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.
Studio Allston Hotel

Studio Allston Hotel

3.5 out of 5
Brighton
Price was CA $1,221, price is now CA $856 per person
CA $856
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.6/10 Excellent! (1,175 reviews)
Staff was friendly. Room was clean

Reviewed on Feb 5, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,075, price is now CA $1,643 per person
CA $1,643
per person
Apr 29 - May 2
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was CA $2,842, price is now CA $1,711 per person
CA $1,711
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out

Reviewed on Jan 25, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,582, price is now CA $1,072 per person
CA $1,072
per person
Mar 20 - Mar 23
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,302, price is now CA $887 per person
CA $887
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,000 reviews)
Staff was great we were treated with warm chocolate chip cookies. but Expedia told us breakfast was included and that was a lie

Reviewed on Feb 2, 2026

Pleasant Point Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is CA $498 per night from Feb 11 to Feb 12
CA $498
CA $570 total
Feb 11 - Feb 12
includes taxes & fees
9.2/10 Wonderful! (808 reviews)
Beautiful property

Reviewed on Jan 24, 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Feb 9 to Feb 10
CA $183
CA $269 total
Feb 9 - Feb 10
includes taxes & fees
9.2/10 Wonderful! (630 reviews)
Courteous staff, helpful with dining suggestions. Loved the room. Very comfortable bed, warm and cozy.

Reviewed on Jan 29, 2026

Chatham Wayside Inn
Modern Beachfront Condo, Gorgeous Views and Centrally Located

Modern Beachfront Condo, Gorgeous Views and Centrally Located

Provincetown MA
9.8/10 Exceptional! (60 reviews)
It was a great view, though we had a good look at a sauna/polar plunge group every day, hosted by a local yoga studio, that operated right behind our harborside window. Parking is a 5 minute walk away, but it is a very walkable area and you can do many things without driving anywhere. The flat is ...

Reviewed on Dec 29, 2025

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Modern Beachfront Condo, Gorgeous Views and Centrally Located
See all 4,169 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.
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Frequently asked questions

How much does a Pleasant Point vacation package cost?
The cheapest Pleasant Point vacation package is CA $856, 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

New stairs at 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

5/5(1 review)

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

Cahoon Hollow 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.