Holiday rentals in Shepherd

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!

New Luxury Apartment in Billings

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.

Western Chic Guest House

Welcome to our charming Western chic guest house in Billings Heights! This cozy and family-friendly accommodation offers a comfortable and accessible stay for all guests. Located in a peaceful neighborhood, this guest house is a quick 10-minute drive from the airport and all major hospitals, you'll have easy access to everything you need during your stay. Whether you're visiting for business or pleasure, our Western chic guest house offers a comfortable and convenient home away from home!

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.

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 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.

Remodeled Retreat | Hot Tub | Parking for Trailers

🏠 Welcome to our newly remodeled retreat! Located in central Billings close to everything. 🚚 We offer extra parking for trucks AND + trailers! 📺 Enjoy seamless entertainment with smart TVs in every room along with WiFi. You'll have a charging station for all your devices! 🛏️ The beds are super comfy! ⭐️ With brand new furnishings, enjoy comfort and modernity in our professionally decorated space. Pristine and very clean!

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.

Garden Hideaway (HOT TUB!)

With craft coffee & a greenhouse downstairs, a private hot tub, & comfy memory foam mattresses, this is the best stay in Billings. Quiet & centrally located, this large & sunny one-of-a-kind home sleeps up to 8, with a clean and relaxing space to chill. Wake to fresh flowers, play ping pong, read about plants and trees, or wander the on-site greenhouse & garden, art gallery, and shop for local artisan crafts.

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.

Waterfront Home Near Downtown Sleeps 8

Escape to a peaceful 4-bed, 2-bath waterfront retreat on a quiet canal, just minutes from downtown Billings. Perfect for families or remote workers, this cozy home comfortably fits your group. Enjoy stunning water and city views from the private deck, a dedicated workspace with high-speed Wi-Fi, and easy access to local attractions. A serene getaway with modern comforts awaits.