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Pittsfield Vacation Packages

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Pittsfield Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Lakeside Inn

Lakeside Inn

2 out of 5
Save 100% on your flight
Price was $397, price is now $261 per person
$261
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Wakefield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attraction MarketStreet Lynnfield is located nearby.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Price was $823, price is now $314 per person
$314
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville

3 out of 5
Save 100% on your flight
Price was $559, price is now $346 per person
$346
per person
Jan 1 - Jan 6
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Somerville. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Harvard Square and TD Garden are located nearby.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $461, price is now $295 per person
$295
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this beach hotel in Beverly. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Beverly Commons and Salem Willows Beach are located nearby.
The Merchant

The Merchant

3 out of 5
Save 100% on your flight
Price was $828, price is now $540 per person
$540
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Salem. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Salem Museum and Witch History Museum are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $908, price is now $594 per person
$594
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Save 100% on your flight
Price was $722, price is now $482 per person
$482
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
The Hotel Marblehead

The Hotel Marblehead

3.5 out of 5
Save 100% on your flight
Price was $443, price is now $300 per person
$300
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this boutique hotel in Marblehead. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Marblehead Museum & Historical Society and Salem Harbor are located nearby.

Pittsfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $461, price is now $295 per person
$295
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $823, price is now $314 per person
$314
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Merchant

The Merchant

3 out of 5
Downtown Salem
Save 100% on your flight
Price was $828, price is now $540 per person
$540
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $908, price is now $594 per person
$594
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Pittsfield Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
Save 100% on your flight
Price was $490, price is now $302 per person
$302
per person
Jan 1 - Jan 6
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $714, price is now $431 per person
$431
per person
Jan 1 - Jan 6
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $648, price is now $398 per person
$398
per person
Jan 1 - Jan 6
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
Price was $1,068, price is now $661 per person
$661
per person
Jan 1 - Jan 6
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Wed, Dec 10 - Sun, Dec 14
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Dec 10 from Orlando Intl. to Portsmouth Intl., returning Sun, Dec 14, priced at $100 found 1 day ago
Breeze Airways
Thu, Dec 18 - Thu, Jan 1
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 18 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Jan 1, priced at $102 found 1 day ago
Breeze Airways
Tue, Dec 30 - Thu, Jan 8
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$133 Roundtrip, found 19 hours ago
$133
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Tue, Dec 30 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Jan 8, priced at $133 found 19 hours ago
Breeze Airways
Sat, Dec 6 - Tue, Dec 9
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Dec 6 from Orlando Intl. to Manchester-Boston Regional, returning Tue, Dec 9, priced at $140 found 6 days ago