Chestnut Hill Vacation Packages

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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.
Best Western Knoxville Airport/Alcoa

Best Western Knoxville Airport/Alcoa

2.5 out of 5
Price was CA $1,248, price is now CA $1,197 per person
CA $1,197
per person
Nov 17 - Nov 21
found 21 hours ago
Roundtrip flight included
Halifax (YHZ) to Knoxville (TYS)
8.4/10 Very Good! (1,005 reviews)
Easy check in. Gave me a broom on the second floor in eyesight of the front desk. I was traveling by myself and I felt so safe.

Reviewed on Aug. 20, 2025

Margaritaville Island Hotel

Margaritaville Island Hotel

4 out of 5
Downtown Pigeon Forge
Price was CA $1,835, price is now CA $1,471 per person
CA $1,471
per person
Nov 17 - Nov 21
found 20 hours ago
Roundtrip flight included
Halifax (YHZ) to Knoxville (TYS)
9.4/10 Exceptional! (1,151 reviews)
We really enjoyed our stay. This is the third year in a row we have brought our granddaughter. We chose River view this time. We didn't enjoy it as much as the Village view so probably won't chose River again. We love Margaritaville.

Reviewed on Aug. 25, 2025

Dollywood's DreamMore Resort

Dollywood's DreamMore Resort

4 out of 5
Price was CA $1,845, price is now CA $1,670 per person
CA $1,670
per person
Nov 17 - Nov 21
found 20 hours ago
Roundtrip flight included
Halifax (YHZ) to Knoxville (TYS)
9.6/10 Exceptional! (1,000 reviews)
It was a wonderful experience to stay at Dreammore.

Reviewed on Aug. 25, 2025

Holiday Inn Express & Suites Alcoa (Knoxville Airport) by IHG

Holiday Inn Express & Suites Alcoa (Knoxville Airport) by IHG

2.5 out of 5
Price was CA $1,272, price is now CA $1,206 per person
CA $1,206
per person
Nov 17 - Nov 21
found 21 hours ago
Roundtrip flight included
Halifax (YHZ) to Knoxville (TYS)
8.6/10 Excellent! (715 reviews)
I would highly recommend anyone stay here. The staff is extremely courteous and friendly. The property is clean. Was an extremely pleasant stay

Reviewed on Jul. 2, 2025

Hilton Knoxville Airport

Hilton Knoxville Airport

3.5 out of 5
Price was CA $1,507, price is now CA $1,443 per person
CA $1,443
per person
Nov 17 - Nov 21
found 20 hours ago
Roundtrip flight included
Halifax (YHZ) to Knoxville (TYS)
9.2/10 Wonderful! (1,005 reviews)
Super friendly staff!

Reviewed on Aug. 27, 2025

Ready to book your vacation to Chestnut Hill?

 

Choose your dates

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 $139 per night from Sep 4 to Sep 5
CA $139
CA $157 total
Sep 4 - Sep 5
includes taxes & fees
8.8/10 Excellent! (1,795 reviews)
"We love staying at the Park Vista. It was quiet and clean. The rooms was spacious. The bed seemed old and a little broken down so it was not the best bed. We slept okay. The parking fee was $15/night. It used to be $10/night so that disappointed us."

Reviewed on Aug. 24, 2025

The Park Vista - a DoubleTree by Hilton Hotel - Gatlinburg
Edgewater Hotel - Gatlinburg

Edgewater Hotel - Gatlinburg

3 out of 5
402 River Rd, Gatlinburg, TN
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Sep 28 to Sep 29
CA $115
CA $130 total
Sep 28 - Sep 29
includes taxes & fees
Edgewater Hotel - Gatlinburg
Compass Hotel by Margaritaville

Compass Hotel by Margaritaville

3 out of 5
125 Music Mountain Drive, Pigeon Forge, TN
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Sep 7 to Sep 8
CA $128
CA $169 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (1,469 reviews)
"A favorite we keep coming back to again and again. The rooms are superb the service and staff is excellent. The breakfast in the morning is amazing. Poolside service is fantastic. Just above and beyond"

Reviewed on Aug. 25, 2025

Compass Hotel by Margaritaville
See all 15,862 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

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
Gatlinburg: Impossibilities Magic and Mind-Reading Show

Pigeon Forge: Impossibilities Magic and Mind-Reading Show

CA $43
per adult
Pigeon Forge: Impossibilities Magic and Mind-Reading Show
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 $1,197 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.