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!

Gail's Guest Suite by MetraPark Arena

CLEAN, COZY, TOP NOTCH spot away from busy traffic streets yet close to the Metra & 10 min from downtown in nice neighborhood. Shared front door only.PLUSH Guest Suite on lower level has private door. Daylight den has beautiful gas fireplace, leather reclining loveseat, microsuede couch & big screen tv. Queen bed has a medium firm Nova foam mattress.Kitchenette has a microwave, small fridge, coffee pot, coffee, tea and snacks. 1-2 Adults only, must be over 21, non smokers, non vapors, no pets.

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

Entire Cozy Condo

Tucked away in the quiet and peaceful Heights neighborhood, the condo features a split level set-up. The cozy condo is a short drive from the airport, grocery stores, MetraPark Arena, Hospitals, and downtown area. Oasis Water park and Lake Elmo are 5 minutes away. The property is a great fit for extended work stays, a place to stay for the weekend while attending events at the arena, or a quiet place to get away while visiting family. We look forward to getting to serve you!

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 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.

Daylight patio & simple Comforts

Welcome to our cozy daylight basement with a private patio, perfect for enjoying simple comforts. The space is thoughtfully designed for relaxation, offering a comfortable living area and peaceful bedrooms. While we don't have a full kitchen, you'll find a mini-fridge, microwave, coffee maker and toaster oven to cover your essentials. Whether you're here to unwind or explore the area, our charming space offers all you need for comfortable, stress-fee stay.

Mountain Man Cabin

Rustic cabin on horse boarding facility. 20 acres of pasture close to a creek. 15 minutes from downtown Billings. 5 minutes from 2 nice restaurants. Pryor Creek Golf course nearby. Quite and peaceful. Outdoor fireplace. Very central to lots of attractions in and around Billings. Note: 1/2 bath inside the cabin. Access to a showerhouse with a private shower room only accessible to this cabin 50 feet from the cabin itself.

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.

Dustin’s Lower Level Heights/Metra/Airport Studio

NO Cleaning Fee… Upon entering through the shared front entryway door of my Townhouse, you'll find your separate entrance leading to your lower-level studio. This ensures complete privacy from the host's living space. Relax in a spacious king-size bed with a plush memory foam topper and enjoy the convenience of a private bathroom. We've provided a microwave, mini-fridge/freezer, and Keurig coffee maker for your comfort.

★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.