Shepherd Vacation Rentals

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Shepherd vacation homes

A living room with a grey sofa, a television on a wooden stand, a ceiling fan, and a large window with curtains.

1. Triangular Casa in Billings

Triangular Casa in Billings
Central - Terry
9.6 out of 10, Exceptional, (137 reviews)
"Nice location. Good space."
United States
Michael
The price is CA $104
CA $222 total
includes taxes & fees
Nov 16 - Nov 17
Triangular Casa in Billings
A deck with wicker furniture, a table, and a lantern.

2. Farmhouse Cottage @ Old Pine Retreats

Farmhouse Cottage @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (24 reviews)
"My girls and I stayed here for one night on our drive from WA to MN. We absolutely loved it and will be back!"
United States
Kim J.
The price is CA $171
CA $320 total
includes taxes & fees
Nov 9 - Nov 10
Farmhouse Cottage @ Old Pine Retreats
A modern building with multiple windows and a balcony.

3. Industrial Loft @ Old Pine Retreats

Industrial Loft @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (16 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 CA $180
CA $341 total
includes taxes & fees
Nov 9 - Nov 10
Industrial Loft @ Old Pine Retreats
A kitchen with a central island, dark cabinets, and a sliding barn-style door.

4. 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, (26 reviews)
"Great place!"
United States
Julie C.
The price is CA $135
CA $187 total
includes taxes & fees
Nov 9 - Nov 10
A clean, comfortable space just off the interstate with easy parking.
A spacious living room with a large window, a sofa, a coffee table, and a television.

5. 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, (17 reviews)
"nice clean house good bed"
United States
james c.
The price is CA $216
CA $243 total
includes taxes & fees
Nov 17 - Nov 18
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
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6. Boho Bungalow @ Old Pine Retreats

Boho Bungalow @ Old Pine Retreats
Billings
9.8 out of 10, Exceptional, (36 reviews)
"Great spot! So unique and we loved having coffee in the morning on the patio!"
United States
Natalie A.
The price is CA $182
CA $318 total
includes taxes & fees
Dec 1 - Dec 2
Boho Bungalow @ Old Pine Retreats
A single-story house with a covered porch and a garage.

7. Pet Friendly 2BR Home w/ fenced backyard

Pet Friendly 2BR Home w/ fenced backyard
Central - Terry
9.4 out of 10, Exceptional, (32 reviews)
"Very clean and nice house. Very close by to the major stores and great places to eat."
United States
Justin D.
The price is CA $161
CA $308 total
includes taxes & fees
Nov 9 - Nov 10
Pet Friendly 2BR Home w/ fenced backyard
A living room with a fireplace, two large windows, a blue couch, a beige sofa, and a coffee table.

8. The Lakehouse: Pool, Theater, Game Room, Lakefront

The Lakehouse: Pool, Theater, Game Room, Lakefront
Billings Heights
9.6 out of 10, Exceptional, (18 reviews)
"Great house / great location "
United States
maggie g.
The price is CA $172
CA $531 total
includes taxes & fees
Nov 10 - Nov 11
The Lakehouse: Pool, Theater, Game Room, Lakefront
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink with bar stools.

9. Modern Two Bedroom Townhouse with garage

Modern Two Bedroom Townhouse with garage
Billings
10.0 out of 10, Exceptional, (2 reviews)
"We really enjoyed our stay."
United States
Janie M.
The price is CA $154
CA $351 total
includes taxes & fees
Nov 11 - Nov 12
Modern Two Bedroom Townhouse with garage
A kitchen with built-in appliances, a window with a view, and organized shelves.

10. Montana Gathering House: Fire Pit, BBQ, HUGE Yard

Montana Gathering House: Fire Pit, BBQ, HUGE Yard
Midtown
10.0 out of 10, Exceptional, (3 reviews)
"Decent place to stay while on the road. Worked well for our family with kids."
United States
Stefan L.
The price is CA $130
CA $479 total
includes taxes & fees
Dec 8 - Dec 9
Montana Gathering House: Fire Pit, BBQ, HUGE Yard
A compact kitchen with a built-in stove, a refrigerator, and a wooden countertop.

11. Quaint sunny cottage that rests in the historical neighborhood of Billings

Quaint sunny cottage that rests in the historical neighborhood of Billings
North Elevation Historic District
10.0 out of 10, Exceptional, (29 reviews)
"Very quaint little house with a lot of character. Very peaceful and quiet neighborhood. Very clean and well taken care of."
United States
Valerie
The price is CA $175
CA $324 total
includes taxes & fees
Nov 9 - Nov 10
Quaint sunny cottage that rests in the historical neighborhood of Billings
A modern kitchen with a central island, pendant lighting, and a view to the dining area.

