South Orleans Vacations from $337

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Your South Orleans Vacation

Well known for its coastal scenery and spectacular views, South Orleans is a fantastic getaway destination. Lock in one of our South Orleans vacation packages and uncover all that this exciting city has to offer. If your trip to South Orleans includes some sightseeing, drop by popular attractions like Nauset Beach, Skaket Beach and Rock Harbor Beach. Stop dreaming and start doing. Browse the range of options on Expedia today and finally put your South Orleans vacation plans into gear!

The Latest South Orleans vacation packages

Price found within the past 48 hours. Click for updated prices.
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was $527, price is now $337 per person
$337
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,013 reviews)
We enjoyed our stay. Would stay again

Reviewed on Nov 24, 2025

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $1,189, price is now $667 per person
$667
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (460 reviews)
The entire experience at The Iris hotel was excellent form the Valet parking, the room, the bar & the restaurant. I would stay there anytime I'm in Brookline

Reviewed on Nov 22, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,135, price is now $646 per person
$646
per person
Feb 13 - Feb 16
found 12 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Clean room, staff is nice and helpful

Reviewed on Nov 29, 2025

Premier Suites - Bay Village

Premier Suites - Bay Village

2 out of 5
Bay Village
Save 100% on your flight
Price was $743, price is now $461 per person
$461
per person
Feb 3 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
6.2/10 (245 reviews)
Great central location, but very over priced for what you get. Felt like I was going to fall through the floor. Super old building and nothing works that well. Internet on tv didn't work. Bath plug/stopper didn't work. Electric hotplate didn't work. Don't bring a large suitcase as the stairs are very narrow and steep and I had to lug it up to the 4th floor.

Reviewed on Nov 10, 2025

The Merchant

The Merchant

3 out of 5
Downtown Salem
Save 100% on your flight
Price was $1,125, price is now $740 per person
$740
per person
Dec 30 - Jan 3
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (375 reviews)
Incredible hospitality. One of our favorite hotel experiences in a while.

Reviewed on Nov 28, 2025

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Discover the most popular places to visit in South Orleans

Skaket Beach showing a beach as well as a family

Skaket Beach

4.5/5(18 reviews)

Warm, clear waters make this beach destination ideal for casual swimming, watersports or a restorative rest on the white sandy shore.

Skaket Beach
Built in 1720

Jonathan Young Windmill

Jonathan Young Windmill is just one of the places to see in Orleans, so why not enjoy the other things to explore during your travels? Stroll along the beautiful beaches or seek out the hiking trails.

Jonathan Young Windmill

Orleans Bowling Center

Enjoy a trip to Orleans Bowling Center and popular activities like hiking in Orleans. Stroll along the area's beautiful beaches, or simply savor its seafood restaurants.

Orleans Bowling Center

What to do in South Orleans

Salem Puzzling Adventure

Plymouth Puzzling Adventure

$35
per traveler
Plymouth Puzzling Adventure
See all activities in South Orleans

South Orleans Hotel Deals

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

2.5 out of 5
867 Iyannough Road Hyannis MA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $122 total per night from Dec 7 to Dec 8
$122 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (646 reviews)
Yes good breakfast kept filled. Friendly staff. Good AC heat system

Reviewed on Nov 20, 2025

Fairfield Inn & Suites by Marriott Cape Cod Hyannis
Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $85 total per night from Dec 1 to Dec 2
$85 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (1,016 reviews)
Beds are comfortable, front desk is prompt & quaint view in back from slider However, walls are thin so ask for room upstairs for best sleep They will charge $20 for late check out which I thought was crummy off season But great value for the money

Reviewed on Nov 26, 2025

Cape Sands Inn
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $193 total per night from Dec 1 to Dec 2
$193 total
Dec 1 - Dec 2
Total with taxes and fees
8.6/10 Excellent! (405 reviews)
The room were clean. The staff were all friendly! I will definitely go back!!!

Reviewed on Nov 10, 2025

Margaritaville Resort Cape Cod
See all 4,753 properties in South Orleans
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 Orleans Vacation Packages

South Orleans Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Barnstable Municipal Airport (HYA)
Max Temp Winter
40ºF
Max Temp Summer
70ºF
Top Sights
Nauset Beach, Skaket Beach and Rock Harbor Beach

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Frequently asked questions

How much does a South Orleans vacation package cost?
Offering excellent value package deals from $337 on Expedia, you'll be surprised at how little a vacation to South Orleans costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to South Orleans?
If you'd like to book a cheap South Orleans vacation package, consider planning a trip in June, July and December. You're likely to find lower prices on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for South Orleans?
Usually, a handful of days is enough to tick off the main attractions during your South Orleans vacation. But if you want to have time to kick back or take day trips, consider extending your itinerary.
How to find the best South Orleans package deals?
Begin your search for a South Orleans package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal South Orleans package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your South Orleans adventure underway.
Is it cheaper to book a South Orleans vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored South Orleans vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to South Orleans?
If you're considering a spur-of-the-moment South Orleans trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later South Orleans vacation packages?
Jet off on your dream escape to South Orleans with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for the next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snag great deals before they disappear.

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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.