Pleasant Point Vacations from ￥159,292

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 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

The Latest Pleasant Point Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was ￥204,354, price is now ￥159,292 per person
￥159,292
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (1,218 reviews)
The lobby and hotel itself are beautiful, and the restaurants were fantastic. The front desk staff was also very friendly and helpful. A few areas could use some improvement: the heater in our room didn’t adjust properly and would reset itself, making the room uncomfortably warm at times. The rooms feel a bit outdated, and the toilet splashed water when flushed. Additionally, when our sheets were changed, we noticed hair left in the bed. Overall, we enjoyed our stay, but addressing these issues would make the experience even better.

Reviewed on Dec 10, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was ￥294,008, price is now ￥164,031 per person
￥164,031
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
8.4/10 Very Good! (188 reviews)
Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥254,772, price is now ￥191,032 per person
￥191,032
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Phenomenon phenomenon will definitely will be back

Reviewed on Nov 26, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was ￥219,770, price is now ￥180,880 per person
￥180,880
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.2/10 Wonderful! (1,196 reviews)
Good, clean, I am satisfied

Reviewed on Dec 3, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was ￥258,324, price is now ￥212,926 per person
￥212,926
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (536 reviews)
Very friendly staff. Amazing location. The room was perfect. Didn’t go to Contessa, but we ran into the Chef in the elevator and he was super fun and courteous. The bar is cool, we ate there a couple nights. We had a very pleasant Thanksgiving week there. Festive and lively hotel. There’s Tatte around the corner and every store you can think of within walking distance. Looking forward to our next stay!

Reviewed on Dec 4, 2025

Pleasant Point Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is ￥40,427 per night from Dec 14 to Dec 15
￥40,427
￥48,583 total
Dec 14 - Dec 15
includes taxes & fees
9.2/10 Wonderful! (797 reviews)
Helpful staff & food & drinks were great !

Reviewed on Dec 12, 2025

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

Modern Beachfront Condo, Gorgeous Views and Centrally Located

Provincetown MA
9.8/10 Exceptional! (57 reviews)
We loved our stay in this condo. It is beautifully designed with a fantastic kitchen. The view is stunning and you are right in the middle of everything. Parking could be a problem during the busy season since there isn’t any directly in front of the condo. Thankfully this wasn’t an issue for us. ...

Reviewed on Dec 2, 2025

Get rates
Modern Beachfront Condo, Gorgeous Views and Centrally Located
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street Brewster MA
The price is ￥25,461 per night from Jan 4 to Jan 5
￥25,461
￥38,053 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8.2/10 Very Good! (999 reviews)
Highly recommend. From check in to check out, the service was friendly, responsive and courteous. The room was also a great surprise. Large room with a large bathroom.Well appointed with a nice balcony. Good bathroom lighting for make-up and easy for two people to get ready at the same time. Beds ...

Reviewed on Sep 22, 2025

The Mansion at Ocean Edge
See all 4,179 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 ￥159,292, 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.