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Gloucester Vacation Packages

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Gloucester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $1,303, price is now $814 per person
$814
per person
Aug 20 - Aug 22
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 Harbor are located nearby.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Save 100% on your flight
Price was $2,201, price is now $1,214 per person
$1,214
per person
Aug 3 - Aug 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and concierge services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $2,045, price is now $1,173 per person
$1,173
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this beach guesthouse in Dennis Port. Enjoy free WiFi, free parking, and a private beach. Popular attractions Sea Street Beach and Pleasant Road Beach are located nearby.
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,387, price is now $889 per person
$889
per person
Jul 7 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Popular attractions Harvard Square and Fenway Park are located nearby.
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,647, price is now $1,700 per person
$1,700
per person
Jul 26 - Jul 30
found 18 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this business-friendly resort in Nantucket. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Nobadeer Beach and Madequecham Pond are located nearby.
Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
Save 100% on your flight
Price was $1,688, price is now $1,089 per person
$1,089
per person
Aug 15 - Aug 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Stay at this hostel in Boston. Enjoy free WiFi, a snack bar/deli, and housekeeping. Popular attractions TD Garden and Boston Harbor are located nearby.
Chatham Tides

Chatham Tides

2.5 out of 5
Save 100% on your flight
Price was $3,727, price is now $2,478 per person
$2,478
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this beach motel in South Chatham. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Red River Beach and Forest Beach are located nearby.
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Save 100% on your flight
Price was $1,325, price is now $890 per person
$890
per person
Jul 5 - Jul 11
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy 2 bars/lounges, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions New England Aquarium and Boston Harbor are located nearby.

Gloucester 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
Save 100% on your flight
Price was $1,303, price is now $851 per person
$851
per person
Aug 19 - Aug 22
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 $1,788, price is now $980 per person
$980
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,647, price is now $1,700 per person
$1,700
per person
Jul 26 - Jul 30
found 18 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Boston (BOS)
Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Save 100% on your flight
Price was $1,688, price is now $1,089 per person
$1,089
per person
Aug 15 - Aug 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)

Gloucester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was $1,919, price is now $1,102 per person
$1,102
per person
Jul 7 - Jul 12
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 $2,966, price is now $1,461 per person
$1,461
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $2,045, price is now $1,173 per person
$1,173
per person
Jul 10 - Jul 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $5,751, price is now $3,534 per person
$3,534
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Boston (BOS)

Top Flight Deals

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

JetBlue Airways
Tue, Aug 11 - Thu, Sep 3
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, found 12 hours ago
$237
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Tue, Aug 11 from Los Angeles Intl. to Logan Intl., returning Thu, Sep 3, priced at $237 found 12 hours ago
Bargain Flight
Sat, Jun 6 - Sat, Jun 13
PDX
Portland Intl.
BOS
Logan Intl.
$302 Roundtrip, found 3 hours ago
$302
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Sat, Jun 6 from Portland Intl. to Logan Intl., returning Sat, Jun 13, priced at $302 found 3 hours ago
Delta
Tue, Jun 23 - Fri, Jul 24
HKG
Hong Kong Intl.
BOS
Logan Intl.
$1,045 Roundtrip, found 1 hour ago
$1,045
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jun 23 from Hong Kong Intl. to Logan Intl., returning Fri, Jul 24, priced at $1,045 found 1 hour ago
Hainan Airlines
Tue, Sep 15 - Wed, Sep 23
PVG
Pudong Intl.
BOS
Logan Intl.
$1,098 Roundtrip, found 15 hours ago
$1,098
Roundtrip
found 15 hours ago
Select Hainan Airlines flight, departing Tue, Sep 15 from Pudong Intl. to Logan Intl., returning Wed, Sep 23, priced at $1,098 found 15 hours ago