Chestnut Hill Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Chestnut Hill

2 outdoor pools
Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park

4.0 star property
8.4 out of 10, Very good, (1124)
"Best Location, new units, Indoor water park"
United States
Shalin
The price is S$187
includes taxes & fees
4 Jan - 5 Jan, 2026
Westgate Smoky Mountain Resort & Water Park
Living area
Deer Ridge Mountain Resort by Jackson Mountain Rentals

Condo in Gatlinburg

3.0 star property
9.0 out of 10, Wonderful, (126)
"Had a great relaxing time, Great view of the mountains from the patio."
United States
Mark
The price is S$530
includes taxes & fees
16 Dec - 17 Dec
Deer Ridge Mountain Resort by Jackson Mountain Rentals
Terrace/patio
Deer Ridge Mountain Resort

Condo resort in Gatlinburg

2.5 star property
9.0 out of 10, Wonderful, (147)
"Property was very nice! Loved my stay here "
United States
Iesha
The price is S$263
includes taxes & fees
9 Dec - 10 Dec
Deer Ridge Mountain Resort
Outdoor dining
Mountain View Condo 1205 - Two Bedroom Condo

Condo in Pigeon Forge

3.5 star property
8.2 out of 10, Very good, (10)
"Love the location. Nice room. Very comfortable atmosphere. "
United States
Emilie
The price is S$422
includes taxes & fees
8 Dec - 9 Dec
Mountain View Condo 1205 - Two Bedroom Condo
Outdoor spa tub
Fireflies and Moonshine

Chalet in Gatlinburg

3.5 star property
9.8 out of 10, Exceptional, (31)
"Place was amazing "
United States
Michael
Fireflies and Moonshine
Private kitchen
Gnoming Around

Cabin in Gatlinburg

3.5 star property
9.4 out of 10, Exceptional, (19)
"Everything about our stay at Gnoming around was perfect. The cabin was more than what I could have pictured wanting for a nice “cool” fall week away in the Smoky Mtns with my mom. Location was perfect with just a short 10 min drive into town. Mike, the owner was very responsive and friendly. I’ll be staying here again the future. I highly recommend to anyone looking for an escape, especially in the fall. "
United States
Matthew
Gnoming Around
2 bedrooms
Sleeps 4 Hot Tub Indoor Pool Mountain Views

Apartment in Gatlinburg

2.0 star property
9.4 out of 10, Exceptional, (6)
"Great view, very clean and relaxing "
United States
Lashaundra
The price is S$625
includes taxes & fees
5 Jan - 6 Jan, 2026
Sleeps 4 Hot Tub Indoor Pool Mountain Views
Living area
Beary Charming

Chalet in Gatlinburg

3.0 star property
8.8 out of 10, Excellent, (13)
"Absolutely love staying at Beary Charming it's our 2nd year and it's always amazing and absolutely beautiful. "
United States
Brittany
Beary Charming
Outdoor spa tub
A Top Notch Lodge

Cabin in Gatlinburg

5.0 star property
9.8 out of 10, Exceptional, (9)
"The cabin was awesome and the kids loved it."
United States
joseph
The price is S$486
includes taxes & fees
7 Dec - 8 Dec
A Top Notch Lodge
Dining
Beary Patch Hill

Cabin in Sevierville

3.5 star property
8.0 out of 10, Very good, (4)
"Excellent cabin. Loved the linen and towel choice. My family felt safe. We would definitely book again !!!"
United States
Celicia
Beary Patch Hill
Living area
Distilled Memories

Cabin in Sevierville

3.0 star property
9.4 out of 10, Exceptional, (14)
" We enjoyed our stay "
United States
Shanata
Distilled Memories
Private kitchen
Whispering Pines by Jackson Mountain Rentals

Condo in Pigeon Forge

3.5 star property
9.4 out of 10, Exceptional, (43)
"Wonderful place to stay ,really clean and peaceful "
United States
Barbara
The price is S$573
includes taxes & fees
13 Dec - 14 Dec
Whispering Pines by Jackson Mountain Rentals
Dining
Tree Tops by HoneyBear Cabins

Holiday Home in Chalet Village

4.0 star property
9.0 out of 10, Wonderful, (4)
"Beautiful view, plenty of space for the whole family. "
United States
Kendra
Tree Tops by HoneyBear Cabins
Exterior
Sweet Surrender

Cabin in Pigeon Forge

3.5 star property
9.2 out of 10, Wonderful, (10)
"Couldn’t find the park but everything else was great"
United States
Rebecca
The price is S$409
includes taxes & fees
10 Dec - 11 Dec
Sweet Surrender
1 bedroom, free WiFi
282 Cozy Cub 1 Bedroom Cabin

Cabin in Gatlinburg

2.5 star property
10.0 out of 10, Exceptional, (2)
"Very beautiful "
United States
Reponsa
The price is S$722
includes taxes & fees
18 Dec - 19 Dec
282 Cozy Cub 1 Bedroom Cabin
Exterior
Viewpoint Condominiums

Apartment in Pigeon Forge

3.5 star property
8.8 out of 10, Excellent, (265)
"We felt like we were in heaven. The views are spectacular and the staff is so helpful and friendly."
United States
Lisa
Viewpoint Condominiums
2 bedrooms, Internet
Pigeon Forge Cabin Game Room Dog Friendly Hot Tub

Apartment in Pigeon Forge

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property offers enough parking for at least 3 vehicles. Accessing the home was simple and easy. The rooms and bathrooms were clean. It is a pet friendly property, but just know you will pay extra for that if you book via third party. I did not notice any animal smells upon entry to the home, but you get a slight hint if you leave for a while and return. Nothing too concerning if youre used to animals anyway. The water is tricky and the shower heads could use a replacement. The pool table is...
United States
Laytoya
The price is S$562
includes taxes & fees
7 Dec - 8 Dec
Pigeon Forge Cabin Game Room Dog Friendly Hot Tub
Exterior
The Willows

Cabin in Sevierville

3.0 star property
9.0 out of 10, Wonderful, (2)
"Awesome , amazing place "
United States
William
The price is S$472
includes taxes & fees
8 Dec - 9 Dec
The Willows
Terrace/patio
Poppys Place Cabin

Cabin in Dandridge

5.0 star property
10.0 out of 10, Exceptional, (5)
"We loved the cabin! Would recommend to everyone! "
United States
Tracy
The price is S$411
includes taxes & fees
5 Jan - 6 Jan, 2026
Poppys Place Cabin
Outdoor spa tub
LOVE SHACK

Cabin in Sevierville

3.0 star property
10.0 out of 10, Exceptional, (12)
"Cozy cabin in a beautiful area! The perfect couple’s getaway!!"
United States
William
LOVE SHACK
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

Country Cascades Waterpark Resort

Country Cascades Waterpark Resort

10/10 Excellent
"Very fun place for kids. "
Brittany 3-night trip
Posted 2 days ago
Country Cascades Waterpark Resort

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 Forbidden Caverns and Douglas Lake.

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.