Pittsfield Vacations from $687
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The Latest Pittsfield vacation packages
Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,699, price is now $941 per person
$941
per person
Jul 21 - Jul 26
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (254 reviews)
Excellent experience- clean and very helpful staff
Reviewed on Mar 9, 2026
The Kendall Hotel at the Engine 7 Firehouse
MIT
Save 100% on your flight
Price was $1,374, price is now $772 per person
$772
per person
Jul 22 - Jul 26
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (1,014 reviews)
Lovely hotel with charming decor and amenities. The staff was quite pl
Reviewed on Apr 27, 2026
The Langham, Boston
Downtown Boston
Save 100% on your flight
Price was $1,829, price is now $1,057 per person
$1,057
per person
Jun 10 - Jun 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Private lounge offered three meals, wine, hard liquor, coffee, fruit, ice cream, etc. Well stocked & staff was superb
Reviewed on Apr 26, 2026
The Boston Hotel
Brighton
Save 100% on your flight
Price was $1,335, price is now $815 per person
$815
per person
Jun 2 - Jun 9
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
7.4/10 Good! (874 reviews)
The best thing about this hotel is its location and its breakfast. It is right in the middle of Brighton and 5 minutes or less from the B Green Line and 10 minutes from the C Green Line. The neighborhood has some cute diners, restaurants and cafes. The included breakfast is decent, with waffles and eggwichs, fruit, yogurt, cereal and plenty of coffee and tea. The free cookies are a big hit.
Housekeeping is available only on request, and the request has to be made by 12 noon.
The rooms are clean but spare. The outlets are few and far between. There is a coffee maker, microwave and fridge in the room.
The hotel is basic but gets the job done. In any other town, it would cost half the price. But it is in Brighton, so you get charged way more.
There is parking.
Reviewed on Apr 23, 2026
Pittsfield Hotel Deals
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!
Pittsfield NH
Steele Hill Resorts
516 Steele Hill Road Sanbornton NH
$189 nightly
The price is $205 total per night from Apr 30 to May 1
$205 total
Apr 30 - May 1
Total with taxes and fees
8.4/10 Very Good! (810 reviews)
Pool and hot tub clean. School vacation week, lots of kids. Staff friendly.
Reviewed on Apr 24, 2026
Fairfield Inn By Marriott Concord
4 Gulf St Concord NH
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $154 total per night from May 3 to May 4
$154 total
May 3 - May 4
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
The stay was good. The staff was nice at checking in. Left early in morning so didn’t have breakfast. The room was good.
Reviewed on Apr 20, 2026
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.
Find the Best Pittsfield Vacation Packages
Pittsfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Manchester-Boston Regional Airport (MHT) |
Population | 1,600 |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
