Pleasant Point Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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

Our pick of the best Pleasant Point Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is NZ$1,079 per night from 1 June to 2 June
NZ$1,079
per night
1 June - 2 June
9.2/10 Wonderful! (825 reviews)
window and door were not closing all the way, got noise complaint after daughter became ill. Food was good staff ok

Reviewed on 13 May 2026

Chatham Bars Inn
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St Provincetown MA
The price is NZ$300 per night from 8 June to 9 June
NZ$300
per night
8 June - 9 June
8.2/10 Very Good! (1,002 reviews)
The second floor, ocean-view suite is worth the extra money! Rooms are neat as a pin, and the gentleman who has checked us in every time we have stayed is simply delightful! Rooms and lobby decor have a mid-century modern vibe, and if you get a suite, you will have 2 huge bathrooms! I cannot rave ...

Reviewed on 12 May 2026

Harbor Hotel Provincetown
Dune Crest Hotel

Dune Crest Hotel

2.5 out of 5
535 Route 6 North Truro MA
The price is NZ$188 per night from 20 May to 21 May
NZ$188
per night
20 May - 21 May
8.8/10 Excellent! (1,000 reviews)
The room was very clean the location was exactly where we wanted not in the middle of anything but very close to all the places we wanted to go. The property is a little dated but kinda in a weird way adds to the charm

Reviewed on 30 Dec 2025

Dune Crest Hotel
See all 4,269 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 holiday package cost?
The cheapest Pleasant Point holiday 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 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.

Discover the most popular places to visit in Pleasant Point

Marconi Beach

Marconi Beach

Why not spend a care-free afternoon at Marconi Beach during your travels in Wellfleet? Discover the area's seafood restaurants or seek out the hiking trails.

Marconi Beach

Mayo Beach

If a restful holiday is part of your travel plans, Mayo Beach might be the perfect place to visit during your trip to Wellfleet. Discover the area's seafood restaurants or seek out the hiking trails.

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