Chestnut Hill Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Top Chestnut Hill Vacation Deals
Price found within the past 48 hours. Click for updated prices.
River Terrace Resort & Convention Center
Downtown Gatlinburg
CA $1,031
per person
Dec 1 - Dec 5
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Knoxville (TYS)
7.8/10 Good! (1,013 reviews)
We had been told the facilities had been renovated in the last few years. The room we had, although clean, looked as though it had new flooring and paint, but the entrance door to the room looked as though it was ready to fall off and hard to open, as well as the door handle to the balcony, the counters in and outside the bathroom looked to be from the 1960s, as did the sinks and mirrors. No secure WIFI. The staff at the desk seemed nice enough but all and all, to us, the room was not worth the price per night we paid. So disappointed. I doubt we ever stay there again.
Reviewed on Oct 17, 2026
Wild Bear Inn
CA $1,614
per person
Dec 30 - Jan 3
found 12 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Knoxville (TYS)
8/10 Very good! (1,008 reviews)
Old motel with a face lift. Loud in the room from traffic, had to play around with the cord on ac/heater to get it to turn in. Good enough for our few hrs of sleep we needed to get!
Reviewed on Oct 19, 2026
Ready to book your vacation to Chestnut Hill?
Chestnut Hill Hotel Deals
Econo Lodge Pigeon Forge Riverside
2440 Parkway Pigeon Forge TN
Fully refundable
CA $119
CA $134 total
Nov 15 - Nov 16
includes taxes & fees
8.8/10 Excellent! (3,452 reviews)
"Very clean and location was great!"
Reviewed on Oct 19, 2026
Best Western Plaza Inn
3755 Parkway Pigeon Forge TN
Fully refundableReserve now, pay when you stay
CA $127
CA $143 total
Oct 25 - Oct 26
includes taxes & fees
Edgewater Hotel - Gatlinburg
402 River Rd Gatlinburg TN
Fully refundableReserve now, pay when you stay
CA $183
CA $206 total
Nov 11 - Nov 12
includes taxes & fees
8.6/10 Excellent! (3,273 reviews)
"Room was clean. Really, the only thing that was terrible was the parking!! 1st we were going to have to park a half mile away and that parking area closed at 9pm and couldn’t get your car till 8 am the next day. That is unacceptable due to what if something happened and you needed your car for an ..."
Reviewed on Oct 19, 2026
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.
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?
What to do in Chestnut Hill
Sevierville VIP Wine, Shine, Bourbon & Lunch Experience
CA $97
per adult
Sevierville: Extreme Mountain Zip Lining Adventure
CA $152
per adult
Sevierville: Smoky Mountains Zipline Near Pigeon Forge
CA $140
per adult
100% of travellers recommend
Frequently asked questions
How much does a Chestnut Hill vacation package cost?
You'll find cheap prices from CA $987 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?
- 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.
- 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.
- 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.
- 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.
