Chestnut Hill Vacations from $333

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Your Chestnut Hill Vacation

Make travel planning hassle-free by booking a vacation package to Chestnut Hill. We'll handle the specifics, so you can focus on appreciating everything this neighborhood can offer. Not sure what to see and do during your trip to Chestnut Hill? Nearby attractions like Nissan Stadium, Vanderbilt University and Ryman Auditorium are excellent places to start. Expedia is here to put your plans into action. Book your perfect Chestnut Hill vacation today.

The Latest Chestnut Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Nashville Airport

Sonesta Nashville Airport

4 out of 5
Save 100% on your flight
Price was $533, price is now $333 per person
$333
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (1,711 reviews)
Nice place. Cosmetic challenges, if you look around. For a resort, there should have been more to offer. Not sure if the resort fees, additional fees, and parking fees were necessary. Casino hotels would charge less and offer more.

Reviewed on Aug 31, 2025

Bluegreen Downtown Nashville

Bluegreen Downtown Nashville

2 out of 5
Downtown Nashville
Save 100% on your flight
Price was $866, price is now $517 per person
$517
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (294 reviews)
The room was spacious and clean. The furniture was uniquely antique. Staff was wonderful and the location was walkable to Broadway and other points of interest. Their A/C unit is a little loud. Overall, nice room, great location and value!

Reviewed on Aug 27, 2025

Element Nashville Vanderbilt West End

Element Nashville Vanderbilt West End

3 out of 5
West End
Save 100% on your flight
Price was $607, price is now $383 per person
$383
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (1,006 reviews)
Loved our stay. Easy access to where we were going. Very clean and neat. Loved the patio area which we used nightly. The only issue we had was the bathroom sink had no water pressure and depending on when you took a shower, you could start out with great water pressure and even in the middle of the shower it could go to barely a drizzle from the shower head. We were on the 6th and top floor however that was disappointing during shower time.

Reviewed on Aug 29, 2025

Caption by Hyatt Downtown Nashville/The Gulch

Caption by Hyatt Downtown Nashville/The Gulch

3 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,150, price is now $731 per person
$731
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (583 reviews)
Hotel was nice and new. Rooms very modern and comfortable. Staff was friendly. It doesn’t have a pool which we didn’t realize upon booking which was a negative for sure

Reviewed on Aug 30, 2025

Bobby Hotel

Bobby Hotel

4 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,216, price is now $774 per person
$774
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (1,007 reviews)
Not far from broadway, super convenient. Loved this hotel.

Reviewed on Aug 26, 2025

Where to stay in Chestnut Hill

Find the best Chestnut Hill areas and neighborhoods for the activities you enjoy most. Learn more about Chestnut Hill
Downtown Nashville which includes a city, a sunset and boating

Downtown Nashville

5 out of top 10 points of interest in this area
4/5(5,801 area reviews)

Sounds of country and honky-tonk resonate around the streets of Music City. Watch a show, attend a hockey match and walk in the footsteps of U.S. presidents.

Find hotels in Downtown Nashville

Chestnut Hill Hotel Deals

Sheraton Grand Nashville Downtown

Sheraton Grand Nashville Downtown

4 out of 5
623 Union St, Nashville, TN
$195 nightly
The price is $230 total per night from Sep 28 to Sep 29
$230 total
Sep 28 - Sep 29
Total with taxes and fees
Sheraton Grand Nashville Downtown
Cambria Hotel Nashville Midtown

Cambria Hotel Nashville Midtown

3 out of 5
1612 Church Street, Nashville, TN
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $148 total per night from Sep 3 to Sep 4
$148 total
Sep 3 - Sep 4
Total with taxes and fees
Cambria Hotel Nashville Midtown
Comfort Inn Downtown Nashville - Music City Center

Comfort Inn Downtown Nashville - Music City Center

3 out of 5
1501 Demonbreun St, Nashville, TN
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $105 total per night from Sep 2 to Sep 3
$105 total
Sep 2 - Sep 3
Total with taxes and fees
Comfort Inn Downtown Nashville - Music City Center
See all 7,703 properties in Chestnut Hill
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Chestnut Hill

Grand Ole Opry showing fall colors

Grand Ole Opry

The pride and joy of Nashville residents and hallowed ground for country music fans the world over.

Grand Ole Opry
Nashville Broadway showing night scenes, nightlife and street scenes

Broadway

The Honky Tonk Highway is known for its great music, drinks and all-night atmosphere, but there’s much more than parties to be had on Nashville’s main artery.

Broadway
Vanderbilt University

Vanderbilt University

Take a campus tour or just explore the area around Vanderbilt University, a top university in Nashville. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Vanderbilt University

Things to do

Hop Walk Nashville's Walking Brewery Tour

Hop Walk Nashville's Walking Brewery Tour

$79
per adult
Hop Walk Nashville's Walking Brewery Tour
Nashville’s Biggest and Wildest Party Tractor Tour

Nashville Biggest & Wildest Party Public Tractor Tour (Ages 21+)

$45
per adult
98% of travellers recommend
Nashville Biggest & Wildest Party Public Tractor Tour (Ages 21+)
Belmont Mansion Entrance

Belmont Mansion General Admission Ticket in Nashville

$18
per adult
96% of travellers recommend
Belmont Mansion General Admission Ticket in Nashville
See all activities in Nashville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.