Chestnut Hill Vacation Rentals

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Vacation Rentals in Chestnut Hill

Deer Ridge Mountain Resort

2.5 star property
9.0 out of 10, Wonderful, (90)
"Clean room, full kitchen, and amazing views. A great place to stay for friends and family."
$142 nightly
The price is $160
Sep 30 - Oct 1
Total with taxes and fees
Deer Ridge Mountain Resort

Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg

3.0 star property
6.2 out of 10, (95)
"Good place"
$54 nightly
The price is $61
Sep 30 - Oct 1
Total with taxes and fees
Timber Ridge Lodge - Walking Distance from Downtown Gatlinburg

Westgate Smoky Mountain Resort & Water Park

4.0 star property
8.4 out of 10, Very Good, (1114)
"This was the best stay ever near the Smoky Mountains. The experience was definitely enjoyable, and I would highly recommend it!"
$160 nightly
The price is $181
Oct 1 - Oct 2
Total with taxes and fees
Westgate Smoky Mountain Resort & Water Park

Deer Ridge Mountain Resort by JMR

3.0 star property
9.0 out of 10, Wonderful, (124)
"Nice place to stay with family."
$266 nightly
The price is $300
Oct 1 - Oct 2
Total with taxes and fees
Deer Ridge Mountain Resort by JMR

Deer Ridge by JMR

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. "
$349 nightly
The price is $394
Oct 2 - Oct 3
Total with taxes and fees
Deer Ridge by JMR

Cedar Lodge

3.5 star property
9.2 out of 10, Wonderful, (59)
"We had a great time on vacation we loved the condo it made us feel at home on vacation I would definitely rent from them again and I probably will next year."
$361 nightly
The price is $406
Oct 3 - Oct 4
Total with taxes and fees
Cedar Lodge

Gatlinburg Adventure Cabins

2.5 star property
7.4 out of 10, Good, (41)
"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!"
$286 nightly
The price is $322
Sep 30 - Oct 1
Total with taxes and fees
Gatlinburg Adventure Cabins

Unique & authentic train depot vacation experience with Free Attraction Tickets

9.2 out of 10, Wonderful, (50)
"We had a wonderful time staying at Smoky Mountain Station. Place was clean, check-in was smooth and as advertised. One listing mentions laundry which is not available, luckily laundromats are nearby. The location was great, minutes from Dollywood and walkable to a fun mountain coaster. Everything we could need was only minutes away. Outdoors was setup perfect for meals and had a fantastic hot tub and fire pit area. Our train loving toddlers are still talking about sleeping in a caboose! Thank...
Unique & authentic train depot vacation experience with Free Attraction Tickets

Bear Crossing by VTrips

3.0 star property
9.4 out of 10, Exceptional, (9)
"The condo was clean. The pool was nice. "
$366 nightly
The price is $411
Oct 5 - Oct 6
Total with taxes and fees
Bear Crossing by VTrips

Luxe Smoky Mountain Cabin: Indoor Pool & Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
Luxe Smoky Mountain Cabin: Indoor Pool & Fire Pit!

Golf View Resort

2.5 star property
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. "
$283 nightly
The price is $318
Oct 14 - Oct 15
Total with taxes and fees
Golf View Resort

A Cabin In The Woods

3.0 star property
8.4 out of 10, Very Good, (32)
"What an absolutely adorable cabin! Perfectly tucked away next to a little creek, the scenery was absolutely gorgeous. It is a little more rustic, but it was absolutely charming. The hot tub was a fantastic bonus!"
$295 nightly
The price is $331
Sep 30 - Oct 1
Total with taxes and fees
A Cabin In The Woods

Whispering Pines Condos by VTrips

2.5 star property
7.2 out of 10, Good, (7)
"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."
$273 nightly
The price is $307
Oct 12 - Oct 13
Total with taxes and fees
Whispering Pines Condos by VTrips

Baskins Creek Condos

4.0 star property
9.0 out of 10, Wonderful, (253)
"The rooms were great."
$305 nightly
The price is $344
Sep 30 - Oct 1
Total with taxes and fees
Baskins Creek Condos

Viewpoint Condominiums

3.5 star property
8.8 out of 10, Excellent, (259)
"We loved staying here and will definitely be back! The only small issue was some hammering in the water pipes, which caused the showers to cut off unexpectedly for a few seconds during use. But the property was so great otherwise that it outweighed that small issue. "
$244 nightly
The price is $258
Sep 30 - Oct 1
Total with taxes and fees
Viewpoint Condominiums

Honeymoon Hills Gatlinburg Cabin Rentals

3.5 star property
8.8 out of 10, Excellent, (212)
"Overall a was a great place!"
Honeymoon Hills Gatlinburg Cabin Rentals

Mountain Lake Lodge! Slide into Fun! Families Love

9.2 out of 10, Wonderful, (28)
"The cabin is great for a large family like mine!!! Would definitely stay again"
Mountain Lake Lodge! Slide into Fun! Families Love

Smith Creek Resort

5.0 star property
$907 nightly
The price is $951
Sep 30 - Oct 1
Total with taxes and fees
Smith Creek Resort

Whispering Pines II

3.0 star property
9.4 out of 10, Exceptional, (6)
"Beautiful property, location convenient for volleyball tournament. Convenient to national park and shopping. "
$276 nightly
The price is $310
Oct 16 - Oct 17
Total with taxes and fees
Whispering Pines II

Mountain Meadows

2.5 star property
6.0 out of 10, (2)
"There was no one working at the registration desk and I was unable to check in. I spent 1.5 hrs calling a number posted number in the office to check in. After 20 plus calls to multiple numbers I had to pay for other lodgings. Very poorly run! I would definitely not recommend!"
$119 nightly
The price is $134
Oct 1 - Oct 2
Total with taxes and fees
Mountain Meadows
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

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 $61 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.