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Chestnut Hill Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Chestnut Hill vacation rentals

A cozy living room with a stone fireplace, a comfortable sofa, a wooden staircase, and a large window offering a mountain view.

1. Deer Ridge Mountain Resort

Deer Ridge Mountain Resort
3.5 star property
Gatlinburg
8.8 out of 10, Excellent, (414 reviews)
"Property is at great location ."
United States
Neetu
$198 nightly
The price is $223
Nov 2 - Nov 3
Total with taxes and fees
Deer Ridge Mountain Resort
A log cabin-style hotel with multiple balconies, a swimming pool, and lush greenery surrounding the property.

2. Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park
4.0 star property
Gatlinburg
8.4 out of 10, Very good, (1,389 reviews)
"Great to stay"
United States
James
$164 nightly
The price is $185
Nov 15 - Nov 16
Total with taxes and fees
Westgate Smoky Mountain Resort & Water Park
A wooden cabin with a deck, surrounded by dense forest and a stream.

3. Honeymoon Hills Gatlinburg Cabin Rentals

Honeymoon Hills Gatlinburg Cabin Rentals
3.5 star property
Gatlinburg
8.8 out of 10, Excellent, (217 reviews)
"Overall a was a great place!"
United States
José M
$384 nightly
The price is $433
Nov 17 - Nov 18
Total with taxes and fees
Honeymoon Hills Gatlinburg Cabin Rentals
A cozy cabin interior with a stone fireplace, leather furniture, and a sign reading "Distilled Meridies."

4. Distilled Memories

Distilled Memories
3.0 star property
Sevierville
9.6 out of 10, Exceptional, (34 reviews)
"Very nice stay"
United States
Mandy
$279 nightly
The price is $314
Oct 26 - Oct 27
Total with taxes and fees
Distilled Memories
A spacious living room with a fireplace, a comfortable sofa, a coffee table, and a balcony with outdoor seating.

5. Deer Ridge Mountain Resort by Jackson Mountain Rentals

Deer Ridge Mountain Resort by Jackson Mountain Rentals
3.0 star property
Gatlinburg
9.0 out of 10, Wonderful, (131 reviews)
"Nice place to stay with family."
United States
Dhvanitkumar
$291 nightly
The price is $328
Oct 25 - Oct 26
Total with taxes and fees
Deer Ridge Mountain Resort by Jackson Mountain Rentals
A wooden cabin kitchen with a dining table set for six, stainless steel appliances, and a large window overlooking greenery.

6. Pinot Splash

Pinot Splash
4.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (6 reviews)
"Everything about this place was perfect!!!! Easy communication with the property and perfect spot for the family!!!"
United States
Chelsea
$646 nightly
The price is $728
Nov 4 - Nov 5
Total with taxes and fees
Pinot Splash
A cozy cabin interior with wooden walls, a fireplace, leather sofas, patterned armchairs, and a dining area with a table and chairs.

7. Fireflies and Moonshine

Fireflies and Moonshine
3.5 star property
Gatlinburg
9.8 out of 10, Exceptional, (35 reviews)
"Lots of space, great atmosphere. Close to town but in the woods. Really relaxing."
United States
Harold
$416 nightly
The price is $469
Oct 28 - Oct 29
Total with taxes and fees
Fireflies and Moonshine
A wooden deck with a hot tub and a bench.

8. Moonshine Holler

Moonshine Holler
3.5 star property
Sevierville
10.0 out of 10, Exceptional, (15 reviews)
"The Stay was perfect and everything was arranged nice."
United States
Leroy
$268 nightly
The price is $302
Nov 4 - Nov 5
Total with taxes and fees
Moonshine Holler
Exterior

9. Lil' Smoky Studio

Lil' Smoky Studio
2.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (1 review)
$319 nightly
The price is $360
Nov 1 - Nov 2
Total with taxes and fees
Lil' Smoky Studio
A cozy log cabin interior with a fireplace, leather seating, a dining area, and large windows offering a view of the outdoors.

10. Cabin On A Cloud

Cabin On A Cloud
3.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (14 reviews)
"We had an amazing stay! The cabin was very convenient to downtown Gatlinburg and only about 25 minutes from Dollywood. It had everything we needed, and the hosts were great communicators. We would definitely stay here again!"
United States
Katie
$437 nightly
The price is $492
Nov 17 - Nov 18
Total with taxes and fees
Cabin On A Cloud
A cozy log cabin interior with a fireplace, leather sofas, a television, and a ceiling fan.

11. A Bearadise

A Bearadise
5.0 star property
Pigeon Forge
10.0 out of 10, Exceptional, (18 reviews)
"Awesome property easy check in can't wait to go back!!"
United States
teresa
$478 nightly
The price is $537
Oct 26 - Oct 27
Total with taxes and fees
A Bearadise
A resort with a large swimming pool, lounge areas, and a building with multiple levels.

