Chestnut Hill Vacations

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Find the Best Chestnut Hill Vacation Packages

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 ₩140,485 per night from Aug 24 to Aug 25
₩140,485
₩158,396 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,771 reviews)
"Older property but very comfortable stay. Stunning views."

Reviewed on Aug 15, 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 ₩161,249 per night from Aug 19 to Aug 20
₩161,249
₩181,809 total
Aug 19 - Aug 20
includes taxes & fees
8.6/10 Excellent! (2,202 reviews)
"I like that the stream is just outside the hotel, haunted mansion is just next to the hotel and walkable distance from the main road."

Reviewed on Aug 17, 2025

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 ₩148,749 per night from Sep 1 to Sep 2
₩148,749
₩192,624 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (1,422 reviews)
"Everyone was very nice and the facility was extremely clean. The only bad thing I would have to say would be the pillows are not firm. I would stay there again and recommend other people to do so as well."

Reviewed on Aug 17, 2025

Compass Hotel by Margaritaville
See all 15,779 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.

Discover the most popular places to visit in Chestnut Hill

Vermont Horse Park

Enjoy the mountain views and explore Vermont Horse Park, a lovely green space in Dandridge. Wander the riverfront in this family-friendly area.

Vermont Horse Park

Frequently asked questions

How much does a Chestnut Hill vacation package cost?
Offering excellent value package deals 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?
You can generally find lower prices and better availability in January, February and March. Explore our cheap Chestnut Hill vacation packages and you could land some great off-season deals.
How many days is enough for Chestnut Hill?
Typically, a handful of days is enough to tick off the main attractions during your Chestnut Hill vacation. But if you prefer to have time to chill out or take day tours, think about extending your trip.
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.
How to plan a trip to Chestnut Hill?

  1. Choose your travel dates: What you want to do in Chestnut Hill and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: As well as the cost of your accommodations, you should factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could arise during your trip to Chestnut Hill.
  3. Work out your trip length: Consider how long you'd like to spend exploring Chestnut Hill. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now 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.