Chestnut Hill Holiday Rentals

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Holiday Rentals in Chestnut Hill

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
The price is AU$292
includes taxes & fees
16 Nov - 17 Nov
Westgate Smoky Mountain Resort & Water Park

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
The price is AU$463
includes taxes & fees
20 Nov - 21 Nov
Deer Ridge by JMR

Dog Friendly Moonfall Cottage Gatlinburg

Gatlinburg
10.0 out of 10, Exceptional, (196)
"Very relaxing cozy stay at the moon fall cottage!"
United States
Cody K.
The price is AU$312
includes taxes & fees
16 Nov - 17 Nov
Dog Friendly Moonfall Cottage Gatlinburg

Jacuzzi 420&Pets welcome

Gatlinburg
9.6 out of 10, Exceptional, (92)
"We had a very nice time. "
United States
Barbara R.
The price is AU$322
includes taxes & fees
1 Dec - 2 Dec
Jacuzzi 420&Pets welcome

Private Cozy DOG FRIENDLY Cabin Home Surrounded by a Variety of Beautiful Trees

Cosby
10.0 out of 10, Exceptional, (73)
"Everything was excellent "
United States
Yuniel
The price is AU$407
includes taxes & fees
16 Nov - 17 Nov
Private Cozy DOG FRIENDLY Cabin Home Surrounded by a Variety of Beautiful Trees

Happily Ever After

5.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (17)
"Beautiful ,clean and it's right between pigeon forge and Gatlinburg just perfect "
United States
Amy
The price is AU$527
includes taxes & fees
30 Nov - 1 Dec
Happily Ever After

Beary Charming

3.0 star property
Gatlinburg
8.8 out of 10, Excellent, (13)
"This place has been an amazing honeymoon stay. The owner is amazing, and always there for any questions or needs! The cabin is beautiful, and has a hot tub to enjoy the night stars. A lot of attractions right near by and a lot of shopping. Great food places to try out, and such a quiet neighborhood! We will definitely be coming back soon! 10/10 amazing!!"
United States
Grace
Beary Charming

Smoky Mountain Log Cabin Just For Two-Gatlinburg TN

Gatlinburg
9.2 out of 10, Wonderful, (225)
"It was amazing, just as it states. Everything was simple, clean, and nice. Will stay again. "
United States
Rose W.
The price is AU$382
includes taxes & fees
15 Dec - 16 Dec
Smoky Mountain Log Cabin Just For Two-Gatlinburg TN

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

Sevierville
9.2 out of 10, Wonderful, (262)
"We loved this cabin! The kids absolutely loved the upstairs area and the Foosball table. Lots of outdoor seating on both front and back porch. The hot tub was also amazing! Easy access to Pigeon Forge. "
United States
Rebecca C.
The price is AU$382
includes taxes & fees
17 Nov - 18 Nov
Beautiful Authentic Log Cabin in the Mountains! Last minute booking deals!

Tiny Owl Cabin – Tranquil Forest Retreat with Hot Tub and Creekside Setting

Newport
9.2 out of 10, Wonderful, (196)
"This is truly a tiny cabin, and we loved it! We got in later than expected, which means that we didnt get to enjoy the hot tub or the peaceful creek right out the door but it was perfect and i would love to return! I do recommend a vehicle with 4 wheel or awd, as there is unpaved access to the property, with some steep hills. I absolutely loved this stay, and highly recommend this to anyone who is in the area Communication with the host was not only easy, but they accommodated my change of plans...
United States
Nicole S.
The price is AU$234
includes taxes & fees
27 Nov - 28 Nov
Tiny Owl Cabin – Tranquil Forest Retreat with Hot Tub and Creekside Setting

Baby Bear Hideaway, rustic, romantic w/a hot Tub

Sevierville
9.6 out of 10, Exceptional, (73)
"The room was very clean and in a great spot! The hot tub was also great, very relaxing place to stay."
United States
Robert E.
The price is AU$344
includes taxes & fees
25 Nov - 26 Nov
Baby Bear Hideaway, rustic, romantic w/a hot Tub

Unforgettable Sunrise View, Dual Living Spaces & on Douglas Lake by Pigeon Forge

Sevierville
10.0 out of 10, Exceptional, (97)
"We really enjoyed our stay. Check in was smooth. The lake view was wonderful. The winding metal staircase was a bit challenging in order to get to the bed as we are both in our 70’s. The place was clean and well taken care of."
United States
Richard S.
The price is AU$661
includes taxes & fees
16 Nov - 17 Nov
Unforgettable Sunrise View, Dual Living Spaces & on Douglas Lake by Pigeon Forge

