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Featured Holiday Homes in Portland

Spacious Riverfront!!! 3 Miles Opryland, 10 Min Downtown Nashville

Spacious Riverfront!!! 3 Miles Opryland, 10 Min Downtown Nashville

Nashville
With a stay at this vacation home, you'll be centrally located in Nashville, within a 15-minute drive of Grand Ole Opry and Gaylord Opryland Resort & Convention ...
Spacious Riverfront!!! 3 Miles Opryland, 10 Min Downtown Nashville
Urban farm on 10 acres 15 minutes to downtown Nashville

Urban farm on 10 acres 15 minutes to downtown Nashville

Nashville
With a stay at this vacation home in Madison, you'll be within a 15-minute drive of Gaylord Opryland Resort & Convention Center and Opryland Hotel Gardens.
Urban farm on 10 acres 15 minutes to downtown Nashville
LAKESIDE RETREAT NEAR DOWNTOWN NASHVILLE

LAKESIDE RETREAT NEAR DOWNTOWN NASHVILLE

Mount Juliet
With a stay at this vacation home in Mount Juliet, you'll be on the waterfront, just a 1-minute walk from Old Hickory Lake and 10 minutes by foot from Cumberland ...
LAKESIDE RETREAT NEAR DOWNTOWN NASHVILLE
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Country living at its best, chickens and a beautiful stocked pond to fish in

Country living at its best, chickens and a beautiful stocked pond to fish in

Springfield
With a stay at this vacation home in Springfield, you'll be 31.5 mi (50.7 km) from Nissan Stadium and 32.3 mi (52 km) from Broadway.
Country living at its best, chickens and a beautiful stocked pond to fish in
Spacious home with POOL, private, safe.

Spacious home with POOL, private, safe.

Nashville
With a stay at this vacation home in Nashville, you'll be within a 10-minute drive of Gaylord Opryland Resort & Convention Center and Opryland Hotel ...
Spacious home with POOL, private, safe.
Cozy & Chic Rustic Retreat-Luxury Log Home ❤️ Near Downtown, Opry and Much More♫

Cozy & Chic Rustic Retreat-Luxury Log Home ❤️ Near Downtown, Opry and Much More♫

Nashville
With a stay at this vacation home, you'll be centrally located in Nashville, within a 10-minute drive of Grand Ole Opry and Gaylord Opryland Resort & Convention ...
Cozy & Chic Rustic Retreat-Luxury Log Home ❤️ Near Downtown, Opry and Much More♫
Swanky Retreat - Mins to Everything

Swanky Retreat - Mins to Everything

Nashville
With a stay at this vacation home, you'll be centrally located in Nashville, within a 10-minute drive of Nissan Stadium and Grand Ole Opry.
Swanky Retreat - Mins to Everything
LAKE FRONT HOME
BOOK 3 GET 1 NITE FREE
MARCH  APRIL TIKI HUT
NEAR NASHVILLE

LAKE FRONT HOME BOOK 3 GET 1 NITE FREE MARCH APRIL TIKI HUT NEAR NASHVILLE

Mt Juliet
When you a stay at this vacation home in Mount Juliet, you'll be on the beach, within a 5-minute walk of Old Hickory Lake and Cumberland River.
LAKE FRONT HOME BOOK 3 GET 1 NITE FREE MARCH APRIL TIKI HUT NEAR NASHVILLE
Cedar Twig Cabin: Serene, cozy & quiet

Cedar Twig Cabin: Serene, cozy & quiet

Mt. Juliet
Located in Mount Juliet, this vacation home is in a rural location, within a 10-minute drive of Mount Juliet Little League Park and Old Hickory Lake.
Cedar Twig Cabin: Serene, cozy & quiet
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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.

Portland 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 Portland vacation homes are the perfect way for you to wing it.

Holiday houses in Portland 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 Portland 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 Portland adventures, obvs.

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

Portland Holiday Homes essential information

Accommodation
357 Holiday Homes
Lowest Price
AU$126
Highest Price
AU$254
Popular accommodation
Spacious Riverfront!!! 3 Miles Opryland, 10 Min Downtown Nashville, Urban farm on 10 acres 15 minutes to downtown Nashville, LAKESIDE RETREAT NEAR DOWNTOWN NASHVILLE, Country living at its best, chickens and a beautiful stocked pond to fish in, Spacious home with POOL, private, safe., Cozy & Chic Rustic Retreat-Luxury Log Home ❤️ Near Downtown, Opry and Much More♫, Swanky Retreat - Mins to Everything , LAKE FRONT HOME BOOK 3 GET 1 NITE FREE MARCH APRIL TIKI HUT NEAR NASHVILLE , Cedar Twig Cabin: Serene, cozy & quiet

Top trending hotels in Portland

SureStay Plus Hotel By Best Western Portland Route 52 West

SureStay Plus Hotel By Best Western Portland Route 52 West

2.5 out of 5
9239 Highway 52, Portland, TN
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 9 Apr to 10 Apr
AU$138
includes taxes & fees
9 Apr - 10 Apr
Located in Portland, SureStay Plus Hotel By Best Western Portland Route 52 West is a 1-minute drive from Sumner Crest WInery and 6 minutes from Kentucky ...
SureStay Plus Hotel By Best Western Portland Route 52 West
Hyatt Place Nashville Opryland

Hyatt Place Nashville Opryland

3 out of 5
220 Rudy Cir, Nashville, TN
Fully refundableReserve now, pay when you stay
The price is AU$254 per night from 16 Apr to 17 Apr
AU$254
includes taxes & fees
16 Apr - 17 Apr
With a stay at Hyatt Place Nashville Opryland in Nashville (Opryland), you'll be within a 5-minute drive of Gaylord Opryland Resort & Convention Center and Opryland ...
Hyatt Place Nashville Opryland
Best Western Suites Near Opryland

Best Western Suites Near Opryland

2.5 out of 5
201 Music City Circle, Nashville, TN
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 20 Apr to 21 Apr
AU$171
includes taxes & fees
20 Apr - 21 Apr
With a stay at Best Western Suites Near Opryland in Nashville (Opryland), you'll be within a 5-minute drive of Gaylord Opryland Resort & Convention Center and ...
Best Western Suites Near Opryland
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Wingate by Wyndham Goodlettsville

Wingate by Wyndham Goodlettsville

2.5 out of 5
202 Northgate Cir, Goodlettsville, TN
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 9 Apr to 10 Apr
AU$126
includes taxes & fees
9 Apr - 10 Apr
Located in Goodlettsville, Wingate by Wyndham Goodlettsville is within a 5-minute drive of Historic Mansker's Station Frontier Life Center and Manskers ...
Wingate by Wyndham Goodlettsville
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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.

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^Subject to availability and chosen travel dates.