Vacation rentals 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.

Warm Woodland Retreat w/ 2 Bed 1 Bath

Tucked into the trees near the rims makes for a great place to make memories on a long weekend. Grill up your favorite food, play some corn hole, & top off the night with s'mores makes for a fun day. Walk to the rim tops for mountain views or downtown for more memory-making activities. This single-family home is within walking distance to local restaurants, coffee shops, museums, rim top trails, the hospital, & the airport. It's a great place to experience Billings and all the best adventures.

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!

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!

Montana Mansion (Theater, Gym, Arcade, Billiards)

Enjoy Big Sky Country in this spacious family home. Packed with amenities and close to Billings top attractions! 🎬 Theater Room w/ Full Surround Sound 🕹️ Game Room w/ Full Length Shuffleboard & Arcade Games 🏋️ Gym w/ Treadmill & Free Weights 🎱 Billiards Room 🍖 Traeger Grill w/ Outdoor Seating 🛏️ Premium Pillow Top Mattresses (4 King, 2 Queen, and 2 Full over Full Bunkbeds (4)) Location: 📍 7 min to Metra Park ✈️ 5 min to Billings Airport 🏥 10 min to Billings Clinic | St Vincent

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!

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.

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!

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.

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.

Garden Hideaway (HOT TUB!)

With craft coffee & a greenhouse downstairs, a private hot tub, & comfy memory foam mattresses, this is the best stay in Billings. Quiet & centrally located, this large & sunny one-of-a-kind home sleeps up to 8, with a clean and relaxing space to chill. Wake to fresh flowers, play ping pong, read about plants and trees, or wander the on-site greenhouse & garden, art gallery, and shop for local artisan crafts.