Pleasant Point Holidays from AU$3,107

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to AU$703 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

Your Pleasant Point Holiday

With a personalised holiday package to Pleasant Point, you'll spend less time planning and more time uncovering this sought-after neighbourhood. From its nature to its views, there's plenty to discover here. Hoping to see the sights during your trip to Pleasant Point? Don't miss nearby attractions such as Marconi Beach, Cahoon Hollow Beach and Indian Neck Beach. Stop daydreaming and start doing. When it's time to book your holiday to Pleasant Point, Expedia will help get you there.

Top Holiday Package Deals in Pleasant Point

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was AU$3,759, price is now AU$3,107 per person
AU$3,107
per person
28 Dec - 3 Jan
found 6 hours ago
Return flight included
Sydney (SYD) to Boston (BOS)
9/10 Wonderful! (1,086 reviews)
Great service from reception staff, and bustling cosy restaurant.

Reviewed on 13 Oct 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was AU$5,306, price is now AU$3,879 per person
AU$3,879
per person
27 Dec - 3 Jan
found 4 hours ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (475 reviews)
Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again.

Reviewed on 13 Oct 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was AU$5,441, price is now AU$4,030 per person
AU$4,030
per person
28 Dec - 2 Jan
found 4 hours ago
Return flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (169 reviews)
Overall, my husband & I enjoyed our stay at the Raffles -- but we weren't thrilled with the level of service we received. Specifically: - We checked in late (~11pm) due to a train delay, and the front desk informed us that our "butler" would reach out the next morning to introduce various services, etc. That never happened, which was disappointing because butler service is a Raffles staple that we were looking forward to experiencing. - Upon getting to our room, which was otherwise lovely, it became clear that the touchscreen-enabled lighting system had malfunctioned. This meant we could only have ALL the lights in the room (+ bathroom) 100% on or 100% off -- no in-between (and no dimming, etc). I alerted the front desk immediately, who offered to send an engineer "within an hour or so" -- but at that point it was nearly 12am, and we were too exhausted to wait so we declined. No one ever followed up with us or offered a solution to the issue, which grew increasingly annoying throughout our stay (e.g., I had to use my phone light to use the bathroom at night because the only other option would have been to turn ALL of the lights on 100% (and wakeup my husband). The issue also extended to the "request service" vs. "privacy please" button, so we had no way of requesting (or denying) maid service. - My husband & I celebrated our anniversary on this trip, and I let the hotel know in advance (hoping for at least a card or little treat) -- but this went 100% unacknowleged.

Reviewed on 20 Oct 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was AU$4,901, price is now AU$3,639 per person
AU$3,639
per person
28 Dec - 3 Jan
found 6 hours ago
Return flight included
Sydney (SYD) to Boston (BOS)
9.4/10 Exceptional! (522 reviews)
Great location but they have no concierge , and for the price you will think they would. Rooms are small

Reviewed on 8 Oct 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was AU$5,101, price is now AU$3,924 per person
AU$3,924
per person
28 Dec - 3 Jan
found 6 hours ago
Return flight included
Sydney (SYD) to Boston (BOS)
9.8/10 Exceptional! (1,008 reviews)
This is a lovely hotel with great facilities in a superb location.

Reviewed on 21 Oct 2025

Our pick of the best Pleasant Point Hotel Deals

Sandcastle Resort and Club

Sandcastle Resort and Club

3 out of 5
929 Commercial Street, Provincetown, MA
The price is AU$173 per night from 26 Oct to 27 Oct
AU$173
26 Oct - 27 Oct
includes taxes & fees
7.2/10 Good! (1,124 reviews)
"Very nice place in front of the beach, beautiful view whole year round ☀️🌊"

Reviewed on 19 Oct 2025

Sandcastle Resort and Club
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is AU$698 per night from 3 Nov to 4 Nov
AU$698
3 Nov - 4 Nov
includes taxes & fees
9/10 Wonderful! (791 reviews)
"Excellent experience all around Gorgeous location and beautiful hotel Lively lobby"

Reviewed on 13 Oct 2025

Chatham Bars Inn
The Villages at Ocean Edge

The Villages at Ocean Edge

3.5 out of 5
One Villages Drive, Brewster, MA
The price is AU$212 per night from 3 Nov to 4 Nov
AU$212
3 Nov - 4 Nov
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Nice room with a kitchen. Bed was large and comfy for two. Room cleaned daily. Coffee was replenished daily as well. The “campus” was beautiful. We were there in early October so the town was pretty much getting ready to close up"

Reviewed on 14 Oct 2025

The Villages at Ocean Edge
See all 3,996 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Pleasant Point holiday package cost?
The cheapest Pleasant Point holiday package is AU$3,107, 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.