Photo by Jana Hankins

Chestnut Hill holiday lettings

We found 575 holiday rentals — enter your dates for availability

Discover a selection of 31 homes, 14 apartments 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:10 Jul - 17 Jul

Image gallery for Nashville's Best View - Private Rooftop Terrace, Steps from Downtown

Rooftop view with custom grill/sink overlooking the Nashville Skyline!
10 out of 10, Exceptional, (83 reviews)
Exceptional
(83 reviews)

Nashville's Best View - Private Rooftop Terrace, Steps from Downtown

Nashville

7% off
Price is £3,090
for 7 nights, 1 home
£441 per night
includes taxes & fees
Nashville's Best View - Private Rooftop Terrace, Steps from Downtown

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    Enjoy full kitchens, pools, gardens and more

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Why visit Chestnut Hill

  • Rich cultural experiences: Explore vibrant music museums and historic colleges that showcase Nashville's artistic heritage.
  • Charming neighbourhood: Enjoy the welcoming atmosphere of Chestnut Hill with friendly locals and trendy spots.
  • Beautiful urban parks: Relax in lovely parks perfect for family outings and outdoor activities.
  • Convenient base: Chestnut Hill serves as an ideal starting point to discover Nashville's lively city life and culture.
  • Diverse accommodation options: Choose from charming private homes to modern apartments for a comfortable stay.

Popular types of accommodation around Chestnut Hill

Embarking on a trip to Chestnut Hill? The next exciting step is selecting your ideal accommodation. From charming houses to modern condos and stylish apartments, there are plenty of options to suit your needs. Explore the best Chestnut Hill apartments in Nashville for a comfortable stay, whether you're seeking a short-term rental or a longer getaway. Your perfect retreat awaits!

  • Houses: A favourite among visitors to Chestnut Hill, these homes offer spacious and comfortable settings for families or groups.
  • Condos: These stylish accommodations are ideal for those seeking modern amenities and a convenient location.
  • Apartments: Perfect for solo travellers or couples, apartments provide a home-away-from-home experience with essential facilities.
  • Cottages: A lovely choice for a quaint and peaceful retreat, cottages are perfect for a romantic getaway.
  • Cabins: For nature enthusiasts, cabins offer a charming escape amidst the beauty of the outdoors.**

Top attractions near Chestnut Hill

Chestnut Hill in Nashville, Tennessee, offers a charming blend of attractions suitable for families and business travellers alike. Visitors can explore the vibrant music museums, historic colleges and universities, and lovely urban parks. This locale is perfect for those seeking cultural experiences, outdoor activities, and family-friendly outings. Whether you're enjoying the local sights or indulging in the rich history, Chestnut Hill promises a delightful escape.

  • Vanderbilt University: A historic institution with beautiful architecture and lush gardens, offering a glimpse into American higher education. The campus is rich in culture, with art galleries and performance spaces that showcase local talent.
  • Broadway: A vibrant tourist precinct renowned for its lively atmosphere, featuring family-friendly attractions, dining options, and outdoor entertainment. Experience the heart of Nashville's music scene with live performances and street musicians.
  • Music City Center: A modern event and conference venue, it hosts a variety of business events and conventions. Its striking design reflects Nashville's musical heritage and provides excellent facilities for networking and exhibitions.

Things to do recommended for couples

If you're seeking a romantic getaway in Chestnut Hill, Nashville, explore the Grand Ole Opry, Ryman Auditorium, and Ascend Amphitheater, all offering vibrant music experiences within a short distance. Enjoy the lively atmosphere together as you create unforgettable memories in this charming locale.

Things to do recommended for families

Families visiting Chestnut Hill can immerse themselves in the excitement at Nissan Stadium and First Horizon Park, both located a mere 1.2km away. For more sports action, FirstBank Stadium, situated 1.9km from Chestnut Hill, offers a fantastic atmosphere for all ages.

Things to do recommended for groups

Visit the Mall at Green Hills for shopping and dining, only 2.5km from Chestnut Hill. Enjoy entertainment at Elliston Place, just 1.9km away, and explore the vibrant Farmer's Market, located 1.2km from your accommodation, perfect for families and friends to experience local culture.

