Pleasant Point Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ฿4,531 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Pleasant Point

Holiday Hill Inn & Suites
Holiday Hill Inn & Suites
2 out of 5
352 Main Street, Dennis Port, MA
The price is ฿4,818 per night from 22 Jul to 23 Jul
฿4,818
฿5,514 total
22 Jul - 23 Jul
includes taxes & fees
8.2/10 Very Good! (858 reviews)
Good value
"It was clean, fairly large room and quiet. The ice cream in the front of the property was not good and the service was terrible, but other than that we had a nice stay. Towels were small and they were very stingy with them."

Reviewed on 27 Jun 2025

Holiday Hill Inn & Suites
The Provincetown Inn
The Provincetown Inn
3 out of 5
1 Commercial Street, Provincetown, MA
The price is ฿10,010 per night from 9 Jul to 10 Jul
฿10,010
฿12,567 total
9 Jul - 10 Jul
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"We usually stay at the Harbor hotel, but we tried this place and loved it.The food was great.The pool was great.The beach was great.We will definitely be back."

Reviewed on 6 Jul 2025

The Provincetown Inn
Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
The price is ฿32,862 per night from 9 Jul to 10 Jul
฿32,862
฿39,491 total
9 Jul - 10 Jul
includes taxes & fees
9.2/10 Wonderful! (769 reviews)
"Absolutely gorgeous property. Everything was top notch and close enough to be able to walk into town. Just what we were looking for."

Reviewed on 30 Jun 2025

Chatham Bars Inn
See all 4,427 properties in Pleasant Point
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.

Frequently asked questions

How much does a Pleasant Point holiday package cost?
The cheapest Pleasant Point holiday package is , so your dream trip can become a reality --- without spending an arm and a leg. Bundle flights, hotels, car rentals and more to tailor a package that's perfect for you.
How do I get a cheap travel package to Pleasant Point?
You'll save tons of cash if you combine your flights, car rentals and hotels into a Pleasant Point holiday package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer more than 550 airlines and 1,000,000 hotels worldwide, so you'll always have plenty of options to choose from. Eager to save even more? Add some exciting activities to your package deal to unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Pleasant Point?
A trip to Pleasant Point wouldn't be complete without stopping by Mayo Beach, Indian Neck Beach and Wellfleet Harbour Actors Theatre. Spend your nights near these popular sights and make sightseeing simple.
What are the top hotels in Pleasant Point?
If it's comfort and convenience you're after, look no further than Waterfront Views Of Creek - Beach Access. Spend your nights relaxing here and your days wandering around Pleasant Point's most well-known attractions.
How far in advance should I book my Pleasant Point holiday?
It's difficult to pick the ideal time for airfares, but we normally say the earlier, the better. Plenty of international journeys on Expedia become available up to 12 months in advance. If you can't book ahead, don't fret. Budget prices appear from time to time just weeks before departure dates.
What does an Expedia Pleasant Point travel package include?
Flights, hotels and rental cars --- we've got them well covered. With Expedia, you can shape your Pleasant Point travel package however you want. All you have to do is figure out just what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the greater your savings!
What should I know before booking a Pleasant Point travel package?
You can save big by combining your flights, hotels and rental cars. Once you've made your booking, you can add on things like tours and activities. Your next unforgettable holiday is only a few clicks away.
Can I choose my airline with a Pleasant Point Expedia holiday package?
Yes, and with more than 550 airlines to pick from throughout the world, you've got lots of choice. Browse the available options and find out which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Pleasant Point holiday package?
Don't worry if you're rethinking your Pleasant Point holiday package --- you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We know your circumstances can suddenly change, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.