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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.
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG

3 out of 5
Price was $687, price is now $431 per person
$431
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $863, price is now $484 per person
$484
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) 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 Bowlero Williamsburg and Williamsburg Premium Outlets are located nearby.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Price was $1,383, price is now $815 per person
$815
per person
Aug 4 - Aug 11
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
Book a stay at this beach hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. 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
Price was $1,167, price is now $716 per person
$716
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Price was $862, price is now $541 per person
$541
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Colonial Houses, an Official Colonial Williamsburg Hotel

Colonial Houses, an Official Colonial Williamsburg Hotel

3 out of 5
Price was $739, price is now $488 per person
$488
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
Book a stay at this spa hotel in Williamsburg. Enjoy 2 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.
Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Price was $1,931, price is now $1,314 per person
$1,314
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
Book a stay at this luxury hotel in Williamsburg. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $844, price is now $576 per person
$576
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) 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 Water Country USA are located nearby.

Gloucester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was $559, price is now $433 per person
$433
per person
Jun 23 - Jun 27
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Richmond (RIC)
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was $1,125, price is now $829 per person
$829
per person
Jun 23 - Jun 27
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Richmond (RIC)
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was $691, price is now $538 per person
$538
per person
Jun 23 - Jun 27
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $803, price is now $630 per person
$630
per person
Jun 23 - Jun 27
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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 $863, price is now $484 per person
$484
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was $1,383, price is now $815 per person
$815
per person
Aug 4 - Aug 11
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,167, price is now $716 per person
$716
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $862, price is now $541 per person
$541
per person
Aug 4 - Aug 11
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)

Top Flight Deals

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

Frontier Airlines
Mon, Jun 29 - Wed, Jul 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$58 Roundtrip, found 19 hours ago
$58
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Mon, Jun 29 from Hartsfield-Jackson Atlanta Intl. to Norfolk Intl., returning Wed, Jul 8, priced at $58 found 19 hours ago
Frontier Airlines
Thu, Sep 24 - Tue, Oct 13
MCO
Orlando Intl.
RIC
Richmond Intl.
$94 Roundtrip, found 3 days ago
$94
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Sep 24 from Orlando Intl. to Richmond Intl., returning Tue, Oct 13, priced at $94 found 3 days ago
Frontier Airlines
Sat, Jul 4 - Sun, Jul 12
MCO
Orlando Intl.
ORF
Norfolk Intl.
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jul 4 from Orlando Intl. to Norfolk Intl., returning Sun, Jul 12, priced at $117 found 6 days ago
Breeze Airways
Wed, Aug 26 - Mon, Sep 14
FLL
Fort Lauderdale - Hollywood Intl.
RIC
Richmond Intl.
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Fort Lauderdale - Hollywood Intl. to Richmond Intl., returning Mon, Sep 14, priced at $176 found 6 days ago