What do I need to keep in mind when booking a vacation around Chestnut Hill

If you're travelling with a group, family, pets, or seeking longer stays, it's important to filter according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Chestnut Hill with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Chestnut Hill with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, as well as ensure access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Chestnut Hill: For many, a family holiday isn't truly complete without their four-legged companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels completely at home.
  • Planning for a long term stay visiting Chestnut Hill: If you're in search of holiday rentals offering discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near Chestnut Hill

Chestnut Hill in Nashville offers a delightful blend of urban charm and historical allure, perfect for families and business travellers alike. Explore the welcoming neighbourhood, where friendly locals and trendy spots create a relaxed atmosphere. Just a stone's throw away, you can discover the vibrant city life and rich culture of Nashville, making it an ideal base for your holiday adventure. Experience the essence of living in Chestnut Hill and uncover its hidden gems.

  • Nashville: Nashville, a vibrant metropolis located 1.2km from Chestnut Hill, is renowned for its rich musical heritage and cultural diversity. Visitors flock to Nashville for a delightful mix of family-friendly activities, business opportunities, and urban adventures. The city boasts a plethora of shopping areas and educational venues, alongside a lively music scene. Notable attractions include the iconic tourist precinct, a bustling stadium, and the picturesque lake, all of which create an engaging travel experience that showcases the essence of Southern hospitality.
  • Downtown Nashville: Just 1.2km from Chestnut Hill, Downtown Nashville is a dynamic neighbourhood pulsating with energy and excitement. This area is perfect for families, business travellers, and city enthusiasts alike. Downtown Nashville features bustling shopping areas, an impressive arena entertainment facility, and a vibrant music concert scene. Local landmarks include a prominent tourist precinct, a large stadium, and a state-of-the-art sports facility, making it a hub of activity that offers an unforgettable experience for visitors.
  • SoBro: SoBro, located a mere mile from Chestnut Hill, is an emerging neighbourhood that perfectly encapsulates the spirit of Nashville. This area is ideal for family outings, business trips, and city explorations. SoBro is home to a variety of shopping areas, an impressive arena entertainment facility, and a thriving music concert scene. Highlights include a lively tourist precinct, a major stadium, and a versatile event conference venue, ensuring that visitors enjoy a diverse range of experiences in this bustling locale.

Best time to go to Chestnut Hill

If you're planning a trip to Chestnut Hill, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in May to June and October, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January37.9°F (3.3°C)Light RainMostly CloudySlightly LowSlightly Low
February42.1°F (5.6°C)Light RainMostly CloudySlightly LowSlightly Low
March50.5°F (10.3°C)Light RainMostly SunnyAverageAverage
April58.8°F (14.9°C)Light RainMostly SunnyAverageAverage
May68.0°F (20.0°C)Light RainMostly SunnySlightly HighSlightly High
June76.5°F (24.7°C)Light RainMostly SunnySlightly HighSlightly High
July79.2°F (26.2°C)Light RainMostly SunnyAverageAverage
August77.7°F (25.4°C)Light RainMostly SunnyAverageAverage
September72.1°F (22.3°C)Light RainMostly SunnyAverageSlightly High
October61.2°F (16.2°C)Light RainMostly SunnySlightly HighAverage
November49.6°F (9.8°C)Light RainMostly SunnyAverageAverage
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowSlightly Low

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming holiday? It may be worthwhile to keep your travel dates flexible, as prices can vary. Additionally, opting for a longer stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a dedicated area for you to plan new getaways, manage your ongoing arrangements, or review and organise your bookings. The properties you have saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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.
How much does it cost to rent a holiday home in Chestnut Hill?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chestnut Hill to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chestnut Hill holiday house rentals?
You can find great discounts on house rentals in Chestnut Hill on Vrbo, 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.
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.
Are there any Chestnut Hill holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
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.
Can I find long-stay holiday rentals in Chestnut Hill?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
How early should I book a Chestnut Hill holiday rental?
Book your Chestnut Hill holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Chestnut Hill home rental booking on Vrbo?
To find Chestnut Hill holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chestnut Hill holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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