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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.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Price was $596, price is now $442 per person
$442
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
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. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Save 100% on your flight
Price was $1,095, price is now $560 per person
$560
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
Book a stay at this family-friendly hotel in Williamsburg. Enjoy free parking, an outdoor pool, 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.
Property and staff were amazing!

Reviewed on Aug 31, 2026

The Commonwealth

The Commonwealth

4 out of 5
Price was $913, price is now $657 per person
$657
per person
Nov 20 - Nov 23
found 6 hours ago
Roundtrip flight included
Dallas (DFW) 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 Richmond Raceway and Richmond Old City Hall are located nearby.

TRAVEL INN

TRAVEL INN

2 out of 5
Price was $699, price is now $532 per person
$532
per person
Oct 11 - Oct 16
found 15 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
Stay at this hotel in Richmond. Enjoy free WiFi, free parking, and a casino. Popular attractions Maymont Park and Byrd Park are located nearby.

Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $791, price is now $607 per person
$607
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.

Williamsburg Sampler B & B

Williamsburg Sampler B & B

3 out of 5
Price was $923, price is now $735 per person
$735
per person
Oct 18 - Oct 21
found 23 hours ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
Stay at this B&B in Williamsburg. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Busch Gardens Williamsburg and Williamsburg Premium Outlets are located nearby.
Very nice B&B, warm and inviting. Comfortable bed.

Reviewed on Jun 7, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Price was $829, price is now $667 per person
$667
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
New York (NYC) 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.

Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
Price was $1,011, price is now $821 per person
$821
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Wanted to play pool but they said the table was reserved.

Reviewed on Aug 30, 2026

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $596, price is now $442 per person
$442
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Midtown
Save 100% on your flight
Price was $1,095, price is now $560 per person
$560
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $913, price is now $657 per person
$657
per person
Nov 20 - Nov 23
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
Williamsburg Sampler B & B

Williamsburg Sampler B & B

3 out of 5
Price was $923, price is now $735 per person
$735
per person
Oct 18 - Oct 21
found 23 hours ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)

Chester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ashland Studio Inn By OYO Richmond North near Kings Dominion

Ashland Studio Inn By OYO Richmond North near Kings Dominion

2.5 out of 5
Price was $715, price is now $522 per person
$522
per person
Oct 11 - Oct 16
found 15 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $1,334, price is now $932 per person
$932
per person
Oct 11 - Oct 16
found 15 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Price was $720, price is now $538 per person
$538
per person
Oct 11 - Oct 16
found 15 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

4 out of 5
Downtown Richmond
Price was $1,071, price is now $814 per person
$814
per person
Oct 11 - Oct 16
found 15 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)

Top Flight Deals

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

American Airlines
Sat, Sep 26 - Mon, Sep 28
MCO
Orlando Intl.
RIC
Richmond Intl.
$193 Roundtrip, found 10 hours ago
$193
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Sep 26 from Orlando Intl. to Richmond Intl., returning Mon, Sep 28, priced at $193 found 10 hours ago
Bargain Flight
Wed, Nov 11 - Sun, Nov 15
BOS
Logan Intl.
RIC
Richmond Intl.
$213 Roundtrip, found 14 hours ago
$213
Roundtrip
found 14 hours ago
Select Bargain Flight flight, departing Wed, Nov 11 from Logan Intl. to Richmond Intl., returning Sun, Nov 15, priced at $213 found 14 hours ago
JetBlue Airways
Tue, Oct 13 - Wed, Oct 14
FLL
Fort Lauderdale - Hollywood Intl.
RIC
Richmond Intl.
$236 Roundtrip, found 14 hours ago
$236
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, Oct 13 from Fort Lauderdale - Hollywood Intl. to Richmond Intl., returning Wed, Oct 14, priced at $236 found 14 hours ago
Bargain Flight
Tue, Oct 27 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
RIC
Richmond Intl.
$249 Roundtrip, found 14 hours ago
$249
Roundtrip
found 14 hours ago
Select Bargain Flight flight, departing Tue, Oct 27 from Hartsfield-Jackson Atlanta Intl. to Richmond Intl., returning Sat, Nov 14, priced at $249 found 14 hours ago