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Check prices for these dates

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Holiday Rentals in Chestnut Hill

Smoke Of The Mountain | Loft Sleeps 8 Views Indoor Pool Access | Terrace/patio
Deer Ridge Mountain Resort

Deer Ridge Mountain Resort

2.5 star property
Gatlinburg
9.0 out of 10, Wonderful, (148)
"Property was very nice! Loved my stay here "
United States
Iesha
The price is 2.240.855 ₫
5.350.371 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Deer Ridge Mountain Resort
Comfort Room, 2 Queen Beds | Premium bedding, individually decorated, individually furnished, desk
Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg

Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg

3.0 star property
Gatlinburg
6.0 out of 10, (113)
"Went for the cheaper room should have spent a little more."
United States
Shaun
Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg
2 outdoor pools
Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park

4.0 star property
Gatlinburg
8.4 out of 10, Very good, (1124)
"Best Location, new units, Indoor water park"
United States
Shalin
The price is 2.586.210 ₫
3.807.344 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Westgate Smoky Mountain Resort & Water Park
Condo, Multiple Beds, Balcony (#324 - No Pets) | Private kitchen | Coffee/tea maker
Whispering Pines II by Jackson Mountain Rentals

Whispering Pines II by Jackson Mountain Rentals

3.0 star property
Pigeon Forge
9.6 out of 10, Exceptional, (10)
"Our condo was clean and roomy. Would definitely stay again. "
United States
Sherry
The price is 2.478.122 ₫
10.102.277 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Whispering Pines II by Jackson Mountain Rentals
BBQ/picnic Area
Baskins Creek Condos

Baskins Creek Condos

4.0 star property
Gatlinburg
9.0 out of 10, Wonderful, (260)
"The rooms were great."
United States
Kent
Baskins Creek Condos
Condo, Multiple Beds, Balcony, Mountain View (#E306 - No Pets) | Living area | 40-inch flat-screen TV with cable channels, TV, fireplace
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, (126)
"Had a great relaxing time, Great view of the mountains from the patio."
United States
Mark
The price is 2.899.930 ₫
10.780.996 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Deer Ridge Mountain Resort by Jackson Mountain Rentals
Condo (1 Bedroom) | Property amenity
Golf View Resort by Jackson Mountain Rentals

Golf View Resort by Jackson Mountain Rentals

2.5 star property
Pigeon Forge
9.0 out of 10, Wonderful, (22)
"Condo was absolutely amazing. Great pool area and very very close to unit. I am a golfer and my finance is a beach/pool person so this fit us perfectly. Proximity to everything was unmatched. Definitely will be back. "
United States
Eric
The price is 5.247.829 ₫
14.585.522 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Golf View Resort by Jackson Mountain Rentals
House (1 Bedroom) | Interior
Luxe Smoky Mountain Cabin: Indoor Pool & Fire Pit!

Luxe Smoky Mountain Cabin: Indoor Pool & Fire Pit!

3.0 star property
Sevierville
10.0 out of 10, Exceptional, (1)
Luxe Smoky Mountain Cabin: Indoor Pool & Fire Pit!
Water park
Smith Creek Reserve Luxury Cabins

Smith Creek Reserve Luxury Cabins

5.0 star property
Sevierville
10.0 out of 10, Exceptional, (1)
Smith Creek Reserve Luxury Cabins
Condo, Multiple Beds, Pool Access, Mountain View (#C305 - No Pets) | Property grounds
Deer Ridge Resort by Jackson Mountain Rentals

Deer Ridge Resort by Jackson Mountain Rentals

3.0 star property
Gatlinburg
8.8 out of 10, Excellent, (84)
"The views are amazing. Very spacious and very quiet will be returning on my next family trip and to stay longer. "
United States
Matthew
Deer Ridge Resort by Jackson Mountain Rentals
Condo (#204 - No Pets) | Private kitchen | Coffee/tea maker, toaster
Bear Crossing by Jackson Mountain Rentals

Bear Crossing by Jackson Mountain Rentals

3.0 star property
Downtown Pigeon Forge
8.8 out of 10, Excellent, (10)
"The condo was clean. The pool was nice. "
United States
Rebecca
Bear Crossing by Jackson Mountain Rentals
Jetted bathtub
Gatlinburg Adventure Cabins

Gatlinburg Adventure Cabins

2.5 star property
Sevierville
7.2 out of 10, Good, (42)
"It was cozy little place... nice and quiet!!! Plenty of woods to explore... a nature trail to walk down! Everything was in good condition and very clean! The communication with the owner was easy and we got responses right away! If you want to have a nice quiet romantic weekend away... this place is perfect!"
United States
Robert
Gatlinburg Adventure Cabins
Property grounds
Cedar Lodge by Jackson Mountain Rentals

Cedar Lodge by Jackson Mountain Rentals

3.5 star property
Pigeon Forge
9.0 out of 10, Wonderful, (62)
"The area was a jewel tucked away from the hustle and bustle. Really enjoyed the quiet time next to the creek and deck compared to the race of main highway. "
United States
Joseph
The price is 2.584.358 ₫
11.158.562 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Cedar Lodge by Jackson Mountain Rentals
Exterior
Viewpoint Condominiums

Viewpoint Condominiums

3.5 star property
Pigeon Forge
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
Cabin, 2 Bedrooms, Jetted Tub (2 King Beds) | Premium bedding, individually decorated, individually furnished
Honeymoon Hills Gatlinburg Cabin Rentals

Honeymoon Hills Gatlinburg Cabin Rentals

3.5 star property
Gatlinburg
8.8 out of 10, Excellent, (214)
"Great communication - and even more amazing stay"
United States
Rayniesha
Honeymoon Hills Gatlinburg Cabin Rentals
Condo, Multiple Beds, Patio (#244 - No Pets) | Outdoor dining
Whispering Pines by Jackson Mountain Rentals

Whispering Pines by Jackson Mountain Rentals

2.5 star property
Pigeon Forge
7.6 out of 10, Good, (9)
"We loved whole set up feeling of home away from home....The mountain view from the patio in the mornings....was very unique and relaxing...I love that the Condo was fully equipped with whatever amenities we needed. Me and family loved it....we most definitely be reserving another condo in the very near future...I would definitely recommend this place."
United States
Kenya
The price is 2.478.874 ₫
7.735.449 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Whispering Pines by Jackson Mountain Rentals
Water park
Smith Creek Resort

Smith Creek Resort

5.0 star property
Sevierville
10.0 out of 10, Exceptional, (1)
"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 7.625.702 ₫
23.365.739 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Smith Creek Resort
BBQ/picnic Area
Pigeon Forge Large Cabins

Pigeon Forge Large Cabins

4.5 star property
Sevierville
Pigeon Forge Large Cabins
Balcony
River's Edge

River's Edge

4.0 star property
Downtown Gatlinburg
River's Edge
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

Hilton Garden Inn Pigeon Forge

Hilton Garden Inn Pigeon Forge

10/10 Excellent
"Very clean"
Jason 2-night trip
Posted 2 days ago
Hilton Garden Inn Pigeon Forge

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 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.