Photo by Jana Hankins

Chestnut Hill holiday rentals

We found 598 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:4 Dec - 11 Dec

Living area
Room
Private kitchen
Dining
Exceptional
(8 reviews)

Dreamy Townhome - Cozy Vibe - Mins to Broadway!

Nashville

8% off
S$6,642
for 7 nights, 1 home
S$949 per night
includes taxes & fees
Dreamy Townhome - Cozy Vibe - Mins to Broadway!
Interior
Property grounds
Private kitchen
Room
Exceptional
(19 reviews)

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

Nashville

7% off
S$6,022
for 7 nights, 1 home
S$860 per night
includes taxes & fees
Nashville skyline Hideaway! Just a few steps away from 12 south and Broadway!
Look into double trundle bedroom off of kitchen!
Large fully stocked kitchen and top of the line appliances!
Rooftop view with custom grill/sink overlooking the Nashville Skyline!
Living area
Exceptional
(103 reviews)

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

Nashville

7% off
S$4,338
for 7 nights, 1 home
S$620 per night
includes taxes & fees
Nashville's Best View - Private Rooftop Terrace, Steps from Downtown
Bedroom 1 Queen Bed
Beautiful private backyard
Living room with comfortable sectional and ample seating.
Coffee/tea Bar w/assorted creamers and various sweeteners.
Exceptional
(70 reviews)

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

Nashville

16% off
S$3,667
for 7 nights, 1 home
S$524 per night
includes taxes & fees
No Cleaning Fee & Breakfast Included! 1/4 Mile to Geodis. 1 exit to Downtown!
Pool
Interior
Interior
Room
Exceptional
(5 reviews)

4BR DT Condo, Oversized Patio, Endless Amenities, Walkable to Everything

Nashville

8% off
S$8,409
for 7 nights, 1 apartment
S$1,201 per night
includes taxes & fees
4BR DT Condo, Oversized Patio, Endless Amenities, Walkable to Everything
Interior
Terrace/patio
Private kitchen
Room
Exceptional
(37 reviews)

Pet friendly, 5 Min to Downtown, gated parking

Nashville

8% off
S$4,331
for 7 nights, 1 home
S$619 per night
includes taxes & fees
Pet friendly, 5 Min to Downtown, gated parking
Living Room w/ City Skyline View
Community lounge/ chefs kitchen
Kitchen Table w/ City Skyline View
Infinity Pool w/ City Skyline View
Exceptional
(25 reviews)

The Malibu Suite Penthouse The Gulch

Nashville

7% off
S$7,365
for 7 nights, 1 apartment
S$1,052 per night
includes taxes & fees
The Malibu Suite Penthouse The Gulch
Living area
Living area
Room
Pool
Wonderful
(7 reviews)

Downtown Nashville/ Gulch Luxury Condo- Sleeps 6

Nashville

7% off
S$2,884
for 7 nights, 1 apartment
S$412 per night
includes taxes & fees
Downtown Nashville/ Gulch Luxury Condo- Sleeps 6
Lobby
Private kitchen
Interior
Pool
Exceptional
(16 reviews)

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

Nashville

8% off
S$7,060
for 7 nights, 1 apartment
S$1,009 per night
includes taxes & fees
Downtown Pool and Cabana's- Walk to Broadway! Luxury Downtown Nashville Suite
Interior
Terrace/patio
Pool
Living area
Excellent
(51 reviews)

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

Nashville

7% off
S$3,096
for 7 nights, 1 apartment
S$442 per night
includes taxes & fees
Luxe Condo - Downtown Nashville - Walk to Broadway / The Gulch - Heated Pool 3/1

  • 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 accommodation in Chestnut Hill?
Houses are the most popular style of holiday rental in Chestnut Hill, according to our data. Even if you've got a different idea about what you want, Vrbo has holiday homes in a variety of shapes and sizes. Compare our options to find your perfect match.
How much does it cost to rent a holiday rental in Chestnut Hill?
Length of stay, season and property type are some things that can determine the price of a holiday home. Simply click on your travel dates to find your ideal escape. From quaint country cottages to expansive villas, all Vrbo holiday rentals offer amazing value.
How much does it cost to rent a beach house in Chestnut Hill?
Prices for beach houses in Chestnut Hill vary depending on the type and size of the property and time of year you're travelling. Simply enter your travel dates into Vrbo and the number of guests to see available options and prices. From there you can use our filters to narrow your search results by ratings, amenities and more.
Are there pet-friendly holiday rentals in Chestnut Hill?
Good news. There are. You'll have a choice of 51 stays that allow pets in Chestnut Hill on Vrbo. Our furry kids deserve a break too, so simply use our search function for pet-friendly holiday rentals to find a perfect pad where your puppy can be near his favourite humans.
What are popular rental amenities in Chestnut Hill?
A fireplace, an ocean view and a firepit are rated the most popular rental amenities in Chestnut Hill. Whether you're taking to the road as a party of one, with a partner or a group of dear friends, Vrbo will help you find a holiday home that fits your tastes with all the features you're looking for.
Are there large group holiday rentals in Chestnut Hill?
Chestnut Hill has 11 holiday homes that can cater to 10 or more guests. These stays come with the privacy and space you need to enjoy good times with loved ones.
Are there holiday rentals in Chestnut Hill that welcome kids?
With 51 family-friendly holiday properties to select from in Chestnut Hill, now is a superb time to introduce your little ones to the thrills of travel. Just check our "Properties good for families" filter box to find stays loaded with amenities perfect for holidaying families, such as kitchens, private pools, hot tubs and entertainment areas.
What are the top attractions for families in Chestnut Hill?
Keeping the kids entertained during your Chestnut Hill holiday is a cinch with these top family-friendly attractions:
  • Broadway
  • Nashville Zoo
  • Adventure Science Centre
Are there one-bedroom holiday rentals in Chestnut Hill?
Yes, Chestnut Hill has seven one-bedroom rentals on offer. Usually located in prime areas due to their smaller size, a one-bedroom rental is perfect if you're getting away with your partner or a buddy. And with home comforts such as full kitchens and more privacy than a standard hotel, you'll be able to chill out while sightseeing around this fabulous destination.
Can I find two-bedroom holiday rentals in Chestnut Hill?
Take off with your loved ones and experience complete comfort and privacy in one of the eight two-bedroom holiday rentals Chestnut Hill has to offer.
Are there holiday rentals with WiFi in Chestnut Hill?
Chestnut Hill has 11 holiday rentals with WiFi, so you'll be able to stay connected while you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movie blockbusters to scrolling social media, these Vrbo homes make it a breeze to go online.
How can I find holiday rentals with air conditioning in Chestnut Hill?
Chestnut Hill has 51 holiday rentals where you'll be able to spend your days in air-conditioned comfort. To book a stay on Vrbo that features this perk, enter your preferred travel dates and use the filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Chestnut Hill?
The minimum age is normally 16, 18 or 21. It can change from one property to another on Vrbo, so check the rules of your chosen Chestnut Hill stay before booking your stay.
How long can I rent a holiday rental in Chestnut Hill for?
The length of time you can rent a holiday rental in Chestnut Hill depends on the property. Just enter your desired dates to view a list of options offering extended stays. With lots of features like full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find a terrific place to call your home away from home in Chestnut Hill.

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