Holiday rentals in Shepherd

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.

Family · Location · Solo travel

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.

Family · Location · Comfort

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!

Family · Value · Parking

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!

Value · Family · Cleanliness

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.

Location · Family · Wifi

*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.

Value · Location · Checkout

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.

Location · Value · Solo travel

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.

Family · Location · Amenities

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.

Location · Family · Pets

★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.

Location · Family · Checkout

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.

Location · Value · Indoor spaces

Billings Best 1BD

This 1 BD ground level is truly one of Billings' hidden gems. Open, spacious, and immaculately kept! Cozy and comfortable furniture and an electric wall fireplace! Includes washer and dryer in the bathroom and Tempurpedic bed! Offers K-Cup coffee and a welcome snack basket! Don't miss this one!

Family · Value · Kitchen