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Holiday rentals in Portland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Upland
4.99 out of 5 average rating, 246 reviews

Brick House Upland

Intentionally designed for short term stays, Brick House Upland is set to welcome you to Upland for your visit to Taylor University, Ivanhoes, Upland, or all that Grant County has to offer. With comfort a hotel cannot offer, we hope this welcoming space will allow you to relax and connect with your family and friends. Rates for most nights begin at $95 and increase for select and premium weekends. Use the search bar at the top of the page to start booking now. *Please note: Most weekends require a two night minimum

Superhost
A spacious living room features a light-colored sofa and two matching armchairs, designed for comfort. A dark wood coffee table sits in the center, accompanied by two cups and a decorative fruit bowl. Natural light streams through the windows, highlighting the patterned area rug.
Flat in Old West End
4.94 out of 5 average rating, 181 reviews

Downtown Old West End-Fun central local with porch

This apt. is one of my favorite spaces. We used to live here and I think you will find it to be a relaxing and comfortable place to spend your time in Muncie. We've provided the basics so that it can be your home away from home: fully functioning kitchen, coffee options, hi speed internet, towels, shampoo, conditioner, soaps, bedding, roku with tv, and board games. 1/2 mile to shops & dining or a walk along the river, 1 mile to BSU. Close the day grilling out while you watch the gorgeous sunset.

Top guest favourite
A warm and inviting living room is reflected in a round mirror. Comfortable orange couches are positioned with light cushions, while a floor lamp and potted plants add to the decor. Natural light filters through the windows, enhancing the tranquil space.
Home in Berne
4.97 out of 5 average rating, 129 reviews

The Franklin Green House in the heart of Berne, IN

This beautiful home in the heart of Berne offers plenty of space for the whole family! Picnic at the Clock Tower, walk downtown, or stroll the new sidewalk all the way to Swiss Village. Stay in town to visit relatives, shop a variety of downtown stores, and enjoy the feel of small town life. The full, eat-in kitchen contains everything you need to make your favorite dish. Plenty of dining options are also available in town! Enjoy your stay in Berne and all this quaint Swiss-inspired town offers.

Top guest favourite
A private theater room is shown with reclining leather chairs arranged in rows facing a wall-mounted TV. Soft, ambient lighting is mounted on the wood-paneled walls, and a plush gray floor cushion is positioned in front, providing additional seating options.
Cabin in Celina
4.96 out of 5 average rating, 128 reviews

Family-Friendly Cabin | Seasonal Pool & Theater

Welcome to Brown Bear Log Cabin—your peaceful wooded escape minutes from restaurants, shops, breweries, landmarks and outdoor fun. Perfect for families, couples and groups to relax and explore. ✔ Movie Theater ✔ Heated Seasonal Pool (5/1–10/1) ✔ Loft Playroom ✔ Dog-Friendly ✔ Living Area ✔ Fully Equipped Kitchen ✔ Workspace ✔ Yard (Fire Pit, BBQ, Dining, Lounge) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Bike Path 0.25 mi ✔ 4 Comfy Bedrooms Book now—or tap ❤️ to save! Learn more below.

Top guest favourite
A serene bedroom features a spacious bed with soft linens and decorative pillows. A reading chair is positioned next to large windows, allowing natural light to illuminate the room. A decorative sign and plants add subtle character to the calming atmosphere.
Guest suite in Muncie
4.97 out of 5 average rating, 388 reviews

The Eagles Nest, two bedroom retreat.

Peaceful, centrally-located historic 1892 Queen Anne Victorian home. The Eagle's Nest has private entrance, off street parking, 2 bedrooms, furnished suite on the 2nd floor overlooking White River. Walk 0.6 miles to downtown Muncie, less than 2 miles to Ball State Univ. and 2 blocks to the Bob Ross Experience (Minnetrista). Nearby eatery and brewery options. Just 29 steps to 62-mile Cardinal Greenway, longest trail in Indiana. Might see an eagle hunting along the river too. You will love it!

Top guest favourite
The exterior of a two-story Techbuilt home is surrounded by lush greenery, showcasing large windows that invite natural light. A mature tree stands nearby, providing shade to the well-kept yard. The cedar siding highlights the home's mid-century architectural style.
Flat in Richmond
4.92 out of 5 average rating, 555 reviews

Private Apartment-800sq ft Next to Earlham College

Upper level separate apartment. Short stroll to Earlham College campus, ball fields, tennis courts, stables and Athletic Center. 5 houses up from the President's house. Windows galore offer natural lighting. Quiet neighborhood. Hardwood floors give that cozy feeling. Guaranteed clean and private. Well-behaved pets welcome. Breakfast not included. Coffee, tea, microwave, toaster oven and refrigerator in apartment. Host lives in lower apartment with dog and 2 cats. Chickens in the back yard.

