Castlewood Vacations

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Find the Best Castlewood Vacation Packages

Castlewood Hotel Deals

Lakefront Vacation Rental With Fire Pit & Dock!

Lakefront Vacation Rental With Fire Pit & Dock!

3 out of 5
Castlewood
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Lakefront Vacation Rental With Fire Pit & Dock!
Lakefront Lake Poinsett Cottage with Private Beach

Lakefront Lake Poinsett Cottage with Private Beach

Castlewood
10/10 Exceptional! (3 reviews)
"Easy check in. The owner was even flexible and let us come early since it was ready. Nice kitchen, a bit small but was amazing to have a spare kitchen in the guest suite. Nice appliances. Nice big beach area with some toys on site. Great to have a blackstone and grill, crockpot, ect for use."

Reviewed on Aug 4, 2025

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Lakefront Lake Poinsett Cottage with Private Beach
Waterfront Lake Poinsett Retreat w/ Fire Pit!

Waterfront Lake Poinsett Retreat w/ Fire Pit!

3 out of 5
100 N Lake Dr, Castlewood, SD
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Waterfront Lake Poinsett Retreat w/ Fire Pit!
See all 85 properties in Castlewood
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 Castlewood vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Castlewood costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Castlewood?
To pick up cheap Castlewood vacation packages, organize your trip outside of peak times such as public holidays. 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 Castlewood?
The ideal length for your Castlewood vacation depends on what you'd like to do and see. Typically, a few days to a week will give you time to check out all the major attractions and discover some hidden treasures along the way.
How to find the best Castlewood package deals?
Use Expedia's handy filters to find some fabulous Castlewood package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Castlewood package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Castlewood vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Castlewood vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Castlewood?
Enjoy incredible bargains by booking your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Castlewood trip.
How to plan a trip to Castlewood?

  1. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to go to Castlewood.
  2. Budget wisely: Besides the price of your hotel, you'll need to consider other expenses too. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Castlewood.
  3. Decide your trip length: Think about how much time you want to spend discovering Castlewood. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored Castlewood vacation package.

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