Chestnut Hill Vacation Rentals

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Our top choices for Chestnut Hill vacation rentals

Condo resort in Gatlinburg

Deer Ridge Mountain Resort
2.5 star property
9.0 out of 10, Wonderful, (152)
"Property was very nice! Loved my stay here "
United States
Iesha
$180 nightly
The price is $203
Dec 15 - Dec 16
Total with taxes and fees
Deer Ridge Mountain Resort
6.0 out of 10, (115)
"Went for the cheaper room should have spent a little more."
United States
Shaun
$59 nightly
The price is $66
Dec 15 - Dec 16
Total with taxes and fees
Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg

Westgate Smoky Mountain Resort & Water Park

Westgate Smoky Mountain Resort & Water Park
4.0 star property
8.4 out of 10, Very Good, (1125)
"Best Location, new units, Indoor water park"
United States
Shalin
$128 nightly
The price is $144
Jan 4 - Jan 5, 2026
Total with taxes and fees
Westgate Smoky Mountain Resort & Water Park
3.0 star property
9.6 out of 10, Exceptional, (10)
"Our condo was clean and roomy. Would definitely stay again. "
United States
Sherry
$503 nightly
The price is $565
Dec 17 - Dec 18
Total with taxes and fees
Whispering Pines II by Jackson Mountain Rentals
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
$363 nightly
The price is $409
Dec 16 - Dec 17
Total with taxes and fees
Deer Ridge Mountain Resort by Jackson Mountain Rentals
3.0 star property
10.0 out of 10, Exceptional, (1)
Luxe Smoky Mountain Cabin: Indoor Pool & Fire Pit!

Condo resort in Gatlinburg

Baskins Creek Condos
4.0 star property
9.0 out of 10, Wonderful, (261)
"The rooms were great."
United States
Kent
Baskins Creek Condos
5.0 star property
10.0 out of 10, Exceptional, (1)
Smith Creek Reserve Luxury Cabins

Cabin in Sevierville

Gatlinburg Adventure Cabins
2.5 star property
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
$313 nightly
The price is $353
Dec 15 - Dec 16
Total with taxes and fees
Gatlinburg Adventure Cabins
3.0 star property
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
$380 nightly
The price is $428
Dec 26 - Dec 27
Total with taxes and fees
Deer Ridge Resort by Jackson Mountain Rentals

Apartment in Pigeon Forge

Viewpoint Condominiums
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
$235 nightly
The price is $247
Dec 15 - Dec 16
Total with taxes and fees
Viewpoint Condominiums
3.5 star property
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
$434 nightly
The price is $488
Dec 25 - Dec 26
Total with taxes and fees
Cedar Lodge by Jackson Mountain Rentals
9.4 out of 10, Exceptional, (30)
"First time staying in a tiny home. Place was cozy and neat. Really nice place. Communication was very good. "
United States
Kevin M.
The Grove 20 by Sojourn Lodging
10.0 out of 10, Exceptional, (155)
"Beautiful place!!! Would definitely book again!!!"
United States
Janet C.
Mountains, Movies & More, Clean!, Xmas Tree, Theater, Game Loft, Quiet Location

Condo in Downtown Pigeon Forge

Bear Crossing by Jackson Mountain Rentals
3.0 star property
8.8 out of 10, Excellent, (10)
"The condo was clean. The pool was nice. "
United States
Rebecca
Bear Crossing by Jackson Mountain Rentals

Vacation Home in Gatlinburg

Standard King Room - NKS
8.0 out of 10, Very Good, (9)
"Excellent location. Helpful staff and responsive owner. "
United States
Mirza Mohammed
$99 nightly
The price is $109
Jan 4 - Jan 5, 2026
Total with taxes and fees
Standard King Room - NKS
9.6 out of 10, Exceptional, (71)
"Place was perfect for three families for a fun Dollywood trip!"
United States
Sterling W.
$639 nightly
The price is $707
Jan 12 - Jan 13, 2026
Total with taxes and fees
Winter Holiday Special!•Hot Tub•Game Room•Sleeps 23•3600 sq ft •Pigeon Forge

Cabin in Sevierville

Smith Creek Resort
5.0 star property
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
$914 nightly
The price is $960
Jan 4 - Jan 5, 2026
Total with taxes and fees
Smith Creek Resort
9.4 out of 10, Exceptional, (31)
"Great home in a nice, quiet neighborhood. The theater was a great amenity in the evenings, and we loved opening the porch doors in the morning for fresh air.Would be happy to stay again one day. :)"
United States
Eric F.
$2,138 nightly
The price is $2,380
Dec 27 - Dec 28
Total with taxes and fees
Slide into Fun! Families Love Mountain Lake Lodge!
2.5 star property
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
$261 nightly
The price is $293
Dec 21 - Dec 22
Total with taxes and fees
Whispering Pines by Jackson Mountain Rentals
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

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 $66 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 Forbidden Caverns and Douglas Lake.

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.