Shepherd holiday rentals

We found 20 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Shepherd that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include parking and a fireplace. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Shepherd getaway

Learn about the unique charm of Shepherd with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Shepherd

Are you hoping to discover attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Shepherd a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Reef Indoor Water Park (19.1 mi / 30.8 km)
  • ZooMontana (19.9 mi / 32.1 km)
  • Four Dances Recreation Area (13.2 mi / 21.3 km)

Exploring the natural features in Shepherd

Whether you're an active traveller or just want to spend some time taking in the scenery, Shepherd is a great spot to appreciate mother nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Lake Elmo State Park (9.9 mi / 15.9 km)
  • Pompeys Pillar National Monument (16.7 mi / 26.8 km)
  • Sacrifice Cliff (13 mi / 20.9 km)
  • Pioneer Park (13.9 mi / 22.3 km)
  • Pictograph Cave State Park (14.9 mi / 24.1 km)
  • The Rimrocks (15.4 mi / 24.8 km)

Transport to and around Shepherd

The nearest airport is in Billings, MT (BIL-Logan Intl.), located 13.5 mi (21.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Shepherd when booking a holiday rental?
When considering a holiday rental in Shepherd, Montana, the area around the town centre is particularly appealing. This neighbourhood not only offers a selection of charming properties, but it also allows easy access to some of the region's key attractions. One of the highlights is the stunning Yellowstone River, which provides opportunities for fishing, kayaking, and enjoying picturesque views. Additionally, the nearby Pictograph Cave State Park offers a fascinating glimpse into the area's prehistoric past with its ancient rock art and scenic hiking trails. Staying in this central area not only places you close to these attractions but also makes it convenient to explore the surrounding natural beauty and local culture.
What is the most popular type of holiday rental accomodation in Shepherd?
In Shepherd, cabins are the most popular type of holiday rental accommodation, with several available in the area. These cabins typically provide a rustic yet comfortable atmosphere, ideal for those looking to immerse themselves in the beautiful natural surroundings. Most cabins come equipped with amenities such as fully stocked kitchens, cozy living areas, and often outdoor spaces like porches or decks for enjoying the fresh air. This makes them a great choice for families or groups seeking a peaceful retreat while being close to outdoor activities and local attractions.
Are there any family house rentals in Shepherd?
In Shepherd, Montana, there are several family-friendly house rentals available. This charming community offers a variety of homes that cater to families, providing ample space for relaxation and activities. Many properties feature well-equipped kitchens, inviting living areas, and outdoor spaces great for children to play and explore.Visitors can enjoy the scenic beauty of the surrounding landscape, with opportunities for outdoor adventures such as hiking, fishing, and exploring local parks. The proximity to Billings also allows for easy access to additional amenities, including shopping, dining, and cultural attractions.
Are there any remote work holiday rentals in Shepherd?
In Shepherd, Montana, there are several remote work holiday rentals available for those looking to combine work and leisure. Many of these properties feature essential amenities such as complimentary Wi-Fi, ensuring a reliable internet connection for remote working. Travellers can expect comfortable living spaces equipped with desks or dedicated work areas, allowing for productivity while enjoying the tranquil surroundings of this charming town.The area itself offers a peaceful atmosphere, great for those seeking a quiet retreat. With its proximity to outdoor activities, such as hiking and fishing, you can easily take breaks to enjoy the natural beauty that Montana has to offer. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Shepherd?
In Shepherd, Montana, popular holiday rental amenities include air conditioning, kitchens equipped for self-catering, and coffee and tea makers for a convenient start to the day. Many rentals also feature sofa beds, providing additional sleeping space for guests. Additionally, the picturesque mountain setting enhances the overall experience, allowing visitors to enjoy the stunning natural surroundings right from their accommodations.
What are the top attractions in Shepherd?
In Shepherd, Montana, visitors can enjoy a taste of the region's natural beauty and local culture. A popular attraction is the nearby Yellowstone River, which provides opportunities for fishing, boating, and scenic walks along the riverbanks. The area is rich in outdoor activities, including hiking and wildlife viewing, especially in the surrounding landscapes that showcase the stunning Montana scenery.For those interested in history, the town is close to the historical sites in Billings, which is just a short drive away. Billings offers cultural attractions like the Yellowstone Art Museum and the Western Heritage Centre, along with various dining and shopping options.Moreover, the proximity to the Beartooth Mountains makes Shepherd a great base for those looking to explore the majestic mountain ranges, with numerous trails for hiking and breathtaking views.
Are all fees included in the Shepherd holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Shepherd holiday homes with parking?
Stayz offers a wide selection of holiday homes in Shepherd with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Shepherd holiday homes?
You can find great discounts on holiday homes in Shepherd on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Shepherd holiday home booking on Stayz?
To find Shepherd holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Shepherd?
A long-stay holiday home in Shepherd is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Shepherd holiday home?
Book your Shepherd holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Shepherd?
Prices for holiday homes in Shepherd vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Shepherd to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas