Chestnut Hill Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Chestnut Hill

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 2.657.413 ₫ per night from 24 Aug to 25 Aug
2.657.413 ₫
2.996.233 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,771 reviews)
"Older property but very comfortable stay. Stunning views."

Reviewed on 15 Aug 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 3.050.179 ₫ per night from 19 Aug to 20 Aug
3.050.179 ₫
3.439.077 ₫ total
19 Aug - 20 Aug
includes taxes & fees
8.6/10 Excellent! (2,197 reviews)
"Great and friendly staff! Very welcoming."

Reviewed on 16 Aug 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
9.6/10 Exceptional! (1,421 reviews)
"This hotel is wonderful! It’s so clean and beautifully decorated. Room- We stayed in a standard room with 2 queen beds. Our room was beautiful and spacious. We were on the 7th floor in a corner where we had a Mountain View from the balcony but a slight pool view from the window. Perfect spot! Nice ..."

Reviewed on 16 Aug 2025

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Compass Hotel by Margaritaville
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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.

Popular places to visit

Shoppes at Roper Mansion

You can learn about the history of Dandridge with a visit to Shoppes at Roper Mansion.

Shoppes at Roper Mansion

Revolutionary War Graveyard

Enjoy a stop at Revolutionary War Graveyard, a landmark worth seeing in Dandridge.

Revolutionary War Graveyard

Frequently asked questions

How much does a Chestnut Hill holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday 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 holiday. 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 holiday as a package?
Expedia holiday 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 holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Chestnut Hill?
If you have your Chestnut Hill holiday 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 accommodation, 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 holiday package that brings all your bookings together.