Explore 77 Luxury Hotels in Western Massachusetts

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Best Luxury Hotels in Western Massachusetts

The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $127 total per night from Dec 12 to Dec 13
$127 total
Dec 12 - Dec 13
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)
"Breakfast was h asic everything else was perfect"

Reviewed on Nov 12, 2026

Opens in a new windowThe Yankee Inn
Lantern House Motel

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

Opens in a new windowLantern House Motel
1896 House Country Inn & Motels

1896 House Country Inn & Motels

910 Cold Spring Road Williamstown MA
$99 nightly
The price is $111 total per night from Nov 15 to Nov 16
$111 total
Nov 15 - Nov 16
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, ...
6.8/10 (460 reviews)
"Checking in was a puzzle as no one was ever in the office. The key was in an envelope attached to the door. All of the 8 cars/guests were housed in rooms adjacent to each other which meant sounds could be heard through the walls! This was a problem re: sleeping!"

Reviewed on Nov 9, 2026

Opens in a new window1896 House Country Inn & Motels
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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 Nov 28 to Nov 29
$462 total
Nov 28 - Nov 29
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 ...
Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Hotel Northampton

Hotel Northampton

36 King Street Northampton MA
$209 nightly
The price is $233 total per night from Nov 27 to Nov 28
$233 total
Nov 27 - Nov 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 ...
Opens in a new windowHotel Northampton
The Orchards Hotel

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 ...
Opens in a new windowThe Orchards Hotel
Hotel On North

Hotel On North

297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $125 total per night from Nov 29 to Nov 30
$125 total
Nov 29 - Nov 30
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self ...
Opens in a new windowHotel On North
D. Hotel Suites & Spa

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA
Fully refundable
$134 nightly
The price is $150 total per night from Dec 13 to Dec 14
$150 total
Dec 13 - Dec 14
Total with taxes and fees
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy the gym and free buffet breakfast each morning. You'll ...
Opens in a new windowD. Hotel Suites & Spa
Don't see what you're looking for?
See all available properties in Western Massachusetts
View all properties
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

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
1,500 hotels
Lowest Price
$111
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, Hotel On North, 1896 House Country Inn & Motels, The Yankee Inn, D. Hotel Suites & Spa

Popular Luxury Stays in Western Massachusetts

Recent Western Massachusetts Hotel Reviews By Fellow Wanderers

Explore More Ways to Travel with Travelocity