Gloucester Vacations
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Gloucester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Hotel and Suites Richmond West End by IHG
Laurel
$474
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Short Pump Town Center and Bowlero West End are located nearby.
Quirk Hotel Richmond
Downtown Richmond
$786
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Maymont Park are located nearby.
it would be nice to have shade on the roof top bar better menu
Reviewed on Aug 15, 2026
The Commonwealth
Downtown Richmond
$648
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
New York (LGA) 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 Maymont Park are located nearby.
Quiet room all night, great meal and friendly staff. A welcoming bath, spacious area..., don't need much else- Thanks to your team !!
Really enjoyed the decor too, we felt special.
Reviewed on Aug 14, 2026
Omni Richmond Hotel
Downtown Richmond
$685
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Maymont Park are located nearby.
Omni Hotel is top notch, this was our first time staying at an Omni Hotel and we loved it. It was clean, the staff was awesome, they provided us with great places to visit, and eat. And I cant say enough about the bed....it was the most comfortable bed we've slept in away from home. We've stayed at other brand properties but none compare to the service and quality at the Omni Richmond.
Reviewed on Aug 13, 2026
Delta Hotels by Marriott Richmond Downtown
Downtown Richmond
$722
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
Book a stay at this business-friendly hotel in Richmond. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Maymont Park are located nearby.
La Quinta Inn & Suites by Wyndham Richmond-Midlothian
North Chesterfield
$506
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
Book a stay at this business-friendly hotel in Midlothian. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chesterfield Towne Center and Mid-Lothian Mines Park are located nearby.
Gloucester Vacation Packages
Looking for ways save both time and money on your upcoming trip to Gloucester? Then look no further, as the AARP Travel Center Powered by Expedia® is here to help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Gloucester incredible. Our Travel Center is a one-stop shop where you can put together the best Gloucester vacation package for you and your family. We have a fabulous selection of flights and hotels, as well as local activities to choose from.
Gloucester Hotels
Our listings include accommodations that are close to all the Gloucester points of interest, and others that are just outside the city center for a more restful retreat.
From Gloucester hotels with pools and on-site restaurants, to boutique accommodations that add all the extra touches, you'll find a hotel here that will make your trip amazing. With AARP Travel Center's Gloucester hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Gloucester
The fact that you are traveling to Gloucester means your vacation is off to a fabulous start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Book Together and Save
As an AARP Member, you can cash in on all the great savings. You'll save on select hotels worldwide, flights, and car rentals. No matter what Gloucester vacation bundle you pick, your membership savings helps you get a great deal. The hardest packing you'll have to do is for your suitcase. Bundle now and get ready for your Gloucester vacation.
Top Hotel Deals
Holiday Inn Express Gloucester by IHG
6639 Forest Hill Ave Gloucester VA
Book a stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Book a stay at this spa aparthotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our ...
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Book a stay at this golf resort in Williamsburg. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the restaurant in our reviews. ...
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
Book a stay at this golf hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Wyndham Garden Williamsburg Busch Gardens Area
201 Water Country Pkwy Williamsburg VA
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
DoubleTree by Hilton Williamsburg
50 Kingsmill Rd Williamsburg VA
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the ...
Kingsmill Resort
1010 Kingsmill Rd Williamsburg VA
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 ...
King’s Creek Resort by Spinnaker
191 Cottage Cove Lane Williamsburg VA
Book a stay at this luxury aparthotel in Williamsburg. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Busch Gardens Williamsburg and ...
Comfort Suites Airport
12570 Jefferson Ave Newport News VA
Book a stay at this beach hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
Great Wolf Lodge Williamsburg
549 East Rochambeau Drive Williamsburg VA
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. ...
Hilton Vacation Club Greensprings Williamsburg
3500 Ludwell Pkwy Williamsburg VA
Book a stay at this golf resort in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Comfort Inn Williamsburg Gateway
331 Bypass Rd Williamsburg VA
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Holiday Inn Hotel & Suites Williamsburg-Historic Gateway by IHG
515 Bypass Rd Williamsburg VA
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 ...
Howard Johnson by Wyndham Williamsburg
6483 Richmond Rd Williamsburg VA
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
Comfort Suites Williamsburg Historic Area
237 Commons Way Williamsburg VA
Book a stay at this business-friendly hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Oct 14 - Fri, Oct 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$119
Roundtrip
found 1 day ago
Tue, Sep 8 - Sat, Sep 26
FLL
Fort Lauderdale - Hollywood Intl.
RIC
Richmond Intl.
$174
Roundtrip
found 3 days ago
Sat, Aug 29 - Tue, Sep 15
LGA
LaGuardia
ORF
Norfolk Intl.
$209
Roundtrip
found 5 days ago
Sat, Sep 19 - Wed, Sep 23
BOS
Logan Intl.
ORF
Norfolk Intl.
$257
Roundtrip
found 16 hours ago
Mon, Dec 21 - Tue, Jan 5
ATL
Hartsfield-Jackson Atlanta Intl.
RIC
Richmond Intl.
$261
Roundtrip
found 2 days ago
Best points of interest in Gloucester
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All accommodation types in Gloucester
More Types of Hotels
- Family Hotels in Gloucester
- Hotels with WiFi in Gloucester
- Pet-friendly Hotels in Gloucester
- Hotels with Air Conditioning in Gloucester
- Hotels with a Pool in Gloucester
- Beach Hotels in Gloucester
- Hotels with Complimentary Breakfast in Gloucester
- Smoke Free Hotels in Gloucester
- Hotel with wifi in Gloucester
- Hotels with Bars in Gloucester
- Hotels with Balconies in Gloucester
- Hotels with Fireplaces in Gloucester
- Hotels with Hot Tubs in Gloucester
- Resorts & Hotels with Spas in Gloucester
- Hotels with smoking rooms in Gloucester
- Hotels with an Indoor Pool in Gloucester