Shepherd Vacation Home Rentals from CA $104: Search Top Private Vacation Homes for Rent

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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

Central - Terry

Michael

CA $222 total

includes taxes & fees

Nov 16 - Nov 17

A deck with wicker furniture, a table, and a lantern.

2. Farmhouse Cottage @ Old Pine Retreats

Billings

Kim J.

CA $333 total

includes taxes & fees

Nov 11 - Nov 12

A modern building with multiple windows and a balcony.

3. Industrial Loft @ Old Pine Retreats

Billings

Nicholas M.

CA $355 total

includes taxes & fees

Nov 11 - Nov 12

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.

Worden

Julie C.

CA $187 total

includes taxes & fees

Nov 11 - Nov 12

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!

Billings

james c.

CA $253 total

includes taxes & fees

Nov 17 - Nov 18

6. Boho Bungalow @ Old Pine Retreats

Billings

Natalie A.

CA $320 total

includes taxes & fees

Dec 5 - Dec 6

A single-story house with a covered porch and a garage.

7. Pet Friendly 2BR Home w/ fenced backyard

Central - Terry

Justin D.

CA $308 total

includes taxes & fees

Nov 11 - Nov 12

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

Billings Heights

maggie g.

CA $545 total

includes taxes & fees

Nov 11 - Nov 12

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

Billings

Janie M.

CA $351 total

includes taxes & fees

Nov 15 - Nov 16

A kitchen with built-in appliances, a window with a view, and organized shelves.

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

Midtown

Stefan L.

CA $484 total

includes taxes & fees

Nov 17 - Nov 18

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

North Elevation Historic District

Valerie

CA $324 total

includes taxes & fees

Nov 11 - Nov 12

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

Billings

Logan H.

CA $327 total

includes taxes & fees

Nov 11 - Nov 12

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

North Elevation Historic District

CA $396 total

includes taxes & fees

Nov 13 - Nov 14

Large sofa and lots of streaming services available. Sofa easily converts to a full bed

14. Garage, King Bed, Quiet, Walkable to Parks Coffee

Billings

Elaina

CA $384 total

includes taxes & fees

Dec 6 - Dec 7

A modern kitchen with stainless steel appliances, a large island with a sink, and pendant lighting.

15. Twin Suites - Walk to Coffee & Green Spaces

Billings

Jennifer S.

CA $386 total

includes taxes & fees

Dec 1 - Dec 2

A room with large windows, a wooden bench, and a grey sofa with a blanket.

16. Townhome • Hospital District • King Bed + Garage

Central - Terry

Chandale F.

CA $418 total

includes taxes & fees

Dec 8 - Dec 9

A porch with a rocking chair, two hanging chairs, and a striped rug.

17. Big Sky Bungalow + Hot Tub/Retro Feels

Billings

Erika P.

CA $474 total

includes taxes & fees

Nov 11 - Nov 12

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

Shiloh

CA $540 total

includes taxes & fees

Nov 11 - Nov 12

A modern living room with a grey sofa, a wooden coffee table, and a TV mounted on the wall.

19. Big Sky Retreat

Midtown

Stacy S.

CA $549 total

includes taxes & fees

Dec 8 - Dec 9

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

Billings

Brad M.

CA $363 total

includes taxes & fees

Nov 11 - Nov 12

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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

Shiloh

10/10 Excellent

Rick

A spacious indoor area with a stone fireplace, wicker furniture, and large windows offering a view of parked cars outside.

Hilltop Inn by Riversage

Downtown Billings

10/10 Excellent

Carol

An outdoor patio area with string lights, seating, and a fire feature.

Home2 Suites by Hilton Billings

Downtown Billings

10/10 Excellent

Dave

A modern hotel with a prominent red accent on the corner, a covered outdoor seating area, and a clear sky.

avid Hotels Billings West by IHG

Shiloh

10/10 Excellent

Great hotel, close to the interstate. Hotel is clean and the rooms are clean and simple. Big TV in the room and mini fridge. No coffee maker in room, but fresh coffee, tea and water in lobby at all times which is nice. Breakfast was good and good variety. We just caught the tail end, so missed the scrambled eggs. Only compliant would be that it would have been helpful if the staff gave us a tutorial on the facilities (ie: ice is only in lobby, coffee available 24/7, breakfast schedule). Two...

Melanie

A dining area with wicker chairs, a long bench, and a view of the street through a window.

Riversage Billings Inn

Downtown Billings

10/10 Excellent

Jurgita

A hotel room with two beds, a desk, a chair, and a small table with a vase of flowers.

Kelly Inn Billings Montana

Southwest Corridor

10/10 Excellent

Dan

A hotel room with two beds, a TV, a window with blinds, a framed picture on the wall, and a bedside lamp.

My Place Hotel - Billings, MT

Southwest Corridor

10/10 Excellent

Roxanne

A hotel with a well-lit outdoor patio area featuring a fire pit, seating, and a variety of plants.

Homewood Suites By Hilton Billings, MT

Shiloh

10/10 Excellent

We only had a 1 night stay but it’s our hotel of choice when traveling across the state. The room was fantastic, very clean and even passed “my inspection” The bed was very comfortable. Unfortunately the tv wasn’t working despite the hotel handyman trying multiple times to fix it. He had placed a work order. Hopefully it’s fixed for the next occupants. We would absolutely stay on our next trip. The breakfast was delicious and the staff amazing.

Joanne

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Shepherd Vacation Rentals

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Shepherd vacation homes

1. Triangular Casa in Billings

2. Farmhouse Cottage @ Old Pine Retreats

3. Industrial Loft @ Old Pine Retreats

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

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

6. Boho Bungalow @ Old Pine Retreats

7. Pet Friendly 2BR Home w/ fenced backyard

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

9. Modern Two Bedroom Townhouse with garage

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

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

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

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

14. Garage, King Bed, Quiet, Walkable to Parks Coffee

15. Twin Suites - Walk to Coffee & Green Spaces

16. Townhome • Hospital District • King Bed + Garage

17. Big Sky Bungalow + Hot Tub/Retro Feels

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

19. Big Sky Retreat

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

Top reviews in Shepherd

Hyatt Place Billings

10/10 Excellent

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