An aerial view of a rural landscape with green fields, a few scattered trees, and two red barns.

Portland Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Portland holiday rentals

A spacious living room with a high ceiling, a chandelier, a staircase, a dining area, and a cozy seating area.

1. 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, (19 reviews)
"This is a beautiful house that is nicely furnished and very comfortable!"
United States
Josh B.
The price is HK$1,334
HK$3,506 total
includes taxes & fees
1 Oct - 2 Oct
The Yellow House - Hidden Gem in heart of Portland
A room with a curved ceiling, a large window, a leather sofa, a coffee table, and a television.

2. Hot Tub, Pool, Game Rooms, & Star Wars Theater!

Hot Tub, Pool, Game Rooms, & Star Wars Theater!
Portland
The price is HK$2,017
HK$4,018 total
includes taxes & fees
5 Oct - 6 Oct
Hot Tub, Pool, Game Rooms, & Star Wars Theater!
A living room with a fireplace, leather sofa, wooden coffee table, and a patterned rug.

3. The Lucky Chance House - Franklin, KY

The Lucky Chance House - Franklin, KY
Franklin
10.0 out of 10, Exceptional, (6 reviews)
"Clean, good communication from host"
United States
Tia E.
The price is HK$1,483
HK$2,672 total
includes taxes & fees
15 Oct - 16 Oct
The Lucky Chance House - Franklin, KY
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a pendant light fixture.

4. Cute Boho Country Bungalow in Central Franklin KY

Cute Boho Country Bungalow in Central Franklin KY
Franklin
9.8 out of 10, Exceptional, (9 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 HK$832
HK$1,738 total
includes taxes & fees
28 Oct - 29 Oct
Cute Boho Country Bungalow in Central Franklin KY
A conference room with a long wooden table, white chairs, and a modern chandelier.

5. Kentucky Comfort Central Retreat, 2 Bedroom Home

Kentucky Comfort Central Retreat, 2 Bedroom Home
Franklin
9.2 out of 10, Wonderful, (9 reviews)
"Great location for a wedding we attended Beautifully decorated and had EVERYTHING we needed-fully stocked "
United States
Lisa G.
The price is HK$798
HK$1,744 total
includes taxes & fees
5 Oct - 6 Oct
Kentucky Comfort Central Retreat, 2 Bedroom Home
A modern living room with a sectional sofa, a wooden coffee table, and a kitchen area with grey cabinets and a stainless steel refrigerator.

6. Lakeshore Living- studio apartment

Lakeshore Living- studio apartment
Gallatin
10.0 out of 10, Exceptional, (15 reviews)
"Room clean and as advertised. Plenty of room for 1-2 people; very comfortable. I stayed here for multiple weeks and would stay here again."
United States
Gary C.
The price is HK$604
HK$1,809 total
includes taxes & fees
5 Oct - 6 Oct
Lakeshore Living- studio apartment
A hotel room with a large bed, two bedside tables with lamps, a wooden door, and two wall-mounted paintings.

7. Vintage modern / boho Gallatin townhome!

Vintage modern / boho Gallatin townhome!
Gallatin
10.0 out of 10, Exceptional, (24 reviews)
"Extremely clean, quiet, well decorated and comfortable. "
United States
Shawn M.
The price is HK$678
HK$1,903 total
includes taxes & fees
5 Oct - 6 Oct
Vintage modern / boho Gallatin townhome!
A bedroom with a wooden bed, a ceiling fan, a bookshelf, and a window with a view of the outdoors.

8. The Creekside Cottage at Honey Run White House, Tennessee est 1918

The Creekside Cottage at Honey Run White House, Tennessee est 1918
White House
The price is HK$1,236
HK$2,585 total
includes taxes & fees
1 Oct - 2 Oct
The Creekside Cottage at Honey Run White House, Tennessee est 1918
A hallway with light blue walls, a wooden floor, and a dark blue accent wall with a cityscape mural.

9. Country Retreat Near Gallatin

Country Retreat Near Gallatin
Bethpage
10.0 out of 10, Exceptional, (4 reviews)
"Great place. Would stay here again."
United States
Mary L.
The price is HK$1,236
HK$2,072 total
includes taxes & fees
1 Oct - 2 Oct
Country Retreat Near Gallatin
A bedroom with a bed, a dark green wall, and string lights.

10. 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, (4 reviews)
"Everything was excellent"
United States
Kandice P.
The price is HK$530
HK$797 total
includes taxes & fees
12 Oct - 13 Oct
The Whispering Oak is a private and cozy getaway with its own private entrance!
Living area

11. Relax Here! Nashville's Northern Retreat

Relax Here! Nashville's Northern Retreat
Gallatin
The price is HK$854
HK$2,109 total
includes taxes & fees
6 Oct - 7 Oct
Relax Here! Nashville's Northern Retreat
A modern living room with a grey sofa, fluffy cushions, a small white side table, and a blue bed.

