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 NZ$312
includes taxes & fees
14 Dec - 15 Dec
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 NZ$540
includes taxes & fees
30 Nov - 1 Dec
Deer Ridge by JMR

Poppys Place Cabin

5.0 star property
Dandridge
10.0 out of 10, Exceptional, (5)
"We loved the cabin! Would recommend to everyone! "
United States
Tracy
Poppys Place Cabin

A Top Notch Lodge

5.0 star property
Gatlinburg
9.8 out of 10, Exceptional, (9)
"The cabin was awesome and the kids loved it."
United States
joseph
The price is NZ$695
includes taxes & fees
7 Dec - 8 Dec
A Top Notch Lodge

Beary Charming

3.0 star property
Gatlinburg
8.8 out of 10, Excellent, (13)
"Absolutely love staying at Beary Charming it's our 2nd year and it's always amazing and absolutely beautiful. "
United States
Brittany
Beary Charming

Happily Ever After

5.0 star property
Gatlinburg
10.0 out of 10, Exceptional, (17)
"Wonderful cabin! Would definitely stay again "
United States
ALEX
Happily Ever After

Cozy Cabin, Mtn Views, Wood Fireplaces, Hot Tub, Pool Table, Pools, Pickleball

Gatlinburg
10.0 out of 10, Exceptional, (184)
"Enjoyed our stay here. Awesome place"
United States
James B.
Cozy Cabin, Mtn Views, Wood Fireplaces, Hot Tub, Pool Table, Pools, Pickleball

Smoky Mountain Log Cabin Just For Two-Gatlinburg TN

Gatlinburg
9.2 out of 10, Wonderful, (225)
"Great place to stay. We will be back."
United States
Troy D.
The price is NZ$440
includes taxes & fees
5 Dec - 6 Dec
Smoky Mountain Log Cabin Just For Two-Gatlinburg TN

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

Gatlinburg
10.0 out of 10, Exceptional, (208)
"Easy check-in, beautiful, clean cabin!"
United States
Susan R.
The price is NZ$509
includes taxes & fees
23 Nov - 24 Nov
MountainView Cutest Bear Cabin in Gatlinburg Cozy Close to Town Hot Tub Romantic

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

Fireflies and Moonshine

3.5 star property
Gatlinburg
9.8 out of 10, Exceptional, (31)
"Place was amazing "
United States
Michael
Fireflies and Moonshine

Blue Mist View

3.5 star property
Gatlinburg
9.4 out of 10, Exceptional, (11)
"Had a great time! Nice cabin! Watch out for the bears!"
United States
Justin
Blue Mist View

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

Cosby
10.0 out of 10, Exceptional, (73)
"Everything was excellent "
United States
Yuniel
The price is NZ$474
includes taxes & fees
7 Dec - 8 Dec
Homey Cozy Dog Friendly Cabin Surrounded By Beautiful Mountain Trees w/Hot Tub+

Riverfront Condo Pigeon Forge/Mt. LeConte Views

Downtown Pigeon Forge
10.0 out of 10, Exceptional, (55)
"Nice location, clean condo, great river view, good rooms, loys to do near condo. Would stay again."
United States
Heather
Riverfront Condo Pigeon Forge/Mt. LeConte Views

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

Sevierville
9.2 out of 10, Wonderful, (263)
"Nice property in the mountains! Quiet and clean!"
United States
Stacey Y.
The price is NZ$440
includes taxes & fees
1 Dec - 2 Dec
Beautiful Authentic Log Cabin in the Mountains! Last minute booking deals!

Pine Needles 6 - One Bedroom Chalet

3.5 star property
Pigeon Forge
9.2 out of 10, Wonderful, (12)
"This place was incredible! Everyone that we were in contact with was kind and helpful. The property itself was stunning, clean, and near everything that we were interested in doing. We will definetly be back! "
United States
Miller
The price is NZ$514
includes taxes & fees
23 Nov - 24 Nov
Pine Needles 6 - One Bedroom Chalet

Great Location! • No Scary Roads • Private Hot Tub

Pigeon Forge
10.0 out of 10, Exceptional, (137)
"Home was clean and a nice stay for our family of 4"
United States
Alicia P.
The price is NZ$546
includes taxes & fees
7 Dec - 8 Dec
Great Location! • No Scary Roads • Private Hot Tub

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

Newport
9.2 out of 10, Wonderful, (196)
"it was a cute little place but too small for us."
United States
Walt B.
The price is NZ$230
includes taxes & fees
2 Dec - 3 Dec
Tiny Owl Cabin – Tranquil Forest Retreat with Hot Tub and Creekside Setting

Jacuzzi 420&Pets welcome

Gatlinburg
9.6 out of 10, Exceptional, (93)
"We had a very nice time. "
United States
Barbara R.
The price is NZ$392
includes taxes & fees
4 Dec - 5 Dec
Jacuzzi 420&Pets welcome

Rustic Mountain Retreat – Breathtaking Views, Private Hot Tub & Grill.

Newport
9.6 out of 10, Exceptional, (131)
"We enjoyed our stay with our daughter and pets. The host welcomed our dog and cat which was such a blessing! The cabin is small but it is beautiful with beautiful views and has everything you need. The loft is super cool too! "
United States
Brianna B.
The price is NZ$286
includes taxes & fees
1 Dec - 2 Dec
Rustic Mountain Retreat – Breathtaking Views, Private Hot Tub & Grill.
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 favorite 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 depends 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 per night. Entering your travel dates in the search wizard you might find 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 family-friendly sights such as Dollywood, or get out into nature at a spot like Chestnut Hill Park. 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.