Pleasant Point Vacations from $296

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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
Raffles Boston
The Charles Hotel
Porter Square Hotel
Beacon Hill Hotel

Pleasant Point Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
$397 nightly
The price is $455 total per night from Oct 30 to Oct 31
$455 total
Oct 30 - Oct 31
Total with taxes and fees
9/10 Wonderful! (790 reviews)
"Wonderful experience"

Reviewed on Oct 6, 2025

Chatham Bars Inn
Sandcastle Resort and Club

Sandcastle Resort and Club

3 out of 5
929 Commercial Street, Provincetown, MA
$98 nightly
The price is $112 total per night from Oct 27 to Oct 28
$112 total
Oct 27 - Oct 28
Total with taxes and fees
7.2/10 Good! (1,117 reviews)
"We often travel to Provincetown from Providence for a night or two, and often stay at the Sandcastle Resort, which is excellent for an inexpensive yet comfortable getaway. The studio apartment is well designed and efficient. The murphy bed is comfortable. We upgraded to a beach view and enjoyed a ..."

Reviewed on Oct 8, 2025

Sandcastle Resort and Club
Captains Quarters Motel & Conference Center

Captains Quarters Motel & Conference Center

2 out of 5
5000 State Highway/Route 6, Eastham, MA
$79 nightly
The price is $91 total per night from Oct 19 to Oct 20
$91 total
Oct 19 - Oct 20
Total with taxes and fees
7.6/10 Good! (1,000 reviews)
"No frills stay but clean and convenient to beaches and restaurants. Very comfortable pillows and beds. We booked for the price when under $100/night and would stay for that price again."

Reviewed on Oct 6, 2025

Captains Quarters Motel & Conference Center
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.

Discover the most popular places to visit in Pleasant Point

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