Portland Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Portland holiday rentals

Smart TV

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 HK$1,374
HK$3,509 total
includes taxes & fees
11 May - 12 May
The Yellow House - Hidden Gem in heart of Portland
Exterior

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, (165 reviews)
"Awesome place! Super clean has everything! "
United States
jake S.
The price is HK$783
HK$1,517 total
includes taxes & fees
12 May - 13 May
Peace And Quiet Of Country Living Yet Close To Modern Convenience.
Exterior detail

Woodsy Cabin Guest House with Spa and Pickleball Court.

Woodsy Cabin Guest House with Spa and Pickleball Court.
Greenbrier
10.0 out of 10, Exceptional, (87 reviews)
"Simple but Beautiful detail. Quiet and peaceful. Wonderful stay will be back again. "
United States
Katie M.
The price is HK$916
HK$1,965 total
includes taxes & fees
13 May - 14 May
Woodsy Cabin Guest House with Spa and Pickleball Court.
Terrace/patio

Wood Shed Tiny House at Twig City Farm!

Wood Shed Tiny House at Twig City Farm!
Lebanon
The price is HK$594
HK$1,029 total
includes taxes & fees
11 May - 12 May
Wood Shed Tiny House at Twig City Farm!
Free WiFi, bed sheets

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 HK$528
HK$795 total
includes taxes & fees
17 May - 18 May
The Whispering Oak is a private and cozy getaway with its own private entrance!
Property grounds

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, (98 reviews)
"Absolutely lovely! Peaceful, large, clean! Nice amenities!! In the countryside but very close to Nashville. We will definitely stay again!! "
United States
Alison R.
The price is HK$728
HK$1,666 total
includes taxes & fees
26 May - 27 May
Newly remodeled, Hot Tub, 70n inch tv Private Entrance, Convenient location
Dining

Kentucky Comfort Central Retreat, 2 Bedroom Home

Kentucky Comfort Central Retreat, 2 Bedroom Home
Franklin
8.8 out of 10, Excellent, (6 reviews)
"Very nice property in a excellent location. Very well appointed and comfortable.Our host Tom responded quickly when we had questions. We would recommend this home for a stay."
United States
Craig C.
The price is HK$867
HK$1,870 total
includes taxes & fees
20 May - 21 May
Kentucky Comfort Central Retreat, 2 Bedroom Home
Interior

Cozy 2-bedroom Milking Parlor in peaceful Logan County near Russellville with AC

Cozy 2-bedroom Milking Parlor in peaceful Logan County near Russellville with AC
Russellville
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful remodeled parlor that gave us an amazing experience staying in Russellville, KY. Easy set up and stay. Great host and experience. It looked brand new. Couldn’t ask for anything better. "
United States
Tim S.
The price is HK$1,057
HK$2,046 total
includes taxes & fees
11 May - 12 May
Cozy 2-bedroom Milking Parlor in peaceful Logan County near Russellville with AC
Fridge, microwave, oven, stovetop

Welcome to #BestStayEver Nashville/Old Hickory TN

Welcome to #BestStayEver Nashville/Old Hickory TN
Nashville
9.8 out of 10, Exceptional, (76 reviews)
"It was clean and a great place to stay."
United States
Alan P.
The price is HK$698
HK$2,516 total
includes taxes & fees
11 May - 12 May
Welcome to #BestStayEver Nashville/Old Hickory TN
2 bedrooms, desk, iron/ironing board, free WiFi

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 HK$775
HK$2,015 total
includes taxes & fees
31 May - 1 Jun
Vintage modern / boho Gallatin townhome!
Private kitchen

1 King 2 Queens Garage Yard Washer Dryer

1 King 2 Queens Garage Yard Washer Dryer
2.0 star property
Lakewood
8.0 out of 10, Very good, (1 review)
"Verify clean and nice neighborhood "
United States
Tyronda
The price is HK$929
HK$3,523 total
includes taxes & fees
26 May - 27 May
1 King 2 Queens Garage Yard Washer Dryer
1 bedroom, iron/ironing board, travel cot, WiFi

Unique Treehouse With Spectacular View.

