Default HTG hotel image

Chestnut Hill Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (445 reviews)
"We absolutely loved our stay beautiful views, very quiet great to be with kids"
United States
Osniel
The price is P5,330
P13,549 total
includes taxes & fees
Nov 16 - Nov 17
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, (1,411 reviews)
"It is a great place to stay and had so much to do..."
United States
BRYCE
The price is P6,821
P9,844 total
includes taxes & fees
Nov 29 - Nov 30
Westgate Smoky Mountain Resort & Water Park
A spacious living room with a fireplace, a comfortable sofa, a coffee table, and a balcony with outdoor seating.

3. 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 P6,496
P20,718 total
includes taxes & fees
Nov 15 - Nov 16
Deer Ridge Mountain Resort by Jackson Mountain 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, (35 reviews)
"We enjoyed our stay. The cabin was clean and the accommodations were great."
United States
Ahmed
The price is P9,228
P19,739 total
includes taxes & fees
Dec 1 - Dec 2
Distilled Memories
A spacious living room with wooden walls and a high ceiling, featuring a sofa set, a coffee table, and a foosball table.

5. Serene Creek Cabin

Serene Creek Cabin
4.5 star property
Sevierville
9.6 out of 10, Exceptional, (4 reviews)
"The cabin was super clean, and i really liked they provided enough towels and blankets for our stay. "
United States
Renee
Serene Creek Cabin
Pool

6. Howling Wolf - One Bedroom Cabin

Howling Wolf - One Bedroom Cabin
3.5 star property
Sevierville
9.4 out of 10, Exceptional, (3 reviews)
"Best experience ever definitely booking another visit "
United States
Tyvon
Howling Wolf - One Bedroom Cabin
A wooden deck with a hot tub and a bench.

7. Moonshine Holler

Moonshine Holler
3.5 star property
Sevierville
10.0 out of 10, Exceptional, (17 reviews)
"The Stay was perfect and everything was arranged nice."
United States
Leroy
The price is P9,228
P20,098 total
includes taxes & fees
Dec 1 - Dec 2
Moonshine Holler
A cozy log cabin interior with a wooden sofa, a coffee table, a television, and a bear statue.

8. Pigeon Forge Vacation Rental: 1 Mi to Dollywood

Pigeon Forge Vacation Rental: 1 Mi to Dollywood
3.0 star property
Pigeon Forge
10.0 out of 10, Exceptional, (2 reviews)
"This cabin was very inviting and clean and very close to Dollywood its like a 7 minute drive and you can see the fire work /drone show everynight that Dollywood puts on. My one and only complaint was the pull out mattress for the couch needs to be upgrade to something better other than that this is a excellent place to stay with your family. "
United States
Scott
Pigeon Forge Vacation Rental: 1 Mi to Dollywood
A cozy cabin interior with wooden walls, a fireplace, leather sofas, patterned armchairs, and a dining area with a table and chairs.

9. Fireflies and Moonshine

Fireflies and Moonshine
3.5 star property
Gatlinburg
9.8 out of 10, Exceptional, (36 reviews)
"Take a moment and let the place make you warm. The air is calming and the cabin is nice and cozy. Take that energy and enjoy yourself. The place is where memories are made."
United States
Tennairius
The price is P12,495
P28,449 total
includes taxes & fees
Nov 30 - Dec 1
Fireflies and Moonshine
A wooden cabin interior with a black leather sofa, a dining table, and a kitchen area.

10. 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 P9,906
P23,650 total
includes taxes & fees
Nov 29 - Nov 30
A Top Notch Lodge
A cozy log cabin interior with a stone fireplace, wooden walls, and a large window with curtains.

11. 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 P8,999
P19,839 total
includes taxes & fees
Dec 1 - Dec 2
The Willows
A room with a leather sofa, a coffee table, and two windows with views of greenery.

