Vacation rentals in Shepherd

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Shepherd

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

An open living space features a sleek kitchen with a granite countertop and two bar stools. A large sectional sofa in dark leather faces a wall-mounted television, while warm wood tones enhance the inviting ambiance. Natural light is filtered through blinds on the windows.

Guesthouse in Billings

4.96 out of 5 average rating, 103 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 spacious wooden deck features a fire table at its center, surrounded by comfortable seating. Lush greenery and trees are visible in the background, providing a serene outdoor setting. A potted plant adds a touch of nature to the inviting space.

Tiny home in Billings

4.99 out of 5 average rating, 161 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

An open kitchen and living area is showcased, featuring a white refrigerator, gas stove, and a blue wall with shelves. A small table with two chairs is present, alongside a light-colored sofa and a coffee table. Natural light enters through nearby windows.

Tiny home in Billings

4.95 out of 5 average rating, 192 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.

Guest favorite

A charming single-story home is set amidst lush greenery, featuring a welcoming entrance with wooden steps leading to a screen door. The exterior showcases dark siding, surrounded by a well-maintained landscape of colorful bushes and stones, offering an inviting first impression.

Home in South Side

4.92 out of 5 average rating, 207 reviews

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!

Top guest favorite

The bathroom features a walk-in shower with a glass door and a modern vanity with a sink. Light fixtures provide illumination above the mirror. Soft bath mats are positioned on the floor, complementing the neutral color scheme of the space.

Guesthouse in Laurel

4.97 out of 5 average rating, 110 reviews

Private Studio Loft

Getaway to our peaceful and centrally-located studio in the heart of Laurel, Montana. Suite Gigi's is an adorable, 100% private, and fully furnished loft atop our detached garage (stairs, no elevator). Suite Gigi's is only 1.5 miles from Main Street with all the fun of downtown USA shopping & amenities. You will have your own keyless entry with private access to one of the garages for secure parking of your vehicle. This property is dog-friendly (max 40 lb) with bbq and outdoor patio seating.

Top guest favorite

A spacious property is presented with a well-maintained lawn and a flower garden featuring various blooming plants. The house features large windows, enhancing natural light, and a stone pathway is visible leading to the entrance, framed by lush greenery.

Guest suite in Billings

5 out of 5 average rating, 212 reviews

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.

Top guest favorite

A corner workspace features a wooden desk with vintage appeal. Above the desk, a framed black-and-white portrait of a horse captures attention. A small potted plant adds a touch of greenery, and a sleek lamp provides task lighting, enhancing the functional aesthetic.

Guesthouse in Billings

4.96 out of 5 average rating, 100 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

The exterior of a two-story building is shown, featuring dark grey siding and white trim. A front door with a small overhang is accessed by a few steps. Snow covers the ground, and a pathway leads along the side of the building, framed by a landscaped area.

Condo in Billings

4.96 out of 5 average rating, 113 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!

Guest favorite

A serene outdoor space features a rustic wooden fence enclosing a garden area. Lush greenery is visible, alongside a trellis lined with blooming flowers. A cozy wooden structure can be seen in the distance, surrounded by trees under an overcast sky.

Guesthouse in Park City

4.96 out of 5 average rating, 340 reviews

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.)

Top guest favorite

A bathroom vanity displays three matching soap dispensers positioned on a black metal rack. A sleek chrome faucet is visible at the sink, alongside a small box of tissues and paper towels. A mirror above the sink is framed by a row of soft, bright lights, enhancing the space.

Apartment in North Park

4.96 out of 5 average rating, 307 reviews

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.

Guest favorite

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.

Tiny home in Billings

4.9 out of 5 average rating, 692 reviews

★Adorable Tiny House near hospitals & breweries ★

This adorable Tiny House is located on the same property as the main house, but has all the amenities of a regular house. Stylishly decorated and cleverly appointed, you'll find you have everything you need for a comfortable stay in this unique space. Located within one mile of the hospital district and one mile from the brewery district, our place is perfectly situated for your convenience.

Top guest favorite

The exterior of a single-story home is showcased, featuring a brown façade and a flat roof. A well-maintained lawn extends in front, complemented by a flower garden with colorful pots. A driveway leads to a dark garage door, and a welcoming porch is adorned with seating.

