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Chester Vacation Packages

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Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
Price was $429, price is now $340 per person
$340
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
Book a stay at this golf resort in Williamsburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Jamestown Settlement and Williamsburg Premium Outlets are located nearby.
Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

3 out of 5
Price was $622, price is now $458 per person
$458
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $541, price is now $409 per person
$409
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $642, price is now $497 per person
$497
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $542, price is now $430 per person
$430
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Hilton Vacation Club Greensprings Williamsburg

Hilton Vacation Club Greensprings Williamsburg

3 out of 5
Price was $432, price is now $345 per person
$345
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
Book a stay at this golf resort in Williamsburg. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Jamestown Settlement and Williamsburg Premium Outlets are located nearby.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $544, price is now $439 per person
$439
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was $456, price is now $375 per person
$375
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) 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.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
Price was $429, price is now $340 per person
$340
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

3 out of 5
Price was $622, price is now $458 per person
$458
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $541, price is now $409 per person
$409
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $642, price is now $497 per person
$497
per person
Apr 23 - Apr 26
found 10 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Richmond (RIC)

Top Flight Deals

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

Spirit Airlines
Wed, Apr 22 - Wed, May 13
MCO
Orlando Intl.
RIC
Richmond Intl.
$69 Roundtrip, found 4 hours ago
$69
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Wed, Apr 22 from Orlando Intl. to Richmond Intl., returning Wed, May 13, priced at $69 found 4 hours ago
Spirit Airlines
Tue, Mar 10 - Sat, Mar 14
FLL
Fort Lauderdale - Hollywood Intl.
RIC
Richmond Intl.
$79 Roundtrip, found 5 days ago
$79
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Tue, Mar 10 from Fort Lauderdale - Hollywood Intl. to Richmond Intl., returning Sat, Mar 14, priced at $79 found 5 days ago
Frontier Airlines
Fri, Feb 13 - Fri, Feb 20
ATL
Hartsfield-Jackson Atlanta Intl.
RIC
Richmond Intl.
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Feb 13 from Hartsfield-Jackson Atlanta Intl. to Richmond Intl., returning Fri, Feb 20, priced at $99 found 3 days ago
Spirit Airlines
Tue, Feb 24 - Wed, Feb 25
LGA
LaGuardia
RIC
Richmond Intl.
$151 Roundtrip, found 2 days ago
$151
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Feb 24 from LaGuardia to Richmond Intl., returning Wed, Feb 25, priced at $151 found 2 days ago