South Wellfleet Vacations from $653

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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.

The Latest South Wellfleet vacation packages

Price found within the past 48 hours. Click for updated prices.
Brass Key Guesthouse - Adults Only

Brass Key Guesthouse - Adults Only

4 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 16
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Provincetown (PVC)
9.6/10 Exceptional! (382 reviews)
We had an amazing stay at the Brass Key. The facility was beautiful. It is conveniently located to everywhere you’d want to be. The staff was friendly and helpful and really added to the experience. It would definitely be my choice for future stays.

Reviewed on Jun 30, 2025

Surfside Hotel and Suites

Surfside Hotel and Suites

2.5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Provincetown (PVC)
8.6/10 Excellent! (1,003 reviews)
Nice will stay again in the future

Reviewed on Jun 30, 2025

Crowne Pointe Historic Inn & Spa - Adults Only

Crowne Pointe Historic Inn & Spa - Adults Only

4 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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

Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Provincetown (PVC)
7.8/10 Good! (1,002 reviews)
We enjoyed the location across from the beach and the amenities at hotel. Also enjoyed all the help from Maurice at the front desk.

Reviewed on Jul 2, 2025

Mercury Hotel Provincetown

Mercury Hotel Provincetown

3 out of 5
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Provincetown (PVC)
9/10 Wonderful! (413 reviews)
The house is beautiful, our room was amazing we loved it, it’s super close to the shops and restaurants, the staff is super nice , my room was ready early in the morning the day of check in, no complaints.

Reviewed on Jun 29, 2025

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Discover the most popular places to visit in South Wellfleet

Marconi Station

You can learn about the history of South Wellfleet when you stop by Marconi Station. Stroll along the beautiful beaches in this family-friendly area, or check out its seafood restaurants.

Marconi Station

Blue Heron Gallery

You can spend an afternoon browsing the exhibits at Blue Heron Gallery in South Wellfleet. Stroll along the beautiful beaches in this family-friendly area, or seek out the hiking trails.

Blue Heron Gallery

South Wellfleet Hotel Deals

Cape Colony Inn
Cape Colony Inn
2.5 out of 5
280 Bradford Street, Provincetown, MA
$249 nightly
The price is $285 total per night from Jul 9 to Jul 10
$285 total
Jul 9 - Jul 10
Total includes taxes and fees
9/10 Wonderful! (1,007 reviews)
"Nicely renovated room with a spacious and well designed layout."

Reviewed on Jul 1, 2025

Cape Colony Inn
Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
$824 nightly
The price is $943 total per night from Jul 23 to Jul 24
$943 total
Jul 23 - Jul 24
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
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 7 to Jul 8
$388 total
Jul 7 - Jul 8
Total includes taxes and fees
8/10 Very Good! (1,025 reviews)
A great waterfront getaway
"A perfect location on the water and close to the pool! All team members were very friendly and helpful."

Reviewed on Jun 30, 2025

The Provincetown Inn
See all 4,984 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.

Find the Best South Wellfleet Vacation Packages

South Wellfleet Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Barnstable Municipal Airport (HYA)
Max Temp Winter
40ºF
Max Temp Summer
70ºF
Top Sights
Cape Cod National Seashore, Nauset Beach and Cape Cod Beaches

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Frequently asked questions

How much does a South Wellfleet vacation package cost?
You can pick up a vacation package to this destination from $653 on Expedia. However, how much your vacation to South Wellfleet costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to South Wellfleet?
If you're hoping to book a cheap South Wellfleet vacation package, consider planning a trip in November, December and January. You'll usually find lower rates on hotels and airfares during these months --- perfect for a budget-friendly break.
How many days is enough for South Wellfleet?
South Wellfleet vacations can be short or long, but to get a true feel for this place, we'd say 2 days is about right. This will mean you can visit headline attractions like Meadow Avenue Beach and Blue Heron Gallery and seek out some hidden gems. Don't miss out on neighborhoods such as Indian Neck Heights and Pleasant Point either. If you're clever with your time, you can even allow for a day trip from South Wellfleet too.
Is it worth booking a vacation package to South Wellfleet?
It's easy to see why a South Wellfleet vacation is on the must-do list of many travelers. Well-known attractions like Lieutenant Island are just the start of things to keep you busy here.
How to find the best South Wellfleet package deals?
Bagging a cheap South Wellfleet package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly South Wellfleet package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a South Wellfleet vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still get the freedom to create a customized South Wellfleet vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to South Wellfleet?
Score amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment South Wellfleet trip.
Does Expedia offer Book Now, Pay Later South Wellfleet vacation packages?
If you're like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your South Wellfleet break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.