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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 Lodge and Suites

Boston Lodge and Suites

4 out of 5
Price was $1,360, price is now $446 per person
$446
per person
Nov 3 - Nov 7
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.
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Price was $1,485, price is now $744 per person
$744
per person
Dec 4 - Dec 7
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 Faneuil Hall Marketplace are located nearby.
Hotel and staff were excellent. The SeaGrill waitstaff was especially friendly and accommodating

Reviewed on Sep 15, 2026

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
Save 100% on your flight
Price was $1,535, price is now $852 per person
$852
per person
Dec 1 - Dec 6
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 Boston Harbor and Faneuil Hall Marketplace are located nearby.

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Price was $3,367, price is now $2,075 per person
$2,075
per person
Nov 21 - Nov 27
found 23 hours 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 room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Price was $2,849, price is now $1,801 per person
$1,801
per person
Nov 21 - Nov 27
found 23 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.
I think I found my fav hotel in Boston. Great location too.

Reviewed on Sep 16, 2026

Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
Price was $1,520, price is now $992 per person
$992
per person
Nov 26 - Nov 29
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 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $1,057, price is now $690 per person
$690
per person
Dec 4 - Dec 7
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
Save 100% on your flight
Price was $883, price is now $626 per person
$626
per person
Dec 6 - Dec 10
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.
Amazing place

Reviewed on Sep 15, 2026

Gloucester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,360, price is now $446 per person
$446
per person
Nov 3 - Nov 7
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 $1,485, price is now $744 per person
$744
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $1,850, price is now $1,075 per person
$1,075
per person
Dec 2 - Dec 5
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
Price was $810, price is now $474 per person
$474
per person
Dec 4 - Dec 7
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.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
Price was $1,535, price is now $852 per person
$852
per person
Dec 1 - Dec 6
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 $2,577, price is now $1,375 per person
$1,375
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was $3,367, price is now $2,075 per person
$2,075
per person
Nov 21 - Nov 27
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was $2,849, price is now $1,801 per person
$1,801
per person
Nov 21 - Nov 27
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.

Southwest Airlines
Wed, Oct 21 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$262 Roundtrip, found 4 hours ago
$262
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Los Angeles Intl. to Logan Intl., returning Sat, Oct 31, priced at $262 found 4 hours ago
American Airlines
Tue, Nov 3 - Sat, Nov 7
PDX
Portland Intl.
BOS
Logan Intl.
$273 Roundtrip, found 4 hours ago
$273
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Nov 3 from Portland Intl. to Logan Intl., returning Sat, Nov 7, priced at $273 found 4 hours ago
Bargain Flight
Wed, Nov 18 - Mon, Nov 23
LAX
Los Angeles Intl.
BOS
Logan Intl.
$289 Roundtrip, found 2 days ago
$289
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Nov 18 from Los Angeles Intl. to Logan Intl., returning Mon, Nov 23, priced at $289 found 2 days ago
United
Wed, Oct 7 - Thu, Oct 29
HKG
Hong Kong Intl.
BOS
Logan Intl.
$852 Roundtrip, found 3 hours ago
$852
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Oct 7 from Hong Kong Intl. to Logan Intl., returning Thu, Oct 29, priced at $852 found 3 hours ago