12. Cozy 1-bedroom country bungalow in quiet Westmoreland with AC

Cozy 1-bedroom country bungalow in quiet Westmoreland with AC
Westmoreland
The price is HK$424
HK$868 total
includes taxes & fees
2 Oct - 3 Oct
Cozy 1-bedroom country bungalow in quiet Westmoreland with AC
A wooden hallway with large windows, a bed in the background, and hanging pendant lights.

13. 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, (88 reviews)
"Beautiful place to stay and enjoy the quiet outside of the Nashville lights! Cozy and updated to today’s standards. Beautifully appointed with a variety of the new and the old! Great story behind this home! Highly recommend!"
United States
Toni
The price is HK$1,561
HK$3,120 total
includes taxes & fees
4 Oct - 5 Oct
Log Cabin Once Owned by Johnny Cash, short drive to Nashville Sleeps 6
A rustic log cabin interior with a wooden staircase, a patterned rug, and a wooden dresser.

14. Spacious Large Cabin at Harding near I-65/Downtown Franklin

Spacious Large Cabin at Harding near I-65/Downtown Franklin
Franklin
9.0 out of 10, Wonderful, (7 reviews)
"Perfect place to stay in the middle of lots of town. Out of town but close to everything. We enjoyed our stay"
United States
Kami B.
The price is HK$2,118
HK$3,684 total
includes taxes & fees
1 Oct - 2 Oct
Spacious Large Cabin at Harding near I-65/Downtown Franklin
A cozy log cabin interior with a stone fireplace, wooden furniture, and a rustic ambiance.

15. 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, (116 reviews)
"Great property and host, very comfortable and the host really cares about their guests, I would rate it higher but 5 is the most it will let me"
United States
George N.
The price is HK$1,373
HK$2,710 total
includes taxes & fees
4 Oct - 5 Oct
JuneBug Log Cabin, Nashville Music History, Dreamy Loft Suite, Stone Frpl.
A wooden cabin with a porch and a staircase leading to the entrance.

16. 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, (174 reviews)
"Amazing property"
United States
Justin M.
The price is HK$785
HK$1,520 total
includes taxes & fees
1 Oct - 2 Oct
Peace And Quiet Of Country Living Yet Close To Modern Convenience.
A covered outdoor patio with a wooden table and benches, a view of a backyard, and a house in the background.

17. Stylish Guest Suite in Gallatin: Close to Nashville, Screened Porch & Firepit

Stylish Guest Suite in Gallatin: Close to Nashville, Screened Porch & Firepit
Gallatin
9.6 out of 10, Exceptional, (19 reviews)
"Yes the place is very nice and welcoming "
United States
Eli H.
The price is HK$1,158
HK$1,515 total
includes taxes & fees
3 Oct - 4 Oct
Stylish Guest Suite in Gallatin: Close to Nashville, Screened Porch & Firepit
A cozy cabin interior with two dark blue armchairs, a wooden dining table, and a kitchen area.

18. Relax & Recharge at Firefly Cabin

Relax & Recharge at Firefly Cabin
Russellville
10.0 out of 10, Exceptional, (9 reviews)
"Very helpfull host! Very nice place to stay!"
United States
Jay E.
The price is HK$657
HK$1,744 total
includes taxes & fees
6 Oct - 7 Oct
Relax & Recharge at Firefly Cabin
A door with a window, a metal exterior, and a wooden door frame.

19. Charming Tiny House in Country

Charming Tiny House in Country
Adairville
The price is HK$706
HK$1,609 total
includes taxes & fees
26 Oct - 27 Oct
Charming Tiny House in Country
A rustic log cabin with a wooden porch, large windows, and a stone foundation.

20. Woodsy Cabin Guest House with Spa.

Woodsy Cabin Guest House with Spa.
Greenbrier
9.8 out of 10, Exceptional, (101 reviews)
"We had a wonderful stay, the cabin was even cuter in person. This way the perfect place for a couples getaway and we especially loved the back deck area. "
United States
Anna P.
The price is HK$1,193
HK$2,283 total
includes taxes & fees
4 Oct - 5 Oct
Woodsy Cabin Guest House with Spa.
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

Comfort Inn Nashville - Opryland Area

Comfort Inn Nashville - Opryland Area

8/10 Good
"It was nice there was shuttle to take downtown and to the Grand Ole Opry for a very reasonable price. The breakfast was good. My only complaint is that I asked twice for someone to look at my clogged bathroom sink , It was never fixed"
Patti 2-night trip
Posted 7 hours ago
Comfort Inn Nashville - Opryland Area

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?

Lakefront property with 7 bedrooms: This holiday home rental outside of Portland is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as an arcade/games room.

How many holiday rentals are there in Portland?

With 6 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 Portland City Hall and Sumner Crest WInery.

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.