Book Holiday Homes in Hillsboro

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Hillsboro

Sewanee,Cavern,Hikes,Waterfalls:Tiny Basecamp New

Sewanee,Cavern,Hikes,Waterfalls:Tiny Basecamp New

Monteagle
The price is AU$349 per night from 3 Mar to 4 Mar
AU$349
includes taxes & fees
3 Mar - 4 Mar
Located in Monteagle, this vacation home is in the mountains, within a 5-minute drive of South Cumberland State Park and Harton Park.
Sewanee,Cavern,Hikes,Waterfalls:Tiny Basecamp New
Summit & Shore House at The Retreat at Deer Lick Falls

Summit & Shore House at The Retreat at Deer Lick Falls

Monteagle
The price is AU$434 per night from 3 Mar to 4 Mar
AU$434
includes taxes & fees
3 Mar - 4 Mar
Located in Monteagle, this vacation home is in the mountains, within a 10-minute drive of South Cumberland State Park and Harton Park.
Summit & Shore House at The Retreat at Deer Lick Falls
Million Dollar Views: Lakefront, Dock, Kayaks+More

Million Dollar Views: Lakefront, Dock, Kayaks+More

Winchester
When you a stay at this vacation home in Winchester, you'll be on the waterfront, just steps from Tims Ford Lake and Elk River.
Million Dollar Views: Lakefront, Dock, Kayaks+More
Save an average of 15% on thousands of hotels when you're signed in
Charming 120 Year Old Sewanee Home on Campus- Walk Everywhere!

Charming 120 Year Old Sewanee Home on Campus- Walk Everywhere!

Sewanee
Located in Sewanee, this vacation home is in a rural location, within a 15-minute walk of University of the South and Lake Finney.
Charming 120 Year Old Sewanee Home on Campus- Walk Everywhere!
The Ascent at The Retreat at Deer Lick Falls II

The Ascent at The Retreat at Deer Lick Falls II

Monteagle
The price is AU$444 per night from 24 Feb to 25 Feb
AU$444
includes taxes & fees
24 Feb - 25 Feb
Located in Tracy City, this vacation home is in the mountains, within a 10-minute drive of South Cumberland State Park and Bigfoot Adventure TN Zipline.
The Ascent at The Retreat at Deer Lick Falls II
Spacious Lakefront Retreat w/ Hot Tub + Dock!

Spacious Lakefront Retreat w/ Hot Tub + Dock!

Winchester
With a stay at this vacation home in Winchester, you'll be on the waterfront, just a 1-minute walk from Tims Ford Lake and 8 minutes by foot from ...
Spacious Lakefront Retreat w/ Hot Tub + Dock!
On the Edge at The Retreat at Deer Lick Falls

On the Edge at The Retreat at Deer Lick Falls

Monteagle
The price is AU$388 per night from 24 Feb to 25 Feb
AU$388
includes taxes & fees
24 Feb - 25 Feb
Located in Monteagle, this vacation home is in the mountains, within a 10-minute drive of South Cumberland State Park and Harton Park.
On the Edge at The Retreat at Deer Lick Falls
Mountain Memories to provide a cozy retreat on your vacation!

Mountain Memories to provide a cozy retreat on your vacation!

Monteagle
The price is AU$332 per night from 24 Feb to 25 Feb
AU$332
includes taxes & fees
24 Feb - 25 Feb
With a stay at this vacation home in Monteagle, you'll be within a 5-minute drive of Harton Park and Monteagle Sunday School Assembly.
Mountain Memories to provide a cozy retreat on your vacation!
Whiskey Trails Cottage

Whiskey Trails Cottage

Tullahoma
With a stay at this vacation home in Tullahoma, you'll be within a 5-minute walk of Tullahoma Rec Center and Rock Creek Park.
Whiskey Trails Cottage
Don't see what you're looking for?
See all available properties in Hillsboro
View all properties
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.

Hillsboro Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Hillsboro vacation homes are the perfect way for you to wing it.

Holiday houses in Hillsboro let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Hillsboro in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Hillsboro adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Hillsboro with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Hillsboro vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Hillsboro Holiday Homes essential information

Accommodation
316 Holiday Homes
Lowest Price
AU$88
Highest Price
AU$444
Popular accommodation
Sewanee,Cavern,Hikes,Waterfalls:Tiny Basecamp New, Summit & Shore House at The Retreat at Deer Lick Falls, Million Dollar Views: Lakefront, Dock, Kayaks+More, Charming 120 Year Old Sewanee Home on Campus- Walk Everywhere!, The Ascent at The Retreat at Deer Lick Falls II, Spacious Lakefront Retreat w/ Hot Tub + Dock!, On the Edge at The Retreat at Deer Lick Falls, Mountain Memories to provide a cozy retreat on your vacation!, Whiskey Trails Cottage

Top trending hotels in Hillsboro

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

3 out of 5
844 W Main Street, Monteagle, TN
Fully refundableReserve now, pay when you stay
The price is AU$88 per night from 25 Feb to 26 Feb
AU$88
includes taxes & fees
25 Feb - 26 Feb
Located in Monteagle, The Smokehouse Lodge and Cabins is within a 10-minute drive of South Cumberland State Park and Sewanee Golf and Tennis Club.
The Smokehouse Lodge and Cabins
Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

2 out of 5
201 Expressway Dr, Manchester, TN
Fully refundableReserve now, pay when you stay
The price is AU$117 per night from 25 Feb to 26 Feb
AU$117
includes taxes & fees
25 Feb - 26 Feb
Located in Manchester, Microtel Inn & Suites by Wyndham Manchester is a 3-minute drive from May Prairie Designated State Natural Area and 7 minutes from Old ...
Microtel Inn & Suites by Wyndham Manchester
The Sewanee Inn

The Sewanee Inn

4 out of 5
1235 University Ave, Sewanee, TN
Fully refundableReserve now, pay when you stay
The price is AU$419 per night from 24 Feb to 25 Feb
AU$419
includes taxes & fees
24 Feb - 25 Feb
When you stay at The Sewanee Inn in Sewanee, you'll be within a 5-minute walk of University of the South.
The Sewanee Inn
Save an average of 15% on thousands of hotels when you're signed in
Sleep Inn And Suites Manchester

Sleep Inn And Suites Manchester

2.5 out of 5
84 Relco Drive, Manchester, TN
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 20 Mar to 21 Mar
AU$138
includes taxes & fees
20 Mar - 21 Mar
A stay at Sleep Inn And Suites Manchester places you in the heart of Manchester, a 2-minute drive from May Prairie Designated State Natural Area and 7 minutes ...
Sleep Inn And Suites Manchester
Don't see what you're looking for?
See all available properties in Hillsboro
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.