Vacation rentals in Shepherd

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Top-rated vacation rentals in Shepherd

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A welcoming living area is shown with a gray sofa and a wooden coffee table positioned on a textured rug. An open kitchen is partially visible, featuring modern appliances. A framed image of a bull adorns the wall, complementing the neutral color palette of the space.
Home in Billings
4.92 out of 5 average rating, 250 reviews

Private Modern 1 Bdr Home W/ Garage

This cozy private 1 Bedroom home has been remodeled for an Airbnb and has everything you may need for a long or short stay. There is a private garage with gated entry as well private parking . You will have everything in this home to yourself . There are all new appliance’s including a new 70inch smart tv in the living room and a smart tv bedroom with high speed internet for all your streaming needs. Comfortable new queen bed and all new furniture. Bathroom heater, living room additional heater.

Top guest favorite
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
4.97 out of 5 average rating, 120 reviews

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.

Top guest favorite
A modern tiny house is depicted with its natural wood exterior, featuring a welcoming covered entrance. A wooden deck extends into the landscape, adorned with outdoor seating and surrounded by trees, creating an inviting connection to nature.
Tiny home in Billings
4.99 out of 5 average rating, 206 reviews

Boho Bungalow @ Old Pine Retreats

If you can imagine a getaway in a uniquely designed tiny house that is built on 60+ acres of wide open and stunning landscape, then you have captured a glimpse of this rare find. This beautiful tiny house is all yours to enjoy such amenities as a glass garage door that can be opened to experience nature from your kitchen table or a fireplace to cozy up to when the temps are cold. You can enjoy coffee in the morning from your private deck and keep your feet warm in the winter with heated floors.

Top guest favorite
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 home in Billings
4.96 out of 5 average rating, 253 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.

Top guest favorite
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
5 out of 5 average rating, 249 reviews

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.

Guest favorite
A spacious living area is equipped with a large sectional sofa and various seating options. Natural light filters through the horizontal blinds covering the windows, illuminating the dark wooden floors. A round wooden table and white dining chairs complete the inviting space.
Home in Billings
4.91 out of 5 average rating, 392 reviews

Cheerful 2 bedroom Centrally Located

Keep it simple at this peaceful and centrally-located space. Less than a 10 minute drive to the hospital, colleges, downtown, airport and west end shopping and dining. On site parking for up to 3 cars, keypad entry, a large fenced backyard, a full kitchen and dining area, with a single bathtub and shower. Comfortable new furniture and beds. High speed internet for all your streaming needs. Within walking distance to two natural food stores, a coffee shop, and a handful of eateries and bars.

Top guest favorite
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
4.97 out of 5 average rating, 137 reviews

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!

Guest favorite
A relaxed living space is featured, showcasing a gray sectional couch adorned with patterned pillows. A small wooden table complements the area, alongside a lamp. Two windows with blinds allow natural light to filter in, highlighting the light green walls and decorative artwork.
Guest suite in Billings
4.76 out of 5 average rating, 164 reviews

Bench Executive Suite - perfect for the traveller!

This is an affordable rental that feels like home and not a generic hotel room! This smaller space accommodates a lot more than what may appear. It is perfect for couples, solo adventurers, and business travelers. In the past, traveling nurses and visitors at the hospital enjoyed this place due to its quick access to the hospital, avoiding any unnecessary traffic. The suite has a private entrance/exit for guests, a private bedroom with queen size bed, and a separate living space to relax.

Top guest favorite
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
4.94 out of 5 average rating, 1,252 reviews

Dusty’s Lower Level Studio

Upon entering through the shared front entryway door of my Townhouse, you'll find your separate entrance leading to your lower-level studio. Besides the top entryway door, there is also a door at the bottom of the stairs. 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.

Guest favorite
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
4.94 out of 5 average rating, 141 reviews

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!

Top guest favorite
A single-story house features a combination of stone and siding, with a two-car garage and a well-maintained front yard. A wrought iron fence surrounds the yard, and two chairs are positioned on the porch. The property is located on a quiet corner lot.
Guest suite in Billings
4.97 out of 5 average rating, 347 reviews

Much More Than a Suite & 2 miles from metra

Home away from home. NON SMOKERS ONLY! The space has a shared entrance that leads into a daylight downstairs, with a wet bars, includes, sink, microwave, toaster, small fridge, keurig, tea pot, and snacks. Enjoy the fireplace, leather furniture, netflix, comfortable queen bed, and a bathroom with soaps & hair products etc. I have tried to anticipate all of your needs. No unapproved guests, no hook-ups. I do live upstairs. NO ONE under 21. second bedroom available for a fee.

Top guest favorite
A vibrant living area features a large sectional sofa positioned in the corner, complemented by colorful decorative elements. The walls are painted in a rich purple, while a potted plant adds a touch of greenery. A warm light pendant creates a cozy ambiance in the room.
Home in Billings
4.95 out of 5 average rating, 366 reviews

Sweet Place for Traveler & Dog to Lay Their Head

This is a nonjudgmental scent free home with a Zen attitude in a modest neighborhood. You must read the additional rules before booking & answer the question in your opening message as well as including any guest coming with you. I am centrally located. Airport 8 min, Hospitals 5 min, Metra 7 min, a short walk to Downtown and easy access to freeway. I provide snacks, drinks, coffee, tea, oatmeal & fully stocked bathroom. No 3rd party bookings. No guest under 18 yrs of age

Popular amenities for Shepherd vacation rentals

  1. Airbnb
  2. United States
  3. Montana
  4. Yellowstone County
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