South Wellfleet Vacation Packages
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Your South Wellfleet Vacation
Let our vacation packages to South Wellfleet inspire your next getaway. There's plenty to like about this lively city, starting with the neighborhood of Pleasant Point, which is great for nature and views. Fill up your itinerary with visits to Nauset Lighthouse, Cape Cod National Seashore and Cape Cod Beaches, some of the attractions you shouldn't miss during your trip to South Wellfleet. A couple of clicks is all it takes to put together your ideal South Wellfleet vacation on Expedia.
Top South Wellfleet Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Provincetown Inn
Price was CA $1,040, price is now CA $802 per person
CA $802
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
8/10 Very Good! (1,000 reviews)
Nice stay. Clean room beautiful view of the ocean. Quiet. Close to PTown if u r a walker!! Or always Pedi Cabs. Yay. Love PTown especially on women’s week. So much fun. Many many things to do. Loved staying at the Inn. Nice ppl working there SO helpful
Reviewed on Jan 9, 2026
Crowne Pointe Historic Inn & Spa - Adults Only
Price was CA $1,040, price is now CA $823 per person
CA $823
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
9.2/10 Wonderful! (833 reviews)
We had a great room (king superior) that was spacious, clean and quiet. The bed was comfortable and the staff and management were incredibly friendly and welcoming. Would definitely stay here again!
Reviewed on Jan 2, 2026
Brass Key Guesthouse - Adults Only
Price was CA $1,158, price is now CA $935 per person
CA $935
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
9.6/10 Exceptional! (445 reviews)
Welcoming staff, great Shipwreck Lounge to meet with friends, lovely accommodations, VERY clean. Great property and surrounding area. Will be staying here for all future visits. Thank you, Dale, for your wonderful hospitality!
Reviewed on Dec 12, 2025
South Wellfleet Hotel Deals
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Wellfleet MA
The price is CA $205 per night from Feb 25 to Feb 26
CA $205
CA $615 total
Feb 25 - Feb 26
includes taxes & fees
9.8/10 Exceptional! (77 reviews)
Great home with amazing location and view. Thank you for a great stay!
Reviewed on Jan 29, 2026
Chatham Bars Inn
297 Shore Rd Chatham MA
The price is CA $498 per night from Feb 26 to Feb 27
CA $498
CA $570 total
Feb 26 - Feb 27
includes taxes & fees
9/10 Wonderful! (811 reviews)
Beautiful property
Reviewed on Jan 24, 2026
Chatham Wayside Inn
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Feb 26 to Feb 27
CA $150
CA $231 total
Feb 26 - Feb 27
includes taxes & fees
9.2/10 Wonderful! (635 reviews)
Friendly staff, clean and spacious room, convenience of having a restaurant on site, and convenience of walking to all the stores and restaurants.
Reviewed on Feb 16, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
