
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
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
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


Fairmont Copley Plaza, Boston
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
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
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

Chatham Bars Inn
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

The Villages at Ocean Edge
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
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.