Pleasantville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Pleasantville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Bluegreen Downtown Nashville
Downtown Nashville
CA $679
per person
Sep 28 - Oct 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Nashville (BNA)
9/10 Wonderful! (509 reviews)
The location was amazing. The staff was lovely and helpful. However, we did not receive any housekeeping. The hotel and the room were very clean, though. Overall, we liked our 3-night stay.
Reviewed on Aug 4, 2026
Reunion Hotel
East Nashville
CA $1,196
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Nashville (BNA)
8.4/10 Very good! (64 reviews)
Great location. Walk to nearby bars and restaurants and some shopping. Nice bar inside the hotel. We were there for the Tomato Art Festival and it was right in the middle of it. Very convenient.
Reviewed on Aug 10, 2026
Ready to book your vacation to Pleasantville?
Pleasantville Hotel Deals
Holiday Inn Express Hurricane by IHG
15368 Highway 13 S Hurricane Mills TN
Fully refundable
CA $177
CA $200 total
Aug 16 - Aug 17
includes taxes & fees
Embassy Inn
235 E Main St Hohenwald TN
Fully refundableReserve now, pay when you stay
CA $105
CA $122 total
Aug 12 - Aug 13
includes taxes & fees
Days Inn by Wyndham Hurricane Mills
15415 Highway 13 S Hurricane Mills TN
Fully refundableReserve now, pay when you stay
CA $120
CA $135 total
Aug 12 - Aug 13
includes taxes & fees
7/10 Good! (497 reviews)
"Very minimal breakfast available, we stayed at the comfort inn last year and they had a wonderful breakfast bar. I was very disappointed that this hotel only had a few bananas and oranges and for the price of the stay for the week, it wasn’t worth it."
Reviewed on Aug 9, 2026
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.
What to do in Pleasantville
Self-Guided Audio Driving Tour in Natchez Trace Parkway
CA $24
per traveller
4 Hour Back Country Can-Am Experience
CA $420
per adult
100% of travellers recommend
Williamsport: 2-Hour Back Country Adventure Ride
CA $348
per adult
Frequently asked questions
How much does a Pleasantville vacation package cost?
You can grab a vacation package to this destination from CA $679 on Expedia. But how much your vacation to Pleasantville costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Pleasantville?
If you'd like to book a cheap Pleasantville vacation package, consider travelling in January, February and October. You'll generally find lower rates on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Pleasantville?
Usually, a handful of days is enough to see the main sights during your Pleasantville vacation. But if you'd like to have more time to relax or go on day trips, think about extending your itinerary.
How to find the best Pleasantville package deals?
Finding a cheap Pleasantville package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Pleasantville package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Pleasantville vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can personalize your Pleasantville escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pleasantville?
Secure fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Pleasantville break.
How to plan a trip to Pleasantville?
- Pick your dates: What you'd like to do in Pleasantville and your preferred season can help you decide when to travel.
- Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to flights and activities. Your accommodations will probably be the largest expense during your trip to Pleasantville.
- Work out your trip length: Think about how much time you'd like to spend discovering Pleasantville. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Bundle your airfare and accommodations: Once you've settled on your dates and duration, book the right Pleasantville vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
