Pleasantville Vacations from $572

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Your Pleasantville Vacation

With every last detail organized before you take off, our Pleasantville vacation packages mean you can focus more on having a good time. Whether you base yourself in the neighborhood of Garden Lots, which is great for watersports, or someplace else, this lively city offers a wealth of discoveries. Any trip to Pleasantville needs a well-designed itinerary. Fill yours with big-name attractions like Halifax and Southwestern Railway Museum, Osprey Ridge Golf Course and Fort Point Museum. A few clicks is all it takes to craft your dream Pleasantville vacation on Expedia.

The Latest Pleasantville vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Halifax Airport by IHG

Holiday Inn Express & Suites Halifax Airport by IHG

2.5 out of 5
Price was $703, price is now $572 per person
$572
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
8.8/10 Excellent! (2,160 reviews)
Upon teaching the hotel we were suprised at the large amount garbage at the inview of the driveway. Other then that the roomwas clean and bed was satisfactory.

Reviewed on Sep 5, 2025

Lux Exec Home HFX Waterfront Pool Hot Tub

Lux Exec Home HFX Waterfront Pool Hot Tub

4.5 out of 5
Save 100% on your flight
Price was $1,825, price is now $1,097 per person
$1,097
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
10/10 Exceptional! (4 reviews)
Our stay was fabulous! The ho

Reviewed on Jul 25, 2025

Prince George Hotel

Prince George Hotel

4 out of 5
Downtown Halifax
Price was $807, price is now $637 per person
$637
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
9.4/10 Exceptional! (1,497 reviews)
Our stay here was a pleasure. Everyone was cheerful and accomodating every step of the way. The place is lively. When our in-room coffee maker stopped working at 6:30 in the morning, there was a brand new one up and running within a few minutes. Special shout out to concierges Raoul and Andy - they were so helpful and gave great suggestions for where to eat and what to do.

Reviewed on Sep 4, 2025

Nalu Retreat & Nordic Spa

Nalu Retreat & Nordic Spa

5 out of 5
Price was $1,368, price is now $1,102 per person
$1,102
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
9.6/10 Exceptional! (24 reviews)
Sandi was very helpful … beautiful views.. bucket list experience !!!! 10/10

Reviewed on Jul 7, 2025

Nalu Retreat Lakeside

Nalu Retreat Lakeside

3 out of 5
Price was $1,201, price is now $994 per person
$994
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
No reviews
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Pleasantville Hotel Deals

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St, Bridgewater, NS
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $162 total per night from Sep 19 to Sep 20
$162 total
Sep 19 - Sep 20
Total with taxes and fees
Travelodge by Wyndham Bridgewater
Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

3.5 out of 5
527 Highway 10 Exit 12, Cookville, NS
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $181 total per night from Sep 14 to Sep 15
$181 total
Sep 14 - Sep 15
Total with taxes and fees
Best Western Plus Bridgewater Hotel & Convention Centre
Miller House By the Bay

Miller House By the Bay

2 out of 5
624 Main street, mahone bay, NS
$102 nightly
The price is $117 total per night from Oct 2 to Oct 3
$117 total
Oct 2 - Oct 3
Total with taxes and fees
Miller House By the Bay
See all 213 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?
You can pick up a vacation package to this popular destination from $572 on Expedia. But how much your vacation to Pleasantville costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Pleasantville?
You can usually find reduced prices and greater availability in November, December and January. Take a look at our cheap Pleasantville vacation packages and you could land some great off-season discounts.
How many days is enough for Pleasantville?
Typically, a handful of days is enough to go to the top attractions during your Pleasantville vacation. However, if you want to have more time to rest or go on day trips, consider extending your itinerary.
How to find the best Pleasantville package deals?
Use Expedia's filters to help you find some tempting Pleasantville package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Pleasantville package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Pleasantville vacation as a package?
You can enjoy significant savings on your next Pleasantville break by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great 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 land a better deal.
When to book a vacation package to Pleasantville?
Secure incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Pleasantville escape.
Does Expedia offer Book Now, Pay Later Pleasantville vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Pleasantville trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.