Pleasantville Vacations from $518

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The Latest Pleasantville vacation packages

Price found within the past 48 hours. Click for updated prices.
The Gilmore, an AvantStay Hotel

The Gilmore, an AvantStay Hotel

4 out of 5
12 South
Price was $693, price is now $518 per person
$518
per person
Jan 25 - Jan 29
found 1 day ago
Roundtrip flight included
Miami (MIA) to Nashville (BNA)
9.8/10 Exceptional! (782 reviews)
The hotel was very clean and there was always plenty of parking in the garage!

Reviewed on Nov 9, 2026

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Price was $1,337, price is now $951 per person
$951
per person
Jan 9 - Jan 12
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (1,005 reviews)

Loews Nashville Hotel at Vanderbilt Plaza

Loews Nashville Hotel at Vanderbilt Plaza

4 out of 5
West End
Price was $994, price is now $729 per person
$729
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (1,007 reviews)

Fairlane Hotel

Fairlane Hotel

4 out of 5
Downtown Nashville
Price was $1,015, price is now $749 per person
$749
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (1,000 reviews)

The Hermitage Hotel

The Hermitage Hotel

5 out of 5
Downtown Nashville
Price was $1,133, price is now $876 per person
$876
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
New York (NYC) to Nashville (BNA)
9.6/10 Exceptional! (937 reviews)

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What to do in Pleasantville

The Ultimate Back Country Adventure: 4 Hour Can-Am Experience

The Ultimate Back Country Adventure: 4 Hour Can-Am Experience

$299
per adult
100% of travellers recommend
The Ultimate Back Country Adventure: 4 Hour Can-Am Experience
See all activities in Pleasantville

Pleasantville Hotel Deals

Holiday Inn Express Hurricane by IHG

Holiday Inn Express Hurricane by IHG

2.5 out of 5
15368 Highway 13 S Hurricane Mills TN
$118 nightly
The price is $133 total per night from Nov 15 to Nov 16
$133 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express Hurricane by IHG
Days Inn by Wyndham Hurricane Mills

Days Inn by Wyndham Hurricane Mills

2 out of 5
15415 Highway 13 S Hurricane Mills TN
$79 nightly
The price is $89 total per night from Nov 10 to Nov 11
$89 total
Nov 10 - Nov 11
Total with taxes and fees
Days Inn by Wyndham Hurricane Mills
Econo Lodge Inn & Suites Centerville

Econo Lodge Inn & Suites Centerville

2.5 out of 5
634 David St Centerville TN
$48 nightly
The price is $56 total per night from Dec 6 to Dec 7
$56 total
Dec 6 - Dec 7
Total with taxes and fees
7/10 Good! (73 reviews)
"It was ok"

Reviewed on Oct 14, 2026

Econo Lodge Inn & Suites Centerville
See all 76 properties in Pleasantville
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 Pleasantville Vacation Packages

Pleasantville Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Pleasantville vacation package cost?
Offering excellent value package deals from $518 on Expedia, you'll be thrilled with how little a vacation to Pleasantville costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Pleasantville?
If you're looking to book a cheap Pleasantville vacation package, consider planning a trip in February, July and November. You'll usually find better rates on hotels and airfares during these months — ideal for a budget-friendly break.
How many days is enough for Pleasantville?
Typically, a handful of days is enough to see the main attractions during your Pleasantville vacation. However, if you want to have some time to chill out or go on day trips, think about extending your itinerary.
How to find the best Pleasantville package deals?
Landing a cheap Pleasantville package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most economical Pleasantville package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Pleasantville vacation as a package?
You can enjoy significant savings on your next Pleasantville break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Pleasantville?
Land fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Pleasantville trip.
Does Expedia offer Book Now, Pay Later Pleasantville vacation packages?
Jet off on your dream getaway to Pleasantville with our Book Now, Pay Later vacations. No need to save like crazy or wait for your next payday — we've teamed up with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.