Family-friendly holiday rentals in Yellowstone County

Boho Bungalow @ Old Pine Retreats

If you can imagine a getaway in a uniquely designed tiny house that is built on 60+ acres of wide open and stunning landscape, then you have captured a glimpse of this rare find. This beautiful tiny house is all yours to enjoy such amenities as a glass garage door that can be opened to experience nature from your kitchen table or a fireplace to cozy up to when the temps are cold. You can enjoy coffee in the morning from your private deck and keep your feet warm in the winter with heated floors.

Cozy Creekside Cabin Near Billings

Enjoy this beautiful fully furnished cabin just minutes outside the Billings city limits. Check in and then unwind with a walk on the private trails just out your front door. We are located a simple drive to the Metra for concerts and events, Ah-Nei State Recreation Area with ATV, walking, and horse trails, historic Pompey's Pillar, the Yellowstone river with fishing accesses, and Lake Elmo State park. Caretakers reside onsite and also host our four-legged friends through their pet resort.

Cozy Retreat - Walk to Downtown, Shops & Breweries

Colorful comfort meets Montana charm — your cozy downtown escape🌿 This cozy and colorful home is the perfect retreat after a day of exploring. Whether you’re visiting for work, family, medical visits, or city events, you’ll love the convenience of our central location 🏙️🍴☕️🏔️🍻 • Downtown Billings – 2 min • Hospitals – 7 min • Billings Airport – 8 min • MetraPark Arena – 7 min • Yellowstone River – 5 min • Starbucks – 6 min • Lake Elmo – 15 min This home is the perfect home base

The Modern Midtown Tiny

Welcome to our charming, centrally located Tiny Home, just minutes from downtown Billings, both hospitals, and the airport. This modern space features high ceilings, large windows that fill the home with natural light, and a queen-size bed that promises a restful night’s sleep. Enjoy the convenience of a fridge, oven/stove, and a new full-size washer and dryer. With stunning tile work and heated bathroom floors, we’ve created a space where you can truly relax and feel at home.

NEW Charming Little Cottage in Park City, Mt

Brand New! Super cute little cottage tucked away in the back yard with a contemporary farmhouse/rustic charm to it. Located right off I-90. Less than 10 minutes from Laurel ( which has Walmart, fast food, grocery store, restaurants). 25 minutes from Billings and 20 minutes to Columbus. Private entrance. Perfect for the traveling worker, couple or solo adventure. Wifi is available with a smart TV so you can watch your shows on your favorite apps (Netflix, HuLu, ect.)

*NEW BUILD* Mini Mountain View Getaway

Mini Mountain View Retreat is a great weekend get away. Just a short walk to downtown, the hospitals, or a view of the Beartooth Mountains. This tiny home makes for a relaxing stay with everything you need and a peaceful and homey atmosphere. Just because it's tiny doesn't mean it isn't full of all your basic home essentials such as a full kitchen, washer and dryer and luxurious features. This shared property is tucked away in a quiet and peaceful neighborhood.

Tranquil 5 bedroom home with large deck and yard

Come relax and unwind in this large home in a quiet Billings neighborhood. Perfectly situated for a family or gathering with open family room and fully stocked kitchen. Main floor has 3 bedrooms and 2 baths. Downstairs hosts a large den with 2 bedrooms, 1 bath, full laundy and a bonus study. Smart TVs throught the house. Dining room opens to a large deck with seating, BBQ and fenced yard. Mature trees provide shade and privacy.

Hospital Corridor Apartment

This special place is close to everything, making it easy to plan your visit. This house was originally built in 1900, then moved to Billings from Broadview in the 1940s. I bought the house in 2004, when my daughter was small, and have lived here ever since. It is a work in progress. Between 2010-13, I had the basement remodeled. I love the yard, and in the summer, I spend a good part of my day outside working in it.

Broadwater house

Newly remodeled 2 bedroom down town home located 2.9 miles from the airport. 6 minutes from Billings Hospitals. 5.3 miles from I-90. Enterprise is located next door for your convenience. NaRa Oriental restaurant, Holliday gas station, and Central High School are all just a short walk away. Easy access to some great spots nearby! This property is located on a busy street, which may result in street noise.

Lewis & Clark Apartment

A clean, comfortable space just off the interstate with parking right outside your door—easy in, easy out. The apartment is set up for a relaxed, no-fuss stay and works well for travelers passing through or staying a few days. The property is in progress as we continue improving the space, but inside you’ll find everything you need for a comfortable stay. Simple, convenient, and easy to settle into.

Stylish, Homey, & Spacious

Don't pass this one up! This home has everything you need to feel just at home! It is a newer home with high-end appliances and all brand new furniture! Pristine and very clean! Sit on the front patio for morning coffee or an evening glass of wine! Enjoy your privacy in the backyard while sitting around the gas fire pit. You will enjoy your time in Billings even more while staying at this home!

★Adorable Tiny House near hospitals & breweries ★

This adorable Tiny House is located on the same property as the main house, but has all the amenities of a regular house. Stylishly decorated and cleverly appointed, you'll find you have everything you need for a comfortable stay in this unique space. Located within one mile of the hospital district and one mile from the brewery district, our place is perfectly situated for your convenience.