Holiday 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.

Location · Family · Check-in

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.

Family · Location · Sleep quality

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!

Family · Value · Sleep quality

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.

Family · Location · Decor

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.

Family · Location · Hospitality

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!

Value · Location · Hot tub

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.

Value · Family · Condition

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.

Location · Value · Hospitality

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.

Value · Location · Condition

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.

Value · Location · EV charging

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.

Value · Family · Quiet

Broadwater house

Newly remodeled 2 bedroom down town home located 2.9 miles from the airport. 6 minutes from Billings Hospitals. 5.3 miles from I-90. Enterprise is located next door for your convenience. NaRa Oriental restaurant, Holliday gas station, and Central High School are all just a short walk away. Easy access to some great spots nearby! This property is located on a busy street, which may result in street noise.

Family · Location · Walkability