South Wellfleet Vacations from $248

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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.
Mercury Hotel Provincetown

Mercury Hotel Provincetown

3 out of 5
Price was $304, price is now $248 per person
$248
per person
Jan 12 - Jan 15
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Provincetown (PVC)
18/10 Exceptional! (466 reviews)
Quaint little hotel with great service. Right in the middle of everything with friendly staff.

Reviewed on Nov 16, 2025

Ellery Hotel Provincetown

Ellery Hotel Provincetown

4 out of 5
Price was $357, price is now $283 per person
$283
per person
Jan 12 - Jan 15
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Provincetown (PVC)
18.8/10 Exceptional! (381 reviews)
The property was modern and clean with plenty of cozy common areas to enjoy. We didn’t have time to go in the hot tub and sauna but they looked inviting. Our room was wonderful! We had a separate cottage suite with a private outside space a nice inside seating area. It was clean and attractive and comfortable. The host was amazing! I wish we had stayed longer.

Reviewed on Oct 25, 2025

The Provincetown Hotel at Gabriel's

The Provincetown Hotel at Gabriel's

3.5 out of 5
Price was $461, price is now $392 per person
$392
per person
Jan 12 - Jan 15
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Provincetown (PVC)
17.2/10 Exceptional! (964 reviews)
The property is charming, staff was very helpful and courteous and the location was amazing. I would definitely stay again next time I am in Provincetown.

Reviewed on Oct 26, 2025

The Masthead Resort

The Masthead Resort

2.5 out of 5
Price was $395, price is now $338 per person
$338
per person
Jan 12 - Jan 15
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Provincetown (PVC)
16.4/10 Exceptional! (492 reviews)
Yes very nice staff

Reviewed on Nov 1, 2025

The Revere Guest House

The Revere Guest House

3.5 out of 5
Price was $509, price is now $472 per person
$472
per person
Jan 12 - Jan 15
found 4 hours ago
Roundtrip flight included
Chicago (CHI) to Provincetown (PVC)
18.4/10 Exceptional! (837 reviews)
I was made to feel like a friend as soon as I walked in, it was homely, comfortable, warm and bright. A million star review

Reviewed on Sep 16, 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

South Wellfleet Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
$273 nightly
The price is $312 total per night from Nov 29 to Nov 30
$312 total
Nov 29 - Nov 30
Total with taxes and fees
9.2/10 Wonderful! (794 reviews)
Great accommodation and staff.

Reviewed on Nov 8, 2025

Chatham Bars Inn
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street Brewster MA
$255 nightly
The price is $283 total per night from Nov 30 to Dec 1
$283 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (999 reviews)
Highly recommend. From check in to check out, the service was friendly, responsive and courteous. The room was also a great surprise. Large room with a large bathroom.Well appointed with a nice balcony. Good bathroom lighting for make-up and easy for two people to get ready at the same time. Beds ...

Reviewed on Sep 22, 2025

The Mansion at Ocean Edge
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $199 total per night from Nov 24 to Nov 25
$199 total
Nov 24 - Nov 25
Total with taxes and fees
9.2/10 Wonderful! (592 reviews)
Room was clean, but quite small vs. our expectations. The location on main st is very convenient, good for shopping and dining.

Reviewed on Nov 17, 2025

Chatham Wayside Inn
See all 4,716 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 $248 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.

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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.