Pleasantville Vacations from $673

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The Latest Pleasantville vacation packages

Price found within the past 48 hours. Click for updated prices.
Caption by Hyatt Downtown Nashville

Caption by Hyatt Downtown Nashville

3 out of 5
Downtown Nashville
Price was $942, price is now $673 per person
$673
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (700 reviews)
Room was perfect for our needs. Staff was attentive and always willing to help or suggest different things for us. Wish bar had more live music but understand thats not what its there for.

Reviewed on Feb 4, 2026

The Gilmore, an AvantStay Hotel

The Gilmore, an AvantStay Hotel

4 out of 5
12 South
Save 100% on your flight
Price was $1,437, price is now $953 per person
$953
per person
Apr 20 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9.8/10 Exceptional! (204 reviews)
Room and hotel were clean. Room was a little smaller than I was expecting but was nice! Mattress was stiff so some like that and some don’t. Room seemed really warm and we had it on 60 and wouldn’t cool off. Had to open door to balcony. Kitchenette is nice if you are staying longer. It is in a really nice little area with plenty of food and beverage choices within walking distance. I would definitely stay again.

Reviewed on Feb 10, 2026

Margaritaville Hotel Nashville

Margaritaville Hotel Nashville

4.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,361, price is now $925 per person
$925
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (1,919 reviews)
My only complaint would be the cost of valet parking. My nephew came to meet us and have dinner and was charged 75$ for a hour and a half…that’s ridiculous as guest of guests staying at this hotel and eating dinner at JWB…

Reviewed on Jan 19, 2026

Bode Nashville

Bode Nashville

3.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,510, price is now $1,070 per person
$1,070
per person
Mar 24 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (1,003 reviews)
nice room, nice location, staff was friendly

Reviewed on Feb 10, 2026

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Price was $1,255, price is now $916 per person
$916
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (924 reviews)
Spotless rooms, amazing staff, beautiful design

Reviewed on Jan 12, 2026

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The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Discover the most popular places to visit in Pleasantville

Grinder's Switch Winery

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

Days Inn by Wyndham Hurricane Mills

Days Inn by Wyndham Hurricane Mills

2 out of 5
15415 Highway 13 S Hurricane Mills TN
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $77 total per night from Feb 27 to Feb 28
$77 total
Feb 27 - Feb 28
Total with taxes and fees
7/10 Good! (463 reviews)
Waste of money

Reviewed on Jan 30, 2026

Days Inn by Wyndham Hurricane Mills
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
$111 nightly
The price is $125 total per night from Mar 1 to Mar 2
$125 total
Mar 1 - Mar 2
Total with taxes and fees
9.2/10 Wonderful! (382 reviews)
The staff were the BEST! Super friendly, helpful, and very knowledgeable. Rooms were clean and beautiful! Breakfast was outstanding! Highly recommend!

Reviewed on Jan 26, 2026

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
$71 nightly
The price is $83 total per night from Feb 20 to Feb 21
$83 total
Feb 20 - Feb 21
Total with taxes and fees
Embassy Inn
See all 86 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 $673 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.