South Orleans Holidays

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Our guide on where to stay in South Orleans

Find the best South Orleans areas and neighborhoods for the activities you enjoy most. Learn more about South Orleans
Nauset Beach which includes a sandy beach as well as a couple

East Orleans

1 out of top 10 points of interest in this area

East Orleans is noteworthy for its beaches, and you can make a stop at top attractions like Nauset Beach and Cape Cod National Seashore.

Find hotels in East Orleans

Our pick of the best South Orleans Hotel Deals

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Orleans MA
9.8/10 Exceptional! (57 reviews)
The house was PERFECT for our family holiday celebration. We loved spending time together in the living rooms and very spacious kitchen. We also really enjoyed the piano, sauna, hot tub and large fireplace. The location is great for getting to Chatham, Orleans and multiple beaches. The hosts went ...

Reviewed on 3 Jan 2026

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Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
The price is NZ$635 per night from 13 Feb to 14 Feb
NZ$635
13 Feb - 14 Feb
includes taxes & fees
8.6/10 Excellent! (428 reviews)
Evrything is so clean! We love staying here with our family with small children. The kids love it and so do we! We go back every year. It's become a tradition!

Reviewed on 10 Jan 2026

Margaritaville Resort Cape Cod
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is NZ$724 per night from 21 Jan to 22 Jan
NZ$724
21 Jan - 22 Jan
includes taxes & fees
9/10 Wonderful! (803 reviews)
Room was very clean but a little dated also there is very little space to put your clothes away…no dressers

Reviewed on 3 Jan 2026

Chatham Bars Inn
See all 4,756 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.

Frequently asked questions

How much does a South Orleans holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday 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?
To pick up cheap South Orleans holiday packages, plan your getaway outside of peak times like public holidays and major festivals. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for South Orleans?
The ideal duration for your South Orleans holiday depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to go to all the leading sights and explore some hidden spots along the way.
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 holiday as a package?
Expedia holiday 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 holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday 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.
How to plan a trip to South Orleans?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the activities on offer will also help you decide when to visit South Orleans.
  2. Plan your budget wisely: On top of the price of your stay, you should factor in other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that may arise during your trip to South Orleans.
  3. Decide how long to go for: Now that you're more familiar with South Orleans, you can figure out the right length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a South Orleans holiday package that brings all your bookings together.

Discover the most popular places to visit in South Orleans

Jonathan Young Windmill

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

Nauset Inlet

Commune with nature and explore the great outdoors at Nauset Inlet during your travels in Orleans. Stroll along the seaside or seek out the hiking trails.

Nauset Inlet

Church of the Transfiguration Orleans

Church of the Transfiguration Orleans is just one of the places to see in Orleans, so why not enjoy the other things to explore during your travels? Amble around the area's beautiful beaches or seek out the hiking trails.

Church of the Transfiguration Orleans

Activities

Salem Puzzling Adventure

Plymouth Puzzling Adventure

NZ$60
per traveller
Plymouth Puzzling Adventure
Private Professional Vacation Photoshoot in Cape Cod

Private Professional Vacation Photoshoot in Cape Cod

NZ$2,025
per adult
Private Professional Vacation Photoshoot in Cape Cod
See all activities in Orleans
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.