Deals on vacations and trips to Pittsfield

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The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $733, price is now $575 per person
$575
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $985, price is now $699 per person
$699
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24 River House by Avantstay

Historic & Secluded Estate on the Hudson River w/ Pool Sleeps 24 River House by Avantstay

3.5 out of 5
Save 100% on your flight
Price was $3,704, price is now $2,802 per person
$2,802
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
An outdoor pool, free self parking, and concierge services are featured at this condo. WiFi in public areas is free. Barbecue grills are provided for your convenience.
Hudson Whaler

Hudson Whaler

2.5 out of 5
Price was $927, price is now $722 per person
$722
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
A gym, free self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A lobby fireplace, a communal living room, and luggage storage are also on offer.
Kingston Carriage House

Kingston Carriage House

4 out of 5
Rondout
Price was $900, price is now $712 per person
$712
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Indianapolis (IND) to Albany (ALB)
This bed & breakfast features free WiFi in public areas, a communal living room, and concierge services. A virtual front desk are provided for your convenience.

Top Pittsfield hotels deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $126 total per night
$126 total
Oct 1 - Oct 2
Total with taxes and fees
This aparthotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free Cancellation
$127 nightly
The price is $141 total per night
$141 total
Sep 13 - Sep 14
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $170 total per night
$170 total
Sep 13 - Sep 14
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 parking and luggage storage are also offered on site.
Pet friendly
Parking included
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
$69 nightly
The price is $77 total per night
$77 total
Sep 13 - Sep 14
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 desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $118 total per night
$118 total
Sep 13 - Sep 14
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 24-hour business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Breakfast included
Pet friendly
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
$115 nightly
The price is $128 total per night
$128 total
Oct 12 - Oct 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, free WiFi in public areas, and free valet parking. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
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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.

Stay near popular Pittsfield attractions

A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Hancock Shaker Village

9.2/10 (101 reviews)
You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.
See properties

Frequently asked questions

How much are vacation packages to Pittsfield?
With a Travelocity vacation package, you can live it up in Pittsfield for as low as $575. Flights, hotels and experiences — we've got you. You can save some cash just for combining your bookings. With all of that taken care of before you even set off, you won't have to worry about a thing.
How long should my Pittsfield vacation be?
Your Pittsfield break can be as short or as long as you'd like it to be, but the majority of travelers stay roughly 2 nights. Hoping to veer off the beaten path and discover some hidden gems? Book a couple more nights and see another side of this place.
Where can I get the best vacation package deals for Pittsfield?
It's hard to beat Travelocity when it comes to putting together your Pittsfield package deal. There are at least 400 airlines and 1,000,000 properties worldwide to select from. Book your trip now and get ready to tick another exciting place off your to-do list.
Why should I book my Pittsfield vacation bundle with Travelocity?
From our 24/7 support to our range of exhilarating destinations, we are dedicated to fulfilling your vacation dreams. All you'll have to do is click and book — our Price Match Guarantee will ensure you get the best deal.
Can I save money on my Pittsfield car rental if I combine it with hotels and flights?
With a Pittsfield vacation package, you can bundle your hotel, car and flight bookings and save a ton. If you want to uncover the best of this fantastic area, why not start with Times Square? This renowned sight is 120 mi from Pittsfield. With your own rental car, you'll be there in no time.
Which airport is best for Pittsfield?
Bradley Intl. Airport (BDL) is 45 mi from the city center and is the starting point for many exciting adventures. Alternatively, Albany Intl. Airport (ALB) is 35 mi away from central Pittsfield and Hartford, CT (HFD-Hartford - Brainard) is 60 mi away from central Pittsfield.
What is there to do in Pittsfield?
Pittsfield has plenty of places to explore, such as Bousquet Ski Area and Barrington Stage Company. These two impressive attractions top most travelers' itineraries.
Where should I stay when visiting Pittsfield?
Many travelers opt to spend their nights at the Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel. It's the perfect base for your Pittsfield vacation.

Photos of local treasures

Browse Pittsfield vacation photos for more inspiration

A historic building with classical architecture, a traffic light, and a yellow taxi.
A stone building with a red door and a tree with pink flowers in front.
A brick building with a clock and an American flag.
A stone church with arched windows and a central tower, surrounded by trees.
A street lined with autumn trees, a street lamp, and parked cars.

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