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Chesterfield Vacation Packages

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Chesterfield Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Kings Dominion/Doswell

Days Inn by Wyndham Kings Dominion/Doswell

2 out of 5
Price was $516, price is now $458 per person
$458
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 family-friendly hotel in Doswell. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Kings Dominion and Meadow Event Park are located nearby.
Was relaxing, got what I need for a decent price. Front desk can be hit or miss

Reviewed on Oct 22, 2026

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 15 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 15 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 17 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.
The property and unit were really nice, but the beds were awful.

Reviewed on Oct 24, 2026

Best Western Premier Richmond City Gateway

Best Western Premier Richmond City Gateway

3 out of 5
Price was $729, price is now $622 per person
$622
per person
Jan 12 - Jan 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Richmond (RIC)
Stay at this hotel in Richmond. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broad Street and Virginia Capital Trail: Richmond Trailhead 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 13 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.
Awesome great bar as well

Reviewed on Oct 24, 2026

Chesterfield Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Best Western Premier Richmond City Gateway

Best Western Premier Richmond City Gateway

3 out of 5
Price was $729, price is now $622 per person
$622
per person
Jan 12 - Jan 15
found 1 day ago
Roundtrip flight included
New York (JFK) 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 15 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 15 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)

Chesterfield 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 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $1,295, price is now $904 per person
$904
per person
Dec 17 - Dec 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 9 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
Mon, Dec 7 - Wed, Dec 16
DFW
Dallas-Fort Worth Intl.
RIC
Richmond Intl.
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Dallas-Fort Worth Intl. to Richmond Intl., returning Wed, Dec 16, priced at $158 found 1 day ago
Bargain Flight
Sat, Jan 9 - Thu, Jan 14
BOS
Logan Intl.
RIC
Richmond Intl.
$215 Roundtrip, found 14 hours ago
$215
Roundtrip
found 14 hours ago
Select Bargain Flight flight, departing Sat, Jan 9 from Logan Intl. to Richmond Intl., returning Thu, Jan 14, priced at $215 found 14 hours ago
Breeze Airways
Sat, Nov 7 - Tue, Nov 10
FLL
Fort Lauderdale - Hollywood Intl.
RIC
Richmond Intl.
$220 Roundtrip, found 14 hours ago
$220
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Fort Lauderdale - Hollywood Intl. to Richmond Intl., returning Tue, Nov 10, priced at $220 found 14 hours ago