Southside All inclusive Vacations

Book a All inclusive Hotel + Flight or Car together to unlock savings

Top All inclusive vacation packages in Southside

Price found within the past 48 hours. Click for updated prices.
The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

Downtown Richmond
$588
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,354 reviews)
Make sure you are not in the rooms front from the restaurant across the street on a weekend, you can hear drunk people until 2AM.

Reviewed on Sep 27, 2026

The Commonwealth

The Commonwealth

Downtown Richmond
$619
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,402 reviews)
Overall okay experience But a great location

Reviewed on Sep 26, 2026

Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

Colonial Williamsburg
$1,652
per person
Dec 13 - Dec 17
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
9.8/10 Exceptional! (410 reviews)
Kingsmill Resort

Kingsmill Resort

Kingsmill
$876
per person
Nov 5 - Nov 8
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
8.6/10 Excellent! (1,004 reviews)
Quirk Hotel Richmond

Quirk Hotel Richmond

Downtown Richmond
$929
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
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5* All inclusive vacations in Southside

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

The Jefferson Hotel

Downtown Richmond
$1,028
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Richmond (RIC)
9.8/10 Exceptional! (1,005 reviews)
Such a great hotel - great staff, interesting, welcoming... we always feel good at the Jefferson. Our only ask is please, please improve the gym (though access to the great YMCA close by helps).

Reviewed on Sep 28, 2026

Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

Colonial Williamsburg
$1,652
per person
Dec 13 - Dec 17
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
9.8/10 Exceptional! (410 reviews)
Don't see what you're looking for?
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3 Night All inclusive vacations in Southside

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

Kingsmill Resort

Kingsmill
$548
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.6/10 Excellent! (1,004 reviews)
The Commonwealth

The Commonwealth

Downtown Richmond
$802
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,402 reviews)
Overall okay experience But a great location

Reviewed on Sep 26, 2026

Quirk Hotel Richmond

Quirk Hotel Richmond

Downtown Richmond
$929
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,001 reviews)
Don't see what you're looking for?
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4 Night All inclusive vacations in Southside

Price found within the past 48 hours. Click for updated prices.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

Midtown
$739
per person
Dec 13 - Dec 17
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
8.6/10 Excellent! (1,000 reviews)
The first room I was booked into had a truly terrible smell — bad enough to ask for a room change. The staff was very cooperative, but they moved me into a pretty musty smelling room with a broken AC/HVAC and a very loud portable AC/filtration unit. I’ve stayed there multiple times in the past and always had great experiences. But after this, not sure I can bring myself to go back.

Reviewed on Sep 20, 2026

The Commonwealth

The Commonwealth

Downtown Richmond
$799
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Richmond (RIC)
8.8/10 Excellent! (1,402 reviews)
Overall okay experience But a great location

Reviewed on Sep 26, 2026

Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

Colonial Williamsburg
$1,652
per person
Dec 13 - Dec 17
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Richmond (RIC)
9.8/10 Exceptional! (410 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Southside
View all trips

All-inclusive Southside vacations: everything you need to know

Can I book a Southside vacation with airfare and meals?

On an all-inclusive vacation, your mind and body can wander far from your wallet. Pay one simple price when you bundle your accommodation and airfare, and you avoid all those yucky bills after conversation-starting cocktails or decadent dinners.

How can I find Southside all-inclusive vacations that are adults only?

All the best all-inclusive, all-adult vacations are a click of a filter or two away. Choose from great grown-up features. Say, a spa for a couple’s massage, a hot tub to soak away the stresses of the day, or a swim-up bar to get the party started.

How much is an all-inclusive trip to Southside?

Affordable all-inclusive is yours, whatever your budget. Packages start tempting you from just $548. Prices and availability are subject to change. Additional terms may apply.

How can I book cheap all-inclusive trips to Southside?

Whenever you book your travel, sorting by price and filtering by budget shows you what’s out there in your price range.

What are the benefits of all-inclusive Southside vacations with airfare?

Create your dream getaway by bundling your flight and hotel and you get delightful deals and discounts. Add your car rental, too, and you save on all three.

What should I think about when I book an all-inclusive Southside family vacation package?

With little tummies taken care of, you just need to put smiles on their faces. Easy! Book an all-inclusive vacation with a full-on water park or epic pools—or book your stay near the world’s biggest theme parks and attractions.

Why should I book an all-inclusive honeymoon package in Southside?

You can start your married life how you mean to go on with an all-inclusive honeymoon package. Eat and drink to your heart’s content, waltz around in happy harmony, and have your fill of delights. Together, you can book up adventure excursions and return to a pool-side cabana for cocktails at sunset.

Can I book an all-inclusive Southside package with free cancellation and/or flexible dates?

When you’re searching for your all-inclusive getaway, filter your results by payment option to find free cancellation and buy now, pay later options. That way, you can rebook without worry, should your plans change.

Why should I book an all-inclusive Southside package vacation with Expedia?

Book amazing all-inclusive adventures, all in one place. Choose from a vast inventory of deals, adding every little extra to build your brilliant break in minutes.

Things to do

Historic Trolley Tour

Historic Trolley Tour

$45
per adult
100% of travellers recommend
Historic Trolley Tour
Down in the Shokoe Bottom, the most haunted neighborhood with 350+ years of history and hauntings!

The Haunted History of Richmond tour

$30
per adult
The Haunted History of Richmond tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$35
per adult
100% of travellers recommend
Richmond: Guided Hike in James River Park
See all activities in Southside

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.