Chestnut Hill Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.

Top Chestnut Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
River Edge Inn

River Edge Inn

2 out of 5
Downtown Gatlinburg
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Knoxville (TYS)
8.6/10 Excellent! (1,004 reviews)
The description on the website isn't quite accurate. The building itself is very old. Room wasn't at all what i expected and the amenities listed in site are also not accurate

Reviewed on Jul. 11, 2025

Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park

4 out of 5
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Knoxville (TYS)
8.4/10 Very Good! (1,093 reviews)
The property was great. It felt like a decently modern cabin in the woods. The people working there are absolutely amazing. Super friendly and curteous. The location is quite easy to find, it is quite steep up the hill. Every hotel we stay I try to give a review based on 3 things. 1. Hospitality, 2. Premise and experience 3. Above and betodn beyond I would give it all a 5 star except the going above and and beyond. There was about 2 occasions where I needed little bit of help and both were failed. I needed to borrow a computer mouse for an hour, I had to check in

Reviewed on Jul. 8, 2025

Laurel Point Resort

Laurel Point Resort

2.5 out of 5
Chalet Village
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Knoxville (TYS)
8.8/10 Excellent! (313 reviews)
They could have been a little more organized. There was no one there to help on January 1st.

Reviewed on Jan. 3, 2025

Hampton Inn Gatlinburg Historic Nature Trail

Hampton Inn Gatlinburg Historic Nature Trail

2.5 out of 5
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Knoxville (TYS)
9.2/10 Wonderful! (1,151 reviews)
Esculent spaciousness in this

Reviewed on Jul. 14, 2025

Courtyard by Marriott Gatlinburg Downtown

Courtyard by Marriott Gatlinburg Downtown

3 out of 5
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Knoxville (TYS)
9/10 Wonderful! (1,003 reviews)
Checking in they tried to put me in a handicap room and not tell us room was paid in advance to..When I got in the room it was terrible smelled like a old folks home and bed was low and the couch and bigger room was not there.. So I called front desk and they tried to give me the run around saying they didn't know who I booked with and I cut her off right and told this will not do I want my room or We would go elsewhere....Then their attitude changed and we got our nice room.....The trees and bushes in the courtyard were way past needing a trimming...This is a great hotel but they must have changed managers for we having been staying here for 6 or 7 years now....And it has changed...

Reviewed on Jul. 14, 2025

Ready to book your vacation to Chestnut Hill?

 

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Chestnut Hill Hotel Deals

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
The price is CA $163 per night from Jul 27 to Jul 28
CA $163
CA $184 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,741 reviews)
"Late checkout was super helpful, and the hotel was better than expected. It is not really walkable from the main drag though. We thought we'd use the trolley, but instead we ended up driving down and parking. We found a central lot for $15, so it worked out fine. Pro tip, with the noon checkout, ..."

Reviewed on Jul. 13, 2025

The Park Vista - a DoubleTree by Hilton Hotel - Gatlinburg
Creekstone Inn
Creekstone Inn
2 out of 5
4034 S River Rd, Pigeon Forge, TN
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Aug 14 to Aug 15
CA $110
CA $126 total
Aug 14 - Aug 15
includes taxes & fees
9/10 Wonderful! (2,478 reviews)
"Staff was great"

Reviewed on Jul. 10, 2025

Creekstone Inn
Grand Smokies Resort Lodge
Grand Smokies Resort Lodge
2.5 out of 5
2385 Parkway, Pigeon Forge, TN
The price is CA $123 per night from Jul 20 to Jul 21
CA $123
CA $138 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very Good! (803 reviews)
"We enjoyed the room and view."

Reviewed on Jul. 13, 2025

Grand Smokies Resort Lodge
See all 15,732 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

What to do in Chestnut Hill

Jet Boat Adventure in the Smoky Mountains Dam Tour

Jet Boat Adventure in the Smoky Mountains Dam Tour

CA $102
per adult
Jet Boat Adventure in the Smoky Mountains Dam Tour
Digital Ocean Adventure in Sevierville

Digital Ocean Adventure in Sevierville

CA $35
per adult
Digital Ocean Adventure in Sevierville
The Ultimate Jet Boat Adventure in Smoky Mountains

The Ultimate Jet Boat Adventure in Smoky Mountains

CA $246
per adult
The Ultimate Jet Boat Adventure in Smoky Mountains
See all activities in Chestnut Hill

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
You'll find cheap prices from CA $1,233 on Expedia for your Chestnut Hill break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Chestnut Hill costs.
What are the cheapest months to go to Chestnut Hill?
You can usually find reduced prices and better availability in January, February and March. Take a look at our cheap Chestnut Hill vacation packages and you could land some great off-season deals.
How many days is enough for Chestnut Hill?
With a well-planned itinerary, you can easily hit the top Chestnut Hill sights in a handful of days. But if you want to discover hidden spots or take day trips, consider booking your Chestnut Hill vacation for longer.
How to find the best Chestnut Hill package deals?
Finding a cheap Chestnut Hill package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Chestnut Hill package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Chestnut Hill vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Chestnut Hill vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Chestnut Hill?
If you've got your Chestnut Hill vacation dates locked in, book as soon as you can to grab some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Chestnut Hill?

  1. Choose when to travel: Check your calendar and get packing. Your favourite time of year and the type of activities available will also help you decide when to escape to Chestnut Hill.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to flights and activities. Your accommodations will probably be the largest expense during your trip to Chestnut Hill.
  3. Determine how many days away: Start by making a list of all the activities and attractions you want to get to in Chestnut Hill. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Chestnut Hill vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.