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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 $1,420, price is now $562 per person
$562
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

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Price was $2,855, price is now $1,532 per person
$1,532
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury apartment in Everett. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Encore Boston Harbor and TD Garden are located nearby.

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Save 100% on your flight
Price was $1,206, price is now $666 per person
$666
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this business-friendly hotel in Brookline. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Fenway Park and Harvard Square are located nearby.

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $2,383, price is now $1,342 per person
$1,342
per person
Oct 28 - Nov 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 Faneuil Hall Marketplace are located nearby.
It was great - def will stay again

Reviewed on Aug 25, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Save 100% on your flight
Price was $1,935, price is now $1,207 per person
$1,207
per person
Nov 5 - Nov 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, 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.
Amazing staff great hotel very comfortable with a great vibe to it.

Reviewed on Aug 25, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Save 100% on your flight
Price was $1,516, price is now $968 per person
$968
per person
Nov 5 - Nov 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 room service in our reviews. Popular attractions Copley Square and Fenway Park are located nearby.

Raffles Boston

Raffles Boston

5 out of 5
Save 100% on your flight
Price was $2,167, price is now $1,451 per person
$1,451
per person
Nov 3 - Nov 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 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 Bow Hotel

The Bow Hotel

4 out of 5
Save 100% on your flight
Price was $1,015, price is now $706 per person
$706
per person
Oct 23 - Oct 26
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Portsmouth. Enjoy free WiFi, concierge services, and bicycle rentals on site. Our guests praise the helpful staff in our reviews. Popular attractions Market Square and Water Country are located nearby.
Great accommodations, walkable to restaurants and shops in Portsmouth, great views, loved the stay!

Reviewed on Aug 24, 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 $1,420, price is now $562 per person
$562
per person
Nov 3 - Nov 7
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
Price was $2,855, price is now $1,532 per person
$1,532
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner
Save 100% on your flight
Price was $1,206, price is now $666 per person
$666
per person
Nov 5 - Nov 8
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 $2,383, price is now $1,342 per person
$1,342
per person
Oct 28 - Nov 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.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Save 100% on your flight
Price was $921, price is now $631 per person
$631
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner
Save 100% on your flight
Price was $2,151, price is now $1,192 per person
$1,192
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was $2,938, price is now $1,937 per person
$1,937
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $1,764, price is now $1,175 per person
$1,175
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)

Top Flight Deals

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

Frontier Airlines
Wed, Oct 21 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$244 Roundtrip, found 3 days ago
$244
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Los Angeles Intl. to Logan Intl., returning Sat, Oct 31, priced at $244 found 3 days ago
Bargain Flight
Tue, Oct 27 - Sat, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$279 Roundtrip, just found
$279
Roundtrip
just found
Select Bargain Flight flight, departing Tue, Oct 27 from Los Angeles Intl. to Logan Intl., returning Sat, Oct 31, priced at $279 just found
Bargain Flight
Tue, Nov 3 - Sat, Nov 7
PDX
Portland Intl.
BOS
Logan Intl.
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Nov 3 from Portland Intl. to Logan Intl., returning Sat, Nov 7, priced at $309 found 3 days ago
Air Canada
Wed, Oct 7 - Thu, Oct 29
HKG
Hong Kong Intl.
BOS
Logan Intl.
$780 Roundtrip, found 18 hours ago
$780
Roundtrip
found 18 hours ago
Select Air Canada flight, departing Wed, Oct 7 from Hong Kong Intl. to Logan Intl., returning Thu, Oct 29, priced at $780 found 18 hours ago