Explore 6 Luxury Hotels in Pittsfield

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Best Luxury Hotels in Pittsfield

Hotel On North

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 10 to Dec 11
$166 total
Dec 10 - Dec 11
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

Opens in a new windowHotel On North
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

20 W Housatonic St. Pittsfield MA
$85 nightly
The price is $95 total per night from Dec 10 to Dec 11
$95 total
Dec 10 - Dec 11
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on ...
8.6/10 Excellent! (346 reviews)
The room was so big it felt like we were in an apartment to be honest. It was well worth the price we paid 😁. If your looking for a place to stay,I would definitely recommend this hotel. The front desk guy was really nice and happy to let us in with a pet for the night. Thanks again 😊🐾

Reviewed on Nov 28, 2025

Opens in a new windowThe Central Downtown Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Dec 11 to Dec 12
$104 total
Dec 11 - Dec 12
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the ...
8.4/10 Very Good! (1,004 reviews)
Loved having coffee and tea 24/7

Reviewed on Nov 29, 2025

Opens in a new windowBest Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA
Fully refundable
$92 nightly
The price is $103 total per night from Dec 12 to Dec 13
$103 total
Dec 12 - Dec 13
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
8/10 Very Good! (980 reviews)
I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly.

Reviewed on Dec 4, 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $99 total per night from Dec 10 to Dec 11
$99 total
Dec 10 - Dec 11
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front ...
5.2/10 (810 reviews)
Room spotless and staff helpful.

Reviewed on Nov 5, 2025

Opens in a new windowFairBridge Inn Express
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More 4 star hotels in Pittsfield

The Inn at Stockbridge

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)

Pittsfield 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 Pittsfield luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in Pittsfield 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 Pittsfield will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in Pittsfield, and plan your next opulent escape.


Pittsfield hotels essential information

Accommodation
1,337 hotels
Lowest Price
$95
Highest Price
$294
Popular hotels
Hotel On North, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Central Downtown Inn & Suites, Best Western Plus Berkshire Hills Inn & Suites, FairBridge Inn Express

Popular Luxury Stays in Pittsfield

5 Stars Luxury stays in Pittsfield
Hotels 5 Stars
Hotels 5 Stars
Luxury stays in Pittsfield with spa
Hotels with Spa
Hotels with Spa

Recent Pittsfield Hotel Reviews By Fellow Wanderers

Vacation Village in the Berkshires

Vacation Village in the Berkshires

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Clean spacious toom"
A verified traveler stayed at Vacation Village in the Berkshires
Vacation Village in the Berkshires

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