12. 2bdrm Cabin 2 Gburg Pet Friendly Fire Pit Game

2bdrm Cabin 2 Gburg Pet Friendly Fire Pit Game
2.0 star property
Gatlinburg
9.8 out of 10, Exceptional, (7 reviews)
"Everything with the cabin was amazing. It was clean and had everything we needed for our stay. Will definitely book again!"
United States
Tiesha
The price is P7,020
P19,978 total
includes taxes & fees
Dec 7 - Dec 8
2bdrm Cabin 2 Gburg Pet Friendly Fire Pit Game
An indoor swimming pool with clear water, surrounded by lounge chairs and a covered seating area.

13. 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, (17 reviews)
"It was a great stay. We love Whispering Pines"
United States
Bambie
The price is P6,496
P20,199 total
includes taxes & fees
Nov 15 - Nov 16
Whispering Pines II by Jackson Mountain Rentals
A spacious cabin interior with a fireplace, comfortable seating, and a large window offering a mountain view.

14. Cabin On A Cloud

Cabin On A Cloud
3.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (17 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 P11,968
P26,777 total
includes taxes & fees
Dec 3 - Dec 4
Cabin On A Cloud
A wooden deck with Adirondack chairs and a large umbrella, overlooking a forested area.

15. Smoky Waters by Hosteeva

Smoky Waters by Hosteeva
3.5 star property
Sevierville
7.4 out of 10, Good, (19 reviews)
"We really enjoyed our stay. Loved this place! Would definitly go back."
United States
Tonya
Smoky Waters by Hosteeva
A kitchen with wooden cabinets, stainless steel appliances, and a granite countertop.

16. Beary Patch Hill

Beary Patch Hill
3.5 star property
Sevierville
9.0 out of 10, Wonderful, (8 reviews)
"Beautiful place to stay! We enjoyed staying here for our vacation. "
United States
Rylea
The price is P9,056
P28,183 total
includes taxes & fees
Dec 1 - Dec 2
Beary Patch Hill
A wooden cabin kitchen with a dining table set for six, stainless steel appliances, and a large window overlooking greenery.

17. 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 P16,335
P46,780 total
includes taxes & fees
Dec 6 - Dec 7
Pinot Splash
A cozy cabin interior with a fireplace, leather furniture, and a ceiling fan.

18. Pinot Paradise

Pinot Paradise
2.0 star property
Pigeon Forge
9.6 out of 10, Exceptional, (8 reviews)
"Cozy cabin, lots of room, very comfortable. I'd stay here again in a heartbeat."
United States
Dolores
The price is P10,661
P26,264 total
includes taxes & fees
Dec 2 - Dec 3
Pinot Paradise
A cozy cabin interior with a fireplace, a television mounted on a wooden wall, a sofa, and a patterned rug.

19. Beary Charming

Beary Charming
3.0 star property
Gatlinburg
9.0 out of 10, Wonderful, (18 reviews)
"Clean cabin, great stay"
United States
Cooper
The price is P7,967
P19,753 total
includes taxes & fees
Nov 15 - Nov 16
Beary Charming
A historic wooden building with a large water wheel, a wooden bridge, and a waterfall.

20. Lil' Smoky Studio

Lil' Smoky Studio
2.0 star property
Gatlinburg
9.0 out of 10, Wonderful, (2 reviews)
"."
United States
Anna
The price is P7,226
P22,956 total
includes taxes & fees
Nov 15 - Nov 16
Lil' Smoky Studio
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestnut Hill Hotel Reviews

Compass Hotel by Margaritaville

Compass Hotel by Margaritaville

10/10 Excellent
"Overall the hotel was perfect! Everyone was very friendly and the room was very clean and comfortable."
Andrea 1-night trip
Posted 1 hour ago
Compass Hotel by Margaritaville

Find out more about Chestnut Hill

Search for holiday rentals in Chestnut Hill on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestnut Hill using one of the methods below:

  • View our selection of featured holiday rentals in Chestnut Hill
  • Use the map to find apartments and other holiday homes in the Chestnut Hill neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chestnut Hill while they last

Look no further and take a look at our great range of rental properties in Chestnut Hill!

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.