Theodosia Vacations from $438

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The Latest Theodosia vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Branson Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

3.5 out of 5
Shepherd of the Hills
Save 100% on your flight
Price was $943, price is now $438 per person
$438
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Springfield (SGF)
8.4/10 Very Good! (1,013 reviews)
Everything seem brand new. Very clean. Great views

Reviewed on May 17, 2026

Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

4 out of 5
Save 100% on your flight
Price was $1,046, price is now $522 per person
$522
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Springfield (SGF)
8.4/10 Very Good! (939 reviews)
Clean, grateful staff and wonderful views of the lake.

Reviewed on May 19, 2026

Holiday Inn Club Vacations Holiday Hills Resort Branson by IHG

Holiday Inn Club Vacations Holiday Hills Resort Branson by IHG

4 out of 5
Save 100% on your flight
Price was $988, price is now $649 per person
$649
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Springfield (SGF)
8.8/10 Excellent! (931 reviews)
We had 3 adults and 1 child. We stayed in a one-bedroom unit. We were right by a playground and pool (that pool wasnt open yet but there were other options). Kitchen and bathroom had everything we needed, as well as additional bedding to make up the pull out couch. It was clean and comfortable. Certainly enjoyed being away from the bustle of town. Would recomment and stay again.

Reviewed on May 12, 2026

Hyatt Vacation Club at The Lodges at Timber Ridge, Branson

Hyatt Vacation Club at The Lodges at Timber Ridge, Branson

4 out of 5
Skyview
Save 100% on your flight
Price was $962, price is now $636 per person
$636
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Springfield (SGF)
9.2/10 Wonderful! (1,106 reviews)
Lovely setting, nice little pond. Great location. We were surprised that the pool was under construction, and they were working on the roof - so a little disappointed, but overall, nice stay

Reviewed on May 16, 2026

Gazebo Inn

Gazebo Inn

2 out of 5
Branson Theater District
Price was $641, price is now $452 per person
$452
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Springfield (SGF)
8.4/10 Very Good! (1,000 reviews)
The property itself is nice the pet friendly atmosphere isn't for me. I have allergies seemed my room had been. Used fir pets prior. For animal lovers with no allergies. This is the place to be.

Reviewed on May 3, 2026

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Theodosia Hotel Deals

Secluded Luxury Retreat | Hot Tub, Lake Access, 37 Acres

Secluded Luxury Retreat | Hot Tub, Lake Access, 37 Acres

Peel AR
10/10 Exceptional! (11 reviews)
"Kitchen had everything you could need"

Reviewed on Mar 16, 2026

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Secluded Luxury Retreat | Hot Tub, Lake Access, 37 Acres
Lake Views, Hot Tub, Games, Spacious Home for all

Lake Views, Hot Tub, Games, Spacious Home for all

Theodosia MO
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Lake Views, Hot Tub, Games, Spacious Home for all
Lakefront Getaway | Dock, ATV Trails & Private Dock

Lakefront Getaway | Dock, ATV Trails & Private Dock

Theodosia AR
10/10 Exceptional! (1 review)
"We had a great stay! The property was easy to find while still maintaining privacy. It was cute, clean, and the beds were super comfortable. As a coffee drinker it was nice to be able to have a complimentary coffee as I enjoyed the lake view from the toasty warmth of the house."

Reviewed on Dec 2, 2025

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Lakefront Getaway | Dock, ATV Trails & Private Dock
See all 567 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.

Find the Best Theodosia Vacation Packages

Theodosia Essential Information

Language
English
Currency
U.S dollars
Population
240
Max Temp Winter
45ºF
Max Temp Summer
90ºF

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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 $438 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.

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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.