Vacation rentals in Shepherd

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Top-rated vacation rentals in Shepherd

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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, 189 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, 233 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, 236 reviews

Gail's Guest Suite by MetraPark Arena

CLEAN, COZY, drama free 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 features a dark sectional couch adorned with decorative pillows. A wooden tray with a potted plant sits on a woven coffee table. Natural light filters through large windows, illuminating the neutral-toned décor and modern kitchen in the background.

Apartment in Billings

4.96 out of 5 average rating, 100 reviews

New Luxury Apartment in Billings

Located in a family friendly neighborhood, you'll find Studio 201 on the second floor just a few doors down from a local coffee shop and around the corner from a new taproom. This home is equipped with a spacious kitchen to prepare meals, private work space, relaxing couch, king sized bed, and a balcony to catch the evening sunsets or sip your morning coffee. Guests can enjoy the nearby walking trails, Yellowstone River and easy access to the interstate, which quickly gets you anywhere in town.

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, 120 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!

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, 340 reviews

Much More Than a Suite & 2 miles from metra

CLEAN & PLUSH. Situated in a newer quiet neighborhood, 5 minutes from the metra, 10 minutes to medical & downtown Enjoy an actual kitchen area, wet bar with fridge, tea Coffee, toast, break- Feast goodies. Fireplace, leather furniture. New queen mattress. All bedding & bathroom rugs laundered after each guest. Additional bedroom at request, and fee. Non-smokers/vapors must be 21, NO hook Ups! No animals. Parking in driveway, (if no oil leaks) front porch to enjoy. Clean, clean, clean!

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

4.95 out of 5 average rating, 128 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 cozy sleeping area features a quilt adorned with wildlife motifs, complemented by decorative pillows. Warm wood paneling creates an inviting space, accompanied by soft lighting from mounted sconces. A framed nature-themed artwork enhances the rustic charm of the room.

Guesthouse in Park City

4.96 out of 5 average rating, 365 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.)

Guest favorite

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

4.93 out of 5 average rating, 231 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.

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, 1,233 reviews

Dusty’s Airbnb Studio-Pet Friendly

Welcome to your cozy and private studio in the heart of Billings! Upon entering through the shared front door, 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.

Top guest favorite

A cozy living space is presented with a light beige wall and an area rug featuring a geometric pattern. A gray sofa is paired with a green armchair, both adorned with decorative pillows. A small side table and lamp provide warm lighting, creating a relaxed atmosphere.

Apartment in Billings

4.96 out of 5 average rating, 376 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.