Top guest favourite
A spacious living area is presented with light-colored walls and large windows that allow natural light to fill the room. Comfortable seating includes a beige armchair and a patterned sofa, positioned around a decorative area rug. A ceiling fan contributes to the room's airy feel.
Home in Celina
4.97 out of 5 average rating, 271 reviews

Bungalow by the Lake

A clean, comfortable spot within walking distance to many of Celina's events, restaurants, clubs and parks. You will have the entire living area to call your own with a full kitchen and laundry if needed. With a view of the lake welcoming you, the Bungalow By The Lake is sure to make your stay in Celina enjoyable, comfortable, and safe. SORRY NO PETS ALLOWED. We are pet lovers ourselves but understand some folks may have allergies so we've dedicated this residence as a NO PET HOME .

Top guest favourite
A spacious home is presented in a scenic outdoor setting, with a charming garden of vibrant flowers in the foreground. The building features a combination of textured stone and siding, framed by a serene sunset sky that enhances the peaceful ambiance.
Guest house in Versailles
4.97 out of 5 average rating, 263 reviews

French B&B - Lower Level Apt w/ 2 bedrooms

The French Bed & Breakfast is nestled in the charming town of Frenchtown, Ohio. This B&B has been operating since 1999 and has accommodated many guests coming to visit Darke County. Lower level of our house - it has spacious and quaint accommodations for a reasonable rate. Included: Continental Breakfast, kitchen, great room & patio. Guest rooms on lower level: 2 bedrooms - can be rented individually or as a 2 bdrm apartment (pricing varies based on events - min $75 ea bdrm).

Top guest favourite
The cottage features a charming exterior with white siding and black shutters. A welcoming front door is adorned with a seasonal wreath. A small, well-maintained garden surrounds the entrance, with shrubs and a decorative pumpkin adding to the inviting appearance.
Home in Decatur
4.99 out of 5 average rating, 126 reviews

Cheerful 2 Bedroom Cottage on 5th in Decatur IN

Quaint cottage style 2 bedroom home located in the downtown area of Decatur IN. This home has a master bedroom with a comfortable queen bed that sleeps 2. Blackout curtains and vintage cottage decor. The second bedroom has two plush twin beds that with advanced noticed can be pushed together to make a King bed. There is a fully stocked kitchen and a washer and dryer to do laundry. The private patio is a nice spot to relax in the morning with coffee or to wind down at sunset.

Guest favourite
The exterior of a modern two-story building is showcased, featuring curved architectural elements and large windows. Lush greenery surrounds the property, complemented by a clear blue sky. A robust tree stands prominently in the foreground, providing visual interest to the setting.
Home in Celina
4.94 out of 5 average rating, 102 reviews

2 bedroom all new~remodeled apartment.

Our 2 bedroom space has been completely renovated & features a modern design with all new furniture & appliances. The open concept living room & kitchen are perfect for entertaining, with comfortable & spacious bedrooms. Located in the heart of downtown Celina, just steps away from all the best restaurants, shops, & attractions. Includes everything you'll need for a comfortable stay, including fresh linens & towels, and we offer professional cleaning before and after every stay.

Top guest favourite
A well-maintained exterior view of a modest structure featuring a green roof and light-colored siding. The entrance is framed by a wooden deck with a railing, accompanied by landscaped stones and decorative elements, including small sculptures and shrubs. Natural light highlights the inviting entryway.
Farm stay in Greens Fork
4.95 out of 5 average rating, 162 reviews

A country night under the stars!

Get away from it all when you stay under the stars. Join us for a peaceful country stay, close enough to drive to nearby shopping and dining, and far enough to hear the crickets and see the stars. Your cozy place will include a kitchenette, coffee pot, microwave & TV. The dining area inside or on the attached deck, full size bed & full bath with shower. Only 3.9 miles from Interstate 70. Should you choose to use 100-foot zipline to exercise your pet.

Top guest favourite
A front porch area is visible, featuring two white wicker chairs with blue pillows positioned around a small dark table. A patterned rug lies underneath. A ceiling fan can be seen above, while greenery is present in the background, enhancing the outdoor setting.
Flat in Greenville
4.97 out of 5 average rating, 204 reviews

Cozy one bedroom apartment in a Century old house

This first floor one bedroom apartment is in a quiet neighborhood just 4 blocks from Wayne Hospital, 5 blocks from Darke County Fairgrounds and a short 5 minute walk to Downtown Greenville. It sleep up 4. The living room has a queen size sofa bed. IT has a TV with Spectrum streaming app. WiFi is available. It has a fully equipped kitchen with coffee maker and microwave. Other features include a washer and dryer and free street parking.

Popular amenities for Portland holiday rentals

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  2. United States
  3. Indiana
  4. Jay County
  5. Portland