Shepherd Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Shepherd vacation rentals

Interior

Relaxing, cozy and comfortable

Relaxing, cozy and comfortable
Worden
9.8 out of 10, Exceptional, (18 reviews)
"Great place!"
United States
Julie C.
The price is ￥12,011
￥18,907 total
includes taxes & fees
May 8 - May 9
Relaxing, cozy and comfortable
Smart TV

Triangular Casa in Billings

Triangular Casa in Billings
Central - Terry
9.6 out of 10, Exceptional, (119 reviews)
"Good location with access to Billings"
United States
Jesse W.
The price is ￥11,729
￥23,690 total
includes taxes & fees
May 7 - May 8
Triangular Casa in Billings
Terrace/patio

Boho Bungalow @ Old Pine Retreats

Boho Bungalow @ Old Pine Retreats
Billings
9.8 out of 10, Exceptional, (24 reviews)
"Absolute gem, after 5 days on the road sight seeing this was the perfect spot to relax for a couple days."
United States
Mike W.
The price is ￥18,959
￥36,214 total
includes taxes & fees
May 10 - May 11
Boho Bungalow @ Old Pine Retreats
Interior

Rims view pet friendly home

Rims view pet friendly home
Rimrock
9.4 out of 10, Exceptional, (73 reviews)
"Host was very quick to respond to messages, the third time we have stayed here and it always good!"
United States
Tonya B.
The price is ￥17,664
￥36,204 total
includes taxes & fees
May 8 - May 9
Rims view pet friendly home
TV

Bo’s Urban Farm House.

Bo’s Urban Farm House.
Central - Terry
9.4 out of 10, Exceptional, (18 reviews)
"This was a great place to stay. "
United States
Christina W.
The price is ￥15,544
￥34,423 total
includes taxes & fees
May 4 - May 5
Bo’s Urban Farm House.
Exterior

Quiet 2BR w/ Backyard, Cozy Home and Covered Parking

Quiet 2BR w/ Backyard, Cozy Home and Covered Parking
Central - Terry
9.4 out of 10, Exceptional, (22 reviews)
"Great value for the price on a quick trip to Billings."
United States
Tim K.
The price is ￥18,113
￥36,858 total
includes taxes & fees
May 11 - May 12
Quiet 2BR w/ Backyard, Cozy Home and Covered Parking
Outdoor dining

Farmhouse Cottage @ Old Pine Retreats

Farmhouse Cottage @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (13 reviews)
"So charming and nicely decorated! Wonderful deck areas quiet area. Would definitely recommend and will be back!"
United States
Jessica L.
The price is ￥22,586
￥42,996 total
includes taxes & fees
Jun 1 - Jun 2
Farmhouse Cottage @ Old Pine Retreats
Terrace/patio

Bo’s Old West Abode with Hot Tub and Sauna

Bo’s Old West Abode with Hot Tub and Sauna
Central - Terry
8.6 out of 10, Excellent, (20 reviews)
"Host friendly and responsive to questions."
United States
Caleb M.
The price is ￥15,363
￥33,380 total
includes taxes & fees
May 4 - May 5
Bo’s Old West Abode with Hot Tub and Sauna
Exterior

Industrial Loft @ Old Pine Retreats

Industrial Loft @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (10 reviews)
"Awesome place with everything you need. Very clean. Highly recommend!"
United States
Matt C.
The price is ￥23,410
￥44,394 total
includes taxes & fees
May 19 - May 20
Industrial Loft @ Old Pine Retreats
Terrace/patio

*New* Montana Dreamin’ Home

*New* Montana Dreamin’ Home
Billings
9.6 out of 10, Exceptional, (30 reviews)
"We loved it here!! Very clean and inviting! "
United States
amanda b.
The price is ￥26,849
￥45,784 total
includes taxes & fees
May 15 - May 16
*New* Montana Dreamin’ Home
TV

Custer Cottage / Fenced Yard

Custer Cottage / Fenced Yard
Midtown
10.0 out of 10, Exceptional, (24 reviews)
"Nice place to stay for the night"
United States
Kalee E.
The price is ￥26,692
￥46,124 total
includes taxes & fees
May 4 - May 5
Custer Cottage / Fenced Yard
Fridge, microwave, oven, stovetop

Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings

Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Billings
9.2 out of 10, Wonderful, (19 reviews)
"Beautiful place!!! Host was wonderful and I would LOVE to stay there again in the future!!"
United States
Laura
The price is ￥18,370
￥34,253 total
includes taxes & fees
May 8 - May 9
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Outdoor spa tub

Rustic Cottage Cozy & Charming

Rustic Cottage Cozy & Charming
Central - Terry
9.4 out of 10, Exceptional, (70 reviews)
"Clean and plenty of kitchen amenities. Comfortable beds and easiest host I have ever worked with."
United States
Susan J.
The price is ￥22,479
￥45,982 total
includes taxes & fees
May 4 - May 5
Rustic Cottage Cozy & Charming
Fridge, microwave, oven, stovetop

Modern townhome minutes from Billings' best shopping, family friendly community!

