
Pleasant Point Vacations from $439
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Find the right fit
Rest easy
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

Margaritaville Resort Cape Cod
Reviewed on Oct 26, 2025

Raffles Boston
Reviewed on Oct 20, 2025

The Whitney Hotel
Reviewed on Oct 13, 2025

Boston Harbor Hotel
Reviewed on Oct 26, 2025

Inn on Main
Reviewed on Aug 7, 2025
Pleasant Point Hotel Deals

Chatham Bars Inn
Excellent experience all around Gorgeous location and beautiful hotel Lively lobby
Reviewed on Oct 13, 2025

The Villages at Ocean Edge
Nice room with a kitchen. Bed was large and comfy for two. Room cleaned daily. Coffee was replenished daily as well. The “campus” was beautiful. We were there in early October so the town was pretty much getting ready to close up
Reviewed on Oct 14, 2025

Surfside Hotel and Suites
It was a very nice room right on the water. Everyone was very nice.
Reviewed on Oct 17, 2025
Discover the most popular places to visit in Pleasant Point

Marconi Beach
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.

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

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


















