Chestnutridge Vacations from $637

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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 Park at Foxborough Resort

The Park at Foxborough Resort

Branson Meadows
$637
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Montrose (MTJ) to Springfield (SGF)
7.2/10 Good! (340 reviews)
Room was decent, pool was nice and clean, all the amenities were great!

Reviewed on Aug 16, 2026

Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

$742
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Springfield (SGF)
8.4/10 Very Good! (1,004 reviews)
We loved it there! Cook, play, sleep- great place to stay!

Reviewed on Oct 1, 2026

Stormy Point Village Lakeside

Stormy Point Village Lakeside

$723
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Springfield (SGF)
7.8/10 Good! (215 reviews)
We paid in full through Expedia when we booked; however, the property charged us additional resort fees at check in. It doubled the price we paid. The amenities are located at the other property and not within walking distance. The ice machine was broken. I will never stay here again.

Reviewed on Sep 25, 2026

The Townhouses

The Townhouses

Green Mountain
$767
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Montrose (MTJ) to Springfield (SGF)
8.2/10 Very Good! (333 reviews)
The staff were friendly. However, At check-in my parking pass was not given to me so we received three calls about it at 7:30 the next morning. The condo looks just like the pictures and was roomy for my large family, but was a little dated. The carpet throughout was old and stained and the stove burners in the kitchen were hard to use because they were bent up. They didn’t provide simple kitchen utensils like pancake turners and they only had a few pans and one sheet pan, which made cooking a bit of a hassle. They didn’t provide dish soap we had to get our own, and they didn’t have extra trash bags available. We have a large family, so that would have been helpful as all of the trash cans were very full when we left. Also, although the rooms were clean at a glance, there were cobwebs and spiders everywhere (some dead, some alive). I recommend that they get their property sprayed by pest control. When we first walked in, we killed 5 spiders within the first 10 minutes. On day two of our stay, I found two more spiders in the laundry area and another bug came crawling in as we were sitting in the living room area. In addition to that, when I went to use a towel from the bathroom downstairs, there was a bug inside of it. Lastly, the shower in the main room had mold inside of it.

Reviewed on Sep 7, 2026

Westgate Branson Woods Resort and Cabins

Westgate Branson Woods Resort and Cabins

Shepherd of the Hills
$645
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Denver (DEN) to Springfield (SGF)
8.6/10 Excellent! (1,186 reviews)
Great value for a cozy place. The decor was outdated but clean, except for some cobwebs in the ceiling corner. Bathtub/shower was small & narrow. Wish there was a bench outside our room to enjoy the woods. Staff were friendly at check in. We liked the gated entrance & security presence.

Reviewed on Oct 2, 2026

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Chestnutridge Hotel Deals

Thousand Hills Resort Hotel

Thousand Hills Resort Hotel

120 Wildwood Dr S Branson MO
Fully refundableReserve now, pay when you stay
$67 nightly
$76 total
Oct 18 - Oct 19
Total with taxes and fees
Thousand Hills Resort Hotel
Chateau On The Lake Resort Spa and Convention Center

Chateau On The Lake Resort Spa and Convention Center

415 North State Highway 265 Branson MO
Fully refundableReserve now, pay when you stay
$168 nightly
$189 total
Oct 20 - Oct 21
Total with taxes and fees
8.4/10 Very Good! (1,392 reviews)
"very nice"

Reviewed on Oct 1, 2026

Chateau On The Lake Resort Spa and Convention Center
Clarion Inn Branson

Clarion Inn Branson

2820 W Highway 76 Branson MO
Fully refundable
$79 nightly
$90 total
Oct 25 - Oct 26
Total with taxes and fees
8.4/10 Very Good! (495 reviews)
"The room was spacious and clean. We were given 3 coupons for 2-for-1 breakfasts for $7.99. Unbelievable good deal on breakfast. No complaints about anything at the Clarion Inn."

Reviewed on Oct 1, 2026

Clarion Inn Branson
See all 7,695 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 $637 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.