Southside Vacations from $667

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Your Southside Vacation

Our vacation packages to Southside give you endless opportunities to discover new sights, sounds and tastes. And with all the details worked out, you can kick back and enjoy your city getaway just like you deserve. During your trip to Southside, give yourself enough time for sightseeing. A great place to begin exploring is Historic Collinsville. Don't delay exploring this city any longer. Your ultimate Southside vacation is a couple of clicks away with Expedia.

The Latest Southside vacation packages

Price found within the past 48 hours. Click for updated prices.
Waymore's Guest House

Waymore's Guest House

3.5 out of 5
East Nashville
Save 100% on your flight
Price was $1,012, price is now $667 per person
$667
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (1,537 reviews)
We stayed for one night while on road trip. Arrived really late and check-in was a really great experience. There’s a nice garage for the cars, which is included in price of the room. Room is comfortable (we got skyline view), loved the hardwood floors. Restaurant was amazing, with creative menu. We got a nice big breakfast before getting back on the road. Will definitely stay at this hotel again and check out rooftop bar!

Reviewed on Mar 7, 2026

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $2,006, price is now $1,318 per person
$1,318
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (1,014 reviews)
This place was amazing! Everyone was sooo nice and helpful! Per friendly and so easy to walk to broadway and the gulch!!! We will be staying here again!

Reviewed on Mar 9, 2026

Caption by Hyatt Downtown Nashville

Caption by Hyatt Downtown Nashville

4 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,289, price is now $863 per person
$863
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (899 reviews)
Room was on the smallerside but adequate. Very good espresso martinis

Reviewed on Mar 12, 2026

The Hermitage Hotel

The Hermitage Hotel

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $2,844, price is now $1,925 per person
$1,925
per person
Apr 22 - Apr 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.6/10 Exceptional! (858 reviews)
Beautiful Hotel and staff was wonderful.

Reviewed on Mar 13, 2026

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Discover the most popular places to visit in Southside

Historic Collinsville

4.5/5(2 reviews)

You can spend an afternoon exploring the galleries in Historic Collinsville in Southside. While you're in the area, stroll along the riverfront.

Historic Collinsville

Southside Hotel Deals

Quality Inn Exit 4

Quality Inn Exit 4

2.5 out of 5
3095 Wilma Rudolph Blvd Clarksville TN
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $96 total per night from Mar 29 to Mar 30
$96 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Beautiful lobby with great buffet breakfast.

Reviewed on Mar 13, 2026

Quality Inn Exit 4
La Quinta Inn & Suites by Wyndham Clarksville

La Quinta Inn & Suites by Wyndham Clarksville

3 out of 5
251 Holiday Dr Clarksville TN
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $115 total per night from Apr 6 to Apr 7
$115 total
Apr 6 - Apr 7
Total with taxes and fees
8.6/10 Excellent! (1,207 reviews)
Clean rooms & pleasant staff

Reviewed on Mar 11, 2026

La Quinta Inn & Suites by Wyndham Clarksville
Baymont by Wyndham Clarksville

Baymont by Wyndham Clarksville

2.5 out of 5
1112 Highway 76 Clarksville TN
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $87 total per night from Mar 30 to Mar 31
$87 total
Mar 30 - Mar 31
Total with taxes and fees
8.6/10 Excellent! (1,586 reviews)
Room was fair. Smelled of cigarette smoke. Contacted office and was instructed to cut on exhaust fan in the bathroom. He said it must be coming from someone in another room and that the rooms were all connected, whatever that means. Hot breakfast was the same every morning. By that I mean sausage ...

Reviewed on Mar 12, 2026

Baymont by Wyndham Clarksville
See all 608 properties in Southside
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.

Find the Best Southside Vacation Packages

Southside Essential Information

Language
English
Currency
U.S dollars
Top Sights
The City Forum, Skyline Lanes and Historic Collinsville

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Frequently asked questions

How much does a Southside vacation package cost?
You'll find cheap prices from $667 on Expedia for your Southside escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Southside costs.
What are the cheapest months to go to Southside?
If you're looking to snag a cheap Southside vacation package, consider planning a trip in November, December and January. You're likely to find better rates on accommodations and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Southside?
With a well-organized schedule, you can easily tick off the main Southside sights in a few days. But if you want to venture off the beaten track or take day trips, think about booking your Southside vacation for longer.
How to find the best Southside package deals?
Bagging a cheap Southside package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Southside package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Southside vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can personalize your Southside escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Southside?
If you have your Southside vacation dates confirmed, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Southside vacation packages?
If you're like us, you love going away but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Southside break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.