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.
Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Price was CA $881, price is now CA $589 per person
CA $589
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (30 reviews)
Very impressed! Very clean, friendly staff, felt safe, the room was far bigger than expected, I’ll be back!

Reviewed on Sep. 1, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,572, price is now CA $1,444 per person
CA $1,444
per person
Nov 5 - Nov 8
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
Staff went above and beyond everyday! The dining options and location were amazing.

Reviewed on Sep. 2, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,229, price is now CA $2,596 per person
CA $2,596
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great harbor views! Room service was superb as well. Everyday we came back to an organized room and sometimes sweets, creams. The reception desk was also good in answering any questions. Excellent location. Would stay again.

Reviewed on Sep. 3, 2025

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was CA $1,510, price is now CA $1,001 per person
CA $1,001
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (2,140 reviews)
It was a great experience. A bit small for four people in one room. But we made due.

Reviewed on Sep. 2, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was CA $2,184, price is now CA $1,457 per person
CA $1,457
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,116 reviews)
The room was clean and well-appointed, the staff courteous and kind. The only thing was that it took 25 min to get our car in the morning from the valet, which I understand with city parking; I would just have requested it earlier. I’d definitely stay here again!

Reviewed on Sep. 3, 2025

Pleasant Point Hotel Deals

Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St, Provincetown, MA
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from Sep 28 to Sep 29
CA $202
CA $278 total
Sep 28 - Sep 29
includes taxes & fees
Harbor Hotel Provincetown
Captains Quarters Motel & Conference Center

Captains Quarters Motel & Conference Center

2 out of 5
5000 State Highway/Route 6, Eastham, MA
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Sep 7 to Sep 8
CA $122
CA $139 total
Sep 7 - Sep 8
includes taxes & fees
Captains Quarters Motel & Conference Center
The Provincetown Inn

The Provincetown Inn

3 out of 5
1 Commercial Street, Provincetown, MA
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Oct 5 to Oct 6
CA $223
CA $303 total
Oct 5 - Oct 6
includes taxes & fees
The Provincetown Inn
See all 4,342 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.
All Inclusive Vacations
All Inclusive Vacations
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Family Vacations

Frequently asked questions

How much does a Pleasant Point vacation package cost?
The cheapest Pleasant Point vacation package is CA $589, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.