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.
Seaglass Inn Provincetown

Seaglass Inn Provincetown

3 out of 5
Price was CA $892, price is now CA $749 per person
CA $749
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
9.6/10 Exceptional! (851 reviews)
Room was clean, staff accommodating, lots of free parking, location convenient, well maintained resort. Only minor issue we had is someone came into our room while the do not disturb sign was on. Otherwise a wonderful relaxing stay and we would definitely return.

Reviewed on Aug 1, 2026

Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
Price was CA $1,620, price is now CA $1,197 per person
CA $1,197
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
8.2/10 Very good! (1,011 reviews)
Location

Reviewed on Aug 4, 2026

The Provincetown Inn

The Provincetown Inn

3 out of 5
Price was CA $1,591, price is now CA $1,257 per person
CA $1,257
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
8/10 Very good! (1,014 reviews)
Property was located in a great area. Nice and quiet.

Reviewed on Aug 5, 2026

Surfside Hotel and Suites

Surfside Hotel and Suites

2.5 out of 5
Price was CA $1,515, price is now CA $1,260 per person
CA $1,260
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
8.6/10 Excellent! (1,007 reviews)

Brass Key Guesthouse - Adults Only

Brass Key Guesthouse - Adults Only

4 out of 5
Price was CA $1,397, price is now CA $1,166 per person
CA $1,166
per person
Sep 11 - Sep 13
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Provincetown (PVC)
9.6/10 Exceptional! (505 reviews)

Ready to book your vacation to South Wellfleet?

 

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South Wellfleet Hotel Deals

Holiday Hill Inn & Suites

Holiday Hill Inn & Suites

2 out of 5
352 Main Street Dennis Port MA
The price is CA $166 per night from Aug 30 to Aug 31
CA $166
CA $190 total
Aug 30 - Aug 31
includes taxes & fees
8.4/10 Very good! (1,010 reviews)
"Ice cream stand and mini golf was walkable. Outdoor pool was clean. Staff was helpful. Housekeeping came late on our second day. Overall a nice stay."

Reviewed on Aug 5, 2026

Holiday Hill Inn & Suites
Lighthouse Inn

Lighthouse Inn

3 out of 5
1 Lighthouse Inn Rd West Dennis MA
8.8/10 Excellent! (232 reviews)
"Great beach front location. The recent addition of the new restaurant and bar are exceptional."

Reviewed on Aug 1, 2026

Get rates
Lighthouse Inn
The Provincetown Inn

The Provincetown Inn

3 out of 5
1 Commercial Street Provincetown MA
The price is CA $305 per night from Sep 1 to Sep 2
CA $305
CA $397 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very good! (1,005 reviews)
"Property was located in a great area. Nice and quiet."

Reviewed on Aug 5, 2026

The Provincetown Inn
See all 4,946 properties in South Wellfleet
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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Stay near popular South Wellfleet attractions

Lieutenant Island

7.6/10 (4 reviews)
Commune with nature and explore the great outdoors at Lieutenant Island during your travels in South Wellfleet. While you're in the area, stroll along the beaches.
See properties

Frequently asked questions

How much does a South Wellfleet vacation package cost?
You can pick up a vacation package to this destination from CA $749 on Expedia. But how much your vacation to South Wellfleet costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to South Wellfleet?
The off-season is the best time to head to South Wellfleet if you're trying to save. Another tip for getting cheap South Wellfleet vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for South Wellfleet?
We suggest planning a South Wellfleet vacation for at least 12 days. This gives you enough time to check off popular sights including Nauset Lighthouse and Wellfleet Harbour Actors Theatre, as well as check out neighbourhoods like Pleasant Point and Indian Neck Heights. You might even be able to squeeze in one or two day trips beyond South Wellfleet.
Is it worth booking a vacation package to South Wellfleet?
South Wellfleet has everything you need for a wonderful escape. Get your South Wellfleet vacation off to a flying start by visiting popular attractions like Lieutenant Island.
How to find the best South Wellfleet package deals?
Begin your search for a South Wellfleet package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal South Wellfleet package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your South Wellfleet escape off to a flying start.
Is it cheaper to book a South Wellfleet vacation as a package?
You can enjoy significant savings on your South Wellfleet retreat by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to South Wellfleet?
If you have your South Wellfleet vacation dates finalized, book as early as you can to bag some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to South Wellfleet?

  1. Pick your travel dates: The things you want to do in South Wellfleet and your favourite season will help you decide when to go.
  2. Calculate your budget: Ensure you have enough money to cover everything from food and transportation to airfares and activities. Your accommodations will likely be the largest expense during your trip to South Wellfleet.
  3. Determine how many days away: Start by making a list of all the sights and activities you want to experience in South Wellfleet. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a South Wellfleet vacation package that brings all your bookings together.

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