Pleasant Point Vacation Packages for 2025

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Top Hotel Deals

The Provincetown Inn

The Provincetown Inn

3 out of 5
1 Commercial Street, Provincetown, MA
21.2 km from Pleasant Point
Stay at this 3-star beach hotel in Provincetown. Enjoy an outdoor pool, 3 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in ...
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St, Provincetown, MA
21.2 km from Pleasant Point
Book a stay at this beach hotel in Provincetown. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the pool and the helpful staff in ...
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
25.57 km from Pleasant Point
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 ...
The Corsair & Cross Rip Oceanfront Resort

The Corsair & Cross Rip Oceanfront Resort

2.5 out of 5
41 Chase Ave, Dennis Port, MA
30.08 km from Pleasant Point
Book a stay at this beach hotel in Dennis Port. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Cape Cod Inflatable Park and Sea Street ...
Surfside Hotel and Suites

Surfside Hotel and Suites

2.5 out of 5
543 Commercial Street, Provincetown, MA
21.56 km from Pleasant Point
Book a stay at this beach hotel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
The Villages at Ocean Edge

The Villages at Ocean Edge

3.5 out of 5
One Villages Drive, Brewster, MA
16.6 km from Pleasant Point
Stay at this 3.5-star beach resort in Brewster. Enjoy 3 outdoor pools, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. ...
Cape Colony Inn

Cape Colony Inn

2.5 out of 5
280 Bradford Street, Provincetown, MA
21.71 km from Pleasant Point
Stay at this hotel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Chatham Tides

Chatham Tides

2.5 out of 5
394 Pleasant St, PO Box 215, South Chatham, MA
27.13 km from Pleasant Point
Book a stay at this beach motel in South Chatham. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms ...
Sandcastle Resort and Club

Sandcastle Resort and Club

3 out of 5
929 Commercial Street, Provincetown, MA
20.64 km from Pleasant Point
Stay at this 3-star beach aparthotel in Provincetown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Breakwater Hotel

Breakwater Hotel

2.5 out of 5
716 Commercial St, Provincetown, MA
21.16 km from Pleasant Point
Book a stay at this beach motel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
26 km from Pleasant Point
Stay at this 4-star golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
2173 Head of the Bay Road, Route 28, Harwich, MA
21.03 km from Pleasant Point
Stay at this 5-star luxury resort in Harwich. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Captain's Cove Golf Course and Captains ...
Dune Crest Hotel

Dune Crest Hotel

2 out of 5
535 Route 6, North Truro, MA
17.63 km from Pleasant Point
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. ...
Crowne Pointe Historic Inn & Spa - Adults Only

Crowne Pointe Historic Inn & Spa - Adults Only

4 out of 5
82 Bradford Street, Provincetown, MA
21.76 km from Pleasant Point
Stay at this 4-star spa hotel in Provincetown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street, Brewster, MA
15.98 km from Pleasant Point
Book a stay at this luxury hotel in Brewster. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Thu, Aug 21 - Wed, Aug 27
LAX
Los Angeles Intl.
BOS
Logan Intl.
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Aug 21 from Los Angeles Intl. to Logan Intl., returning Wed, Aug 27, priced at $173 found 1 day ago
JetBlue Airways
Tue, Aug 26 - Sun, Aug 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 26 from Los Angeles Intl. to Logan Intl., returning Sun, Aug 31, priced at $215 found 1 day ago
American Airlines
Wed, Jul 16 - Mon, Jul 21
PDX
Portland Intl.
BOS
Logan Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 16 from Portland Intl. to Logan Intl., returning Mon, Jul 21, priced at $217 found 1 day ago
Delta
Wed, Jul 16 - Wed, Jul 16
PDX
Portland Intl.
BOS
Logan Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 16 from Portland Intl. to Logan Intl., returning Wed, Jul 16, priced at $237 found 1 day ago