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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Portland holiday rentals

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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, (18 reviews)
"The home is clean, beautiful, and conveniently located to stores and restaurants. The beds were very comfortable. The rooms were spacious. We recommend staying here for your next trip to Portland/Nashville area. I will book again if I’m back in town. "
United States
Angela D.
The price is HK$1,506
HK$3,338 total
includes taxes & fees
1 Sept - 2 Sept
The Yellow House - Hidden Gem in heart of Portland
Private kitchen

2. Cute Boho Country Bungalow in Central Franklin KY

Cute Boho Country Bungalow in Central Franklin KY
Franklin
9.8 out of 10, Exceptional, (8 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$748
HK$1,690 total
includes taxes & fees
10 Aug - 11 Aug
Cute Boho Country Bungalow in Central Franklin KY
Dining

3. Kentucky Comfort Central Retreat, 2 Bedroom Home

Kentucky Comfort Central Retreat, 2 Bedroom Home
Franklin
9.0 out of 10, Wonderful, (7 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$770
HK$1,765 total
includes taxes & fees
18 Aug - 19 Aug
Kentucky Comfort Central Retreat, 2 Bedroom Home
Interior

4. Country Retreat Near Gallatin

Country Retreat Near Gallatin
Bethpage
10.0 out of 10, Exceptional, (3 reviews)
"Extremely clean and homey space. Kristen is a great host. We would certainly stay here again"
United States
Jared W.
The price is HK$1,236
HK$1,921 total
includes taxes & fees
10 Aug - 11 Aug
Country Retreat Near Gallatin
Interior

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

Spacious Large Cabin at Harding near I-65/Downtown Franklin
Franklin
8.8 out of 10, Excellent, (6 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$1,804
HK$3,511 total
includes taxes & fees
10 Aug - 11 Aug
Spacious Large Cabin at Harding near I-65/Downtown Franklin
2 bedrooms, desk, iron/ironing board, free WiFi

6. Vintage modern / boho Gallatin townhome!

Vintage modern / boho Gallatin townhome!
Gallatin
10.0 out of 10, Exceptional, (22 reviews)
"Extremely clean, quiet, well decorated and comfortable. "
United States
Shawn M.
The price is HK$734
HK$1,821 total
includes taxes & fees
13 Aug - 14 Aug
Vintage modern / boho Gallatin townhome!
Interior

7. 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, (82 reviews)
"The property was great. It had everything we needed, was clean, and very relaxing."
United States
Kristen C.
The price is HK$1,561
HK$3,031 total
includes taxes & fees
13 Aug - 14 Aug
Log Cabin Once Owned by Johnny Cash, short drive to Nashville Sleeps 6
Smart TV, fireplace, books

8. 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, (112 reviews)
"We enjoyed our stay will defenatly tell others about the cabin"
United States
Terry R.
The price is HK$1,373
HK$2,491 total
includes taxes & fees
10 Aug - 11 Aug
JuneBug Log Cabin, Nashville Music History, Dreamy Loft Suite, Stone Frpl.
Coffee/tea maker, fridge, microwave, oven

9. 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, (24 reviews)
"This was a lovely space for our ladies' getaway."
United States
Debrina D.
The price is HK$1,327
HK$2,571 total
includes taxes & fees
11 Aug - 12 Aug
Historic Stonewall Stays • Room for 12 w/ New Bunk Room
Exterior detail

10. 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, (94 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$2,184 total
includes taxes & fees
16 Aug - 17 Aug
Woodsy Cabin Guest House with Spa and Pickleball Court.
Outdoor dining

11. 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, (17 reviews)
"Clean, comfortable and convenient. Very thankful to have been here."
United States
Karen W.
The price is HK$967
HK$1,202 total
includes taxes & fees
11 Aug - 12 Aug
Stylish Guest Suite in Gallatin: Close to Nashville, Screened Porch & Firepit
TV, offices

12. Relax Here! Nashville's Northern Retreat

Relax Here! Nashville's Northern Retreat
Gallatin
The price is HK$1,182
HK$2,583 total
includes taxes & fees
8 Sept - 9 Sept
Relax Here! Nashville's Northern Retreat
1 bedroom, free WiFi, bed sheets

13. 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, (3 reviews)
"Everything was excellent"
United States
Kandice P.
The price is HK$530
HK$745 total
includes taxes & fees
10 Aug - 11 Aug
The Whispering Oak is a private and cozy getaway with its own private entrance!
Exterior

14. 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, (173 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 HK$784
HK$1,529 total
includes taxes & fees
11 Aug - 12 Aug
Peace And Quiet Of Country Living Yet Close To Modern Convenience.
Interior

15. 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, (5 reviews)
"Couldn’t ask for better!"
United States
Karen
The price is HK$1,098
HK$2,102 total
includes taxes & fees
10 Aug - 11 Aug
Cozy 2-bedroom Milking Parlor in peaceful Logan County near Russellville with AC
4 bedrooms, memory-foam beds, iron/ironing board, travel cot

16. Creekside Getaway - Close to DT & Lake

Creekside Getaway - Close to DT & Lake
Gallatin
9.8 out of 10, Exceptional, (9 reviews)
"Property was clean and in a good location for our short stay. Would not hesitate to choose this location again."
United States
Tara M.
The price is HK$1,758
HK$3,334 total
includes taxes & fees
10 Aug - 11 Aug
Creekside Getaway - Close to DT & Lake
Property grounds

17. 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, (106 reviews)
"Beautiful property! We had a peaceful and relaxing stay with a beautiful view. The hot tub was perfect and the towel warmer was a nice addition. The hosts were quick to respond and checked in before and during the trip. WORTH IT!"
United States
Tif G.
The price is HK$663
HK$1,471 total
includes taxes & fees
7 Sept - 8 Sept
Newly remodeled, Hot Tub, 70n inch tv Private Entrance, Convenient location
Coffee/tea maker, fridge, microwave, oven

18. Welcome to #BestStayEver Nashville/Old Hickory TN

Welcome to #BestStayEver Nashville/Old Hickory TN
Nashville
9.8 out of 10, Exceptional, (91 reviews)
"Very good accomodations for our stay, clean and well decorated, would definitely stay here again"
United States
mike h.
Welcome to #BestStayEver Nashville/Old Hickory TN
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 Nashville-Hendersonville by IHG

Holiday Inn Express Nashville-Hendersonville by IHG

10/10 Excellent
"It was pretty much an excellent stay. Relaxing for sure! Everybody was helpful and great personalities. Get a great price, would definitely go back."
Kelley 10-night trip
Posted less than an hour ago
Holiday Inn Express Nashville-Hendersonville 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?

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 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 Sumner Crest WInery and Cold Springs Museum.

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.