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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.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Price was $940, price is now $422 per person
$422
per person
Mar 29 - Apr 1
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.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Save 100% on your flight
Price was $833, price is now $534 per person
$534
per person
Mar 29 - Apr 1
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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $2,574, price is now $1,710 per person
$1,710
per person
Apr 30 - May 4
found 18 hours ago
Roundtrip flight included
Nashville (BNA) 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 Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Save 100% on your flight
Price was $874, price is now $584 per person
$584
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this spa aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Wild Animal Lagoon and Bay View Street Beach are located nearby.
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
Save 100% on your flight
Price was $2,914, price is now $1,950 per person
$1,950
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chatham Seaside Links and Chatham Fish Pier are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $1,044, price is now $713 per person
$713
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and Boston Common are located nearby.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
Save 100% on your flight
Price was $949, price is now $684 per person
$684
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $896, price is now $653 per person
$653
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TD Garden and New England Aquarium are located nearby.

Pittsfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Cove At Yarmouth

The Cove At Yarmouth

3 out of 5
Price was $635, price is now $417 per person
$417
per person
Apr 3 - Apr 7
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 $940, price is now $422 per person
$422
per person
Mar 29 - Apr 1
found 1 day 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 $833, price is now $534 per person
$534
per person
Mar 29 - Apr 1
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 $2,574, price is now $1,710 per person
$1,710
per person
Apr 30 - May 4
found 18 hours ago
Roundtrip flight included
Nashville (BNA) to Boston (BOS)

Pittsfield Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was $1,296, price is now $852 per person
$852
per person
Apr 5 - Apr 10
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
Save 100% on your flight
Price was $2,176, price is now $1,252 per person
$1,252
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was $2,440, price is now $1,426 per person
$1,426
per person
May 15 - May 22
found 20 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was $1,851, price is now $1,184 per person
$1,184
per person
May 15 - May 22
found 20 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Boston (BOS)

Top Flight Deals

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

Breeze Airways
Sat, Jun 6 - Sat, Jun 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 23 hours ago
$102
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Sat, Jun 6 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 6, priced at $102 found 23 hours ago
Breeze Airways
Thu, Mar 5 - Thu, Mar 12
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$116 Roundtrip, found 5 days ago
$116
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Mar 5 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Mar 12, priced at $116 found 5 days ago
JetBlue Airways
Tue, Apr 7 - Sat, Apr 11
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$142 Roundtrip, found 15 hours ago
$142
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Tue, Apr 7 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Apr 11, priced at $142 found 15 hours ago
Breeze Airways
Thu, Mar 19 - Sun, Mar 22
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$177 Roundtrip, found 18 hours ago
$177
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, Mar 19 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, Mar 22, priced at $177 found 18 hours ago