A white structure with a sign reading "Portland Mills Bridge" and a warning to "Cross this bridge at a walk."

Portland Holiday 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 holiday rentals

1. Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14
Fort Recovery
10.0 out of 10, Exceptional, (14 reviews)
"Our family had a great stay! "
United States
todd b.
The price is NZ$754
includes taxes & fees
27 Sept - 28 Sept
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

2. The Loft at Grand Lake - In the Heart of Downtown Celina, Steps from the Lake

The Loft at Grand Lake - In the Heart of Downtown Celina, Steps from the Lake
Celina
8.6 out of 10, Excellent, (46 reviews)
"It really was a great place in a great location. We really enjoyed the entire trip. It was clean and the bed was comfortable. We loved walking around Celina. The bikes were a great addition. We rode them all over the place. Just a really fun little trip. "
United States
Bryan D.
The price is NZ$399
includes taxes & fees
5 Oct - 6 Oct
The Loft at Grand Lake - In the Heart of Downtown Celina, Steps from the Lake

3. Excellent Lake View 2Bdrm Cottage in Small Neighborhood Near Shopping & Dining

Excellent Lake View 2Bdrm Cottage in Small Neighborhood Near Shopping & Dining
Celina
10.0 out of 10, Exceptional, (46 reviews)
"The house was clean and so adorable, we enjoyed the location and comfort! Our second time in this area and do enjoy it! The host is great! "
United States
Jennifer P.
The price is NZ$468
includes taxes & fees
28 Sept - 29 Sept
Excellent Lake View 2Bdrm Cottage in Small Neighborhood Near Shopping & Dining

4. Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (46 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is NZ$297
includes taxes & fees
27 Sept - 28 Sept
Cardinal Cottage - 2 bedroom cozy home

5. Trojan Hideaway on First Street

Trojan Hideaway on First Street
Upland
10.0 out of 10, Exceptional, (11 reviews)
"Loved this cute home in a quiet neighborhood. Great for our family and had everything we needed for our stay. "
United States
Matthew B.
The price is NZ$399
includes taxes & fees
30 Sept - 1 Oct
Trojan Hideaway on First Street

6. mi casa es TU casa (WEST)

mi casa es TU casa (WEST)
Upland
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful accommodations!! Enjoyed our stay! "
United States
Nathan R.
The price is NZ$263
includes taxes & fees
27 Oct - 28 Oct
mi casa es TU casa (WEST)

7. 'Downtown Delight' w/ Patio! 1 Mi to Ball State

'Downtown Delight' w/ Patio! 1 Mi to Ball State
Muncie
10.0 out of 10, Exceptional, (27 reviews)
"It was an amazing place to stay and we had a wonderful weekend!! "
United States
Stace Y.
The price is NZ$601
includes taxes & fees
29 Sept - 30 Sept
'Downtown Delight' w/ Patio! 1 Mi to Ball State

8. Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (18 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is NZ$530
includes taxes & fees
30 Sept - 1 Oct
Retro Home Close to Campus

9. mi casa es TU casa (EAST)

mi casa es TU casa (EAST)
Upland
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful Experience Everything Up to Par Thank You for the Pleasure"
United States
Paul D.
The price is NZ$299
includes taxes & fees
30 Sept - 1 Oct
mi casa es TU casa (EAST)

10. The Guest House: Charming Local Comfort

The Guest House: Charming Local Comfort
Coldwater
The price is NZ$589
includes taxes & fees
5 Oct - 6 Oct
The Guest House: Charming Local Comfort

11. Grand Lake Getaway Cozy 2 - Bedroom Lake Retreat Near Grand Lake St. Marys

Grand Lake Getaway Cozy 2 - Bedroom Lake Retreat Near Grand Lake St. Marys
Celina
9.8 out of 10, Exceptional, (8 reviews)
"This was the perfect spot for our weekend together. Very clean and well furnished."
United States
Cheryl
The price is NZ$514
includes taxes & fees
27 Oct - 28 Oct
Grand Lake Getaway Cozy 2 - Bedroom Lake Retreat Near Grand Lake St. Marys

12. Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
Muncie
10.0 out of 10, Exceptional, (8 reviews)
"The property was absolutely beautiful, just as pictured!!! it’s a must stay."
United States
Simonne S.
The price is NZ$396
includes taxes & fees
20 Oct - 21 Oct
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

13. 'downtown Delight' w/ Patio! 1 Mi to Ball State

'downtown Delight' w/ Patio! 1 Mi to Ball State
2.5 star property
Muncie
The price is NZ$567
includes taxes & fees
28 Sept - 29 Sept
'downtown Delight' w/ Patio! 1 Mi to Ball State

14. Cozy Country Escape with all the Amenities, Close to Taylor U, IWU, BSU

Cozy Country Escape with all the Amenities, Close to Taylor U, IWU, BSU
Upland
The price is NZ$313
includes taxes & fees
28 Sept - 29 Sept
Cozy Country Escape with all the Amenities, Close to Taylor U, IWU, BSU

15. Heated Seasonal Pool, Hot Tub & Theater • Rustic Cabin by Bike Path

Heated Seasonal Pool, Hot Tub & Theater • Rustic Cabin by Bike Path
Celina
10.0 out of 10, Exceptional, (24 reviews)
"A perfect location for our retreat."
United States
Jason H.
The price is NZ$1,283
includes taxes & fees
14 Oct - 15 Oct
Heated Seasonal Pool, Hot Tub & Theater • Rustic Cabin by Bike Path

16. Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
Muncie
The price is NZ$435
includes taxes & fees
2 Oct - 3 Oct
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

17. Private Seasonal Pool, Dock & Hot Tub • Spacious Dog-Friendly Near Lake

Private Seasonal Pool, Dock & Hot Tub • Spacious Dog-Friendly Near Lake
Celina
10.0 out of 10, Exceptional, (31 reviews)
"Had an amazing excellent stay. The home is spacious, well-appointed and the immaculate. Easy check-in and good communication with host. Would definitely stay again. "
United States
Marsha Q.
The price is NZ$1,235
includes taxes & fees
12 Oct - 13 Oct
Private Seasonal Pool, Dock & Hot Tub • Spacious Dog-Friendly Near Lake

18. Cozy 2-bedroom next to Cardinal Greenway Trail

Cozy 2-bedroom next to Cardinal Greenway Trail
Muncie
10.0 out of 10, Exceptional, (1 review)
"Stay was awesome. House was so clean and host was awesome."
United States
Sharon C.
The price is NZ$372
includes taxes & fees
26 Oct - 27 Oct
Cozy 2-bedroom next to Cardinal Greenway Trail

19. mi casa es TU casa (Center)

mi casa es TU casa (Center)
Upland
10.0 out of 10, Exceptional, (12 reviews)
"Great stay"
United States
Kelley G.
The price is NZ$405
includes taxes & fees
27 Sept - 28 Sept
mi casa es TU casa (Center)

20. Serene 3-bedroom house Cartier with AC in the Village at Ball State University

Serene 3-bedroom house Cartier with AC in the Village at Ball State University
Muncie
The price is NZ$726
includes taxes & fees
27 Sept - 28 Sept
Serene 3-bedroom house Cartier with AC in the Village at Ball State University
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Portland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Portland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Portland. Seeing all the best attractions is bound to make you fall in love with Portland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Portland short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there 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 shopping and churches.

What are some of the best holiday rentals that Portland has to offer?

Lake Access, Seasonal Heated Pool,Hot Tub. Sleeps up to 22.: This holiday home rental outside of Portland is located on a lake, and has an outdoor pool, a balcony 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. Kick off your shoes and enjoy yourself with an arcade/games room and 1 hot tub.

What’s there to see and do in Portland?

While you're exploring the area, Lehman Park and Coldwater Nature Preserve are a couple of picturesque spots to get outside and enjoy nature. Winchester Speedway and Eldora Speedway are a couple of places you'll find in the wider area.

What’s a holiday rental in Portland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Portland. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.