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

Holiday Rentals in Shepherd

Cozy, Stylish 2-Bedroom Retreat in Prime Location – Walk to Shops & Dining!
2.0 star property
The price is AU$206
includes taxes & fees
20 Oct - 21 Oct
Cozy, Stylish 2-Bedroom Retreat in Prime Location – Walk to Shops & Dining!
Antique Charm by Hospital and Parks
2.0 star property
The price is AU$490
includes taxes & fees
20 Oct - 21 Oct
Antique Charm by Hospital and Parks
Quaint Cottage @ Fort Nibbe
2.0 star property
9.8 out of 10, Exceptional, (16)
"The cottage is awesome, ended up staying 2 extra nights. The cottage is completely furnished. Will highly recommend, and like to come back again."
United States
charles
The price is AU$203
includes taxes & fees
20 Oct - 21 Oct
Quaint Cottage @ Fort Nibbe
Relaxing, cozy and comfortable
9.8 out of 10, Exceptional, (18)
"This place is a hidden gem. Totally cute and immaculate. We enjoyed sitting on the porch and watching a storm roll in."
United States
Robert
The price is AU$203
includes taxes & fees
20 Oct - 21 Oct
Relaxing, cozy and comfortable
Restored Vintage Mobile Home on our small Private Ranch
9.0 out of 10, Wonderful, (8)
"Perfect lodging for our trip. Kurt was very responsive and hospitable. We will certainly be back on future trips to the area."
United States
Jake D.
The price is AU$269
includes taxes & fees
23 Oct - 24 Oct
Restored Vintage Mobile Home on our small Private Ranch
Cozy cabin - pet friendly
The price is AU$203
includes taxes & fees
21 Oct - 22 Oct
Cozy cabin - pet friendly
*New* Montana Dreamin’ Home
9.6 out of 10, Exceptional, (27)
"Nice little home to stay in! Clean, crisp look."
United States
Melissa S.
The price is AU$355
includes taxes & fees
20 Oct - 21 Oct
*New* Montana Dreamin’ Home
Bo’s Bungalow with Hot Tub and Sauna
9.6 out of 10, Exceptional, (11)
"Was perfect for our 2 day stay in Billings!"
United States
Tiffany G.
The price is AU$294
includes taxes & fees
22 Oct - 23 Oct
Bo’s Bungalow with Hot Tub and Sauna
Barb’s Cozy Home with Office and Covered Parking!
2.0 star property
9.6 out of 10, Exceptional, (19)
"Awesome and management. Would gladly stay there again. "
United States
Rodney H.
The price is AU$331
includes taxes & fees
20 Oct - 21 Oct
Barb’s Cozy Home with Office and Covered Parking!
Industrial Loft @ Old Pine Retreats
10.0 out of 10, Exceptional, (8)
"We had a great time at the Industrial Loft! Beautiful, cozy, and well appointed house situated in a quiet area with beautiful views on the surroundings. We had nice walks from the house and a very pleasant stay. We look forward to coming back!"
United States
Caroline B.
The price is AU$401
includes taxes & fees
20 Oct - 21 Oct
Industrial Loft @ Old Pine Retreats
Triangular Casa in Billings
9.6 out of 10, Exceptional, (100)
"This property was nicely furnished, clean and well maintained…the beds were comfortable too…also easy to access, thanks. And close to lots of shopping areas. We enjoyed a leisurely breakfast and then went about our day with the knowledge of a comfortable stay at the end of our day."
United States
Laura
The price is AU$258
includes taxes & fees
24 Oct - 25 Oct
Triangular Casa in Billings
Farmhouse Cottage @ Old Pine Retreats, Farmhouse Cottage @ Old Pine Retreats
10.0 out of 10, Exceptional, (12)
"Place was wonderful. It was clean had everything needed and amazing views. Hosts were kind enough to let us check in a little early and were very kind. "
United States
Emma C.
The price is AU$401
includes taxes & fees
22 Oct - 23 Oct
Farmhouse Cottage @ Old Pine Retreats, Farmhouse Cottage @ Old Pine Retreats
Bo’s Old West Abode with Hot Tub and Sauna
8.4 out of 10, Very good, (16)
"Great place and responsive owner. Love the hot tub."
United States
c h.
The price is AU$308
includes taxes & fees
26 Oct - 27 Oct
Bo’s Old West Abode with Hot Tub and Sauna
Rims view pet friendly home
9.6 out of 10, Exceptional, (54)
"Great place "
United States
Frank N.
The price is AU$314
includes taxes & fees
23 Oct - 24 Oct
Rims view pet friendly home
Come and stay at Emerald Cottage, your mini home away from home.
9.0 out of 10, Wonderful, (39)
"Owners were very responsive. Neighorhood super quiet. Easy to get to places."
United States
Carl T.
The price is AU$304
includes taxes & fees
20 Oct - 21 Oct
Come and stay at Emerald Cottage, your mini home away from home.
Modern townhome minutes from Billings' best shopping, family friendly community!
10.0 out of 10, Exceptional, (37)
"This VRBO was absolutely beautiful! It was close to shopping and was within walking distance of a great little coffee spot, The Maple Moose. The place had everything you need! Check-in and out was a breeze! We will definitely stay here again! "
United States
kim i.
Modern townhome minutes from Billings' best shopping, family friendly community!
Big Sky Retreat
10.0 out of 10, Exceptional, (14)
"Nice central location. Super comfy beds and nice updates in the house."
United States
Blake S.
The price is AU$483
includes taxes & fees
22 Oct - 23 Oct
Big Sky Retreat
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
9.2 out of 10, Wonderful, (12)
"Great home, with fenced yard and hot tub! Very clean and comfy! Thank you so much for a lovely stay."
United States
Stephanie H.
The price is AU$430
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Bo's Rusty Relic Billings |Hot Tub | Rustic decor | Central Billings
9.6 out of 10, Exceptional, (40)
"I enjoyed staying at this property. It was clean and comfortable. It was nice to have the hot tub, which was also kept clean and worked well. The location is close to downtown and hospitals. The neighborhood is lots of older homes with some of them in good condition and some of them pretty rundown. "
United States
amy t.
The price is AU$353
includes taxes & fees
20 Oct - 21 Oct
Bo's Rusty Relic Billings |Hot Tub | Rustic decor | Central Billings
Luxury Living Next Door to Hospital
2.0 star property
10.0 out of 10, Exceptional, (3)
"Great little place to stay."
United States
Allison N.
The price is AU$529
includes taxes & fees
22 Oct - 23 Oct
Luxury Living Next Door to Hospital
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 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?

Triangular Casa in Billings: This holiday home rental outside of Shepherd offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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.