Search Deals on
Gloucester Vacation Packages

Build your package with 2 more options

Gloucester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Boston - Woburn/ Burlington

Red Roof Inn PLUS+ Boston - Woburn/ Burlington

2.5 out of 5
Price was $727, price is now $478 per person
$478
per person
Jun 9 - Jun 13
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Woburn. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Burlington Mall and MarketStreet Lynnfield are located nearby.
The Langham, Boston

The Langham, Boston

5 out of 5
Save 100% on your flight
Price was $1,291, price is now $798 per person
$798
per person
May 22 - May 25
found 2 days 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 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 $1,074, price is now $680 per person
$680
per person
Jun 25 - Jun 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Lexington Battle Green and Burlington Mall are located nearby.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $784, price is now $497 per person
$497
per person
Jun 1 - Jun 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this beach hotel in Beverly. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Salem Willows Beach and Lacrom Theatre are located nearby.
Life House, Nantucket

Life House, Nantucket

3.5 out of 5
Save 100% on your flight
Price was $2,556, price is now $1,700 per person
$1,700
per person
May 21 - May 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Stay at this hotel in Nantucket. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Jethro Coffin House and White Heron Theatre are located nearby.
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was $3,100, price is now $2,075 per person
$2,075
per person
Jun 20 - Jun 26
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
XV Beacon

XV Beacon

5 out of 5
Save 100% on your flight
Price was $3,282, price is now $2,206 per person
$2,206
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, 24-hour room service, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Boston Common and TD Garden are located nearby.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $799, price is now $546 per person
$546
per person
May 18 - May 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Mount Tom State Reservation and Nash's Dinosaur Track Quarry are located nearby.

Gloucester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Boston - Woburn/ Burlington

Red Roof Inn PLUS+ Boston - Woburn/ Burlington

2.5 out of 5
Price was $727, price is now $478 per person
$478
per person
Jun 9 - Jun 13
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,291, price is now $798 per person
$798
per person
May 22 - May 25
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
XV Beacon

XV Beacon

5 out of 5
Beacon Hill
Save 100% on your flight
Price was $3,282, price is now $2,206 per person
$2,206
per person
Jun 11 - Jun 15
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $799, price is now $546 per person
$546
per person
May 18 - May 22
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.
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,224, price is now $764 per person
$764
per person
May 30 - Jun 6
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 $1,691, price is now $855 per person
$855
per person
May 19 - May 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $2,674, price is now $1,613 per person
$1,613
per person
Jun 20 - Jun 26
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $4,990, price is now $3,070 per person
$3,070
per person
Jun 20 - Jun 26
found 14 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.

American Airlines
Tue, Jul 7 - Tue, Jul 14
LAX
Los Angeles Intl.
BOS
Logan Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jul 7 from Los Angeles Intl. to Logan Intl., returning Tue, Jul 14, priced at $217 found 1 hour ago
American Airlines
Sat, May 23 - Wed, Jun 10
PDX
Portland Intl.
BOS
Logan Intl.
$222 Roundtrip, found 2 hours ago
$222
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, May 23 from Portland Intl. to Logan Intl., returning Wed, Jun 10, priced at $222 found 2 hours ago
Delta
Thu, May 7 - Sat, May 9
PDX
Portland Intl.
BOS
Logan Intl.
$227 Roundtrip, found 2 hours ago
$227
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, May 7 from Portland Intl. to Logan Intl., returning Sat, May 9, priced at $227 found 2 hours ago
United
Tue, Aug 25 - Sat, Sep 5
LAX
Los Angeles Intl.
BOS
Logan Intl.
$227 Roundtrip, found 11 hours ago
$227
Roundtrip
found 11 hours ago
Select United flight, departing Tue, Aug 25 from Los Angeles Intl. to Logan Intl., returning Sat, Sep 5, priced at $227 found 11 hours ago