Chestnut Hill Vacations from $483

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Your Chestnut Hill Vacation

When an adventure in the city is calling, answer it with a Chestnut Hill vacation package. With all your travel arrangements taken care of before you go, all you have to do here is focus on having a blast. When it's time to get out and see the sights, be sure to include Douglas Lake and Vermont Horse Park on the itinerary for your trip to Chestnut Hill. Check out Expedia's extensive range of travel options and start organizing your dream vacation to Chestnut Hill today.

The Latest Chestnut Hill vacation packages

Price found within the past 48 hours. Click for updated prices.
River Terrace Resort & Convention Center

River Terrace Resort & Convention Center

3.5 out of 5
Downtown Gatlinburg
Price was $658, price is now $483 per person
$483
per person
Aug 23 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Knoxville (TYS)
7.6/10 Good! (1,007 reviews)
The front desk staff are very helpful, kindness and really nice thxyou

Reviewed on Jul 17, 2026

Laurel Point Resort

Laurel Point Resort

2.5 out of 5
Chalet Village
Save 100% on your flight
Price was $1,122, price is now $792 per person
$792
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Knoxville (TYS)
9/10 Wonderful! (328 reviews)
We had a great stay overall. The room was clean and comfortable, and the air conditioning worked well, which made our stay very pleasant. The staff was friendly, welcoming, and quick to answer any questions we had. The kitchen was convenient and had everything we needed for a short family stay. The property was quiet, well maintained, and in a good location. The only small improvement would be to update a few furnishings, but it did not affect our stay. We would definitely consider staying here again.

Reviewed on Jul 9, 2026

Wild Bear Inn

Wild Bear Inn

3 out of 5
Price was $766, price is now $555 per person
$555
per person
Oct 5 - Oct 9
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Knoxville (TYS)
7.8/10 Good! (1,001 reviews)
Wonderfully quiet little place. We had a great experiance! Helpful Staff and clean rooms, the tavern was great!

Reviewed on Jul 13, 2026

The Lodges at the Great Smoky Mountains

The Lodges at the Great Smoky Mountains

4 out of 5
Price was $878, price is now $647 per person
$647
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Knoxville (TYS)
9/10 Wonderful! (76 reviews)
Room was very clean and spacious. Decent view from building 7. They do not clean daily or restock anything during your stay.

Reviewed on Jul 12, 2026

Mountain Meadows

Mountain Meadows

2.5 out of 5
Price was $792, price is now $594 per person
$594
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
8.2/10 Very Good! (12 reviews)
This was our second time staying at this location. It has an older design and isn't the most modern property but it is well kept. The location is close enough to all the attractions but far enough to be nice and quiet.

Reviewed on Jun 28, 2026

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Stay near popular Chestnut Hill attractions

Chestnut Hill Park

10.0/10 (1 review)
Chestnut Hill Park is just one of the places to see in Chestnut Hill, so why not enjoy the other things to explore during your travels?
See properties

What to do in Chestnut Hill

Goliath: Extreme Mountain Zip Lining Adventure

Sevierville: Extreme Mountain Zip Lining Adventure

$109
per adult
Sevierville: Extreme Mountain Zip Lining Adventure
The Ultimate Jet Boat Adventure in Smoky Mountains

The Ultimate Jet Boat Adventure in Smoky Mountains

$215
per adult
The Ultimate Jet Boat Adventure in Smoky Mountains
Cades Cove Guided Tour from Pigeon Forge

Cades Cove Guided Tour from Pigeon Forge

$167
per adult
Cades Cove Guided Tour from Pigeon Forge
See all activities in Chestnut Hill

Chestnut Hill Hotel Deals

Country Cascades Waterpark Resort

Country Cascades Waterpark Resort

3.5 out of 5
204 Sharon Dr Pigeon Forge TN
$138 nightly
The price is $155 total per night from Jul 26 to Jul 27
$155 total
Jul 26 - Jul 27
Total with taxes and fees
Country Cascades Waterpark Resort
Wilderness at the Smokies – River Lodge Suites

Wilderness at the Smokies – River Lodge Suites

4 out of 5
1424 Old Knoxville Highway Sevierville TN
$168 nightly
The price is $189 total per night from Aug 17 to Aug 18
$189 total
Aug 17 - Aug 18
Total with taxes and fees
8.6/10 Excellent! (416 reviews)
"Excellent experience all the way! The staff was kind and helpful and the water park was so well staffed—we felt very safe with our child there. Would highly recommend—excellent value."

Reviewed on Jul 17, 2026

Wilderness at the Smokies – River Lodge Suites
Econo Lodge Pigeon Forge Riverside

Econo Lodge Pigeon Forge Riverside

2.5 out of 5
2440 Parkway Pigeon Forge TN
Fully refundable
$72 nightly
The price is $81 total per night from Aug 5 to Aug 6
$81 total
Aug 5 - Aug 6
Total with taxes and fees
8.6/10 Excellent! (3,051 reviews)
"Convenient location. I suggest to have variety of food for breakfast. They have the same breakfast for 4 days of stay"

Reviewed on Jul 17, 2026

Econo Lodge Pigeon Forge Riverside
See all 17,055 properties in Chestnut Hill
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 Chestnut Hill Vacation Packages

Chestnut Hill Essential Information

Language
English
Currency
U.S dollars
Top Sights
Dandridge Golf & Country Club and Vermont Horse Park

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Frequently asked questions

How much does a Chestnut Hill vacation package cost?
Offering excellent value package deals from $483 on Expedia, you'll be thrilled with how little a vacation to Chestnut Hill costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chestnut Hill?
If you're looking to score a cheap Chestnut Hill vacation package, consider traveling in January, February and March. You'll typically find better prices on airfares and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Chestnut Hill?
With a well-organized schedule, you can easily hit the main Chestnut Hill sights in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, think about booking your Chestnut Hill vacation for longer.
How to find the best Chestnut Hill package deals?
Begin your search for a Chestnut Hill package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to tailor 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 Chestnut Hill package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chestnut Hill adventure underway.
Is it cheaper to book a Chestnut Hill vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Chestnut Hill vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Chestnut Hill?
If you have your Chestnut Hill vacation dates confirmed, book early to grab some unbeatable deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Chestnut Hill vacation packages?
Jet off on your perfect trip to Chestnut Hill with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait for your next paycheck — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.