Modern townhome minutes from Billings' best shopping, family friendly community!
Billings
10.0 out of 10, Exceptional, (38 reviews)
"Very nice property..comfortable "
United States
Juli L.
Modern townhome minutes from Billings' best shopping, family friendly community!
Terrace/patio

Bo's Old West Landing w/Hot Tub and Sunrise Views

Bo's Old West Landing w/Hot Tub and Sunrise Views
Central - Terry
9.6 out of 10, Exceptional, (27 reviews)
"This was the perfect place for our family. "
United States
Aaron J.
The price is ￥20,097
￥40,018 total
includes taxes & fees
May 4 - May 5
Bo's Old West Landing w/Hot Tub and Sunrise Views
Smart TV, DVD player, video library

Lovely 4-bedroom house in Lockwood with large yard and covered patio!

Lovely 4-bedroom house in Lockwood with large yard and covered patio!
Billings
9.6 out of 10, Exceptional, (5 reviews)
"House was perfect for our group. Beds were comfortable. Communication from property manager was accurate and on point."
United States
Amber R.
The price is ￥28,262
￥34,932 total
includes taxes & fees
May 5 - May 6
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
Interior

Townhome • Hospital District • King Bed + Garage

Townhome • Hospital District • King Bed + Garage
Central - Terry
9.8 out of 10, Exceptional, (7 reviews)
"The property was very clean and quiet and very well stocked with plenty of cleaning supplies kitchen utensils and necessities. Very Pet friendly, easy off street parking attached garage. Warm and welcoming."
United States
Carmela H.
The price is ￥14,131
￥38,832 total
includes taxes & fees
May 6 - May 7
Townhome • Hospital District • King Bed + Garage
Smart TV, fireplace

Bo`s Private 1BR Guesthouse Retreat | Hot Tub • Sauna • Gym

Bo`s Private 1BR Guesthouse Retreat | Hot Tub • Sauna • Gym
Central - Terry
10.0 out of 10, Exceptional, (15 reviews)
"Great location in Billings. Adorable home, tiny but much better than hotel options. "
United States
Melani V.
The price is ￥16,172
￥32,388 total
includes taxes & fees
May 7 - May 8
Bo`s Private 1BR Guesthouse Retreat | Hot Tub • Sauna • Gym
Fridge, microwave, oven, stovetop

Charming 3-bedroom townhome in Billings

Charming 3-bedroom townhome in Billings
Billings
10.0 out of 10, Exceptional, (17 reviews)
"Nice place. As described. "
United States
Russ M.
The price is ￥20,772
￥44,647 total
includes taxes & fees
May 4 - May 5
Charming 3-bedroom townhome in Billings
Exterior

Parkhill Bungalow • Pioneer Park

Parkhill Bungalow • Pioneer Park
Midtown
9.6 out of 10, Exceptional, (4 reviews)
"Veey nice property "
United Kingdom
Juli L.
The price is ￥15,544
￥48,328 total
includes taxes & fees
May 17 - May 18
Parkhill Bungalow • Pioneer Park
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shepherd Hotel Reviews

avid Hotels Billings West by IHG

avid Hotels Billings West by IHG

10/10 Excellent
"Breakfast good. Clean"
Scott 3-night trip
Posted 2 hours ago
avid Hotels Billings West by IHG

Find out more about Shepherd

Search for holiday rentals in Shepherd on Expedia! You can easily find your home rentals, villas, holiday apartments in Shepherd using one of the methods below:

  • View our selection of featured holiday rentals in Shepherd
  • Use the map to find apartments and other holiday homes in the Shepherd neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shepherd while they last

Look no further and take a look at our great range of rental properties in Shepherd!

Frequently asked questions

Can I find a vacation rental in Shepherd?

Yes, we have vacation rentals near top sights in Shepherd, or you can go with a more secluded option if you're looking for relaxation.

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

Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings: This vacation home rental near 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 the hot tub 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 larger area, you’ll find Lake Elmo State Park and First Interstate Arena at MetraPark.

What are vacation rentals like in Shepherd?

Vacation rentals are privately owned properties you can book for several days or more in Shepherd. Vacation rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for family trips or small group gatherings.