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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.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was $459, price is now $337 per person
$337
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly motel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Save 100% on your flight
Price was $599, price is now $404 per person
$404
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this spa hotel in Williamsburg. Enjoy 3 outdoor pools, a full-service spa, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Wedmore Place

Wedmore Place

3.5 out of 5
Save 100% on your flight
Price was $809, price is now $552 per person
$552
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this spa hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Busch Gardens Williamsburg and Jamestown Settlement are located nearby.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $534, price is now $394 per person
$394
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free parking, an outdoor pool, and free water park access. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and Bowlero Williamsburg are located nearby.
Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Price was $519, price is now $389 per person
$389
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free parking, 2 outdoor pools, and 3 hot tubs. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Inn at 605

Inn at 605

3.5 out of 5
Save 100% on your flight
Price was $826, price is now $620 per person
$620
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Stay at this B&B in Williamsburg. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $481, price is now $365 per person
$365
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly resort in Williamsburg. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Great Wolf Lodge Williamsburg

Great Wolf Lodge Williamsburg

3.5 out of 5
Price was $746, price is now $574 per person
$574
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this family-friendly resort in Williamsburg. Enjoy 5 indoor pools, 2 restaurants, and 2 hot tubs. Our guests praise the helpful staff in our reviews. Popular attractions Williamsburg Premium Outlets and MagiQuest are located nearby.

Gloucester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Virginia Crossings Hotel, Tapestry Collection by Hilton

Virginia Crossings Hotel, Tapestry Collection by Hilton

3.5 out of 5
Price was $544, price is now $441 per person
$441
per person
Mar 16 - Mar 19
just found
Roundtrip flight included
New York (LGA) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $661, price is now $513 per person
$513
per person
Mar 16 - Mar 19
just found
Roundtrip flight included
New York (LGA) to Richmond (RIC)
Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was $785, price is now $621 per person
$621
per person
Mar 16 - Mar 19
just found
Roundtrip flight included
New York (LGA) to Richmond (RIC)
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was $574, price is now $461 per person
$461
per person
Mar 16 - Mar 19
just found
Roundtrip flight included
New York (LGA) to Richmond (RIC)

Gloucester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was $459, price is now $337 per person
$337
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
Price was $599, price is now $404 per person
$404
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Wedmore Place

Wedmore Place

3.5 out of 5
Save 100% on your flight
Price was $809, price is now $552 per person
$552
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $534, price is now $394 per person
$394
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)

Top Flight Deals

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

Spirit Airlines
Thu, Feb 5 - Mon, Feb 9
MCO
Orlando Intl.
RIC
Richmond Intl.
$61 Roundtrip, found 3 days ago
$61
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, Feb 5 from Orlando Intl. to Richmond Intl., returning Mon, Feb 9, priced at $61 found 3 days ago
Spirit Airlines
Wed, Mar 4 - Sat, Mar 14
FLL
Fort Lauderdale - Hollywood Intl.
RIC
Richmond Intl.
$77 Roundtrip, found 23 hours ago
$77
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Wed, Mar 4 from Fort Lauderdale - Hollywood Intl. to Richmond Intl., returning Sat, Mar 14, priced at $77 found 23 hours ago
Spirit Airlines
Sat, Jan 24 - Mon, Feb 2
ATL
Hartsfield-Jackson Atlanta Intl.
RIC
Richmond Intl.
$91 Roundtrip, found 3 days ago
$91
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sat, Jan 24 from Hartsfield-Jackson Atlanta Intl. to Richmond Intl., returning Mon, Feb 2, priced at $91 found 3 days ago
Spirit Airlines
Wed, Jan 21 - Thu, Jan 29
LGA
LaGuardia
RIC
Richmond Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Jan 21 from LaGuardia to Richmond Intl., returning Thu, Jan 29, priced at $100 found 1 day ago