Pleasant Point Vacation Packages

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Top Holiday Package Deals in Pleasant Point

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Aug 26 - Sep 1
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
Door into the room was swelled and very difficult to open.

Reviewed on Jul. 17, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
This property by far exceeded my expectations. We will no doubt be back and have recommended this hotel to many others.

Reviewed on Jul. 18, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Save 100% on your flight
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (135 reviews)
Nobody on property to talk to

Reviewed on May 20, 2025

The Cove At Salem

The Cove At Salem

3 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 22
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (595 reviews)
Great experience! Staff was super friendly, Room was pretty and smelled good! Game room was so nice with comfy, adorable chairs and hocus pocus decor, which I loved! I would definitely go back again.

Reviewed on Jul. 18, 2025

Frequently asked questions

How much does a Pleasant Point vacation package cost?
The cheapest Pleasant Point vacation package is CA $774, 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.

Discover the most popular places to visit in Pleasant Point

Marconi Beach

Marconi Beach

Why not spend a carefree afternoon at Marconi Beach during your travels in Wellfleet? Discover the area's seafood restaurants or seek out the hiking trails.

Marconi Beach
Cahoon Hollow Beach

Cahoon Hollow Beach

Enjoy a relaxing day at the beach and a lively night at the bar at this favorite daytrip destination.

Cahoon Hollow Beach
Mayo Beach

Mayo Beach

If a restful vacation is part of your travel plans, Mayo Beach might be the perfect place to seek out during your trip to Wellfleet. Discover the area's seafood restaurants or seek out the hiking trails.

Mayo Beach