Portland Holiday Rentals

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Our top choices for Portland holiday rentals

The Yellow House - Hidden Gem in heart of Portland

The Yellow House - Hidden Gem in heart of Portland
Portland
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful house with lots of charm. We had a great New Year's hosting our local family, and they all enjoyed the property."
United States
Kevin D.
The price is NZ$873
includes taxes & fees
29 June - 30 June
The Yellow House - Hidden Gem in heart of Portland

Vintage modern / boho Gallatin townhome!

Vintage modern / boho Gallatin townhome!
Gallatin
10.0 out of 10, Exceptional, (21 reviews)
"Extremely clean, quiet, well decorated and comfortable. "
United States
Shawn M.
The price is NZ$432
includes taxes & fees
28 June - 29 June
Vintage modern / boho Gallatin townhome!

Peace And Quiet Of Country Living Yet Close To Modern Convenience.

Peace And Quiet Of Country Living Yet Close To Modern Convenience.
Scottsville
9.8 out of 10, Exceptional, (168 reviews)
"All around great place. It was clean and peaceful. The hosts were excellent. My family wishes we had longer than a weekend to explore the area. "
United States
Andrea B.
The price is NZ$337
includes taxes & fees
24 June - 25 June
Peace And Quiet Of Country Living Yet Close To Modern Convenience.

Newly remodeled, Hot Tub, 70n inch tv Private Entrance, Convenient location

Newly remodeled, Hot Tub, 70n inch tv Private Entrance, Convenient location
Lebanon
10.0 out of 10, Exceptional, (102 reviews)
"This place is a very nice and quiet place "
United States
Shirlene M.
The price is NZ$367
includes taxes & fees
25 June - 26 June
Newly remodeled, Hot Tub, 70n inch tv Private Entrance, Convenient location

Charming 4-bedroom in Russellville Kentucky with Hot Tub

Charming 4-bedroom in Russellville Kentucky with Hot Tub
Russellville
10.0 out of 10, Exceptional, (21 reviews)
"everything was great. Clean, comfortable bed, they even had scented candles. Hot tub too. Nice neighborhood."
United States
Janie W.
Charming 4-bedroom in Russellville Kentucky with Hot Tub

Cute Boho Country Bungalow in Central Franklin KY

Cute Boho Country Bungalow in Central Franklin KY
Franklin
9.8 out of 10, Exceptional, (7 reviews)
"We had a great stay and felt very welcomed. The house was thoughtfully decorated and very cute. "
United States
sherie g.
The price is NZ$383
includes taxes & fees
24 June - 25 June
Cute Boho Country Bungalow in Central Franklin KY

Modern and Charming Cottage

Modern and Charming Cottage
Heron Walk
9.8 out of 10, Exceptional, (43 reviews)
"Security system and screen door did not seem to work properly. Bed was very comfortable and overall cleanliness of the property was excellent. Plenty of room and the location met our needs."
United States
Michele K.
The price is NZ$395
includes taxes & fees
25 June - 26 June
Modern and Charming Cottage

The Backstage Tiny House by Impossible Forrest!

The Backstage Tiny House by Impossible Forrest!
Lebanon
9.0 out of 10, Wonderful, (4 reviews)
"Cute place for the night. Very small with two dogs and us but was comfortable and nice surroundings."
United States
Shannon R.
The price is NZ$229
includes taxes & fees
1 July - 2 July
The Backstage Tiny House by Impossible Forrest!

Wood Shed Tiny House at Twig City Farm!

Wood Shed Tiny House at Twig City Farm!
Lebanon
The price is NZ$230
includes taxes & fees
6 July - 7 July
Wood Shed Tiny House at Twig City Farm!

Nashville Lake Chalet, Waterfront Sunset Views!

Nashville Lake Chalet, Waterfront Sunset Views!
Mt Juliet
9.2 out of 10, Wonderful, (85 reviews)
"This is the perfect location for a peaceful and scenic getaway. Nestled in nature but close enough to the big city. We had a perfect stay!"
United States
Stacy S.
The price is NZ$630
includes taxes & fees
5 July - 6 July
Nashville Lake Chalet, Waterfront Sunset Views!

Tranquil 1-bedroom country house perfect for a peaceful getaway

Tranquil 1-bedroom country house perfect for a peaceful getaway
Russellville
The price is NZ$291
includes taxes & fees
24 June - 25 June
Tranquil 1-bedroom country house perfect for a peaceful getaway

The Whispering Oak is a private and cozy getaway with its own private entrance!