Unique Treehouse With Spectacular View.
Springfield
10.0 out of 10, Exceptional, (52 reviews)
"Absolutely loved our stay! This room is so comfy and we loved the little sitting room. Can’t wait to come back for a longer stay!"
United States
Erica M.
The price is HK$1,233
HK$2,147 total
includes taxes & fees
11 May - 12 May
Unique Treehouse With Spectacular View.
Interior

Modern and Charming Cottage

Modern and Charming Cottage
Heron Walk
9.8 out of 10, Exceptional, (41 reviews)
"Very clean nice place to stay while visiting Nashville."
United States
Ricky L.
The price is HK$575
HK$1,762 total
includes taxes & fees
17 May - 18 May
Modern and Charming Cottage
Interior

Log Cabin Once Owned by Johnny Cash, short drive to Nashville Sleeps 6

Log Cabin Once Owned by Johnny Cash, short drive to Nashville Sleeps 6
Hendersonville
10.0 out of 10, Exceptional, (76 reviews)
"What an amazing cabin. Clean, quaint, quiet, and felt like home. Thank you so much!"
United States
James G.
The price is HK$1,558
HK$3,263 total
includes taxes & fees
11 May - 12 May
Log Cabin Once Owned by Johnny Cash, short drive to Nashville Sleeps 6
Interior

The Whiskey River Lodge

The Whiskey River Lodge
Nashville
The price is HK$759
HK$4,401 total
includes taxes & fees
11 May - 12 May
The Whiskey River Lodge
Exterior

Hank's Hangout 24–Rooftop Deck–Sleeps 8

Hank's Hangout 24–Rooftop Deck–Sleeps 8
Madison
9.8 out of 10, Exceptional, (23 reviews)
"Love everything about it.... will book again"
United States
Shaniece
The price is HK$1,205
HK$4,704 total
includes taxes & fees
11 May - 12 May
Hank's Hangout 24–Rooftop Deck–Sleeps 8
Exterior

Tranquil 1-bedroom country house perfect for a peaceful getaway

Tranquil 1-bedroom country house perfect for a peaceful getaway
Russellville
The price is HK$691
HK$1,452 total
includes taxes & fees
14 May - 15 May
Tranquil 1-bedroom country house perfect for a peaceful getaway
Beach nearby

The Backstage Tiny House by Impossible Forrest!

The Backstage Tiny House by Impossible Forrest!
Lebanon
8.8 out of 10, Excellent, (3 reviews)
"It was a great place to stop and relax on a long drive! A tiny gem just outside Nashville."
United States
Kathryn H.
The price is HK$594
HK$1,029 total
includes taxes & fees
26 May - 27 May
The Backstage Tiny House by Impossible Forrest!
Interior

Music City Medley is ready for your next adventure!

Music City Medley is ready for your next adventure!
Old Hickory
9.8 out of 10, Exceptional, (68 reviews)
"Wonderful pet-friendly stay in Nashville!"
United States
Amanda L.
The price is HK$1,135
HK$2,436 total
includes taxes & fees
17 May - 18 May
Music City Medley is ready for your next adventure!
Property grounds

Lake House w/ Rooftop Views! 20 to Downtown Nash!

Lake House w/ Rooftop Views! 20 to Downtown Nash!
Nashville
10.0 out of 10, Exceptional, (7 reviews)
"We fully enjoyed your beautiful home!"
United States
K P.
The price is HK$1,327
HK$4,809 total
includes taxes & fees
12 May - 13 May
Lake House w/ Rooftop Views! 20 to Downtown Nash!
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

Holiday Inn Express White House by IHG

Holiday Inn Express White House by IHG

10/10 Excellent
"Room was vet clean, friendly staff. "
Sharon 1-night trip
Posted 2 hours ago
Holiday Inn Express White House by IHG

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

  • View our selection of featured holiday rentals in Portland
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Portland while they last

Look no further and take a look at our great range of rental properties in Portland!

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?

Luxurious 5-Bedroom Lakeside Retreat with Hot Tub, Fire Pit and Dolly Room: This holiday home rental outside of Portland offers a patio, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Portland?

With 5 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.