Chestnutridge Vacations from $345

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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.
Gazebo Inn

Gazebo Inn

2 out of 5
Branson Theater District
Price was $478, price is now $345 per person
$345
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to Springfield (SGF)
8.4/10 Very Good! (1,007 reviews)
Thank you

Reviewed on Jul 16, 2026

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 $700, price is now $406 per person
$406
per person
Sep 18 - Sep 22
found 10 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (SGF)
8.6/10 Excellent! (1,011 reviews)
Dirty towel in bathroom, hanging behind bathroom door. Mold on ceiling ,wall and shower curtain. So I wonder how clean it really was.

Reviewed on Jul 16, 2026

Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

4 out of 5
Price was $769, price is now $512 per person
$512
per person
Sep 18 - Sep 22
found 10 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Springfield (SGF)
8.4/10 Very Good! (983 reviews)
I only stayed for two nights but the room was clean, the shower had great water pressure (very important), and the staff was extremely friendly and helpful. My only complaint was that it was like living in an apartment, so it was noisy with the neighbors upstairs walking around, but for the price and service, it was worth it.

Reviewed on Jul 13, 2026

Hilton Grand Vacations Club Long Creek Ridgedale

Hilton Grand Vacations Club Long Creek Ridgedale

2.5 out of 5
Save 100% on your flight
Price was $2,761, price is now $1,936 per person
$1,936
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Denver (DEN) to Springfield (SGF)
10/10 Exceptional! (1 review)
Great View

Reviewed on Apr 12, 2026

The Ozarker Lodge

The Ozarker Lodge

4 out of 5
Foggy River Woods
Price was $764, price is now $556 per person
$556
per person
Sep 5 - Sep 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Springfield (SGF)
9/10 Wonderful! (811 reviews)
Room was not clean , location is great and good for young kids

Reviewed on Jul 14, 2026

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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
$67 nightly
The price is $76 total per night from Aug 5 to Aug 6
$76 total
Aug 5 - Aug 6
Total with taxes and fees
8/10 Very Good! (6,189 reviews)
"Wonderful place to stay, we loved the pool and the staff was so helpful and friendly"

Reviewed on Jul 16, 2026

Thousand Hills Resort Hotel
Hotel Grand Victorian

Hotel Grand Victorian

3.5 out of 5
2325 W Highway 76 Branson MO
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $118 total per night from Aug 3 to Aug 4
$118 total
Aug 3 - Aug 4
Total with taxes and fees
9.2/10 Wonderful! (1,891 reviews)
"Pool was nice. Rooms just okay kind of small. Found straw underneath bed with white substance."

Reviewed on Jul 16, 2026

Hotel Grand Victorian
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
$136 nightly
The price is $153 total per night from Aug 2 to Aug 3
$153 total
Aug 2 - Aug 3
Total with taxes and fees
9.2/10 Wonderful! (1,141 reviews)
"This is a 3 star type of property. So long as your expectations are for that, you’ll be happy. Pros: comfortable bed, climate control worked well, in room laundry and well-equipped kitchenette with full-size fridge. Nice game room at the lodge. Cons: aging property is going to need some updates soon. ..."

Reviewed on Jul 16, 2026

Hyatt Vacation Club at The Lodges at Timber Ridge, Branson
See all 7,581 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 $345 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.