Chestnutridge Vacations from $559

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Your Chestnutridge Vacation

The fascinating city of Chestnutridge is calling your name. Uncover both its hidden gems and highlights with a Chestnutridge vacation package that's customized to you. National Tiger Sanctuary and Bonniebrook Gallery, Museum and Homestead are among the must-see sights to check out during your trip to Chestnutridge. Stop dreaming and start adventuring. Check out the many options on Expedia today and finally put your Chestnutridge vacation plans into gear!

The Latest Chestnutridge vacation packages

Price found within the past 48 hours. Click for updated prices.
The Townhouses

The Townhouses

3 out of 5
Green Mountain
Price was $720, price is now $559 per person
$559
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (SGF)
8.2/10 Very Good! (326 reviews)
There is a weird noise coming from the pipes when ever someone flushed the toilet or took a shower so if someone went to use the restroom in the middle of the night it woke everybody up. Other then that the place was perfect.

Reviewed on May 11, 2026

Westgate Branson Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

3.5 out of 5
Shepherd of the Hills
Price was $917, price is now $566 per person
$566
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (SGF)
8.4/10 Very Good! (1,032 reviews)
Didn't like that the room was on an upper floor, 16 steps up and down every time you left the room. Amenities in room were excellent

Reviewed on May 21, 2026

Homestead Motel

Homestead Motel

2 out of 5
Hiawatha Heights
Price was $807, price is now $618 per person
$618
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (SGF)
9.2/10 Wonderful! (365 reviews)
It was perfect for what we needed. A reasonably priced no frills family friendly establishment close to everything.

Reviewed on Mar 21, 2026

The Ozarker Lodge

The Ozarker Lodge

4 out of 5
Foggy River Woods
Price was $832, price is now $642 per person
$642
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (SGF)
9/10 Wonderful! (763 reviews)
Fun, beautiful and unique place where Families can bond over games and s’mores!

Reviewed on May 24, 2026

Roark Creek Resort

Roark Creek Resort

4.5 out of 5
Downtown Branson
Price was $1,194, price is now $929 per person
$929
per person
Jul 6 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Springfield (SGF)
9/10 Wonderful! (2 reviews)
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Chestnutridge Hotel Deals

Thousand Hills Resort Hotel

Thousand Hills Resort Hotel

3 out of 5
120 Wildwood Dr S Branson MO
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $84 total per night from Jun 7 to Jun 8
$84 total
Jun 7 - Jun 8
Total with taxes and fees
8/10 Very Good! (5,942 reviews)
"Only intended to stay two nights, but ended up staying another four nights! Great location! Clean!"

Reviewed on May 24, 2026

Thousand Hills Resort Hotel
Lodge Of The Ozarks

Lodge Of The Ozarks

3 out of 5
3431 W 76 Country Blvd. Branson MO
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $107 total per night from May 31 to Jun 1
$107 total
May 31 - Jun 1
Total with taxes and fees
9.8/10 Exceptional! (3,003 reviews)
"Air Conditioner quit working in the middle of the night. Front desk pretty much said sorry touch luck. It was very unprofessional. Luckily Im a Electrical engineer I reset the unit and it started working again 15 minutes later. Actually working alot better. No thank to the staff on duty. The breakfast ..."

Reviewed on May 24, 2026

Lodge Of The Ozarks
Hyatt Vacation Club at The Lodges at Timber Ridge, Branson

Hyatt Vacation Club at The Lodges at Timber Ridge, Branson

4 out of 5
147 Welk Resort Circle Branson MO
Fully refundable
$145 nightly
The price is $163 total per night from May 25 to May 26
$163 total
May 25 - May 26
Total with taxes and fees
9.2/10 Wonderful! (1,107 reviews)
"The staff was excellent here. Even the maintenance dudes were cool. Front desk ladies were great. The young lady in the activities center was super nice and really cool. We did the escape room they had. EVERYONE who stays here should do it. It’s only $5 and the people who work there made up the puzzles ..."

Reviewed on May 21, 2026

Hyatt Vacation Club at The Lodges at Timber Ridge, Branson
See all 7,570 properties in Chestnutridge
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 Chestnutridge Vacation Packages

Chestnutridge Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Springfield-Branson National Airport (SGF)
Top Sights
Sight and Sound Theatres, Shepherd of the Hills Outdoor Theater and The Mansion

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Frequently asked questions

How much does a Chestnutridge vacation package cost?
Offering excellent value package deals from $559 on Expedia, you'll be thrilled with how little a vacation to Chestnutridge costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chestnutridge?
December, January and February are great times to search for cheap Chestnutridge vacation packages. Opting to travel in less busy months means you can typically find better prices on hotels and flights.
How many days is enough for Chestnutridge?
The ideal duration for your Chestnutridge vacation depends on what you'd like to do and see. Usually, a few days to a week will give you time to visit all the top sights and discover some hidden treasures along the way.
How to find the best Chestnutridge package deals?
Begin your search for a Chestnutridge package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Chestnutridge package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chestnutridge adventure underway.
Is it cheaper to book a Chestnutridge vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Chestnutridge vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Chestnutridge?
If you're planning a spur-of-the-moment Chestnutridge trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Chestnutridge vacation packages?
Your Chestnutridge break should be a relaxing escape from your busy life, not a source of money-related stress. So to allow you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.