A calm lake with a forested shoreline and a clear blue sky.

Portland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Portland vacation homes

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, (20 reviews)
"A great alternative to a hotel. We had 8 and pets, and had ample room. The house is older, but very clean and charming with nice updates. Would definitely visit again. What a great value!"
United States
David K.
The price is CA $282
CA $667 total
includes taxes & fees
Nov 15 - Nov 16
The Yellow House - Hidden Gem in heart of Portland

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

Hot Tub, Pool, Game Rooms, & Star Wars Theater!
Portland
The price is CA $466
CA $822 total
includes taxes & fees
Nov 16 - Nov 17
Hot Tub, Pool, Game Rooms, & Star Wars Theater!

3. The Lucky Chance House - Franklin, KY

The Lucky Chance House - Franklin, KY
Franklin
10.0 out of 10, Exceptional, (6 reviews)
"This is a very nice place to stay. Easy to find and close to everything we needed."
United States
Diana M.
The price is CA $270
CA $579 total
includes taxes & fees
Nov 30 - Dec 1
The Lucky Chance House - Franklin, KY

4. Cute Boho Country Bungalow in Central Franklin KY

Cute Boho Country Bungalow in Central Franklin KY
Franklin
10.0 out of 10, Exceptional, (11 reviews)
"Cute little house, perfect for what we needed!"
United States
Maggie L.
The price is CA $164
CA $326 total
includes taxes & fees
Nov 21 - Nov 22
Cute Boho Country Bungalow in Central Franklin KY

5. Kentucky Comfort Central Retreat, 2 Bedroom Home

Kentucky Comfort Central Retreat, 2 Bedroom Home
Franklin
9.2 out of 10, Wonderful, (10 reviews)
"Great location for a wedding we attended Beautifully decorated and had EVERYTHING we needed-fully stocked "
United States
Lisa G.
The price is CA $171
CA $338 total
includes taxes & fees
Nov 15 - Nov 16
Kentucky Comfort Central Retreat, 2 Bedroom Home

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

Cozy 1-bedroom country bungalow in quiet Westmoreland with AC
Westmoreland
The price is CA $77
CA $146 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom country bungalow in quiet Westmoreland with AC

7. Vintage modern / boho Gallatin townhome!

Vintage modern / boho Gallatin townhome!
Gallatin
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful stay at a great price. Highly recommend!"
United States
Caity S.
The price is CA $123
CA $342 total
includes taxes & fees
Nov 16 - Nov 17
Vintage modern / boho Gallatin townhome!

8. 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, (116 reviews)
"Over all was a great place. We would come back and rent again"
United States
Ken K.
The price is CA $130
CA $298 total
includes taxes & fees
Nov 16 - Nov 17
Newly remodeled, Hot Tub, 70n inch tv Private Entrance, Convenient location

9. Old Hickory 4BR Retreat, Near Lake & Sleeps 8

Old Hickory 4BR Retreat, Near Lake & Sleeps 8
Lakewood
The price is CA $143
CA $910 total
includes taxes & fees
Nov 17 - Nov 18
Old Hickory 4BR Retreat, Near Lake & Sleeps 8

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

Stylish Guest Suite in Gallatin: Close to Nashville, Screened Porch & Firepit
Gallatin
9.8 out of 10, Exceptional, (22 reviews)
"Nice place outside of town, host was super nice."
United States
Evan M.
The price is CA $209
CA $262 total
includes taxes & fees
Nov 24 - Nov 25
Stylish Guest Suite in Gallatin: Close to Nashville, Screened Porch & Firepit

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

Historic Stonewall Stays • Room for 12 w/ New Bunk Room
Gallatin
9.6 out of 10, Exceptional, (25 reviews)
"This was a lovely space for our ladies' getaway."
United States
Debrina D.
The price is CA $289
CA $619 total
includes taxes & fees
Nov 16 - Nov 17
Historic Stonewall Stays • Room for 12 w/ New Bunk Room

