Pleasant Point Vacations from $319

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

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $637, price is now $319 per person
$319
per person
Nov 1 - Nov 3
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,333, price is now $786 per person
$786
per person
Nov 3 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!

Reviewed on Aug 24, 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,096, price is now $650 per person
$650
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,711 reviews)
Great staff and great location. Rooms where clean and comfortable

Reviewed on Aug 27, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,062, price is now $1,847 per person
$1,847
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
Lovely property and staff. Great location and spa. Will return!

Reviewed on Aug 26, 2025

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
Price was $882, price is now $569 per person
$569
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (2,072 reviews)
Good value for the price and our family of 5. I would prefer rooms with no carpet. It was fine, but questionable as I smelled chorine. Overall, it was fine. The front desk was helpful and the service was very good.

Reviewed on Aug 21, 2025

Pleasant Point Hotel Deals

Captains Quarters Motel & Conference Center

Captains Quarters Motel & Conference Center

2 out of 5
5000 State Highway/Route 6, Eastham, MA
$88 nightly
The price is $101 total per night from Sep 3 to Sep 4
$101 total
Sep 3 - Sep 4
Total with taxes and fees
7.6/10 Good! (1,007 reviews)
"The pool was not usable; it needed cleaning."

Reviewed on Aug 24, 2025

Captains Quarters Motel & Conference Center
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St, Provincetown, MA
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $226 total per night from Sep 21 to Sep 22
$226 total
Sep 21 - Sep 22
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
"The rooms were super nice, clean, and well appointed."

Reviewed on Aug 25, 2025

Harbor Hotel Provincetown
The Provincetown Inn

The Provincetown Inn

3 out of 5
1 Commercial Street, Provincetown, MA
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $244 total per night from Sep 21 to Sep 22
$244 total
Sep 21 - Sep 22
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
"Love it"

Reviewed on Aug 23, 2025

The Provincetown Inn
See all 4,338 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Pleasant Point

New stairs at Marconi Beach

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.

Marconi Beach
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
This mornings walk

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.

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