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

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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 £313
includes taxes & fees
8 Sept - 9 Sept
Underground Speakeasy Experience in Historic Fort Recovery - Sleeps 14

2. 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, (41 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 £175
includes taxes & fees
13 Sept - 14 Sept
Excellent Lake View 2Bdrm Cottage in Small Neighborhood Near Shopping & Dining

3. 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)
"This house is a must stay! Very clean, great amenities, and a very helpful, responsive host. We stayed for 4 days in the middle of winter and had a wonderful time. The theater room and children's party area were great for the kids!"
United States
Lori B.
The price is £675
includes taxes & fees
6 Oct - 7 Oct
Heated Seasonal Pool, Hot Tub & Theater • Rustic Cabin by Bike Path

4. 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, (44 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 £174
includes taxes & fees
13 Sept - 14 Sept
The Loft at Grand Lake - In the Heart of Downtown Celina, Steps from the Lake

5. 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, (6 reviews)
The price is £210
includes taxes & fees
8 Sept - 9 Sept
Grand Lake Getaway Cozy 2 - Bedroom Lake Retreat Near Grand Lake St. Marys

6. mi casa es TU casa (WEST)

mi casa es TU casa (WEST)
Upland
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful accommodations!! Enjoyed our stay! "
United States
Nathan R.
The price is £113
includes taxes & fees
7 Sept - 8 Sept
mi casa es TU casa (WEST)

7. mi casa es TU casa (Center)

mi casa es TU casa (Center)
Upland
10.0 out of 10, Exceptional, (11 reviews)
"Great stay"
United States
Kelley G.
The price is £172
includes taxes & fees
13 Sept - 14 Sept
mi casa es TU casa (Center)

8. 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)
"The house and property were perfect for us. The house was clean when we got there and everything in it’s place the pool and hot tub and yard were perfect. Our dog loved the space and it was a great vacation. Would come back again and bring friends."
United States
Amy P.
The price is £558
includes taxes & fees
21 Sept - 22 Sept
Private Seasonal Pool, Dock & Hot Tub • Spacious Dog-Friendly Near Lake

9. 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 £180
includes taxes & fees
28 Sept - 29 Sept
Trojan Hideaway on First Street

10. The Guest House: Charming Local Comfort

The Guest House: Charming Local Comfort
Coldwater
The price is £250
includes taxes & fees
28 Sept - 29 Sept
The Guest House: Charming Local Comfort

11. Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (16 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is £214
includes taxes & fees
7 Sept - 8 Sept
Retro Home Close to Campus

12. Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (44 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is £127
includes taxes & fees
19 Sept - 20 Sept
Cardinal Cottage - 2 bedroom cozy home

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 £237
includes taxes & fees
7 Sept - 8 Sept
'downtown Delight' w/ Patio! 1 Mi to Ball State

14. Heated Seasonal Pool, Hot Tub, Golf Course Home with Putting Green, Dogs Welcome

Heated Seasonal Pool, Hot Tub, Golf Course Home with Putting Green, Dogs Welcome
Celina
10.0 out of 10, Exceptional, (14 reviews)
"Great location and very communicative host! Thank you!"
United States
Lori T.
The price is £551
includes taxes & fees
16 Sept - 17 Sept
Heated Seasonal Pool, Hot Tub, Golf Course Home with Putting Green, Dogs Welcome

15. '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 £255
includes taxes & fees
7 Sept - 8 Sept
'Downtown Delight' w/ Patio! 1 Mi to Ball State

16. 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 £203
includes taxes & fees
30 Sept - 1 Oct
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

17. Heated Seasonal Pool + Hot Tub Grand Lake Getaway With Boat Dock Near Bike Path

Heated Seasonal Pool + Hot Tub Grand Lake Getaway With Boat Dock Near Bike Path
Celina
10.0 out of 10, Exceptional, (5 reviews)
"This was one of the best properties we’ve ever stayed at! Katie, the Host, was exceptionally responsive with the few questions we had! I would recommend staying here to anyone who values an as advertised property!"
United States
Matt V.
The price is £706
includes taxes & fees
15 Sept - 16 Sept
Heated Seasonal Pool + Hot Tub Grand Lake Getaway With Boat Dock Near Bike Path

18. 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 £187
includes taxes & fees
7 Sept - 8 Sept
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

19. 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 £190
includes taxes & fees
14 Sept - 15 Sept
Serene 3-bedroom house Cartier with AC in the Village at Ball State University

20. Cozy 2-bedroom next to Cardinal Greenway Trail

Cozy 2-bedroom next to Cardinal Greenway Trail
Muncie
The price is £168
includes taxes & fees
15 Sept - 16 Sept
Cozy 2-bedroom next to Cardinal Greenway Trail
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, apart-hotels, 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 £127 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

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?

Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA: This holiday home rental outside of Portland is located in a rural location, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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. Berne Clock Tower and Winchester 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.