Chestnut Hill Vacations from $566

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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
Save 100% on your flight
Price was $945, price is now $566 per person
$566
per person
Jun 5 - Jun 9
found 22 hours ago
Roundtrip flight included
Denver (DEN) to Knoxville (TYS)
7.6/10 Good! (1,005 reviews)
Great location and good value for the money. Room was very spacious. The floor of the bathtub seemed to have water trapped under the surface so it was a bit wobbly and the decor is a bit dated but overall a great value for the price!

Reviewed on Apr 8, 2026

Holiday Inn Club Vacations Smoky Mountain Resort by IHG

Holiday Inn Club Vacations Smoky Mountain Resort by IHG

3 out of 5
Save 100% on your flight
Price was $1,441, price is now $981 per person
$981
per person
Jun 11 - Jun 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Knoxville (TYS)
9/10 Wonderful! (484 reviews)
Very clean room, soft beds, wonderful pillows, excellent showers. The indoor pools were a little cold, and strong chlorine smell. Staff was wonderful, very pleasant. I would come back again, and do recommend. Walking distance from the main drag is a huge plus!

Reviewed on Mar 31, 2026

The Ramsey Hotel and Convention Center Pigeon Forge

The Ramsey Hotel and Convention Center Pigeon Forge

3 out of 5
Downtown Pigeon Forge
Price was $969, price is now $676 per person
$676
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Knoxville (TYS)
8.4/10 Very Good! (1,440 reviews)
Maybe switch breakfast choices up for ppl that are staying more than three days also clean the pool more often

Reviewed on Apr 8, 2026

Country Cascades Waterpark Resort

Country Cascades Waterpark Resort

3.5 out of 5
Downtown Pigeon Forge
Price was $1,169, price is now $836 per person
$836
per person
Jun 27 - Jul 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Knoxville (TYS)
9/10 Wonderful! (2,475 reviews)
Great location and staff was friendly.

Reviewed on Apr 8, 2026

The Oliver Hotel

The Oliver Hotel

3.5 out of 5
Downtown Knoxville
Save 100% on your flight
Price was $1,631, price is now $1,171 per person
$1,171
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Knoxville (TYS)
9.8/10 Exceptional! (747 reviews)
Valet parking made it easy at this city location. Just steps to Market Square. Peter Kern Library, a a Prohibition style bar was fun. Comfortable bed. Move bathroom amenities.

Reviewed on Apr 8, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chestnut Hill
View all trips

Discover the most popular places to visit in Chestnut Hill

Dandridge Golf & Country Club

4/5(3 reviews)

Enjoy a round of golf in Dandridge at Dandridge Golf & Country Club. Attend a baseball game while you're in the area, or simply enjoy its bars.

Dandridge Golf & Country Club

Vermont Horse Park

You can take time to visit Vermont Horse Park during your travels to Dandridge. Wander the riverfront or discover the mountain views in this family-friendly area.

Vermont Horse Park

Chestnut Hill Hotel Deals

Edgewater Hotel - Gatlinburg

Edgewater Hotel - Gatlinburg

3 out of 5
402 River Rd Gatlinburg TN
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $168 total per night from Apr 12 to Apr 13
$168 total
Apr 12 - Apr 13
Total with taxes and fees
8.6/10 Excellent! (2,751 reviews)
We enjoyed our stay, the room was clean and beds comfortable. The breakfast was ok it was the same options every morning. It’s very convenient to downtown

Reviewed on Apr 8, 2026

Edgewater Hotel - Gatlinburg
Country Cascades Waterpark Resort

Country Cascades Waterpark Resort

3.5 out of 5
204 Sharon Dr Pigeon Forge TN
$123 nightly
The price is $139 total per night from Apr 23 to Apr 24
$139 total
Apr 23 - Apr 24
Total with taxes and fees
9/10 Wonderful! (2,499 reviews)
Great location and staff was friendly.

Reviewed on Apr 8, 2026

Country Cascades Waterpark Resort
The Park Vista - a DoubleTree by Hilton Hotel - Gatlinburg

The Park Vista - a DoubleTree by Hilton Hotel - Gatlinburg

4 out of 5
705 Cherokee Orchard Road Gatlinburg TN
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $115 total per night from May 10 to May 11
$115 total
May 10 - May 11
Total with taxes and fees
9/10 Wonderful! (2,153 reviews)
No glass cups are provided in the room which seems really weird but they said they had problems with people dropping them from the balconies. The breakfast buffet is fine but not worth paying for unless you get it with your room.

Reviewed on Apr 8, 2026

The Park Vista - a DoubleTree by Hilton Hotel - Gatlinburg
See all 16,425 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
Offering excellent value package deals from $566 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.