Pleasant Point Vacations from $459

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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.
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Provincetown (PVC)
7.8/10 Good! (1,002 reviews)
Phenomenal management and beautiful property. We will return every year!!

Reviewed on Jul 7, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
per person
Sep 8 - Sep 15
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,999 reviews)
Great location- like the covered a/c overpass bridge to shopping center and walking distance to Newbury street for lots more shopping and restaurants Hotel has nice rooms with a bit of charm and speedy elevators

Reviewed on Jul 8, 2025

Brass Key Guesthouse - Adults Only

Brass Key Guesthouse - Adults Only

4 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Provincetown (PVC)
9.6/10 Exceptional! (382 reviews)
Best place to stay in Provincetown. Grounds are immaculate, rooms are clean though on the smaller side, and the staff is fantastic. Nice breakfast each day. And it’s convenient to everything.

Reviewed on Jul 7, 2025

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
10/10 Exceptional! (8 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

Crowne Pointe Historic Inn & Spa - Adults Only

Crowne Pointe Historic Inn & Spa - Adults Only

4 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Provincetown (PVC)
9.2/10 Wonderful! (779 reviews)
Beautiful resort tucked away in the middle of all the fun that is Ptown. Delicious breakfast (included), lovely pool and hot tubs, and excellent service, esp from Chris and Richard. We highly recommend it!

Reviewed on Jun 29, 2025

Pleasant Point Hotel Deals

The Provincetown Inn
The Provincetown Inn
3 out of 5
1 Commercial Street, Provincetown, MA
$339 nightly
The price is $388 total per night from Jul 9 to Jul 10
$388 total
Jul 9 - Jul 10
Total includes taxes and fees
8/10 Very Good! (1,002 reviews)
"We usually stay at the Harbor hotel, but we tried this place and loved it.The food was great.The pool was great.The beach was great.We will definitely be back."

Reviewed on Jul 6, 2025

The Provincetown Inn
Holiday Hill Inn & Suites
Holiday Hill Inn & Suites
2 out of 5
352 Main Street, Dennis Port, MA
$155 nightly
The price is $177 total per night from Jul 9 to Jul 10
$177 total
Jul 9 - Jul 10
Total includes taxes and fees
8.2/10 Very Good! (858 reviews)
Good value
"It was clean, fairly large room and quiet. The ice cream in the front of the property was not good and the service was terrible, but other than that we had a nice stay. Towels were small and they were very stingy with them."

Reviewed on Jun 27, 2025

Holiday Hill Inn & Suites
Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
$1,067 nightly
The price is $1,221 total per night from Jul 9 to Jul 10
$1,221 total
Jul 9 - Jul 10
Total includes taxes and fees
9.2/10 Wonderful! (769 reviews)
"Absolutely gorgeous property. Everything was top notch and close enough to be able to walk into town. Just what we were looking for."

Reviewed on Jun 30, 2025

Chatham Bars Inn
See all 4,380 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

5/5(7 reviews)

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

4.5/5(27 reviews)

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.