Holiday houses in Shepherd

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.

Private & Cozy 2BR Home W/ Hot Tub & Sauna

Cozy and private 2 Bedroom home that has been renovated and modernized for an Airbnb. There is a private hot tub and sauna, fully fenced back yard and a heated front patio. All private nothing shared. New appliance’s as well as a 65inch Samsung TV, outlet & usb charging beds and high speed internet for all your streaming needs. Comfortable new queen beds and all new furniture. Convenience Store - Walking distance about 2 blocks Grocery store- 1.2 miles Airport- 3 miles Downtown- Under 1 mile

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!

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!

Sleeps 6 | Waterfront Deck + Near Downtown

Escape to a peaceful waterfront retreat along a quiet canal, just minutes from downtown Billings. This bright and cozy 1-bedroom top-unit is perfect for solo travelers, couples, or remote workers, offering a calm, comfortable space to relax with stunning water and city views. Sip your morning coffee on your private deck, enjoy board games with family or friends, and take advantage of premium amenities like high-speed Wi-Fi, a dedicated workspace, and an EV charger.

*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.

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 parties/gatherings. 2 person 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.

Industrial Loft@Old Pine Retreat

Here is your opportunity to experience a remote getaway just minutes away from downtown Billings. This beautiful, vintage-industrial themed house has features that include a 21 foot high ceiling in the living room, a gas fireplace, a loft master bedroom and a second bedroom, large bathrooms on both levels and a private deck. If this isn't enough, the views and remote space that you will get to experience will be enough to take your breath away!

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.

Louise Lodge

Family- and pet-friendly 2 bedroom 1 bathroom apartment on Poly Drive. Charming and convenient location on Billings Westend, this space is perfect for singles, couples and small families. Relax in our stylish and cozy living space or snuggle on the sofa bed for movie night. Local grocery and coffee shop within walking distance with hospitals, colleges and airport just minutes away.

Lewis & Clark Apartment

This cute and comfortable place is perfect to kick your feet up and relax. 3 minutes to I-94, 2 minutes to Pompey’s Pillar National Monument and 25 minutes to Billings. This apartment is comfortable and roomy and has everything to enjoy your stay even if it’s just for a night.