Vacation rentals in Shepherd

4.96 out of 5 average rating, 113 reviews

A spacious living area features a dark leather sectional sofa facing a wooden kitchen island with granite countertops. The room is illuminated by overhead lights, and a white area rug is positioned on warm-toned hardwood flooring. Cabinets and appliances are situated along one wall.

Guesthouse in Billings

Private modern loft in country setting.

Take it easy at this extremely private and quiet setting with no close neighbors. Our little home with only one queen bed is the perfect space for solo adventures or a couple. This simple cozy loft is not only beautiful but offers views of Montana's Emerald Hills and the Prior Mountain Range. The perfect getaway from the hustle of the city with access to Billings, Shepherd and Huntley in minutes while never leaving the paved roads and parking lot ready for your vehicle with or without a trailer.

A rustic cabin entrance is framed by wooden beams, showcasing a cozy porch with two chairs and a barbecue grill. Potted flowers add a touch of color at the base, while a gravel path leads to the door, inviting visitors to explore the surrounding nature.

4.96 out of 5 average rating, 220 reviews

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.

4.92 out of 5 average rating, 225 reviews

A cozy living room features a comfortable chair and a dark blue sofa, accented with decorative cushions. A round table with a lamp is positioned beside the sofa. The space is brightened by natural light streaming through large windows, illuminating a patterned area rug.

Home in Billings

Downtown Billings Retreat

Explore Downtown Billings’ vibrant streets with this comfortable and cozy home as your base. This cute little home is tastefully decorated with colorful patterns and boho accents. Your home away from home is a perfect central location! 🤌 • Two of Montana’s largest hospitals - 7 min. • Airport - 8 min. • MetraPark Arena - 7 min. • River - 5 min. • Starbucks - 6 min. • Lake Elmo - 15 min. You’ll find a great variety of breweries, restaurants, cafes, and shopping only minutes away also :) Enjoy!

5 out of 5 average rating, 226 reviews

A cozy den features a stone fireplace with a wooden mantel. A coffee maker and small fridge are positioned nearby. A leather reclining loveseat sits next to a dark ottoman, and a wall clock and decorative mirror are displayed on the walls.

Guest suite in Billings

Gail's Guest Suite by MetraPark Arena

CLEAN, COZY 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, toaster, coffee pot, coffee, tea and snacks. 1-2 Adults only, must be over 21, non smokers, non vapors, no pets.

4.97 out of 5 average rating, 117 reviews

A spacious guest room features a metal frame bed with decorative blankets. Flanking the bed are two bedside tables topped with decorative lamps. Large windows allow ample natural light, while soft, textured curtains add a cozy touch. A patterned rug enhances the warmth of the space.

Guesthouse in Billings

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!

4.95 out of 5 average rating, 124 reviews

A comfortably arranged living area features a large gray sectional sofa and a white media console. A wall-mounted television is positioned above a compact electric fireplace. A textured area rug lies on the dark wood flooring, with natural light softly illuminating the room.

Condo in Billings

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!

4.96 out of 5 average rating, 353 reviews

A cozy sleeping area features a quilt adorned with wildlife motifs, complemented by decorative pillows. Warm wood paneling creates an inviting space, accompanied by soft lighting from mounted sconces. A framed nature-themed artwork enhances the rustic charm of the room.

Guesthouse in Park City

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.)

A single-story tiny home is shown with a welcoming green door and a front porch featuring a bench. Light-colored siding is complemented by large windows that offer views of the surrounding landscape, consisting of gentle hills and trees.

4.96 out of 5 average rating, 274 reviews

*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.

The exterior of the house is presented, showcasing a blend of natural wood and modern materials. Large windows reflect sunlight, while a spacious deck extends from the structure, surrounded by trees and open sky.

4.98 out of 5 average rating, 116 reviews

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!

4.94 out of 5 average rating, 1,229 reviews

A spacious bed is centered in the room, adorned with a light blue bedspread and vibrant throw pillows in orange and blue. Two bedside tables with lamps frame the bed, and colorful artwork decorates the wall above.

Apartment in Billings

Dusty’s Airbnb Studio-Pet Friendly

Welcome to your cozy and private studio in the heart of Billings! Upon entering through the shared front door, 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.

4.96 out of 5 average rating, 357 reviews

A cozy living space is presented with a light beige wall and an area rug featuring a geometric pattern. A gray sofa is paired with a green armchair, both adorned with decorative pillows. A small side table and lamp provide warm lighting, creating a relaxed atmosphere.

Apartment in Billings

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.

The sleeping area features a spacious bed adorned with a patterned blanket and decorative pillows. Sunlight filters in, highlighting the barn door leading to the bathroom. A kitchenette is visible in the background, showcasing essential appliances and kitchenware.