Pleasant Point Holidays from AU$3,024

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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.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was AU$3,574, price is now AU$3,024 per person
AU$3,024
per person
28 Dec - 3 Jan
just found
Return flight included
Sydney (SYD) to Boston (BOS)
8.6/10 Excellent! (1,323 reviews)
The property is in good condition & it’s a safe area, but overall cleanliness lacks. At first glance it’s fine, but when you look in corners, behind toilet, shower floor, some furniture surfaces, window ledges, etc. it’s just not clean. Our door lock battery failed and it was eventually resolved by maintenance; however, the communication from front desk staff was nil and we had a flight to catch. She said very little to us and we had no idea if they were going to resolve the situation. The one thing she did say was that it was our fault by putting our hotel keys by our phones. Turns out the lock battery was dead and there was no apology and no communication on if/when it would be resolved. I won’t say don't stay here as it wasn’t awful, but they claim to be 4-star and I didn’t find cleanliness and service to be 4-star. Great location and walkable to North End/Little Italy & other areas like Boston Public Market, Quincy Market & The Garden if you want to go to a game. Dining is convenient and lots to choose from within walking distance.

Reviewed on 18 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
just found
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
just found
Return flight included
Sydney (SYD) to Boston (BOS)
9.8/10 Exceptional! (1,019 reviews)
This is a lovely hotel with great facilities in a superb location.

Reviewed on 21 Oct 2025

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
just found
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

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was AU$3,684, price is now AU$3,114 per person
AU$3,114
per person
28 Dec - 3 Jan
just found
Return flight included
Sydney (SYD) to Boston (BOS)
9.2/10 Wonderful! (1,175 reviews)
The place was nice, but the breakfast dropped the ball. Not many options for health conscious. I ordered some items in person for delivery and of course 2 of the 3 items were missing.

Reviewed on 19 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$172 per night from 23 Oct to 24 Oct
AU$172
23 Oct - 24 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 30 Oct to 31 Oct
AU$698
30 Oct - 31 Oct
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 3,991 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 holiday package cost?
The cheapest Pleasant Point holiday package is AU$3,024, 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.