Search Deals on
Chester Vacation Packages

Build your package with 2 more options

Leaving from

Going to

Departing

Returning

Travelers

Room 1

Adults

ChildrenAges 2 to 17

InfantsYounger than 2

Add specific hotel dates

An aerial view of a town with a prominent water tower, industrial buildings, and a main road.

Chester
Richmond
Virginia
United States of America
North America
Hotwire.com

Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5

Price was $580, price is now $436 per person

$436

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

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

Club Wyndham Governor’s Green

3 out of 5

Price was $977, price is now $767 per person

$767

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

Club Wyndham Kingsgate

3 out of 5

Price was $756, price is now $597 per person

$597

per person

Oct 18 - Oct 23

found 1 day ago

Roundtrip non-stop 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.

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 18 hours 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.

Wedmore Place

3.5 out of 5

Price was $817, price is now $662 per person

$662

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 Historic Jamestowne are located nearby.

Rochambeau Roadside Inn

2 out of 5

Price was $753, price is now $615 per person

$615

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

Stay at this hotel in Williamsburg. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Busch Gardens Williamsburg and Water Country USA are located nearby.

What a hidden gem! I’ll admit we were a little skeptical when we saw how great all the reviews were, but this place totally deserves it! It’s nothing like those typical chain hotels, so don’t expect a big lobby with old carpets and a subpar breakfast buffet. This place is for people who want cleanliness and a place that thought of all the little things! First and foremost…SO CLEAN! The room smells nice when you enter. Beds are soft. A proper amount of towels (no calling down for extras). A nice modern tile shower with incredible water pressure. Outlets everywhere. Free WiFi. An ice house with (ice, obviously) with free bike rentals and a little closet with all the stuff you might need but forgot. What a great place!!

Reviewed on Aug 31, 2026

Holiday Inn Club Vacations Williamsburg Resort by IHG

3.5 out of 5

Price was $664, price is now $544 per person

$544

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

Book a stay at this family-friendly resort in Williamsburg. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Popular attractions Williamsburg Premium Outlets and MagiQuest are located nearby.

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

3 out of 5

Colonial Williamsburg

Price was $580, price is now $436 per person

$436

per person

Oct 14 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)