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, 193 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 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, 239 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.

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, 124 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, 132 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 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, 355 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

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, 370 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 single-story tiny home is shown with a welcoming green door and a front porch featuring a bench. Light-colored siding is complemented by large windows that offer views of the surrounding landscape, consisting of gentle hills and trees.

Tiny home in Billings

4.97 out of 5 average rating, 286 reviews

*NEW BUILD* Mini Mountain View Getaway

Mini Mountain View Retreat is a great weekend get away. Just a short walk to downtown, the hospitals, or a view of the Beartooth Mountains. This tiny home makes for a relaxing stay with everything you need and a peaceful and homey atmosphere. Just because it's tiny doesn't mean it isn't full of all your basic home essentials such as a full kitchen, washer and dryer and luxurious features. This shared property is tucked away in a quiet and peaceful neighborhood.

Superhost

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

4.91 out of 5 average rating, 238 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, 1,236 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, 389 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.

Top guest favorite

An outdoor deck area features a comfortable seating arrangement with several chairs and a sofa, accompanied by a decorative table. Colorful cushions enhance the seating, and a patterned rug lies beneath. Lush greenery and a serene landscape are visible in the background, contributing to a relaxing ambiance.

Home in Billings

4.94 out of 5 average rating, 101 reviews

Peace in the city

Relax at this tranquil upper unit getaway, surrounded by calming waters and abundant wildlife. Just 5 minutes from the airport and MetraPark, it’s nestled in a quiet, private neighborhood close to downtown Billings, local restaurants, and walking/biking trails. Guests love how it feels tucked away yet near all the amenities. The cozy basement unit is also available for booking.