Southside Vacation Packages 2026 from $444

Southside flight + hotel vacation packages

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

The Colonies at Williamsburg

$444

per person

Dec 10 - Dec 12

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Richmond (RIC)

2 outdoor tennis courts, an indoor pool, and a lazy river are all featured at this smoke-free hotel. Bring the family and enjoy the free water park, children's pool, and playground. Enjoy the gym and perks like free self parking.

Westgate Historic Williamsburg Resort

Midtown

$462

per person

Dec 12 - Dec 14

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Richmond (RIC)

This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free self parking and free WiFi.

Quirk Hotel Richmond

Downtown Richmond

$1,178

per person

Oct 26 - Nov 1

found 23 hours ago

Roundtrip flight included

Chicago (ORD) to Richmond (RIC)

This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.

Kingsmill Resort

Kingsmill

$554

per person

Dec 10 - Dec 12

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Richmond (RIC)

This smoke-free hotel features a golf course, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.

Wedmore Place

$549

per person

Dec 10 - Dec 12

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Richmond (RIC)

An attached winery and a restaurant are featured at this boutique hotel. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the gym and free perks like continental breakfast and free self parking.

Top Southside hotels deals

Red Roof Inn Richmond South

4350 Commerce Rd Richmond VA

Free Cancellation

Reserve now, pay when you stay

$66 nightly

$76 total

Sep 23 - Sep 24

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, express check-out, and concierge services are also on offer.

Pet friendly

Parking included

Four Points by Sheraton Richmond

9901 Midlothian Tpke Richmond VA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$126 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

Hyatt Place Richmond/Arboretum

201 Arboretum Place Richmond VA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$128 total

Sep 27 - Sep 28

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free buffet breakfast each morning.

Pool

Breakfast included

Country Inn & Suites by Radisson, Richmond I-95 South, VA

2401 Willis Rd Richmond VA

Free Cancellation

$89 nightly

$103 total

Oct 18 - Oct 19

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and laundry facilities and free newspapers are also offered.

Breakfast included

Free WiFi

Best Western Premier Richmond City Gateway

4303 Commerce Road Richmond VA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$118 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and free perks like full breakfast and free self parking. Free parking, a 24-hour business center, and a coffee shop are also offered.

Pool

Breakfast included

Candlewood Suites Richmond-South by IHG

4301 Commerce Rd Richmond VA

$98 nightly

$114 total

Oct 5 - Oct 6

Total with taxes and fees

A 24-hour gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Business travelers can take advantage of the 24-hour business center.

Pet friendly

Free WiFi

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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.

Stay near popular Southside attractions

A street intersection with a crosswalk, trees, and a building with a restaurant named "Panera Bread."

Stony Point Fashion Park

8.6/10 (16 reviews)

You can browse for the perfect souvenirs at Stony Point Fashion Park during your trip to Richmond. Attend a sporting event or simply enjoy the charming coffeehouses while you're in the area.

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Frequently asked questions

How much are vacation packages to Southside?

Get ready to be pleasantly surprised — you can find yourself in Southside for a mere $444. Let Travelocity save you money and hassle with our excellent vacation packages. With hotels, flights and tours all ready to go, why put it off?

Where can I get the best vacation package deals for Southside?

It's hard to look past Travelocity when it comes to finding your Southside package deal. There are as many as 400 partner airlines and 1,000,000 properties worldwide to select from. Book your trip now and get ready to cross another exciting destination off your must-visit list.

Why should I purchase my Southside vacation package with Travelocity?

We take the stress out of travel planning. Whether you're seeking an amazing new place to wander around or want to ensure you get the best price on offer, we're here to help. Our 24/7 customer support, top-quality service and Price Match Guarantee mean you can book with confidence with Travelocity.

Can I save on my Southside car rental if I bundle it with my hotel or flight?

Booking a Southside vacation package with Travelocity is a simple way to save you time and money. You can bundle a flight, hotel and car, or any combination of them, and land awesome discounts. You can also add on tours and experiences. After you've picked up the keys to your rental car, head out of the neighborhood and discover what this place has to offer. Roughly 100 mi from Southside, White House justifies a road trip.

What is the best time of year to go to Southside?

Take your vacation in and spend more of your cash on awesome experiences, not your hotel. This is the most inexpensive month to arrange your stay. Prices are highest in , so avoid traveling during this time if your budget is tight. April, August and October is the busiest period for Southside. You'll need to book ahead of time and be prepared to pay premium rates. November, December and January are the least popular months to visit.