Shepherd Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Shepherd holiday rentals

Holiday Home in Rimrock

Rims view pet friendly home
9.6 out of 10, Exceptional, (57)
"Very clean awesome stay!"
United States
Jessie S.
The price is AU$281
includes taxes & fees
15 Dec - 16 Dec
Rims view pet friendly home
10.0 out of 10, Exceptional, (26)
"Was clean and great set up!"
United States
Shawn W.
The price is AU$675
includes taxes & fees
14 Dec - 15 Dec
Enjoy the hot tub and gas fire pit in this 5 bedroom 2.5 bath house
10.0 out of 10, Exceptional, (45)
"We really enjoyed the spaciousness of the home and the cozy environment you have created. It was perfect for our stay needs and you were so accommodating. "
United States
Vickie G.
Pets & Kids Love this Montana Dream Home!

Holiday Home in Central - Terry

Triangular Casa in Billings
9.6 out of 10, Exceptional, (108)
"Wonderful little house. Very comforting and close to everything "
United States
jack k.
The price is AU$215
includes taxes & fees
16 Dec - 17 Dec
Triangular Casa in Billings

Cottage in Billings

Custer Cottage / Fenced Yard
9.8 out of 10, Exceptional, (17)
"Very nice home in a good location."
United States
Charles P.
The price is AU$435
includes taxes & fees
7 Jan - 8 Jan 2026
Custer Cottage / Fenced Yard

Holiday Home in Billings

Modern West-End Haven
9.6 out of 10, Exceptional, (68)
"Great stay. "
United States
Kris K.
Modern West-End Haven
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great nice place to stay"
United States
Samuel David
Charming Montana Home w/ Grill: 6 Mi to Lake Elmo!
10.0 out of 10, Exceptional, (44)
"We had a wonderful stay and it was really close to the airport. "
United States
Krystal F.
Tranquil 5 bedroom home with large deck and yard
2.0 star property
9.4 out of 10, Exceptional, (21)
"Great value for the price on a quick trip to Billings."
United States
Tim K.
The price is AU$324
includes taxes & fees
14 Dec - 15 Dec
Quiet 2BR w/ Backyard, Cozy Home and Covered Parking
10.0 out of 10, Exceptional, (21)
"Nice and cozy place to stay in! "
United States
Jose G.
The price is AU$375
includes taxes & fees
16 Dec - 17 Dec
Bo's Old West Landing w/Hot Tub and Sunrise Views
3.0 star property
10.0 out of 10, Exceptional, (1)
"A very nice aroma inside , very clean bathroom & kitchen"
United States
Samuel David
Billings Abode w/ Grill: Walk to Park & Shops

Holiday Home in Central - Terry

Bo’s Urban Farm House.
9.4 out of 10, Exceptional, (18)
"This was a great place to stay. "
United States
Christina W.
Bo’s Urban Farm House.
3.0 star property
6 Mi to Zoomontana: Family Home w/ Fenced Yard
3.0 star property
8.0 out of 10, Very good, (6)
"Perfect location and easy everything."
United States
Ewan
Wfh-friendly Billings Apt ~ 1 Mi to Downtown!
2.0 star property
9.2 out of 10, Wonderful, (12)
"Wonderful large home that everyone enjoyed, very accommodating and clean. "
United States
Joseph C.
The price is AU$593
includes taxes & fees
14 Dec - 15 Dec
Montana Mansion: Theater, Gym, Arcade, Billiards
10.0 out of 10, Exceptional, (48)
"Very nice stay . "
United States
Lori K.
The price is AU$491
includes taxes & fees
12 Jan - 13 Jan 2026
Centrally located, huge shaded patio with hot tub! Entire place to yourself!

Holiday Home in Central - Terry

Bo’s Bungalow with Hot Tub and Sauna
9.6 out of 10, Exceptional, (13)
"Was perfect for our 2 day stay in Billings!"
United States
Tiffany G.
The price is AU$290
includes taxes & fees
14 Dec - 15 Dec
Bo’s Bungalow with Hot Tub and Sauna

Holiday Home in Central - Terry

Bo’s White House with Fenced Yard
9.6 out of 10, Exceptional, (24)
"Comfortable and welcoming, we enjoyed our stay!"
United States
Jim P.
The price is AU$412
includes taxes & fees
13 Dec - 14 Dec
Bo’s White House with Fenced Yard
10.0 out of 10, Exceptional, (30)
"Absolutely amazing views!! Beautiful house and great host!! Thank you!"
United States
lala w.
Yellowstone Valley Overlook - 10 acres 5 minutes from Billings
8.6 out of 10, Excellent, (17)
"Great place and responsive owner. Love the hot tub."
United States
c h.
The price is AU$316
includes taxes & fees
20 Dec - 21 Dec
Bo’s Old West Abode with Hot Tub and Sauna
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Shepherd Hotel Reviews

Find out more about Shepherd

Everything you need to know about Shepherd holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherd holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shepherd holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Shepherd holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shepherd. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shepherd holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shepherd holiday rentals we have selected for you start as low as AU$215 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Shepherd rentals

At Expedia, we put the best Shepherd holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shepherd rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shepherd holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shepherd. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Shepherd?

Yes, there are holiday rentals close to the most popular sights in Shepherd, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Shepherd has to offer?

Rims view pet friendly home : This holiday home rental outside of Shepherd offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Shepherd?

While exploring the area, visit family-friendly sights like Reef Indoor Water Park, or get outside and enjoy nature at Yellowstone River. In the wider area, you’ll find Lake Elmo State Park and MetraPark.

What are holiday rentals like in Shepherd?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shepherd. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for families.