Theodosia Vacations from $373

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The Latest Theodosia vacation packages

Price found within the past 48 hours. Click for updated prices.
Still Waters Resort

Still Waters Resort

4 out of 5
Price was $526, price is now $373 per person
$373
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (SGF)
8.8/10 Excellent! (4,251 reviews)
Clean, quite; friendly staff; perfect for families with kids; marina and 3 pools; food trucks on property; valleyball and basketball court; plenty of grills available; kids loved it. We will be back.

Reviewed on Aug 22, 2025

Westgate Branson Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

3.5 out of 5
Price was $626, price is now $396 per person
$396
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Springfield (SGF)
7.8/10 Good! (1,017 reviews)
Love everything!! Will be back.

Reviewed on Aug 23, 2025

Homestead Motel

Homestead Motel

2 out of 5
Hiawatha Heights
Price was $732, price is now $520 per person
$520
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Springfield (SGF)
9.2/10 Wonderful! (353 reviews)
Awesome diamond in the rough! Small cozy place, SUPER clean, beds were comfortable, host was extremely nice and accommodating! Will be staying again!

Reviewed on Aug 4, 2025

Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

4 out of 5
Price was $554, price is now $397 per person
$397
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (SGF)
8.2/10 Very Good! (766 reviews)
Needed a code for the subdivision gate that i was not informed of. Took 15min to get code once we got ahold of property manager. Not happy.

Reviewed on Aug 22, 2025

Club Wyndham Mountain Vista

Club Wyndham Mountain Vista

3.5 out of 5
Price was $726, price is now $529 per person
$529
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Springfield (SGF)
9/10 Wonderful! (379 reviews)
The room was nice and spacious. Room was clean other than really dusty cieling fans and furnace closet vent. I liked view of the pond and watching the ducks. The pools were really nice and we had alot fun at the club house. Every employee we spoke to from check in to checkout was really nice and helpful. Thankyou for a relaxing vacation space.

Reviewed on Aug 21, 2025

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Theodosia Hotel Deals

Americinn By Wyndham Mountain Home

Americinn By Wyndham Mountain Home

2.5 out of 5
290 Drillers Road, Mountain Home, AR
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $115 total per night from Sep 14 to Sep 15
$115 total
Sep 14 - Sep 15
Total with taxes and fees
9.6/10 Exceptional! (357 reviews)
"When I arrived, the staff greeted me and made sure I felt welcome at the property. I needed to do some business work and I was able to use the business area for making copies to present at my meeting the next day. At no extra charge! That was amazing. The desk attendant, Chevelle, helped me with ..."

Reviewed on Aug 19, 2025

Americinn By Wyndham Mountain Home
Days Inn by Wyndham Mountain Home

Days Inn by Wyndham Mountain Home

2 out of 5
1746 Highway 62 B, Mountain Home, AR
Fully refundableReserve now, pay when you stay
$58 nightly
The price is $67 total per night from Sep 7 to Sep 8
$67 total
Sep 7 - Sep 8
Total with taxes and fees
7.8/10 Good! (856 reviews)
"Very quiet and very nice prices"

Reviewed on Aug 20, 2025

Days Inn by Wyndham Mountain Home
Cedar house

Cedar house

2 out of 5
156 Lake Ridge Rd, Rockaway Beach, MO
$142 nightly
The price is $154 total per night from Sep 10 to Sep 11
$154 total
Sep 10 - Sep 11
Total with taxes and fees
8.4/10 Very Good! (5 reviews)
"Cedar house review Spacious and nice layout craftsman ship good. Cedar smell very strong upon arrival, diminished after time . Kitchen was nice but did not have necessary items to prepare a meal. Iron provided but no ironing board. No soap or shampoo in bathroom Queen size bed in a very large room ..."

Reviewed on Aug 17, 2025

Cedar house
See all 520 properties in Theodosia
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.

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Frequently asked questions

How much does a Theodosia vacation package cost?
You can snap up a vacation package to this popular destination from $373 on Expedia. However, how much your vacation to Theodosia costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Theodosia?
If you'd like to book a cheap Theodosia vacation package, consider traveling in January, October and December. You'll typically find better rates on accommodations and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Theodosia?
With a well-planned itinerary, you can easily visit the most popular Theodosia attractions in a few days. But if you want to discover hidden gems or take day trips, think about booking your Theodosia vacation for longer.
How to find the best Theodosia package deals?
Begin your search for a Theodosia package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Theodosia 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 Theodosia escape off to a flying start.
Is it cheaper to book a Theodosia vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and accommodations individually. Better still, you can personalize your Theodosia escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Theodosia?
Land fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Theodosia getaway.
Does Expedia offer Book Now, Pay Later Theodosia vacation packages?
Your Theodosia trip should be a relaxing escape from your daily routine, not a source of money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.