Pleasantville Vacations from $333

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The Latest Pleasantville vacation packages

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

Sonesta Nashville Airport

4 out of 5
Save 100% on your flight
Price was $533, price is now $333 per person
$333
per person
Nov 7 - Nov 10
found 2 days ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (1,711 reviews)
Nice place. Cosmetic challenges, if you look around. For a resort, there should have been more to offer. Not sure if the resort fees, additional fees, and parking fees were necessary. Casino hotels would charge less and offer more.

Reviewed on Aug 31, 2025

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $2,739, price is now $1,557 per person
$1,557
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (837 reviews)
Fantastic and unique property. Walking distance to broadway.

Reviewed on Aug 27, 2025

Margaritaville Hotel Nashville

Margaritaville Hotel Nashville

4.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $976, price is now $621 per person
$621
per person
Nov 7 - Nov 10
found 2 days ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (1,834 reviews)
Had an amazing time. Beautiful hotel. The staff was awesome! Love the bartenders at the pool deck!!

Reviewed on Aug 28, 2025

The Sobro Guest House by AvantStay

The Sobro Guest House by AvantStay

4 out of 5
Downtown Nashville
Save 100% on your flight
Price was $2,055, price is now $1,334 per person
$1,334
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (1,000 reviews)
Great location Walkable to downtown and Nissan Stadium Free parking

Reviewed on Aug 1, 2025

Virgin Hotels Nashville

Virgin Hotels Nashville

4.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $831, price is now $540 per person
$540
per person
Nov 7 - Nov 10
found 2 days ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (2,234 reviews)
Love everything a out this hotel except it s not walking distance from broadway but really close by taxi ! The pool is super cool and the food was amazing

Reviewed on Aug 30, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Pleasantville

Grinder's Switch Winery

2.5/5(3 reviews)

You can enjoy a tasting or tour at Grinder's Switch Winery during your travels to Centerville. Discover the area's waterfalls and countryside.

Grinder's Switch Winery

Pleasantville Hotel Deals

Econo Lodge Inn & Suites

Econo Lodge Inn & Suites

2.5 out of 5
634 David St, Centerville, TN
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $72 total per night from Sep 7 to Sep 8
$72 total
Sep 7 - Sep 8
Total with taxes and fees
Econo Lodge Inn & Suites
Holiday Inn Express Hurricane by IHG

Holiday Inn Express Hurricane by IHG

2.5 out of 5
15368 Highway 13 S, Hurricane Mills, TN
Fully refundable
$132 nightly
The price is $149 total per night from Sep 7 to Sep 8
$149 total
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express Hurricane by IHG
Embassy Inn

Embassy Inn

2.5 out of 5
235 E Main St, Hohenwald, TN
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $81 total per night from Sep 1 to Sep 2
$81 total
Sep 1 - Sep 2
Total with taxes and fees
Embassy Inn
See all 84 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.

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Frequently asked questions

How much does a Pleasantville vacation package cost?
Offering excellent value package deals from $333 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.