Pleasant Point 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*
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Top Holiday Package Deals in Pleasant Point
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
CA $1,601
per person
Dec 13 - Dec 17
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
Great location. A bit pricey for the size room. Easy to get most places by walking .
Reviewed on Oct 4, 2026
Four Seasons Hotel Boston
Bay Village
CA $1,584
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (485 reviews)
Beautiful hotel
Wonderful rooms and kids absolutely loved the vault ! Looking forward to staying again :)
Reviewed on Oct 3, 2026
The Langham, Boston
Downtown Boston
CA $1,606
per person
Dec 13 - Dec 17
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
The staff were incredibly helpful & nice. The hotel was beautiful & great location
Reviewed on Oct 4, 2026
Pleasant Point Hotel Deals
Chatham Bars Inn
297 Shore Rd Chatham MA
CA $557
CA $638 total
Nov 3 - Nov 4
includes taxes & fees
Harbor Hotel Provincetown
698 Commercial St Provincetown MA
Fully refundableReserve now, pay when you stay
CA $181
CA $256 total
Nov 1 - Nov 2
includes taxes & fees
8.4/10 Very good! (1,005 reviews)
"Terrific service. Hardwood floors in room are terrific idea to keep sand in check when returning from the beach. Room was very comfortable. When going downtown I highly recommend taking the provided shuttle. Everything is near the drop off point, and trying to find parking is almost impossible."
Reviewed on Oct 5, 2026
Cape Colony Inn
280 Bradford Street Provincetown MA
CA $141
CA $161 total
Oct 6 - Oct 7
includes taxes & fees
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 vacation package cost?
The cheapest Pleasant Point vacation package is CA $1,376, 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 vacation 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 Harbor Actors Theater. 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 vacation?
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 vacation is only a few clicks away.
Can I choose my airline with a Pleasant Point Expedia vacation 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 vacation package?
Don't worry if you're rethinking your Pleasant Point vacation 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.
Things to do
Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour
CA $35
per traveller
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
CA $70
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
CA $70
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.