Pleasant Point Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Pleasant Point

Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
The price is S$377 per night from 2 Dec to 3 Dec
S$377
includes taxes & fees
2 Dec - 3 Dec
9/10 Wonderful! (730 reviews)
"Location, service, food, and amenities are all top notch. The complimentary limo service needs extra mention as it was impeccable: brand new cars, local drivers, fast and reliable. Made for a very enjoyable stay. Thanks"

Reviewed on 2 Nov,2024

Chatham Bars Inn
Harbor Hotel Provincetown
Harbor Hotel Provincetown
3 out of 5
698 Commercial St, Provincetown, MA
7.6/10 Good! (1,001 reviews)
"hotel was nice - only downside was there was nothing walking distance to go to and their restaurant was closed for the season so we had to drive to get to anything. rooms were ok - they did have a nice firepit outside which was nice. seemed very safe area which is important to me traveling as a single ..."

Reviewed on 26 Nov,2024

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Harbor Hotel Provincetown
Crowne Pointe Historic Inn & Spa - Adults Only
Crowne Pointe Historic Inn & Spa - Adults Only
4 out of 5
82 Bradford Street, Provincetown, MA
The price is S$227 per night from 2 Dec to 3 Dec
S$227
includes taxes & fees
2 Dec - 3 Dec
9.2/10 Wonderful! (725 reviews)
"Great service and relaxing"

Reviewed on 17 Nov,2024

Crowne Pointe Historic Inn & Spa - Adults Only
See all 4,104 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.

Popular places to visit

Cahoon Hollow Beach

Cahoon Hollow Beach

Enjoy a relaxing day at the beach and a lively night at the bar at this favorite daytrip destination.

Cahoon Hollow Beach
Mayo 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.