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Chestnut Hill Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chestnut Hill vacation rentals

Exterior

1. Pond side Tiny Cabin + Sauna

Pond side Tiny Cabin + Sauna
Newport
9.8 out of 10, Exceptional, (158 reviews)
"Wonderful visit! Tammy was very responsive & a gracious host!"
United States
Kelly
$107 nightly
The price is $120
Dec 1 - Dec 2
Total with taxes and fees
Pond side Tiny Cabin + Sauna
Outdoor spa tub

2. Cozy Beavercreek Cabin Retreat – Smoky Mountain Serenity Awaits!

Cozy Beavercreek Cabin Retreat – Smoky Mountain Serenity Awaits!
Newport
9.8 out of 10, Exceptional, (65 reviews)
"Great place to stay"
United States
Matthew G.
$147 nightly
The price is $164
Nov 10 - Nov 11
Total with taxes and fees
Cozy Beavercreek Cabin Retreat – Smoky Mountain Serenity Awaits!
A cozy cabin interior with a stone fireplace, leather furniture, and a sign reading "Distilled Meridies."

3. 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
$254 nightly
The price is $286
Nov 9 - Nov 10
Total with taxes and fees
Distilled Memories
A rustic cabin surrounded by snow-covered trees.

4. SAVE! ROMATIC GATLINBURG GETAWAY!!

SAVE! ROMATIC GATLINBURG GETAWAY!!
Gatlinburg
9.2 out of 10, Wonderful, (187 reviews)
"Thank you so much! We had a wonderful time and your property was very charming. The only thing I would say negative was the lack of lighting in the kitchen. Loved the front porch"
United States
Jill C.
$182 nightly
The price is $202
Nov 9 - Nov 10
Total with taxes and fees
SAVE! ROMATIC GATLINBURG GETAWAY!!
A large, historic building with a symmetrical facade, multiple chimneys, and a central tower. In front, there is a well-manicured lawn with a circular fountain.

5. Luxury living Amazing Mtn Views! indoor pool & spa

Luxury living Amazing Mtn Views! indoor pool & spa
Gatlinburg
9.6 out of 10, Exceptional, (230 reviews)
"Great experience, very well maintained and clean "
United States
Erin H.
$211 nightly
The price is $236
Nov 15 - Nov 16
Total with taxes and fees
Luxury living Amazing Mtn Views! indoor pool & spa
A spacious cabin interior with a kitchen island, dining area, and a cozy living room.

6. Homey Cozy Dog Friendly Cabin Surrounded By Beautiful Mountain Trees w/Hot Tub+

Homey Cozy Dog Friendly Cabin Surrounded By Beautiful Mountain Trees w/Hot Tub+
Cosby
10.0 out of 10, Exceptional, (91 reviews)
"We love this place. Away from tourists but close to stores and restaurants. It only takes about 25 minutes to get to Gatlinburg. You will not regret staying here!"
United States
Amy K.
$232 nightly
The price is $259
Nov 30 - Dec 1
Total with taxes and fees
Homey Cozy Dog Friendly Cabin Surrounded By Beautiful Mountain Trees w/Hot Tub+
A wooden cabin kitchen with a white dishwasher, a stove with four burners, and a microwave.

7. Bear Secrets

Bear Secrets
5.0 star property
Sevierville
8.8 out of 10, Excellent, (6 reviews)
"Wonderful cabin. Decorated beautifully "
United States
Lela
$310 nightly
The price is $349
Nov 10 - Nov 11
Total with taxes and fees
Bear Secrets
A cabin interior with a stone fireplace, a wooden ceiling fan, a stone-tub hot tub, a leather sofa, and a wooden coffee table.

8. Gatlinburg Log Cabin For a Perfect Honeymoon- Pet Friendly

Gatlinburg Log Cabin For a Perfect Honeymoon- Pet Friendly
Gatlinburg
9.2 out of 10, Wonderful, (186 reviews)
"This was the perfect spot for our trip! Great location, kind of hidden away but also a good driving distance to all the thing’s Gatlinburg has to offer. We will definitely be back."
United States
Bethany
$180 nightly
The price is $200
Nov 23 - Nov 24
Total with taxes and fees
Gatlinburg Log Cabin For a Perfect Honeymoon- Pet Friendly
A cabin interior with a stone fireplace, a wooden ceiling fan, a stone-tub hot tub, a leather sofa, and a wooden coffee table.

9. Gatlinburg Honeymoon Cabin Just For You!

Gatlinburg Honeymoon Cabin Just For You!
Gatlinburg
9.4 out of 10, Exceptional, (219 reviews)
"It was a wonderful small pet friendly cabin that was still close enough to downtown Gatlinburg."
United States
Shay C.
$182 nightly
The price is $202
Nov 10 - Nov 11
Total with taxes and fees
Gatlinburg Honeymoon Cabin Just For You!
A log cabin with a metal roof, surrounded by snow-covered trees.

10. Smoky Mountain Getaway for Two-Gatlinburg Tennessee

Smoky Mountain Getaway for Two-Gatlinburg Tennessee
Gatlinburg
9.0 out of 10, Wonderful, (218 reviews)
"My husband and I stayed here for 10 days, we loved it! It was very clean, quiet and had everything we needed. In a quiet area only about 10 minutes from Gatlinburg. The host was excellent, replied quickly to our questions and requests for additional supplies needed since it was a longer stay. Would highly recommend and would definitely book again."
United States
Deborah
$167 nightly
The price is $187
Nov 11 - Nov 12
Total with taxes and fees
Smoky Mountain Getaway for Two-Gatlinburg Tennessee
A wooden deck with a hot tub and a bench.

