Photo by Jon Ross

Portland Holiday Rentals

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Our top choices for Portland holiday rentals

10.0 out of 10, Exceptional, (13)
"This is a beautiful house that is nicely furnished and very comfortable!"
United States
Josh B.
The price is NZ$814
includes taxes & fees
20 Jan - 21 Jan 2026
The Yellow House - Hidden Gem in heart of Portland
10.0 out of 10, Exceptional, (18)
"We truly enjoyed our stay in this unique place and will plan another trip. "
United States
TIna B.
The price is NZ$555
includes taxes & fees
24 Jan - 25 Jan 2026
Fantastic Ark minutes away from Nashville
2.0 star property
10.0 out of 10, Exceptional, (16)
"We had a great stay - it’s well decorated, comfortable, and clean. Would stay again!"
United States
Erin S.
The price is NZ$419
includes taxes & fees
28 Dec - 29 Dec
Vintage modern / boho Gallatin townhome!
10.0 out of 10, Exceptional, (1)
"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 NZ$176
includes taxes & fees
25 Dec - 26 Dec
The Backstage Tiny House by Impossible Forrest!
9.8 out of 10, Exceptional, (163)
"beautiful area on 200 acres to explore, would definitely do it again"
United States
jalen r.
The price is NZ$302
includes taxes & fees
22 Jan - 23 Jan 2026
Peace And Quiet Of Country Living Yet Close To Modern Convenience.
2.0 star property
The price is NZ$478
includes taxes & fees
4 Jan - 5 Jan 2026
1 King 2 Queens Garage Yard Washer Dryer
9.0 out of 10, Wonderful, (7)
"Was a beautiful stay would recommend to any couple that wants to stay close to Nashville I’d for sure stay again loved the place super cute !!!!"
United States
Anonymous traveller
The price is NZ$263
includes taxes & fees
30 Dec - 31 Dec
Stylish Guest Suite in Gallatin: Close to Nashville, Screened Porch & Firepit

Holiday Home in Old Hickory

Old Hickory Retreat 2-Sleeps 8
2.0 star property
9.6 out of 10, Exceptional, (4)
"We had a great stay at the home in Old Hickory. Right near the water and close to downtown Nashville. Plenty of space for the 6 of us and the place is true to the photos in the listing. "
United States
Derek C.
The price is NZ$1,082
includes taxes & fees
4 Jan - 5 Jan 2026
Old Hickory Retreat 2-Sleeps 8
10.0 out of 10, Exceptional, (9)
"Wouldn’t hesitate to stay and not a bad drive to Nashville. Everything depicted in the pictures is the exact same as what was there. Overall a great experience. "
United States
Justin S.
The price is NZ$339
includes taxes & fees
25 Dec - 26 Dec
Lakeshore Living- studio apartment
8.0 out of 10, Very good, (1)
"This is perfect if you’re in to your country music, Great place, great feel to it , we even did some song writing too, super hosts very easy to get on with. It was great to jam on their back porch. We look forward to seeing them another time "
United Kingdom
Paul W.
The price is NZ$351
includes taxes & fees
3 Jan - 4 Jan 2026
Honky Tonk Haven Cozy Nashville Apartment Country Feel in The Middle of The City
10.0 out of 10, Exceptional, (1)
"Thank you for a great “unique” stay experience! Room was clean, cool and quiet! Breakfast delicious! "
United States
Evonne W.
The price is NZ$182
includes taxes & fees
25 Dec - 26 Dec
Horse Stall Suite 3 Trotter Range Adventure Spot!
10.0 out of 10, Exceptional, (66)
"We loved staying at this house! So much history! Everything was perfect "
United States
Stacey W.
The price is NZ$430
includes taxes & fees
8 Jan - 9 Jan 2026
Mammoth Cave-Game Room-Buc-ee’s-Mint Casino-6 Beds-Stocked- wifi-StockedFirepit!
10.0 out of 10, Exceptional, (90)
"Great stay! "
United States
Melony G.
The price is NZ$339
includes taxes & fees
4 Jan - 5 Jan 2026
Newly remodeled, Hot Tub, 70n inch tv Private Entrance, Convenient location
9.8 out of 10, Exceptional, (65)
"This Vrbo was perfect for our stay! It was very clean and comfortable and it was in a good location for us. The host was great with communicating as well. We would definitely stay here again!"
United States
Shayna M.
The price is NZ$567
includes taxes & fees
4 Jan - 5 Jan 2026
Welcome to #BestStayEver Nashville/Old Hickory TN
2.0 star property
8.8 out of 10, Excellent, (6)
"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 NZ$504
includes taxes & fees
2 Jan - 3 Jan 2026
Kentucky Comfort Central Retreat, 2 Bedroom Home
2.0 star property
The price is NZ$478
includes taxes & fees
4 Jan - 5 Jan 2026
1 King 1 Queen 2 Double Garage Washer Dryer

Apartment in Bethpage

Country Retreat Near Gallatin
10.0 out of 10, Exceptional, (3)
"Extremely clean and homey space. Kristen is a great host. We would certainly stay here again"
United States
Jared W.
The price is NZ$456
includes taxes & fees
25 Dec - 26 Dec
Country Retreat Near Gallatin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house! Super cool location near the Opry and right on the river! Very accommodating owners. Would stay again for sure! "
United States
Rachel B.
Nashville River Retreat 3BR 5 minutes to the Grand Ole Opry
9.6 out of 10, Exceptional, (9)
"The home is beautiful and nice size for a family. The house is centrally located which is great. Home owner was easy to get in touch with and very kind. Wewill stay here again"
United States
Cassandra F.
The price is NZ$794
includes taxes & fees
24 Jan - 25 Jan 2026
Beautiful 3Bedroom Townhome off Old Hickory Lake.

Holiday Home in Bowling Green

Family Game Night II - 3BD/2.5BA
9.6 out of 10, Exceptional, (13)
"The home was perfect for our stay! "
United States
Tania P.
The price is NZ$776
includes taxes & fees
31 Dec - 1 Jan 2026
Family Game Night II - 3BD/2.5BA
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

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as NZ$339 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

‼️3BR Lakefront in Nashville w/ BBQ & Hot Tub: This holiday home rental outside of Portland is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and 1 hot tub.

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 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.