Vacation rentals in Shepherd

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Top-rated vacation rentals in Shepherd

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Top guest favourite

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.

Tiny homes in Billings

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.

4.97 out of 5 average rating, 314 reviews

Top guest favourite

Home in Billings

Billings Cottage

Welcome to The Billings Cottage. A cozy retreat within walking distance to a Coffee Shop and a Pizza/Bar. Designed for comfort and convenience, this charming Montana home is the perfect base for your Big Sky adventures. With 3 Bedrooms & 2 baths. It sleeps up to 6 adults. With an additional child's mattress if needed. Whether you’re here to ski in Red Lodge, explore Yellowstone, visit Cody, Wyoming, Devils Tower or plan a scenic drive to Glacier NP. This home puts you in the heart of it all.

5.0 out of 5 average rating, 108 reviews

Top guest favourite

Home in Billings Heights

Lake Hills Luxury

Bring the whole family to this great place with lots of room for fun. This home offers so much for the Entire family, from adults to kids. You can relax out back on the fully covered and furnished patio with a large yard or hang out in the lower level that has plenty of space for family fun and relaxation. Best yet, this home is 1 block from Lake Hills Golf Course! A golfer's paradise! This home is near so many outdoor activities including walking trails, Lake Elmo state park, and the Rims!

4.96 out of 5 average rating, 25 reviews

Top guest favourite

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 Heights

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!

4.96 out of 5 average rating, 182 reviews

Top guest favourite

Home in Billings

CozyLiving

Enjoy the entire home to yourself with a beautiful outdoor space to relax in, without compromising on location. This house is perfectly located in the heart of Billings, just walking distance from the mall, groceries, restaurants, a park, and a par 3 golf course. ✓ Fully equipped kitchen ✓ King size bed ✓ Playground ✓ 31" Outdoor gas fire pit with adirondack and rocking chairs ✓ Traeger pellet grill ✓ Huge deck ✓ Outdoor couches and tables ✓ Board games ✓ Toys for small

4.98 out of 5 average rating, 162 reviews

Top guest favourite

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.

Tiny homes in Billings

*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.

4.97 out of 5 average rating, 368 reviews

Guest favourite

The living area features a modern sofa with neutral upholstery, complemented by a cozy throw. Two artwork pieces are displayed on the wall. A wooden coffee table sits in front of the sofa, accompanied by a floor lamp and a decorative plant in the corner.

Home in Billings

Montana Modern Home

This is a family-friendly home. We made sure to include all of our favorite touches that we look for when we travel. 1) Great Sleep! We got brand-new Tuft & Needle mattresses, comfy pillows, luxurious bedding, and darkening shades. 2) Amazing Coffee. We got you a Nespresso and a Keurig with K Cups. We will provide a few options, but bring your favs if you have them! 3) Professionally Decorated. We think you will love all the Montana Modern special touches.

4.9 out of 5 average rating, 569 reviews

Top guest favourite

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.

Tiny homes in Billings

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!

4.99 out of 5 average rating, 201 reviews

Guest favourite

A spacious family room features a large sectional sofa with a modern design, complemented by a soft throw blanket. A mounted flat-screen TV is above a decorative fireplace. Adjacent, a dining area with wooden chairs and a table is partially visible, leading to sliding glass doors allowing natural light.

Home in Billings Heights

Tranquil 5 bedroom home with large deck and yard

Come relax and unwind in this large home in a quiet Billings neighborhood. Perfectly situated for a family or gathering with open family room and fully stocked kitchen. Main floor has 3 bedrooms and 2 baths. Downstairs hosts a large den with 2 bedrooms, 1 bath, full laundy and a bonus study. Smart TVs throught the house. Dining room opens to a large deck with seating, BBQ and fenced yard. Mature trees provide shade and privacy.

4.93 out of 5 average rating, 124 reviews

Guest favourite

A rustic interior is displayed, featuring a spacious bed adorned with a patterned bedspread. Natural wood paneling lines the walls, enhancing the cabin's character. A ladder leads to a loft area, while a wooden dresser and rocking chairs provide additional seating. Natural light filters through the door and windows.

Cabin in Huntley

Buffalo 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.

5.0 out of 5 average rating, 7 reviews

Top guest favourite

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.

4.96 out of 5 average rating, 568 reviews

Top guest favourite

Apartment in Billings Heights

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.

4.94 out of 5 average rating, 1319 reviews