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Shepherd Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Shepherd vacation rentals

Interior

A clean, comfortable space just off the interstate with easy parking.

A clean, comfortable space just off the interstate with easy parking.
Worden
9.8 out of 10, Exceptional, (20 reviews)
"Great place!"
United States
Julie C.
The price is AED 350
AED 517 total
includes taxes & fees
5 Jul - 6 Jul
A clean, comfortable space just off the interstate with easy parking.
Terrace/patio

Cozy 2 bedroom cabin! Country charm with comfort and scenery!

Cozy 2 bedroom cabin! Country charm with comfort and scenery!
Ballantine
The price is AED 506
AED 626 total
includes taxes & fees
28 Jun - 29 Jun
Cozy 2 bedroom cabin! Country charm with comfort and scenery!
Smart TV

Triangular Casa in Billings

Triangular Casa in Billings
Central - Terry
9.6 out of 10, Exceptional, (124 reviews)
"This is a really neat place in billings that is fairly close to downtown."
United States
Anthony C.
The price is AED 370
AED 725 total
includes taxes & fees
23 Jun - 24 Jun
Triangular Casa in Billings
Terrace/patio

Boho Bungalow @ Old Pine Retreats

Boho Bungalow @ Old Pine Retreats
Billings
9.8 out of 10, Exceptional, (26 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 AED 444
AED 847 total
includes taxes & fees
23 Jun - 24 Jun
Boho Bungalow @ Old Pine Retreats
Terrace/patio

Bo’s Bungalow with Hot Tub and Sauna

Bo’s Bungalow with Hot Tub and Sauna
Central - Terry
9.8 out of 10, Exceptional, (17 reviews)
"Host reached out on took good care of us."
United States
Greg I.
The price is AED 359
AED 753 total
includes taxes & fees
23 Jun - 24 Jun
Bo’s Bungalow with Hot Tub and Sauna
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
9.4 out of 10, Exceptional, (23 reviews)
"Great place and wish we could have stayed longer. Very clean! Will stay again!"
United States
Juli W.
The price is AED 536
AED 924 total
includes taxes & fees
6 Jul - 7 Jul
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Terrace/patio

*New* Montana Dreamin’ Home

*New* Montana Dreamin’ Home
Billings
9.6 out of 10, Exceptional, (32 reviews)
"Great location, cozy and clean."
United States
Laura R.
The price is AED 612
AED 1,049 total
includes taxes & fees
23 Jun - 24 Jun
*New* Montana Dreamin’ Home
Interior

Rims view pet friendly home

Rims view pet friendly home
Rimrock
9.4 out of 10, Exceptional, (80 reviews)
"Great place with an amazing backyard! "
United States
Mitchell S.
The price is AED 413
AED 847 total
includes taxes & fees
29 Jun - 30 Jun
Rims view pet friendly home
Outdoor dining

Farmhouse Cottage @ Old Pine Retreats

Farmhouse Cottage @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (15 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 AED 555
AED 1,047 total
includes taxes & fees
29 Jun - 30 Jun
Farmhouse Cottage @ Old Pine Retreats
Interior

Townhome • Hospital District • King Bed + Garage

Townhome • Hospital District • King Bed + Garage
Central - Terry
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, comfy, clean. I’d stay here again. "
United States
Crystal C.
The price is AED 409
AED 1,116 total
includes taxes & fees
23 Jun - 24 Jun
Townhome • Hospital District • King Bed + Garage
TV

Bo’s Urban Farm House.

Bo’s Urban Farm House.
Central - Terry
9.2 out of 10, Wonderful, (21 reviews)
"This was a great place to stay. "
United States
Christina W.
The price is AED 364
AED 801 total
includes taxes & fees
23 Jun - 24 Jun
Bo’s Urban Farm House.
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)
"Everything was great! Very nice, clean and cozy. Awesome host."
United States
Cheryle K.
The price is AED 359
AED 781 total
includes taxes & fees
23 Jun - 24 Jun
Bo’s Old West Abode with Hot Tub and Sauna
TV

Contemporary Downtown Retreat 2-bedroom condo in Billings

Contemporary Downtown Retreat 2-bedroom condo in Billings
Central - Terry
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful space and excellent location quiet and ultra comfortable "
United States
David L.
The price is AED 344
AED 808 total
includes taxes & fees
23 Jun - 24 Jun
Contemporary Downtown Retreat 2-bedroom condo in Billings
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
9.8 out of 10, Exceptional, (8 reviews)
"Perfect for a family of 6, comfy and clean. Far enough outside of Billings but not to far. "
United States
Dustin
The price is AED 631
AED 777 total
includes taxes & fees
25 Jun - 26 Jun
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
Exterior

Industrial Loft @ Old Pine Retreats

Industrial Loft @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (11 reviews)
"We loved this place! It was very clean and the hot tub was kept clean as well. I definitely will stay here again for our next Billings weekends"
United States
Nicholas M.
The price is AED 586
AED 1,080 total
includes taxes & fees
30 Jun - 1 Jul
Industrial Loft @ Old Pine Retreats
Children's area

Bo's Rusty Relic Billings |Hot Tub | Rustic decor | Central Billings

Bo's Rusty Relic Billings |Hot Tub | Rustic decor | Central Billings
Central - Terry
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay! "
United States
Brynn W.
The price is AED 582
AED 1,038 total
includes taxes & fees
23 Jun - 24 Jun
Bo's Rusty Relic Billings |Hot Tub | Rustic decor | Central Billings
TV

Custer Cottage / Fenced Yard

Custer Cottage / Fenced Yard
Midtown
10.0 out of 10, Exceptional, (28 reviews)
"It was a great experience will definitely want to stay there again when we come back "
United States
Chris R.
The price is AED 624
AED 1,079 total
includes taxes & fees
28 Jun - 29 Jun
Custer Cottage / Fenced Yard
Children's area

Bo`s Heart of Central Billings Green Retreat w/ Hot Tub | near park | Game Room | Office

Bo`s Heart of Central Billings Green Retreat w/ Hot Tub | near park | Game Room | Office
Central - Terry
9.4 out of 10, Exceptional, (28 reviews)
"The house was perfect for our family. Great location, clean and comfortable"
United States
Chris H.
Bo`s Heart of Central Billings Green Retreat w/ Hot Tub | near park | Game Room | Office
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
9.8 out of 10, Exceptional, (31 reviews)
"This was the perfect place for our family. "
United States
Aaron J.
The price is AED 470
AED 1,031 total
includes taxes & fees
23 Jun - 24 Jun
Bo's Old West Landing w/Hot Tub and Sunrise Views
TV

Big Sky Retreat

Big Sky Retreat
Midtown
9.6 out of 10, Exceptional, (23 reviews)
"It was great place to stay. "
United States
Stacy S.
The price is AED 392
AED 1,129 total
includes taxes & fees
23 Jun - 24 Jun
Big Sky Retreat
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.
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Top Shepherd Hotel Reviews

Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

10/10 Excellent
"Room was clean, spacious, and comfortable. Staff was friendly and assistive with any check-in/stay issues we had. Convenient location and easy to navigate parking lot. Would stay here again!"
Jen 7-night trip
Posted 5 hours ago
Ledgestone Suites Hotel Billings

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?

Triangular Casa in 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 selection 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 Four Dances Recreation Area, 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.