Explore 77 Luxury Hotels in Western Massachusetts
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Best Luxury Hotels in Western Massachusetts
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
$358 nightly
The price is $399 total per night from Aug 31 to Sep 1
$399 total
Aug 31 - Sep 1
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! (114 reviews)
"Very lovely beautiful Room and property The outside pool was not available"
Reviewed on Jul 30, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $184 total per night from Sep 7 to Sep 8
$184 total
Sep 7 - Sep 8
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! (1,001 reviews)
"Nice facility, good location, clean room, helpful staff. The pool was great as well. The breakfast could be enhanced with real eggs, some gluten free option. Also, I asked one of the servers who was replenishing food containers if there was an alternative to dairy milk for my oatmeal and she said ..."
Reviewed on Aug 13, 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
$110 nightly
The price is $123 total per night from Aug 16 to Aug 17
$123 total
Aug 16 - Aug 17
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, ...
6.6/10 (455 reviews)
"I booked this motel for the amenities: spa, pool, pond, but all I saw was broken down pool. As soon as I opened the door to rm 110 it stank of mildew. It was cold at night so tried the heat but it was not working! I asked for another room with heat but they were booked. They gave me a room heater ..."
Reviewed on Aug 9, 2026
Hotel Northampton
36 King Street Northampton MA
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $184 total per night from Aug 24 to Aug 25
$184 total
Aug 24 - Aug 25
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 ...
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 ...
Hotel On North
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $200 total per night from Sep 7 to Sep 8
$200 total
Sep 7 - Sep 8
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 ...
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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
Devonfield Inn B&B
85 Stockbridge Rd. Lee MA
$389 nightly
The price is $435 total per night from Sep 3 to Sep 4
$435 total
Sep 3 - Sep 4
Total with taxes and fees
10/10 Exceptional! (140 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 | 1,506 hotels |
|---|---|
Lowest Price | $123 |
Highest Price | $435 |
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
The Yankee Inn
5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Nice facility, good location, clean room, helpful staff. The pool was great as well. The breakfast could be enhanced with real eggs, some gluten free option. Also, I asked one of the servers who was replenishing food containers if there was an alternative to dairy milk for my oatmeal and she said no. Another guest heard my question and pointed me to the almond milk. It would be helpful if your staff could be aware of all of the offerings! Otherwise, we had a wonderful stay."
A verified traveler stayed at The Yankee Inn
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