The price is $462 total per night from Jan 5 to Jan 6
$462 total
Jan 5 - Jan 6, 2026
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! (85 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!
Reviewed on Oct 27, 2025
Hotel Northampton
36 King Street Northampton MA
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $184 total per night from Dec 14 to Dec 15
$184 total
Dec 14 - Dec 15
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)
We liked everything!
Reviewed on Nov 29, 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $84 total per night from Dec 24 to Dec 25
$84 total
Dec 24 - Dec 25
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! (1,000 reviews)
My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there
Reviewed on Dec 10, 2025
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)
Good overall.
Reviewed on Oct 26, 2025
1896 House Country Inn & Motels
910 Cold Spring Road Williamstown MA
$99 nightly
The price is $111 total per night from Dec 14 to Dec 15
$111 total
Dec 14 - Dec 15
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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View all propertiesLowest 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 Inn at Stockbridge
30 East Street Lee MA
$263 nightly
The price is $294 total per night from Jan 1 to Jan 2
$294 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.6/10 Exceptional! (99 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 | 1,482 hotels |
|---|---|
Lowest Price | $84 |
Highest Price | $462 |
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
D. Hotel Suites & Spa
5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Stayed 3 nights, really great hotel and value. "
A verified traveler stayed at D. Hotel Suites & Spa
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