Pleasant Point Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Standard Room, 1 Queen Bed | Premium bedding, in-room safe, iron/ironing board, free WiFi
    Aug 1 - Aug 7

    Hotel Ivy Boston Common + Flight

    Bay Village
    6 nights
    2.5 star property
    8.4/10 - Very Good (1,453 reviews)
    "Clean rooms, staff friendly"
    Reviewed May 21, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - NRT • 1 stop
    ￥471,205
    ￥345,537
    per traveler
    found 1 day ago
    Hotel Ivy Boston Common
  • Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillowtop beds, minibar
    Aug 1 - Aug 7

    Boston Harbor Hotel + Flight

    North End
    6 nights
    5.0 star property
    9.8/10 - Exceptional (1,001 reviews)
    "This was 10/10 with everything top tier"
    Reviewed May 20, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - NRT • 1 stop
    Save 100% on your flight
    ￥746,083
    ￥464,672
    per traveler
    found 1 day ago
    Boston Harbor Hotel
  • Lobby
    Aug 1 - Aug 7

    Fairmont Copley Plaza, Boston + Flight

    Back Bay
    6 nights
    4.5 star property
    9.0/10 - Wonderful (1,241 reviews)
    "Gorgeous hotel in a fabulous location. Highly recommend!"
    Reviewed May 19, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - NRT • 1 stop
    ￥503,899
    ￥390,844
    per traveler
    found 1 day ago
    Fairmont Copley Plaza, Boston
  • Front of property
    Aug 1 - Aug 7

    Eurostars The Boxer + Flight

    West End
    6 nights
    4.0 star property
    8.8/10 - Excellent (1,489 reviews)
    "I liked the location. The room itself was small and it had a dank smell. Otherwise everything was fine. Nice lobby and restaurant on site."
    Reviewed May 21, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - NRT • 1 stop
    ￥457,844
    ￥363,556
    per traveler
    found 1 day ago
    Eurostars The Boxer
  • 3 restaurants; breakfast, lunch, dinner, and brunch served
    Aug 1 - Aug 7

    The Charles Hotel + Flight

    West Cambridge
    6 nights
    4.0 star property
    9.4/10 - Exceptional (1,003 reviews)
    "I remain impressed with the Charles Hotel. The rooms are very comfortable. The location perfect when doing things around Harvard Square. The restaurant and bars are great and the the staff very helpful. Well worth the price."
    Reviewed May 21, 2026
    Roundtrip • Tokyo (HND) - Boston (BOS)
    HND - BOS • 1 stop BOS - NRT • 1 stop
    ￥523,759
    ￥422,814
    per traveler
    found 1 day ago
    The Charles Hotel

Pleasant Point Hotel Deals

Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St Provincetown MA
Fully refundableReserve now, pay when you stay
The price is ￥20,073 per night from Jun 8 to Jun 9
￥20,073
￥28,431 total
Jun 8 - Jun 9
includes taxes & fees
Harbor Hotel Provincetown
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is ￥84,469 per night from May 26 to May 27
￥84,469
￥96,676 total
May 26 - May 27
includes taxes & fees
9.2/10 Wonderful! (826 reviews)
"window and door were not closing all the way, got noise complaint after daughter became ill. Food was good staff ok"

Reviewed on May 13, 2026

Chatham Bars Inn
Dune Crest Hotel

Dune Crest Hotel

2.5 out of 5
535 Route 6 North Truro MA
Fully refundableReserve now, pay when you stay
The price is ￥17,158 per night from Jun 1 to Jun 2
￥17,158
￥19,637 total
Jun 1 - Jun 2
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Beautiful sunset view from deck in evening, peaceful setting, view of natural landscape and Provincetown in distance. Breakfast included in clean dining. Crisp clean resort."

Reviewed on May 22, 2026

Dune Crest Hotel
See all 4,278 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 , 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

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.