The Whispering Oak is a private and cozy getaway with its own private entrance!
Springfield
10.0 out of 10, Exceptional, (2 reviews)
"Private, cozy, and so cute! Very welcoming and comfortable."
United States
Sheila A.
The price is NZ$178
includes taxes & fees
28 June - 29 June
The Whispering Oak is a private and cozy getaway with its own private entrance!

Woodsy Cabin Guest House with Spa and Pickleball Court.

Woodsy Cabin Guest House with Spa and Pickleball Court.
Greenbrier
9.8 out of 10, Exceptional, (90 reviews)
"We absolutely loved our stay at this property. The cabin was so cute and well decorated. The property was beautiful and we loved walking down to the creek, grilling on the back deck and spending time in the hot tub. The bed was super comfortable and the cabin had plenty of clean linens and kitchenware. We loved our visit from the dog and cat that stopped by outside to greet us. If you are looking for a quiet place to relax, unwind and rest, this cabin is perfect!!"
United States
Kimberley H.
The price is NZ$481
includes taxes & fees
29 June - 30 June
Woodsy Cabin Guest House with Spa and Pickleball Court.

The Magic Cottage: Artsy Nashville Escape w/ Hot Tub, Sleeps 10, & Near Downtown

The Magic Cottage: Artsy Nashville Escape w/ Hot Tub, Sleeps 10, & Near Downtown
Nashville
The price is NZ$1,400
includes taxes & fees
29 June - 30 June
The Magic Cottage: Artsy Nashville Escape w/ Hot Tub, Sleeps 10, & Near Downtown

Lakeshore Living- studio apartment

Lakeshore Living- studio apartment
Gallatin
10.0 out of 10, Exceptional, (14 reviews)
"Unit was clean and exactly as pictured. Quiet residential location. Will definitely stay here again!"
United States
Carla C.
The price is NZ$457
includes taxes & fees
30 June - 1 July
Lakeshore Living- studio apartment

The Whiskey River Lodge

The Whiskey River Lodge
Nashville
The price is NZ$997
includes taxes & fees
6 July - 7 July
The Whiskey River Lodge

Nashville Lakehouse on Old Hickory, Two Foot Cove!

Nashville Lakehouse on Old Hickory, Two Foot Cove!
Mt Juliet
9.2 out of 10, Wonderful, (126 reviews)
"Really enjoyed the Lake House. Was in town celbrating my sons 21st birthday and really enjoyed our time here. "
United States
Emilea W.
The price is NZ$671
includes taxes & fees
30 June - 1 July
Nashville Lakehouse on Old Hickory, Two Foot Cove!

JuneBug Log Cabin, Nashville Music History, Dreamy Loft Suite, Stone Frpl.

JuneBug Log Cabin, Nashville Music History, Dreamy Loft Suite, Stone Frpl.
Hendersonville
10.0 out of 10, Exceptional, (107 reviews)
"We enjoyed our stay will defenatly tell others about the cabin"
United States
Terry R.
The price is NZ$592
includes taxes & fees
28 June - 29 June
JuneBug Log Cabin, Nashville Music History, Dreamy Loft Suite, Stone Frpl.

Springfield Haven - Modern Comfort Near Nashville

Springfield Haven - Modern Comfort Near Nashville
Springfield
10.0 out of 10, Exceptional, (1 review)
"A beautiful home located in a great location of Springfield. The home has plenty of space, comfortable bedding, and an amazing master bathroom. We appreciated the spacious kitchen and the plentiful towels provided for guest."
United States
Rebecca D.
The price is NZ$1,199
includes taxes & fees
24 June - 25 June
Springfield Haven - Modern Comfort Near Nashville

Historic Stonewall Stays • Room for 12 w/ New Bunk Room

Historic Stonewall Stays • Room for 12 w/ New Bunk Room
Gallatin
9.8 out of 10, Exceptional, (23 reviews)
"This was a lovely space for our ladies' getaway."
United States
Debrina D.
The price is NZ$607
includes taxes & fees
24 June - 25 June
Historic Stonewall Stays • Room for 12 w/ New Bunk Room
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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Top Portland Hotel Reviews

Find out more about Portland

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Portland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Portland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Portland. Seeing all the best attractions is bound to make you fall in love with Portland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Portland short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Portland?

Yes, there are holiday rentals close to the most popular sights in Portland, or you can select a more secluded option if you're looking for a relaxing stay. Portland is known for its festivals and university setting.

What are some of the best holiday rentals that Portland has to offer?

Cozy, Modern, Safe, Quiet Neighborhood, Minutes From Nashville's Top Attractions: This holiday home rental outside of Portland offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a private garden and a selection of games.

How many holiday rentals are there in Portland?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Portland stay.

What can I see and do in Portland?

Portland City Park and Richland Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Cold Springs Museum and Portland City Hall.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a family trip.