Pleasant Point Vacations from $617
Book a Hotel + Flight or Car together to unlock savings
Your Pleasant Point Vacation
With a personalized vacation package to Pleasant Point, you'll spend less time planning and more time uncovering this sought-after neighborhood. From its nature to its views, there's plenty to discover here. Hoping to see the sights during your trip to Pleasant Point? Don't miss nearby attractions such as Marconi Beach, Cahoon Hollow Beach and Indian Neck Beach. Stop daydreaming and start doing. When it's time to book your vacation to Pleasant Point, Expedia will help get you there.
The Latest Pleasant Point Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
$653
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Pleasant Point Hotel Deals
Harbor Hotel Provincetown
698 Commercial St Provincetown MA
Fully refundableReserve now, pay when you stay
$202 nightly
$231 total
Oct 18 - Oct 19
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Perfect little mini resort in Provincetown. Clean room, fun pool and cabana area, and firepit and water sprinklers for the little ones. Right across the street from the harbor but before the crowds on Commercial Street. Friendly staff."
Reviewed on Sep 18, 2026
The Villages at Ocean Edge
One Villages Drive Brewster MA
$172 nightly
$197 total
Oct 4 - Oct 5
Total with taxes and fees
Holiday Hill Inn & Suites
352 Main Street Dennis Port MA
Fully refundableReserve now, pay when you stay
$117 nightly
$133 total
Sep 27 - Sep 28
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
"Nice"
Reviewed on Sep 18, 2026
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.
Things to do
Cape Cod Self-Guided Driving Audio Tour
$17
per traveler
100% of travellers recommend
Massachusetts: Smartphone-Based Audio Tour Bundle
$50
per traveler
Helltown Horrors and Pirates: A Self-Guided Tour of Provincetown
$10
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.