Guest suite in Billings

4.96 out of 5 average rating, 239 reviews

Sunsets & City Lights

Sunsets and city lights await in this spacious guest suite that sleeps six. Quick access to I-90/I-94 interchanges. Enjoy two big bedrooms, a full private bathroom, desk with high speed internet, continental kitchenette and a large open living room with a leather sofa sleeper, comfortable sitting chairs, 65" smart TV, gas fireplace, dining table and an outdoor patio!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Shepherd vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Shepherd

Superhost

A deer stands amidst tall grass and trees, illuminated by sunlight filtering through the forest. The surrounding landscape features a mix of greenery and scattered underbrush, highlighting the wildlife habitat in a natural setting.

Cottage in Lavina

4.64 out of 5 average rating, 73 reviews

Big Sky Ranch Stay

ReneeRating, 5 stars9 months ago

We really enjoyed our stay. Was exactly as described. And perfect for what we needed. Directions were easy to understand and follow. Kurt was quick to respond to my questions. Sunrise was beautiful and we enjoyed watching the horses in the field.

Top guest favorite

A vivid rainbow arcs across the sky above a lush green field, with a solitary tree and an extensive wooden fence in the background. Soft sunlight illuminates the grass, while a stormy atmosphere is hinted at by visible lightning in the distance.

Home in Billings

4.94 out of 5 average rating, 62 reviews

Peaceful, Country Living. Modern Remodel (Hot Tub)

LisaRating, 5 stars1 week ago

The house was amazing. Super comfortable and cozy. Well stocked kitchen with everything we needed to cook meals. The best part for us was the outside space. The garden was beautiful and our pups had so much space to run and play. It was magical for our family. We cannot wait to come back! We have stayed at quite a few places and this was one of the best. We had the opportunity to meet the owners. Really enjoyed talking with them. They were very helpful and the communication was very much appreciated.

The exterior of the camper features a sleek design with light and dark grey finishes. An awning extends from the side, providing shade over the entrance. Steps lead up to the door, which opens to a cozy interior. Gravel surrounds the base of the camper.

Camper/RV in Billings

4.68 out of 5 average rating, 19 reviews

Creek View Camper

IngridRating, 5 stars5 days ago

Amazing host and beautiful setting!

Apartment in Billings

5 out of 5 average rating, 6 reviews

Modern 1BR • Great Stay Near Airport & Hospitals

EllieRating, 5 stars1 week ago

We really enjoyed our stay here! It was very clean and cute! Communication was great too! Would for sure stay here again!!

A compact living area is visible, featuring a sleek dining table with two stools positioned beneath a mounted television. A small window allows natural light, while air conditioning is provided below. Textured wood paneling creates a cozy ambiance throughout the space.

Tiny home in Worden

4.93 out of 5 average rating, 27 reviews

Burnt Cross Cabin

JessikaRating, 5 stars12 months ago

Our family of three loved this stay! Perfect for our short getaway and the space was versitile enough for adjusting to my toddlers sleeping habits. The kitchen had all the amenities to cook and clean up easily. Would definitely stay again if we return to the Billings area.

Guesthouse in Park City

4.89 out of 5 average rating, 56 reviews

Montana Ranch Guest House

ZoeRating, 5 stars1 month ago

Very spacious and peaceful, with magnificent view and cozy feel. Micheal is super helpful and very open. Overall just an amazing stay.

Superhost

A well-appointed bathroom features a clean white toilet next to a modern vanity with a light wood finish. The walls are adorned with textured gray tiles, and a framed landscape painting adds a decorative touch. Soft lighting enhances the inviting ambiance.

Apartment in North Park

4.89 out of 5 average rating, 19 reviews

#18 The Narrow One

MadyRating, 5 stars1 week ago

David was by far the kindest and most accommodating host we have ever had. His place went above and beyond all expectations. The apartment was in immaculate condition when we arrived. We were so impressed by the high quality appliances, a super comfortable bed and a stunning renovated bathroom. David hosted us for a very long stay and stayed in touch with us the entire time helping out with anything we needed. I highly recommend staying at any of David‘s properties to anyone travelling through Billings. His properties are one of a kind.

Guest favorite

Guesthouse in Pioneer Park

4.9 out of 5 average rating, 29 reviews

The Modern Midtown Tiny

AsiaRating, 5 stars1 day ago

Very clean and comfortable tiny home. Everything looks as pictured and the host was extremely helpful and responsive. Everything is so modern down to the tankless water heater. Provided a list of to do’s and the proactiveness on all steps of your stay. Close to BIL (10 minutes) this is the perfect peaceful place to enjoy your vacation.

Show all

Vacation rentals in Shepherd

Top-rated vacation rentals in Shepherd

Vacation rentals for every style

Popular amenities for Shepherd vacation rentals

Other great vacation rentals in Shepherd

Destinations to explore