Pleasant Point
Wellfleet
Visit Pleasant Point
Things to do
Cape Cod & Provincetown: Self-Guided Drive & Walk Audio Tour
CA $35
per traveller
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
CA $70
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
CA $71
per traveller
Pleasant Point Hotel Deals
Holiday Hill Inn & Suites
352 Main Street Dennis Port MA
The price is CA $162 per night from Aug 30 to Aug 31
CA $162
CA $185 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this family-friendly motel in Dennis Port. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Harbor Hotel Provincetown
698 Commercial St Provincetown MA
The price is CA $290 per night from Sep 7 to Sep 8
CA $290
CA $380 total
Sep 7 - Sep 8
includes taxes & fees
Stay at this hotel in Provincetown. Enjoy free parking, an outdoor pool, and a fireplace in the lobby. Our guests praise the pool and the helpful staff in our ...
8.4/10 Very good! (1,012 reviews)
"Pool was closed for maintenance reasons but this stuff should be disclosed at booking. Other than that very good. Beautiful beach to sit on in the evening just across the road. Free shuttles to downtown. Room could have better closet / storage space. But we would stay again. Grab Brothers played ..."
Reviewed on Aug 18, 2026
Dune Crest Hotel
535 Route 6 North Truro MA
The price is CA $224 per night from Sep 7 to Sep 8
CA $224
CA $257 total
Sep 7 - Sep 8
includes taxes & fees
Stay at this hotel in North Truro. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,016 reviews)
"Nice breakfast and the room said parking lot view but there was a full view of the ocean."
Reviewed on Aug 18, 2026
The Villages at Ocean Edge
One Villages Drive Brewster MA
The price is CA $256 per night from Aug 31 to Sep 1
CA $256
CA $357 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this beach resort in Brewster. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very good! (1,005 reviews)
"Very far from everything, definitely need a car. outdated and"
Reviewed on Aug 19, 2026
The Provincetown Inn
1 Commercial Street Provincetown MA
The price is CA $228 per night from Sep 14 to Sep 15
CA $228
CA $308 total
Sep 14 - Sep 15
includes taxes & fees
Book a stay at this beach hotel in Provincetown. Enjoy an outdoor pool, 3 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in ...
8/10 Very good! (1,023 reviews)
"I like the pool amenities"
Reviewed on Aug 18, 2026
Chatham Bars Inn
297 Shore Rd Chatham MA
The price is CA $802 per night from Sep 14 to Sep 15
CA $802
CA $918 total
Sep 14 - Sep 15
includes taxes & fees
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
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.
Where to stay in Pleasant Point
Find the best Pleasant Point areas and neighborhoods for the activities you enjoy most.
Indian Neck Heights
Though Indian Neck Heights might not have many top sights, you can venture to the surrounding area to see attractions like Cape Cod National Seashore and Lieutenant Island.