12. Smith Creek Resort

Smith Creek Resort
5.0 star property
Sevierville
10.0 out of 10, Exceptional, (3 reviews)
"Unbelievable place!!! We thoroughly enjoyed our stay here. Top of the line everything. Highend, exclusive and overall just perfect. You can’t go wrong staying at this AMAZING RESORT!!!!"
United States
Jenny
$934 nightly
The price is $981
Nov 3 - Nov 4
Total with taxes and fees
Smith Creek Resort
Pool

13. Happily Ever After

Happily Ever After
5.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (22 reviews)
"We love the cabin"
United States
shaun
$538 nightly
The price is $606
Nov 14 - Nov 15
Total with taxes and fees
Happily Ever After
A cozy log cabin interior with a stone fireplace, wooden walls, and a large window with curtains.

14. The Willows

The Willows
3.0 star property
Sevierville
9.8 out of 10, Exceptional, (7 reviews)
"Was an ideal getaway cabin far enough from crowds but close enough to the attractions. Highly recommend and will be staying here again when we return!"
United States
Jerid
$281 nightly
The price is $317
Nov 3 - Nov 4
Total with taxes and fees
The Willows
A balcony with a table and chairs, overlooking a cityscape with buildings and greenery.

15. Whispering Pines by Jackson Mountain Rentals

Whispering Pines by Jackson Mountain Rentals
3.5 star property
Pigeon Forge
9.4 out of 10, Exceptional, (51 reviews)
"nice location, "
United States
Louise
$366 nightly
The price is $411
Nov 1 - Nov 2
Total with taxes and fees
Whispering Pines by Jackson Mountain Rentals
A cabin with a deck, outdoor seating, and a fire pit.

16. Romantic Cabin Retreat By Ghosal Luxury Lodging

Romantic Cabin Retreat By Ghosal Luxury Lodging
4.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (8 reviews)
"The property was very easy to get to and while feeling secluded in the mountains, we were also only 10-15 minutes away from the downtown life. The cabin was clean, the pool and hot tub were well maintained. There was a lot to do at the cabin so we could just stay in if we wanted to. Would recommend to any couple looking for a get away!"
United States
Michael
$820 nightly
The price is $925
Oct 30 - Oct 31
Total with taxes and fees
Romantic Cabin Retreat By Ghosal Luxury Lodging
A cozy cabin interior with a fireplace, leather furniture, and a ceiling fan.

17. Pinot Paradise

Pinot Paradise
2.0 star property
Pigeon Forge
9.6 out of 10, Exceptional, (7 reviews)
"Beautiful place to visit and they’re on my anniversary had a good time. It’s clean and well kept very comfortable and I travel a lot."
United States
Athena
$380 nightly
The price is $427
Nov 3 - Nov 4
Total with taxes and fees
Pinot Paradise
A wooden cabin interior with a black leather sofa, a dining table, and a kitchen area.

18. A Top Notch Lodge

A Top Notch Lodge
5.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful cottage in peaceful location. Relatively close to Gatlinburg, 5 minutes drive. I would definitely stay there again."
United States
Fred
$349 nightly
The price is $393
Oct 25 - Oct 26
Total with taxes and fees
A Top Notch Lodge
A neatly arranged bedroom with a bed, two bedside tables, a framed sign above the bed, and a view of the outdoors through a window.

19. Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg

Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg
3.0 star property
Gatlinburg
5.8 out of 10, (182 reviews)
"Great location. Downfall cleaning wasn't done in timely manner during check in and hardly anyone in the office. But the staff I seen was nice."
United States
Elizabeth
$56 nightly
The price is $64
Nov 1 - Nov 2
Total with taxes and fees
Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg
A wooden deck with a hot tub, red chairs, and a wooden pergola.

20. Gnoming Around

Gnoming Around
3.5 star property
Gatlinburg
9.4 out of 10, Exceptional, (23 reviews)
"super nice"
United States
Danielle
$340 nightly
The price is $384
Oct 29 - Oct 30
Total with taxes and fees
Gnoming Around
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.
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Top Chestnut Hill Hotel Reviews

Edgewater Hotel - Gatlinburg

Edgewater Hotel - Gatlinburg

10/10 Excellent
"Parking was nice. Pool area was nice. Location is the best. It was walkable pretty much anywhere we wanted to go in Gatlinburg. Breakfast was average. We would stay here again."
Robin 2-night trip
Posted 2 hours ago
Edgewater Hotel - Gatlinburg

Find out more about Chestnut Hill

Everything you need to know about Chestnut Hill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestnut Hill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestnut Hill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestnut Hill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestnut Hill. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chestnut Hill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $64 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chestnut Hill rentals

At Expedia, we put the best Chestnut Hill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chestnut Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestnut Hill vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestnut Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Chestnut Hill?

Yes, you can find vacation rentals where you'll be only 14.4 mi (23.2 km) from Dollywood, providing a more remote option if you'd like a quiet spot to stay.

What's the top vacation rental in Chestnut Hill?

Westgate Smoky Mountain Resort & Water Park: This vacation home rental outside of Chestnut Hill offers 2 hot tubs, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Chestnut Hill?

Explore the area and family-friendly sights such as Dollywood, or get out into nature at a spot like Chestnut Hill Park. In the larger area, you’ll find Island at Pigeon Forge and Forbidden Caverns.

What are vacation rentals like in Chestnut Hill?

Vacation rentals are privately owned properties you can reserve for several days or longer in Chestnut Hill. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.