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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 $601, price is now $536 per person
$536
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly aparthotel 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.

The Commonwealth

The Commonwealth

4 out of 5
Price was $1,161, price is now $875 per person
$875
per person
Nov 25 - Nov 29
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this luxury hotel in Richmond. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.

Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Price was $934, price is now $789 per person
$789
per person
Nov 25 - Nov 29
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Short Pump Town Center and Short Pump Village are located nearby.

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $738, price is now $627 per person
$627
per person
Dec 10 - Dec 15
found 24 hours ago
Roundtrip non-stop 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 Merchants Square are located nearby.

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was $828, price is now $717 per person
$717
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Book a stay at this luxury aparthotel in Williamsburg. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.

Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Price was $827, price is now $729 per person
$729
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Price was $954, price is now $846 per person
$846
per person
Dec 27 - Jan 3
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Broad Street and Richmond Raceway are located nearby.

Rochambeau Williamsburg

Rochambeau Williamsburg

3 out of 5
Price was $775, price is now $692 per person
$692
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
Stay at this hotel in Williamsburg. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Busch Gardens Williamsburg and Merchants Square are located nearby.
Very clean rolm and well lovated. Just a short drive to the historic centre. Only down side for us was the lack of a kettle to make a drink and the aircon unit was noisy and difficult to use. Otherwise it’s a lovely little place to stay. Bike hire available and an ice house on site.

Reviewed on Oct 24, 2026

Gloucester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Rochambeau Williamsburg

Rochambeau Williamsburg

3 out of 5
Price was $775, price is now $692 per person
$692
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $1,161, price is now $875 per person
$875
per person
Nov 25 - Nov 29
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was $934, price is now $789 per person
$789
per person
Nov 25 - Nov 29
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Price was $827, price is now $729 per person
$729
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)

Gloucester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $738, price is now $627 per person
$627
per person
Dec 10 - Dec 15
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Rochambeau Williamsburg

Rochambeau Williamsburg

3 out of 5
Price was $874, price is now $713 per person
$713
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was $862, price is now $736 per person
$736
per person
Dec 27 - Jan 3
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $1,267, price is now $1,095 per person
$1,095
per person
Dec 27 - Jan 3
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

Top Flight Deals

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

Frontier Airlines
Thu, Nov 12 - Wed, Dec 2
MCO
Orlando Intl.
RIC
Richmond Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Orlando Intl. to Richmond Intl., returning Wed, Dec 2, priced at $63 found 1 day ago
Frontier Airlines
Sat, Nov 14 - Wed, Dec 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$113 Roundtrip, found 23 hours ago
$113
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Hartsfield-Jackson Atlanta Intl. to Norfolk Intl., returning Wed, Dec 2, priced at $113 found 23 hours ago
Frontier Airlines
Tue, Nov 10 - Mon, Nov 16
MCO
Orlando Intl.
ORF
Norfolk Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Nov 10 from Orlando Intl. to Norfolk Intl., returning Mon, Nov 16, priced at $119 found 2 days ago
Frontier Airlines
Wed, Dec 2 - Fri, Dec 11
DFW
Dallas-Fort Worth Intl.
ORF
Norfolk Intl.
$125 Roundtrip, found 2 hours ago
$125
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Dallas-Fort Worth Intl. to Norfolk Intl., returning Fri, Dec 11, priced at $125 found 2 hours ago