12. 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, (7 reviews)
"Great place."
United States
Jamie D.
The price is CA $210
CA $379 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 2-bedroom Milking Parlor in peaceful Logan County near Russellville with AC

13. 20 Min to Nashville | Secluded 12 Acres | Game Room + Fire Pit | Sleeps 16

20 Min to Nashville | Secluded 12 Acres | Game Room + Fire Pit | Sleeps 16
Goodlettsville
The price is CA $288
CA $1,565 total
includes taxes & fees
Nov 15 - Nov 16
20 Min to Nashville | Secluded 12 Acres | Game Room + Fire Pit | Sleeps 16

14. Private Hilltop Retreat 20 Min to Nashville | 3 Acres, Fire Pit & Movie Room

Private Hilltop Retreat 20 Min to Nashville | 3 Acres, Fire Pit & Movie Room
Goodlettsville
The price is CA $261
CA $1,531 total
includes taxes & fees
Nov 17 - Nov 18
Private Hilltop Retreat 20 Min to Nashville | 3 Acres, Fire Pit & Movie Room

15. Tranquil 1-bedroom country house perfect for a peaceful getaway

Tranquil 1-bedroom country house perfect for a peaceful getaway
Russellville
8.0 out of 10, Very good, (1 review)
"This place was great, cozy little cabin out in the country , quiet , peaceful!!! Would definitely stay here again. They even made some complimentary cinnamon buns,Sooooo gooood!!!!!!"
United States
Anonymous traveller
The price is CA $128
CA $239 total
includes taxes & fees
Nov 19 - Nov 20
Tranquil 1-bedroom country house perfect for a peaceful getaway

16. Peaceful 2-bedroom townhome with AC in vibrant Nashville

Peaceful 2-bedroom townhome with AC in vibrant Nashville
Nashville
The price is CA $166
CA $503 total
includes taxes & fees
Dec 1 - Dec 2
Peaceful 2-bedroom townhome with AC in vibrant Nashville

17. Cute Three Bedroom

Cute Three Bedroom
Nashville
10.0 out of 10, Exceptional, (30 reviews)
"Very cozy bungalow. It has everything we needed."
United States
blake b.
The price is CA $148
CA $363 total
includes taxes & fees
Nov 16 - Nov 17
Cute Three Bedroom

18. Modern and Charming Cottage

Modern and Charming Cottage
Heron Walk
9.6 out of 10, Exceptional, (51 reviews)
"The home was well appointed and very comfortable. The owner addressed our needs quickly and effectively. We will be back."
United States
Lisa S.
The price is CA $125
CA $333 total
includes taxes & fees
Nov 18 - Nov 19
Modern and Charming Cottage

19. Quiet Residential Family Hideaway, Big Backyard

Quiet Residential Family Hideaway, Big Backyard
River Trace
10.0 out of 10, Exceptional, (2 reviews)
"It was a cozy place to stay outside of downtown Nashville. Would stay again if we ever went back."
United States
Amanda S.
The price is CA $136
CA $683 total
includes taxes & fees
Nov 17 - Nov 18
Quiet Residential Family Hideaway, Big Backyard

20. The Southern Pearl | Rooftop Lounge, 2 Parking Spaces & Dog-Friendly Comfort

The Southern Pearl | Rooftop Lounge, 2 Parking Spaces & Dog-Friendly Comfort
Madison
8.8 out of 10, Excellent, (5 reviews)
The price is CA $195
CA $714 total
includes taxes & fees
Nov 17 - Nov 18
The Southern Pearl | Rooftop Lounge, 2 Parking Spaces & Dog-Friendly Comfort
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Portland Hotel Reviews

Find out more about Portland

Portland Vacation Homes information

Number of reviews
321
Accommodation
348 Vacation Homes
Lowest Price
CA $146
Highest Price
CA $1,565

Explore a world of travel with Expedia