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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.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was $530, price is now $369 per person
$369
per person
May 4 - May 7
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this spa aparthotel in West Yarmouth. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hyannis Harbor and Mayflower Beach are located nearby.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Price was $1,894, price is now $934 per person
$934
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy a rooftop terrace, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Price was $1,792, price is now $1,067 per person
$1,067
per person
Apr 23 - Apr 26
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 Langham, Boston

The Langham, Boston

5 out of 5
Price was $1,145, price is now $763 per person
$763
per person
Apr 23 - Apr 26
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.
Beachside Village Resort

Beachside Village Resort

3 out of 5
Price was $1,181, price is now $803 per person
$803
per person
May 11 - May 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this beach apartment in Falmouth. Enjoy free WiFi, an outdoor pool, and daily housekeeping. Our guests praise the property condition in our reviews. Popular attractions Surf Drive Beach and Falmouth Beach are located nearby.
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
Save 100% on your flight
Price was $1,657, price is now $1,129 per person
$1,129
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fenway Park and Copley Square are located nearby.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Save 100% on your flight
Price was $1,395, price is now $970 per person
$970
per person
Jun 2 - Jun 8
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 full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New England Aquarium and TD Garden are located nearby.
Hampton Inn & Suites Portsmouth Downtown

Hampton Inn & Suites Portsmouth Downtown

3 out of 5
Save 100% on your flight
Price was $1,506, price is now $1,059 per person
$1,059
per person
May 31 - Jun 7
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Portsmouth. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Nahcotta and Moffatt-Ladd House are located nearby.

Pittsfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,145, price is now $763 per person
$763
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was $1,894, price is now $934 per person
$934
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,792, price is now $1,067 per person
$1,067
per person
Apr 23 - Apr 26
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 $1,252, price is now $870 per person
$870
per person
May 21 - May 25
found 16 hours 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.
Beachside Village Resort

Beachside Village Resort

3 out of 5
Price was $1,181, price is now $803 per person
$803
per person
May 11 - May 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was $2,889, price is now $1,120 per person
$1,120
per person
Jun 1 - Jun 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Save 100% on your flight
Price was $1,657, price is now $1,129 per person
$1,129
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
Bay Village
Save 100% on your flight
Price was $1,216, price is now $830 per person
$830
per person
May 27 - Jun 1
found 16 hours ago
Roundtrip flight included
Cleveland (CLE) to Boston (BOS)

Top Flight Deals

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

Breeze Airways
Thu, Mar 26 - Sun, Mar 29
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$128 Roundtrip, found 6 days ago
$128
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Mar 26 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Mar 29, priced at $128 found 6 days ago
Breeze Airways
Sat, Jun 6 - Sat, Jun 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$144 Roundtrip, found 1 hour ago
$144
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sat, Jun 6 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 6, priced at $144 found 1 hour ago
Breeze Airways
Wed, Apr 1 - Wed, Apr 8
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$211 Roundtrip, found 2 hours ago
$211
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Apr 1 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Apr 8, priced at $211 found 2 hours ago
American Airlines
Mon, May 4 - Sat, May 9
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$249 Roundtrip, found 2 hours ago
$249
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Mon, May 4 from Ronald Reagan Washington National to Manchester-Boston Regional, returning Sat, May 9, priced at $249 found 2 hours ago