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Chestnut Hill Holiday Rentals

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Check prices for these dates

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

Our top choices for Chestnut Hill holiday 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, (411 reviews)
"Property is at great location ."
United States
Neetu
The price is S$285
includes taxes & fees
21 Oct - 22 Oct
Deer Ridge Mountain Resort
A log cabin-style hotel with multiple buildings, a restaurant, and a parking area surrounded by greenery.

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, (1,386 reviews)
"Great to stay"
United States
James
The price is S$237
includes taxes & fees
15 Nov - 16 Nov
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
The price is S$554
includes taxes & fees
17 Nov - 18 Nov
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
The price is S$425
includes taxes & fees
19 Nov - 20 Nov
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
The price is S$423
includes taxes & fees
25 Oct - 26 Oct
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
The price is S$914
includes taxes & fees
20 Oct - 21 Oct
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
The price is S$571
includes taxes & fees
28 Oct - 29 Oct
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
Moonshine Holler
Exterior

9. Lil' Smoky Studio

Lil' Smoky Studio
2.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (1 review)
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
The price is S$605
includes taxes & fees
18 Nov - 19 Nov
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, (17 reviews)
"Awesome property easy check in can't wait to go back!!"
United States
teresa
The price is S$668
includes taxes & fees
20 Oct - 21 Oct
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
The price is S$1,281
includes taxes & fees
21 Oct - 22 Oct
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
The price is S$818
includes taxes & fees
14 Nov - 15 Nov
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
The price is S$384
includes taxes & fees
3 Nov - 4 Nov
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
The price is S$538
includes taxes & fees
1 Nov - 2 Nov
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
The price is S$1,021
includes taxes & fees
30 Oct - 31 Oct
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
The price is S$497
includes taxes & fees
3 Nov - 4 Nov
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
The price is S$478
includes taxes & fees
25 Oct - 26 Oct
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, (178 reviews)
"Location is what you’re paying for here. No towels, no soap, shampoo or toiletries. Had issues checking in with Expedia reservation. Wouldn’t pay this price for this accommodation again."
United States
Travis
The price is S$74
includes taxes & fees
1 Nov - 2 Nov
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
The price is S$464
includes taxes & fees
21 Oct - 22 Oct
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

Wilderness at the Smokies – River Lodge Suites

Wilderness at the Smokies – River Lodge Suites

10/10 Excellent
"Definitely will be back!"
james 2-night trip
Posted less than an hour ago
Wilderness at the Smokies – River Lodge Suites

Frequently asked questions

Can I find a holiday rental in Chestnut Hill?

Yes, you can find holiday rentals where you'll be only 14.4 mi (23.2 km) from Dollywood, providing a secluded option if you want a quiet place to stay.

What are some of the best holiday rentals that Chestnut Hill has to offer?

Westgate Smoky Mountain Resort & Water Park: This holiday home rental outside of Chestnut Hill offers 2 hot tubs, a BBQ 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 wider area, you’ll find Island at Pigeon Forge and Forbidden Caverns.

What are holiday rentals like in Chestnut Hill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestnut Hill. Holiday rentals offer extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family gatherings.