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

Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Billings
9.6 out of 10, Exceptional, (45 reviews)
"Great stay!"
United States
Logan H.
The price is CA $197
CA $327 total
includes taxes & fees
Nov 10 - Nov 11
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
A modern kitchen with a central island, bar stools, stainless steel appliances, and a wooden staircase leading to a loft.

13. BRAND NEW Willow Suite-Luxury 2BR Near Hospitals and MSU-B

BRAND NEW Willow Suite-Luxury 2BR Near Hospitals and MSU-B
North Elevation Historic District
The price is CA $190
CA $412 total
includes taxes & fees
Nov 9 - Nov 10
BRAND NEW Willow Suite-Luxury 2BR Near Hospitals and MSU-B
A house with a covered porch, two Adirondack chairs, a door, and a small garden area with stepping stones.

14. Mocha Haven King Bed Quiet Walkable To Parks, Coffee, Yellowstone River

Mocha Haven King Bed Quiet Walkable To Parks, Coffee, Yellowstone River
Billings
10.0 out of 10, Exceptional, (9 reviews)
"Brand new and clean, quiet neighborhood."
United States
Elaina
The price is CA $182
CA $310 total
includes taxes & fees
Nov 30 - Dec 1
Mocha Haven King Bed Quiet Walkable To Parks, Coffee, Yellowstone River
A modern kitchen with stainless steel appliances, a large island with a sink, and pendant lighting.

15. Twin Suites - Walk to Coffee & Green Spaces

Twin Suites - Walk to Coffee & Green Spaces
Billings
10.0 out of 10, Exceptional, (5 reviews)
"Lovely community, beautiful space, easy access"
Canada
Jennifer S.
The price is CA $167
CA $388 total
includes taxes & fees
Dec 1 - Dec 2
Twin Suites - Walk to Coffee & Green Spaces
A room with large windows, a wooden bench, and a grey sofa with a blanket.

16. Townhome • Hospital District • King Bed + Garage

Townhome • Hospital District • King Bed + Garage
Central - Terry
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful home and close to downtown so that was a bonus! "
United States
Chandale F.
The price is CA $169
CA $402 total
includes taxes & fees
Nov 16 - Nov 17
Townhome • Hospital District • King Bed + Garage
A porch with a rocking chair, two hanging chairs, and a striped rug.

17. Big Sky Bungalow + Hot Tub/Retro Feels

Big Sky Bungalow + Hot Tub/Retro Feels
Billings
10.0 out of 10, Exceptional, (2 reviews)
"Adorable unit, so nicely decorated. Nice and safe community that is easy to get to but keeps you away from the noise of downtown."
United States
Erika P.
The price is CA $179
CA $474 total
includes taxes & fees
Nov 11 - Nov 12
Big Sky Bungalow + Hot Tub/Retro Feels
A living room with a sofa, coffee table, and a dining area with a table and chairs.

18. Peaceful & Private 2 Bed West End Home on a Gated Acre

Peaceful & Private 2 Bed West End Home on a Gated Acre
Shiloh
The price is CA $194
CA $540 total
includes taxes & fees
Nov 9 - Nov 10
Peaceful & Private 2 Bed West End Home on a Gated Acre
A modern living room with a grey sofa, a wooden coffee table, and a TV mounted on the wall.

19. Big Sky Retreat

Big Sky Retreat
Midtown
9.4 out of 10, Exceptional, (28 reviews)
"It was great place to stay. "
United States
Stacy S.
The price is CA $338
CA $640 total
includes taxes & fees
Nov 29 - Nov 30
Big Sky Retreat
A two-story house with a front porch, a central door, and a small front yard with steps leading to the entrance.

20. NEW! Sparkling 1-Level 2-BDRM King

NEW! Sparkling 1-Level 2-BDRM King
Billings
10.0 out of 10, Exceptional, (10 reviews)
"Megan's place is extraordinary! Very clean, quiet and comfortable. Great location as well!!"
United States
Brad M.
The price is CA $211
CA $363 total
includes taxes & fees
Nov 11 - Nov 12
NEW! Sparkling 1-Level 2-BDRM King
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 reviews in Shepherd

A modern bar area with a long counter, bar stools, and a seating area with tables and chairs.
Hyatt Place Billings

Hyatt Place Billings

Hyatt Place Billings
Shiloh

10/10 Excellent

Clean, great staff
Canada
Rick
Reviewed October 8, 2026
Hyatt Place Billings

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