Photo by Jana Hankins

Chestnut Hill holiday rentals

We found 599 holiday rentals — enter your dates for availability
Discover a selection of 24 homes and other holiday rentals in Chestnut Hill that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and garden. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Chestnut Hill

Showing deals for:13 Nov - 20 Nov

Exterior
Room
Dining
Private kitchen
Exceptional
(8 reviews)

Dreamy Townhome - Cozy Vibe - Mins to Broadway!

Nashville

8% off
AU$7,131
for 7 nights, 1 home
AU$1,019 per night
includes taxes & fees
Dreamy Townhome - Cozy Vibe - Mins to Broadway!
Private kitchen
Property grounds
Room
Living area
Exceptional
(19 reviews)

Nashville skyline Hideaway! Just a few steps away from 12 south and Broadway!

Nashville

8% off
AU$7,390
for 7 nights, 1 home
AU$1,056 per night
includes taxes & fees
Nashville skyline Hideaway! Just a few steps away from 12 south and Broadway!
Living room with comfortable sectional and ample seating.
Beautiful private backyard
Formal dining room seats six (up to 8 if requested prior to checkin)
Bedroom 1 Queen Bed
Exceptional
(70 reviews)

No Cleaning Fee & Breakfast Included! 1/4 Mile to Geodis. 1 exit to Downtown!

Nashville

17% off
AU$3,883
for 7 nights, 1 home
AU$555 per night
includes taxes & fees
No Cleaning Fee & Breakfast Included! 1/4 Mile to Geodis. 1 exit to Downtown!
Private kitchen
Interior
Pool
Interior
Exceptional
(14 reviews)

Brand New w/Pool/Walk to Broadway!

Nashville

8% off
AU$7,462
for 7 nights, 1 apartment
AU$1,066 per night
includes taxes & fees
Brand New w/Pool/Walk to Broadway!
Interior
Terrace/patio
Private kitchen
Room
Exceptional
(35 reviews)

Pet friendly, 5 Min to Downtown, gated parking

Nashville

8% off
AU$4,247
for 7 nights, 1 home
AU$607 per night
includes taxes & fees
Pet friendly, 5 Min to Downtown, gated parking
Gym/ Yoga studio
Community lounge/ chefs kitchen
Kitchen Table w/ City Skyline View
Living Room w/ City Skyline View
Exceptional
(25 reviews)

The Malibu Suite Penthouse The Gulch

Nashville

7% off
AU$7,954
for 7 nights, 1 apartment
AU$1,136 per night
includes taxes & fees
The Malibu Suite Penthouse The Gulch
Room
Exterior
Pool
Living area
Exceptional
(11 reviews)

~NEW~ Downtown Nashville! Walk to Broadway + FREE parking • Balcony • Pool

Nashville

8% off
AU$2,387
for 7 nights, 1 apartment
AU$341 per night
includes taxes & fees
~NEW~ Downtown Nashville! Walk to Broadway + FREE parking • Balcony • Pool
Living area
Living area
Pool
Private kitchen
Wonderful
(7 reviews)

Downtown Nashville/ Gulch Luxury Condo- Sleeps 6

Nashville

7% off
AU$3,045
for 7 nights, 1 apartment
AU$435 per night
includes taxes & fees
Downtown Nashville/ Gulch Luxury Condo- Sleeps 6
Enjoy top-of-the-line amenities like this cozy outdoor fireplace.
Stunning high ceilings, open floor plan, and lots of natural light in this premium downtown condo. Smart TV in the living room with all the streaming apps and a comfortable sleeper sofa. Glass sliding doors leading to the spacious private patio.
Stunning high ceilings, open floor plan, and lots of natural light. Smart TV in the living room with all the streaming apps and a comfortable sleeper sofa. The stairs lead to the loft-style King bedroom.
Brand new pool with comfortable lounge chairs, cabanas, and umbrellas.
Wonderful
(12 reviews)

Luxury Penthouse w/ 2 Floors - Pool, Patio, Gym, Walk to Broadway

Nashville

8% off
AU$2,758
for 7 nights, 1 apartment
AU$394 per night
includes taxes & fees
Luxury Penthouse w/ 2 Floors - Pool, Patio, Gym, Walk to Broadway
Beautiful lobby and common spaces in this newly constructed condo building.
LA Jackson is a stylish rooftop bar and restaurant known for its stunning views of the skyline and vibrant atmosphere.  The menu is filled with creative cocktails and delicious bites.
Bright and spacious living room off the kitchen. Smart TV, remote controlled room darkening shades, and pull-out sleeper sofa for ultimate comfort. Dining table that can seat 8 people.
Pool with comfortable lounge chairs, cabanas and umbrellas.
Exceptional
(39 reviews)

Penthouse Luxury w/ Pool, Patio & City View - Walk to Broadway

Nashville

8% off
AU$4,677
for 7 nights, 1 apartment
AU$668 per night
includes taxes & fees
Penthouse Luxury w/ Pool, Patio & City View - Walk to Broadway
Private kitchen
Terrace/patio
Interior
Living area
Excellent
(50 reviews)

Luxe Condo - Downtown Nashville - Walk to Broadway / The Gulch - Heated Pool 3/1

Nashville

8% off
AU$2,950
for 7 nights, 1 apartment
AU$421 per night
includes taxes & fees
Luxe Condo - Downtown Nashville - Walk to Broadway / The Gulch - Heated Pool 3/1
Interior
Private kitchen
Terrace/patio
Lobby
Exceptional
(16 reviews)

