Pleasant Point Vacations from ￥250,268

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The Latest Pleasant Point Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was ￥326,024, price is now ￥250,268 per person
￥250,268
per person
Dec 26 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,687 reviews)
Perfect location, modern and nice surroundings.

Reviewed on Oct 17, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥435,640, price is now ￥296,117 per person
￥296,117
per person
Dec 26 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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 Oct 13, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was ￥432,806, price is now ￥305,010 per person
￥305,010
per person
Dec 26 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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 Oct 8, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was ￥473,992, price is now ￥337,164 per person
￥337,164
per person
Dec 26 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,019 reviews)
One of the best I’ve stayed at in a while

Reviewed on Oct 11, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was ￥387,836, price is now ￥276,904 per person
￥276,904
per person
Dec 26 - Jan 2
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,021 reviews)
Clean and stylish room

Reviewed on Oct 13, 2025

Pleasant Point Hotel Deals

Sandcastle Resort and Club

Sandcastle Resort and Club

3 out of 5
929 Commercial Street, Provincetown, MA
The price is ￥14,775 per night from Oct 20 to Oct 21
￥14,775
￥16,911 total
Oct 20 - Oct 21
includes taxes & fees
7.2/10 Good! (1,123 reviews)
"The view doesn't get any better in ocean front rooms. Close to the outdoor pool which was spotless and the rooms are clean and well stocked."

Reviewed on Oct 15, 2025

Sandcastle Resort and Club
The Villages at Ocean Edge

The Villages at Ocean Edge

3.5 out of 5
One Villages Drive, Brewster, MA
The price is ￥13,663 per night from Oct 21 to Oct 22
￥13,663
￥20,810 total
Oct 21 - Oct 22
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 Oct 14, 2025

The Villages at Ocean Edge
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is ￥56,968 per night from Oct 20 to Oct 21
￥56,968
￥68,459 total
Oct 20 - Oct 21
includes taxes & fees
9/10 Wonderful! (790 reviews)
"Wonderful experience"

Reviewed on Oct 6, 2025

Chatham Bars Inn
See all 3,998 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.

Frequently asked questions

How much does a Pleasant Point vacation package cost?
The cheapest Pleasant Point vacation package is ￥250,268, 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

5/5(7 reviews)

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