Chestnut Hill Vacation Rentals

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Vacation Rentals in Chestnut Hill

Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg

3.0 star property
Gatlinburg
6.0 out of 10, (110)
"Most comfortable bed the outside look ok but the room was nice 10 out of 10 "
United States
Melissa
$50 nightly
The price is $56
Nov 16 - Nov 17
Total with taxes and fees
Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg

Deer Ridge Mountain Resort

2.5 star property
Gatlinburg
9.0 out of 10, Wonderful, (129)
"Clean, amazing view, amenities.."
United States
Galina
$180 nightly
The price is $203
Dec 2 - Dec 3
Total with taxes and fees
Deer Ridge Mountain Resort

Whispering Pines II

3.0 star property
Pigeon Forge
9.6 out of 10, Exceptional, (9)
"Our condo was clean and roomy. Would definitely stay again. "
United States
Sherry
$505 nightly
The price is $567
Nov 16 - Nov 17
Total with taxes and fees
Whispering Pines II

Westgate Smoky Mountain Resort & Water Park

4.0 star property
Gatlinburg
8.4 out of 10, Very Good, (1122)
"Best Location, new units, Indoor water park"
United States
Shalin
$167 nightly
The price is $189
Nov 19 - Nov 20
Total with taxes and fees
Westgate Smoky Mountain Resort & Water Park

Baskins Creek Condos

4.0 star property
Gatlinburg
9.0 out of 10, Wonderful, (258)
"Great place to stay"
United States
Andrian
$308 nightly
The price is $347
Nov 20 - Nov 21
Total with taxes and fees
Baskins Creek Condos

Deer Ridge Mountain Resort by JMR

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
Deer Ridge Mountain Resort by JMR

Golf View Resort

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
Golf View Resort

Bear Crossing by VTrips

3.0 star property
Downtown Pigeon Forge
8.8 out of 10, Excellent, (10)
"We had an excellent stay! The condo was very nicely decorated and had everything we needed and was very clean. Loved the location! Enjoyed walking to the island."
United States
kristine
$352 nightly
The price is $396
Nov 16 - Nov 17
Total with taxes and fees
Bear Crossing by VTrips

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!

Cedar Lodge

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
$377 nightly
The price is $423
Nov 16 - Nov 17
Total with taxes and fees
Cedar Lodge

Smith Creek Reserve Luxury Cabins

5.0 star property
Sevierville
10.0 out of 10, Exceptional, (1)
$855 nightly
The price is $893
Nov 16 - Nov 17
Total with taxes and fees
Smith Creek Reserve Luxury Cabins

Gatlinburg Adventure Cabins

2.5 star property
Sevierville
7.2 out of 10, Good, (42)
"Cabin had mice in the walls, a very hard mattress and half the burners on the stove didn’t work would suggest renting this one"
United States
Joshua
$286 nightly
The price is $322
Nov 17 - Nov 18
Total with taxes and fees
Gatlinburg Adventure Cabins

The Grove 20 by Sojourn Lodging

Sevierville
9.4 out of 10, Exceptional, (22)
"A/c filter needed cleaning was dirty and restricted air flow "
United States
Darren
The Grove 20 by Sojourn Lodging

Unique & authentic train depot vacation experience with Free Attraction Tickets

Pigeon Forge
9.2 out of 10, Wonderful, (56)
"Such a cool concept of transforming an old train car into this rental property. The location is great and the host was so easy to work with. If your planning a family vacation this place is an ideal spot."
United States
Christopher K.
Unique & authentic train depot vacation experience with Free Attraction Tickets

Deer Ridge by JMR

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
$268 nightly
The price is $302
Nov 20 - Nov 21
Total with taxes and fees
Deer Ridge by JMR

Romantic Cabin w/ Hot Tub in Pigeon Forge!

3.0 star property
Sevierville
Romantic Cabin w/ Hot Tub in Pigeon Forge!

Viewpoint Condominiums

3.5 star property
Pigeon Forge
8.8 out of 10, Excellent, (264)
"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
Nov 17 - Nov 18
Total with taxes and fees
Viewpoint Condominiums

Winter Holiday Special!•Hot Tub•Game Room•Sleeps 23•3600 sq ft •Pigeon Forge

Pigeon Forge
9.6 out of 10, Exceptional, (68)
"This house is as advertised and has great accommodations along with a great location. "
United States
Bradley D.
$629 nightly
The price is $697
Nov 16 - Nov 17
Total with taxes and fees
Winter Holiday Special!•Hot Tub•Game Room•Sleeps 23•3600 sq ft •Pigeon Forge

Mountains, Movies & More, Clean!, Xmas Tree, Theater, Game Loft, Quiet Location

Sevierville
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

Amazing Views•King Beds•HotTub•FirePit•PuttPutt•Arcades•Tether Ball

Pigeon Forge
9.8 out of 10, Exceptional, (6)
"The cabin was beautiful and the location was perfect. Super clean. The beds were so comfy. Would definitely stay here again. "
United States
Haley W.
Amazing Views•King Beds•HotTub•FirePit•PuttPutt•Arcades•Tether Ball
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 $56 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 cultural attractions such as Titanic Museum, or visit a family-friendly sight such as Dollywood. 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.