11. Moonshine Holler

Moonshine Holler
3.5 star property
Sevierville
10.0 out of 10, Exceptional, (16 reviews)
"The Stay was perfect and everything was arranged nice."
United States
Leroy
$266 nightly
The price is $300
Nov 9 - Nov 10
Total with taxes and fees
Moonshine Holler
A wooden cabin with a porch, two small Christmas trees, and a rocking chair.

12. Beautiful Authentic Log Cabin in the Mountains! Last minute booking deals!

Beautiful Authentic Log Cabin in the Mountains! Last minute booking deals!
Sevierville
9.2 out of 10, Wonderful, (306 reviews)
"We had an amazing time! The cabin was great & comfy!"
United States
Sierra N.
$218 nightly
The price is $243
Nov 12 - Nov 13
Total with taxes and fees
Beautiful Authentic Log Cabin in the Mountains! Last minute booking deals!
A cozy cabin interior with a stone fireplace, wooden walls, a television, and a dining area.

13. 1 Mile 2 DwTn Gatlinburg/Park-Like Setting/Rustic

1 Mile 2 DwTn Gatlinburg/Park-Like Setting/Rustic
Gatlinburg
9.6 out of 10, Exceptional, (90 reviews)
"Great location; very quiet; clean"
United States
Kimberly J.
1 Mile 2 DwTn Gatlinburg/Park-Like Setting/Rustic
A cozy log cabin interior with a fireplace, leather sofas, a television, and a ceiling fan.

14. A Bearadise

A Bearadise
5.0 star property
Pigeon Forge
10.0 out of 10, Exceptional, (19 reviews)
"What a wonderful place to stay clean well-maintained I will be back. We absolutely love it here. Thank you for having us."
United States
Alfred
$478 nightly
The price is $537
Nov 10 - Nov 11
Total with taxes and fees
A Bearadise
A hot tub on a wooden deck with a view of autumn foliage.

15. Secluded Romance, Hot Tub, Fireplace, Decor, Honeymoons

Secluded Romance, Hot Tub, Fireplace, Decor, Honeymoons
Sevierville
10.0 out of 10, Exceptional, (252 reviews)
"Overall a great stay very friendly hosts . Very clean cabin and very comfortable beds . 10/10 would stay again"
United States
Justin C.
$219 nightly
The price is $245
Nov 15 - Nov 16
Total with taxes and fees
Secluded Romance, Hot Tub, Fireplace, Decor, Honeymoons
A modern living room with a sofa, blue armchairs, a fireplace, a TV, a ceiling fan, and a staircase.

16. Deer Ridge Resort by Jackson Mountain Rentals

Deer Ridge Resort by Jackson Mountain Rentals
3.0 star property
Gatlinburg
8.6 out of 10, Excellent, (97 reviews)
"Everything was great. The only issue we had was how hard the beds were but other than that. the view was amazing and the space for 5 people was very good."
United States
Flora
$244 nightly
The price is $275
Nov 8 - Nov 9
Total with taxes and fees
Deer Ridge Resort by Jackson Mountain Rentals
A wooden deck with a railing, surrounded by dense green foliage.

17. AFFORDABLE. Gatlinburg Honeymoon Cabin

AFFORDABLE. Gatlinburg Honeymoon Cabin
Gatlinburg
9.2 out of 10, Wonderful, (92 reviews)
"Host was courteous and even left us a gift in the cabin. Check in and check out was a breeze. The location was perfect, close enough to Gatlinburg to enjoy but secluded enough to relax. We will book there anytime we return."
United States
Chad
$193 nightly
The price is $215
Nov 9 - Nov 10
Total with taxes and fees
AFFORDABLE. Gatlinburg Honeymoon Cabin
A hot tub with a view of autumn foliage and a clear sky.

18. Big Views of Mt. LeConte/Near Downtown Gatlinburg

Big Views of Mt. LeConte/Near Downtown Gatlinburg
Gatlinburg
9.6 out of 10, Exceptional, (100 reviews)
"We loved this place! Check in was super easy, along with fast replies and communication with the host. We also used the hot tub every night. The only thing that needs improvement is more supplies like trash bags, toilet paper, and wash cloths/towels. Other than that everything else was great and I would definitely stay there again."
United States
Madison
$269 nightly
The price is $300
Nov 9 - Nov 10
Total with taxes and fees
Big Views of Mt. LeConte/Near Downtown Gatlinburg
A cozy cabin interior with a fireplace, wooden walls, a ceiling fan, and a television.

19. Amazing Views! Hot Tub,Pool Table,Fireplace,Relax!

Amazing Views! Hot Tub,Pool Table,Fireplace,Relax!
Gatlinburg
10.0 out of 10, Exceptional, (283 reviews)
"Amazing stay!"
United States
Audrie R.
$262 nightly
The price is $290
Nov 18 - Nov 19
Total with taxes and fees
Amazing Views! Hot Tub,Pool Table,Fireplace,Relax!
A wooden cabin interior with a dining area, a staircase with a wheel, and a view of the outdoors through large windows.

20. Sunrise Woods Retreat

Sunrise Woods Retreat
5.0 star property
Sevierville
9.4 out of 10, Exceptional, (6 reviews)
"Absolutely beautiful cabin very close to all activities "
United States
Jessica
$326 nightly
The price is $367
Nov 8 - Nov 9
Total with taxes and fees
Sunrise Woods Retreat
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

Compass Hotel by Margaritaville

Compass Hotel by Margaritaville

10/10 Excellent
"Loved it"
Nicholas 2-night trip
Posted less than an hour ago
Compass Hotel by Margaritaville

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 $63 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.