Downtown Pool and Cabana's- Walk to Broadway! Luxury Downtown Nashville Suite

Nashville

8% off
AU$6,983
for 7 nights, 1 apartment
AU$998 per night
includes taxes & fees
Downtown Pool and Cabana's- Walk to Broadway! Luxury Downtown Nashville Suite
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental in Chestnut Hill?
In Chestnut Hill, both apartments and holiday houses are equally popular, with around 16 of each type available in the area. These accommodations are typically situated in serene neighbourhoods, providing a peaceful getaway for visitors. Most units come with essential amenities such as fully equipped kitchens, comfortable living spaces, and outdoor areas for enjoying the tranquil surroundings. Additionally, several condos are available, offering a more communal living experience with shared facilities.
What are popular rental amenities in Chestnut Hill?
In Chestnut Hill, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy home-cooked dining experiences. Many properties also feature coffee and tea makers for a quick morning brew. Outdoor spaces such as decks or patios are common, providing a pleasant area to relax and take in the surroundings. Onsite parking is typically available, making it convenient for travellers with vehicles. Additionally, some rentals offer balconies, great for enjoying the fresh air and scenic views.
Can I find family house rentals in Chestnut Hill?
In Chestnut Hill, Tennessee, there are several family-friendly house rentals available, ideal for those looking to enjoy a relaxing getaway. Visitors can expect spacious homes with multiple bedrooms, allowing for ample room for everyone. Many properties come equipped with full kitchens, making it easy to prepare meals together, as well as inviting living areas superb for family gatherings.Surrounding the area, guests can explore the beautiful landscapes that East Tennessee has to offer, including nearby parks and lakes, which provide opportunities for outdoor activities such as hiking, fishing, and picnicking.
Can I rent a holiday home with a pool or hot tub in Chestnut Hill?
In Chestnut Hill, Tennessee, there are several holiday homes available for rent that feature both pools and hot tubs. This serene area offers a picturesque setting for a relaxing getaway, with properties often set amidst beautiful landscapes. Travellers can expect amenities such as private pools, hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens, making it ideal for families or groups seeking comfort and convenience. Additionally, many of these rentals provide Wi-Fi and modern furnishings, ensuring a pleasant stay.
Can I book pet-friendly holiday rentals in Chestnut Hill?
In Chestnut Hill, Tennessee, there are several pet-friendly holiday rentals available for those looking to enjoy a getaway with their furry companions. Visitors can expect a variety of amenities in these accommodations, such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely. Many of these rentals are situated in serene settings, often surrounded by nature, providing a peaceful retreat for both humans and pets alike.The area itself offers opportunities for outdoor activities, with nearby parks and trails suitable for walks and exploration. Chestnut Hill is a charming place, ideal for those wanting to unwind and connect with nature while enjoying the company of their pets.
When is the best time to visit Chestnut Hill for a holiday rental?
The best time to visit Chestnut Hill for a holiday rental is during the peak season from February to April, with March being particularly popular. This period welcomes nature enthusiasts and those seeking a peaceful retreat, as the landscape comes alive with vibrant blooms and mild temperatures ranging from 5 to 15 degrees Celsius. The pleasant weather creates ideal conditions for outdoor activities such as hiking and birdwatching, allowing visitors to fully appreciate the natural beauty of the area.March offers a delightful atmosphere, great for exploring the scenic trails and enjoying the serene surroundings. With the arrival of spring, you'll find opportunities for picturesque walks and the chance to witness the blossoming flora in full splendour.For those looking to save, consider visiting in November when the tourist crowds thin out, providing a more tranquil experience. While the temperatures may be cooler, this month allows for peaceful hikes and an opportunity to enjoy the stunning autumn colours as the leaves change.Ultimately, your ideal time to visit Chestnut Hill will depend on whether you prefer the lively energy of springtime adventures or the quiet charm of late autumn.
Are there any remote work holiday rentals in Chestnut Hill?
In Chestnut Hill, Tennessee, there are numerous remote work-friendly holiday rentals available, with around 36 options to choose from. These accommodations are particularly well-suited for those who need to balance work and leisure. Many properties come equipped with high-speed Wi-Fi, dedicated workspaces, and comfortable desk chairs, ensuring a productive environment.Travellers can expect various amenities that cater to business needs, such as event-friendly spaces and limo or town car services for convenient transport. The serene surroundings of Chestnut Hill provide a peaceful backdrop for remote work, while still being close to local attractions and natural beauty. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are the top attractions in Chestnut Hill, Tennessee, United States of America?
In Chestnut Hill, Tennessee, visitors can enjoy the tranquil beauty of the surrounding countryside, with attractions that highlight the area's natural charm. The Great Smoky Mountains National Park is a short drive away, offering breathtaking views, hiking trails, and opportunities for wildlife observation. In the nearby town of Gatlinburg, attractions such as the SkyLift Park and the Gatlinburg Arts and Crafts Community provide a mix of outdoor adventure and local culture.Chestnut Hill itself is known for its peaceful landscapes and rural charm, making it a superb spot for those looking to relax and unwind. Exploring the local area may lead to quaint shops and charming dining options that reflect the hospitality of the region.
Are all fees included in the Chestnut Hill holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chestnut Hill holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chestnut Hill with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chestnut Hill holiday homes?
You can find great discounts on holiday homes in Chestnut Hill on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chestnut Hill holiday home booking on Stayz?
To find Chestnut Hill holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chestnut Hill?
A long-stay holiday home in Chestnut Hill is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chestnut Hill holiday home?
Book your Chestnut Hill holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chestnut Hill?
Prices for holiday homes in Chestnut Hill vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chestnut Hill to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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