Holiday Homes in Portland

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Apartments
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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Portland holiday homes

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, (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 €446
includes taxes & fees
15 Nov - 16 Nov
The Yellow House - Hidden Gem in heart of Portland
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a marble island.

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

Hot Tub, Pool, Game Rooms, & Star Wars Theater!
Portland
The price is €520
includes taxes & fees
16 Nov - 17 Nov
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)
"This is a very nice place to stay. Easy to find and close to everything we needed."
United States
Diana M.
The price is €330
includes taxes & fees
18 Nov - 19 Nov
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
10.0 out of 10, Exceptional, (11 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 €207
includes taxes & fees
13 Nov - 14 Nov
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, (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 €216
includes taxes & fees
12 Nov - 13 Nov
Kentucky Comfort Central Retreat, 2 Bedroom Home
A two-story house with a deck, large windows, and a covered outdoor seating area.

6. Converted MiniFarm North of Nashville with Hot Tub

Converted MiniFarm North of Nashville with Hot Tub
Gallatin
10.0 out of 10, Exceptional, (5 reviews)
"Awesome place to stay, highly recommend booking this home!"
United States
Jacob L.
The price is €846
includes taxes & fees
21 Nov - 22 Nov
Converted MiniFarm North of Nashville with Hot Tub
A compact room with a bunk bed, a desk with a computer, a chair, a small plant, and a ladder.

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

Cozy 1-bedroom country bungalow in quiet Westmoreland with AC
Westmoreland
The price is €94
includes taxes & fees
13 Nov - 14 Nov
Cozy 1-bedroom country bungalow in quiet Westmoreland with AC
A hotel room with a large bed, two bedside tables with lamps, a wooden door, and two wall-mounted paintings.

8. 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 €220
includes taxes & fees
16 Nov - 17 Nov
Vintage modern / boho Gallatin townhome!
A small waterfall cascading over rocks into a pond surrounded by lush greenery.

9. 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 €198
includes taxes & fees
8 Dec - 9 Dec
Newly remodeled, Hot Tub, 70n inch tv Private Entrance, Convenient location
A spacious kitchen with white cabinets, a granite countertop, and a dining area with a wooden table and chairs.

10. 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 €380
includes taxes & fees
16 Nov - 17 Nov
Historic Stonewall Stays • Room for 12 w/ New Bunk Room
A covered outdoor patio with a wooden table and benches, a view of a backyard, and a house in the background.

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

Stylish Guest Suite in Gallatin: Close to Nashville, Screened Porch & Firepit
Gallatin
9.8 out of 10, Exceptional, (22 reviews)
"Nice place outside of town, host was super nice."
United States
Evan M.
The price is €168
includes taxes & fees
23 Nov - 24 Nov
Stylish Guest Suite in Gallatin: Close to Nashville, Screened Porch & Firepit
A wooden building with a closed sign, a ramp, and a gravel ground.

12. 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 €153
includes taxes & fees
12 Nov - 13 Nov
Tranquil 1-bedroom country house perfect for a peaceful getaway
A hallway with a wooden floor, white walls, and a door leading to a bathroom with a sink and mirror.

13. Modern and Charming Cottage

Modern and Charming Cottage
Heron Walk
9.6 out of 10, Exceptional, (50 reviews)
"This was the fourth time we have stayed here. The location is close to our Madison family and we love the front porch!"
United States
sarah r.
The price is €214
includes taxes & fees
18 Nov - 19 Nov
Modern and Charming Cottage
A spacious living area with a wooden staircase, a leather recliner, and a round coffee table.

14. 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 €241
includes taxes & fees
12 Nov - 13 Nov
Cozy 2-bedroom Milking Parlor in peaceful Logan County near Russellville with AC
A modern living room with a sofa, a coffee table, and a dining area with a kitchen in the background.

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

Old Hickory 4BR Retreat, Near Lake & Sleeps 8
Lakewood
The price is €580
includes taxes & fees
15 Nov - 16 Nov
Old Hickory 4BR Retreat, Near Lake & Sleeps 8
A spacious living room with a large sectional sofa, a fireplace, and a television mounted on the wall.

16. 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 €971
includes taxes & fees
12 Nov - 13 Nov
Private Hilltop Retreat 20 Min to Nashville | 3 Acres, Fire Pit & Movie Room
A spacious living area with a sofa, coffee table, and a ceiling fan.

17. 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 €995
includes taxes & fees
15 Nov - 16 Nov
20 Min to Nashville | Secluded 12 Acres | Game Room + Fire Pit | Sleeps 16
A living room with a sofa, a TV, a wooden side table, a rug, a painting, and a hallway leading to a dining area.

18. Cute Three Bedroom

Cute Three Bedroom
Nashville
10.0 out of 10, Exceptional, (30 reviews)
"Great back yard for our dog! And easy to get downtown for the show we came to see. Would book again"
United States
Cassidy L.
The price is €231
includes taxes & fees
12 Nov - 13 Nov
Cute Three Bedroom
A modern kitchen with white cabinets, a central island, and a dining area with a long table and chairs.

19. Stunning Private Retreat 25mins North of Nashville

Stunning Private Retreat 25mins North of Nashville
Hendersonville
10.0 out of 10, Exceptional, (17 reviews)
"Great private and secluded property for groups looking to enjoy Nashville."
United States
Alec M.
The price is €900
includes taxes & fees
23 Nov - 24 Nov
Stunning Private Retreat 25mins North of Nashville
A living room with a sofa, chairs, a TV, a fireplace, and string lights.

20. 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 €432
includes taxes & fees
17 Nov - 18 Nov
Quiet Residential Family Hideaway, Big Backyard
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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Learn more about Portland

Sip local vintages at Sumner Crest Winery before delving into the area's past at Cold Springs Museum. Sunny days invite exploration of Richland Park or a round of golf at nearby Kenny Perry's Country Creek, where small-town charm meets outdoor adventure.

See all hotels in Portland
A calm lake with a forested shoreline and a clear blue sky.