Family-friendly holiday rentals in Billings

Farmhouse Cottage @ Old Pine Retreats

This is your house if you are looking to experience the beauty of rugged Montana landscape just minutes outside of Billings, while in a uniquely designed tiny home. The Farmhouse Cottage @ Old Pine Retreats is a rustic, farmhouse themed home that is loaded with breathtaking views. Guests can take in the landscape next to the wall of windows and fireplace in the living room or enjoy a meal with friends on the main level deck. If this isn't enough, there is a roof-top deck that is sure to please!

Owls Nest by Landed - New Luxury Apartment

Located in a family friendly neighborhood, you'll find Studio 201 on the second floor just a few doors down from a local coffee shop and around the corner from a new taproom. This home is equipped with a spacious kitchen to prepare meals, private work space, relaxing couch, king sized bed, and a balcony to catch the evening sunsets or sip your morning coffee. Guests can enjoy the nearby walking trails, Yellowstone River and easy access to the interstate, which quickly gets you anywhere in town.

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

Cottage near Yellowstone River

This cozy cottage gives you easy access to our west end shopping and wonderful restaurants. You are also minutes from our downtown with delicious local restaurants and breweries. We are a small walk, or a quick drive away from the Yellowstone River. Take a walk through the neighborhood and grab a coffee, soda or ice cream at our friendly neighborhood coffee house, {Maple Moose}. The cottage has a comfortable , relaxing atmosphere. A queen bed and a bunk bed. A peaceful front deck.

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.

Charming three-bedroom townhome

This charming three-bedroom townhome is in the sought-after Annafeld Neighborhood in Billings. It features luxury amenities, including a Samsung 65-inch Frame TV, oversized sectional couch, king bed, and a spacious walk-in closet. Enjoy the perks of local living with a popular coffee shop and a delightful pizza taproom just a short stroll away. Plus, its prime location provides easy access to Billings West End shopping and is just minutes from the vibrant downtown area.

Charming Private Guest House

This special place is close to everything, making it easy to plan your visit. Close to Downtown, Airport, Hospitals and Shopping. No children. No visitors, parties or gatherings. 2 adult occupancy. Full kitchen stocked with necessities. Smaller dogs allowed (30 lbs or less). 2 pet max. Queen Bed. Blackout curtains for soothing sleep. WiFi and Utilities. TV and netflix are available. Extra linens and blankets. The owners live in the front house and have a small dog.

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.

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.

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.