Mountain Heaven Cabin in Pigeon Forge

Sevierville
9.8 out of 10, Exceptional, (248)
"Great property close to town."
United States
hannah d.
The price is AU$651
includes taxes & fees
22 Nov - 23 Nov
Mountain Heaven Cabin in Pigeon Forge

Gnoming Around

3.5 star property
Gatlinburg
9.4 out of 10, Exceptional, (18)
"Everything about our stay at Gnoming around was perfect. The cabin was more than what I could have pictured wanting for a nice “cool” fall week away in the Smoky Mtns with my mom. Location was perfect with just a short 10 min drive into town. Mike, the owner was very responsive and friendly. I’ll be staying here again the future. I highly recommend to anyone looking for an escape, especially in the fall. "
United States
Matthew
Gnoming Around

MountainView Cutest Bear Cabin in Gatlinburg Cozy Close to Town Hot Tub Romantic

Gatlinburg
10.0 out of 10, Exceptional, (208)
"We loved the cabin! Great location and very clean and cozy. Thank you for the amazing stay, we will be back!"
United States
Haley W.
MountainView Cutest Bear Cabin in Gatlinburg Cozy Close to Town Hot Tub Romantic

Pine Needles 6 - One Bedroom Chalet

3.5 star property
Pigeon Forge
9.2 out of 10, Wonderful, (12)
"First off the chalet was very nice and clean. It felt very cozy and private. The rooms were good sized and the jacuzzi was heavenly. The kitchen did have pots and and some appliances and silverware but no strainer or oven pans. It is dog friendly , which is important to us but not much green space to walk them at all. The reason i posted just okay is in your listings you say washer and dryers and fitness room . Also on some websites, it shows it is suppose to have an indoor pool and it does...
United States
Alan
The price is AU$412
includes taxes & fees
18 Nov - 19 Nov
Pine Needles 6 - One Bedroom Chalet

Discover Serenity at TinyFox Cabin: Your Perfect Getaway Surrounded by Nature

Newport
9.8 out of 10, Exceptional, (146)
"We had a wonderful stay at this tiny home campground in the beautiful rural Tennessee mountains. Less than an hour from the national park yet feels a world away from touristy Gatlinburg. Our host Tammy was a lovely and gracious host."
United States
Angela W.
The price is AU$242
includes taxes & fees
23 Nov - 24 Nov
Discover Serenity at TinyFox Cabin: Your Perfect Getaway Surrounded by Nature

Snuggle Bug by Beyond Expectations: Cozy 1BR Cabin w/ Hot Tub & Golf Nearby

Gatlinburg
9.8 out of 10, Exceptional, (204)
"This cabin is everything we were expecting and more! It was beautiful, clean and in a good location! We loved the pool table and hot tub!"
United States
Leslie D.
The price is AU$548
includes taxes & fees
30 Nov - 1 Dec
Snuggle Bug by Beyond Expectations: Cozy 1BR Cabin w/ Hot Tub & Golf Nearby

The Pine Knot Cabin, November 16-21st only 115/night book now!

Sevierville
9.6 out of 10, Exceptional, (84)
"Thoroughly enjoyed our stay here! "
United States
Sara P.
The Pine Knot Cabin, November 16-21st only 115/night book now!

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

Gatlinburg
10.0 out of 10, Exceptional, (244)
"Loved our stay… well equipped…beautiful place.."
United States
Rose Anne U.
The price is AU$416
includes taxes & fees
7 Dec - 8 Dec
Amazing Views! Hot Tub,Pool Table,Fireplace,Relax!
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestnut Hill holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chestnut Hill holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestnut Hill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestnut Hill holiday rentals we have selected for you start as low as AU$292 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chestnut Hill rentals

At Expedia, we put the best Chestnut Hill holiday 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 holiday.

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 holiday rental in Chestnut Hill?

Yes, you can find holiday rentals where you'll be only 14.4 mi (23.2 km) from Dollywood, providing a secluded option if you want a quiet place to stay.

What are some of the best holiday rentals that Chestnut Hill has to offer?

Westgate Smoky Mountain Resort & Water Park: This holiday home rental outside of Chestnut Hill offers 2 hot tubs, a BBQ 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 one of the family-friendly sights such as Dollywood. In the wider area, you’ll find Forbidden Caverns and Douglas Lake.

What are holiday rentals like in Chestnut Hill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestnut Hill. Holiday rentals offer extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family gatherings.