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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.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Save 100% on your flight
Price was $801, price is now $553 per person
$553
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Price was $1,691, price is now $925 per person
$925
per person
Aug 29 - Sep 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, 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.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,271, price is now $719 per person
$719
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Boston (BOS)
Book a stay at this luxury hotel in Lexington. Enjoy room service, free bicycles on site, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions Burlington Mall and Minute Man National Historical Park are located nearby.
The Charles Hotel

The Charles Hotel

4 out of 5
Save 100% on your flight
Price was $2,322, price is now $1,354 per person
$1,354
per person
Aug 28 - Sep 5
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
Raffles Boston

Raffles Boston

5 out of 5
Price was $4,106, price is now $2,580 per person
$2,580
per person
Aug 29 - Sep 5
found 3 hours 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 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Price was $3,601, price is now $2,344 per person
$2,344
per person
Aug 29 - Sep 5
found 3 hours 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 room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Price was $1,147, price is now $748 per person
$748
per person
Aug 29 - Sep 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 Faneuil Hall Marketplace and New England Aquarium are located nearby.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $889, price is now $607 per person
$607
per person
Aug 29 - Sep 1
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.

Gloucester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,271, price is now $719 per person
$719
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,691, price is now $925 per person
$925
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Save 100% on your flight
Price was $1,405, price is now $810 per person
$810
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,147, price is now $748 per person
$748
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

Gloucester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $1,132, price is now $710 per person
$710
per person
Sep 3 - Sep 8
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was $4,106, price is now $2,580 per person
$2,580
per person
Aug 29 - Sep 5
found 3 hours 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 $2,651, price is now $1,678 per person
$1,678
per person
Jul 23 - Jul 28
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,428, price is now $921 per person
$921
per person
Sep 6 - Sep 12
found 23 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.

JetBlue Airways
Tue, Sep 15 - Tue, Sep 15
LAX
Los Angeles Intl.
BOS
Logan Intl.
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 15 from Los Angeles Intl. to Logan Intl., returning Tue, Sep 15, priced at $242 found 1 day ago
United
Tue, Nov 3 - Sat, Nov 7
PDX
Portland Intl.
BOS
Logan Intl.
$278 Roundtrip, found 2 days ago
$278
Roundtrip
found 2 days ago
Select United flight, departing Tue, Nov 3 from Portland Intl. to Logan Intl., returning Sat, Nov 7, priced at $278 found 2 days ago
Delta
Wed, Jun 24 - Tue, Jul 21
HKG
Hong Kong Intl.
BOS
Logan Intl.
$1,043 Roundtrip, found 1 day ago
$1,043
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 24 from Hong Kong Intl. to Logan Intl., returning Tue, Jul 21, priced at $1,043 found 1 day ago
Hainan Airlines
Tue, Sep 15 - Wed, Sep 23
PVG
Pudong Intl.
BOS
Logan Intl.
$1,092 Roundtrip, found 6 days ago
$1,092
Roundtrip
found 6 days ago
Select Hainan Airlines flight, departing Tue, Sep 15 from Pudong Intl. to Logan Intl., returning Wed, Sep 23, priced at $1,092 found 6 days ago