Shepherd Vacation Rentals

Where to?

Dates

November 2026

December 2026

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

In two months

In three months

In four months

Our top choices for Shepherd vacation rentals

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

￥25,089 total

includes taxes & fees

Nov 9 - Nov 10

2. Boho Bungalow @ Old Pine Retreats

Billings

Natalie A.

￥36,018 total

includes taxes & fees

Nov 8 - Nov 9

A hallway with wooden sliding doors leading to a bathroom.

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

Worden

Julie C.

￥19,566 total

includes taxes & fees

Nov 7 - Nov 8

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

4. Farmhouse Cottage @ Old Pine Retreats

Billings

Kim J.

￥39,495 total

includes taxes & fees

Nov 30 - Dec 1

A single-story house with a front yard, a visible mailbox, and a street sign indicating '18th St W' and 'Wyoming Ave'.

5. Cozy 2BR Home in Central Billings

Midtown

Why So C.

￥18,299 total

includes taxes & fees

Nov 18 - Nov 19

A modern building with multiple windows and a balcony.

6. Industrial Loft @ Old Pine Retreats

Billings

Nicholas M.

￥40,481 total

includes taxes & fees

Nov 30 - Dec 1

A residential area with houses, green lawns, and a clear sky.

7. Moss & Blush King Bed Quiet Walkable to Parks, Coffee, Yellowstone River

Billings

Perry G.

￥42,413 total

includes taxes & fees

Nov 16 - Nov 17

8. Cozy 1-bedroom apartment in amazing Billings with AC

Downtown Billings

￥35,230 total

includes taxes & fees

Nov 6 - Nov 7

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

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

Midtown

Stefan L.

￥54,778 total

includes taxes & fees

Nov 17 - Nov 18

A spacious living room with a large window, a sofa, a coffee table, and a television.

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

Billings

james c.

￥29,004 total

includes taxes & fees

Nov 9 - Nov 10

A dining area with a table, chairs, a painting, a potted plant, and a floor lamp.

11. over the sugar pine retreat

West End

￥33,178 total

includes taxes & fees

Nov 12 - Nov 13

A living room with a gray sofa, a fireplace, a ceiling fan, a TV, and a white cabinet.

12. Private 1BR Guesthouse Retreat

Central - Terry

nasheena

￥32,587 total

includes taxes & fees

Nov 8 - Nov 9

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink with bar stools.

13. Modern Two Bedroom Townhouse with garage

Billings

Janie M.

￥39,163 total

includes taxes & fees

Nov 30 - Dec 1

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

14. Pet Friendly 2BR Home w/ fenced backyard

Central - Terry

Justin D.

￥33,494 total

includes taxes & fees

Nov 6 - Nov 7

A modern kitchen with a large island, bar stools, and pendant lighting.

15. Carriage House on 32nd

North Elevation Historic District

"We had a very comfortable stay at this charming newly remodeled home. Missy was very easy to communicate with and made us feel welcome. The hosts haven't missed any details in creating a lovely space to gather with friends and family. This home is beautifully decorated and clean. Plan on coffee and all of the cookware and utensils to provide meals in the kitchen. The neighborhood is quaint and historical. Thank you for a wonderful stay!!"

Josie M.

￥52,492 total

includes taxes & fees

Nov 6 - Nov 7

A covered porch with a grill, outdoor seating, and a number sign.

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

Ballantine

Christy

￥25,652 total

includes taxes & fees

Nov 9 - Nov 10

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

17. Big Sky Retreat

Midtown

Stacy S.

￥52,546 total

includes taxes & fees

Nov 10 - Nov 11

A compact kitchen with a built-in stove, a refrigerator, and a wooden countertop.

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

North Elevation Historic District

Valerie

￥36,804 total

includes taxes & fees

Nov 9 - Nov 10

A room with a wooden table, a shelf with books and a basket of flowers, a television on a wooden stand, and a window with white curtains.

19. Bo’s Urban Farm House | 2bed | 1 bath | Large Yard

Central - Terry

Christina W.

￥35,546 total

includes taxes & fees

Nov 8 - Nov 9

A modern kitchen with a central island, pendant lighting, and a view to the dining area.

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

Billings

Logan H.

￥36,855 total

includes taxes & fees

Nov 8 - Nov 9

View all properties

Find vacation rentals that suit your style

Top Shepherd Hotel Reviews

An outdoor patio with a stone fireplace, metal chairs, and a view of the city skyline at dusk.

Boothill Inn And Suites

Billings Heights

10/10 Excellent

Valorie

A spacious indoor area with a large tree, a fireplace, and seating arrangements.

Best Western Plus Clocktower Inn

Downtown Billings

10/10 Excellent

Sean

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

Lavinia

A hotel room with a large bed, a desk, a chair, a small table, a microwave, and a refrigerator.

Ledgestone Suites Hotel Billings

Southwest Corridor

10/10 Excellent

Laura

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

Home2 Suites by Hilton Billings

Downtown Billings

10/10 Excellent

Janet

An indoor swimming pool with a slide, a wooden ceiling, and a stone wall.

Best Western Plus Kelly Inn & Suites

Southwest Corridor

10/10 Excellent

Hotels.com failed to note that we were supposed to have a handicap room...even tho I emphasized that my Mom is in a wheelchair and when I made the reservation he assured me that was what he put on the reservation. We had a very difficult time getting her in the bathroom at night. The hotel had no handicap rooms left when I called to make sure about our reservation, but they did move us nearer the hall bathrooms...but Mom would not go out in the hall in her nightclothes. We probably won't...

Linn A

A restaurant interior with wooden furniture, hanging lights, and large windows.

Dude Rancher Lodge

Downtown Billings

10/10 Excellent

Laurie

A modern kitchen with a central island, bar stools, and a dining area with tables and chairs.

SureStay Plus Hotel by Best Western Billings

West End

10/10 Excellent

Maria

A spacious lobby with leather sofas, a reception desk, and modern lighting fixtures.

La Quinta Inn & Suites by Wyndham Billings

Southwest Corridor

10/10 Excellent

Erica

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

Joanna

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

Jerelyn

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

This was the first time i've ever stayed at this hotel in particular but I definitely will be staying here more often due to it's cleanliness and the courtesy of the staff. Granted not everyone will share my opinion but I for one was pretty impressed. I usually stay at the same hotel's when staying overnight cause of my back and now that I know hotels' beds aren't complete concrete, I have officially found another place to stay when spending another night in billings, mt.

J-Walker

A modern hotel with a 'Courtyard by Marriott' sign, featuring a covered entrance, large windows, and a well-lit facade.

Courtyard BY Marriott Billings

West End

10/10 Excellent

wendy

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.

Shepherd Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Shepherd vacation rentals

1. Triangular Casa in Billings

2. Boho Bungalow @ Old Pine Retreats

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

4. Farmhouse Cottage @ Old Pine Retreats

5. Cozy 2BR Home in Central Billings

6. Industrial Loft @ Old Pine Retreats

7. Moss & Blush King Bed Quiet Walkable to Parks, Coffee, Yellowstone River

8. Cozy 1-bedroom apartment in amazing Billings with AC

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

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

11. over the sugar pine retreat

12. Private 1BR Guesthouse Retreat

13. Modern Two Bedroom Townhouse with garage

14. Pet Friendly 2BR Home w/ fenced backyard

15. Carriage House on 32nd

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

17. Big Sky Retreat

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

19. Bo’s Urban Farm House | 2bed | 1 bath | Large Yard

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

Find vacation rentals that suit your style

Top Shepherd Hotel Reviews

Boothill Inn And Suites

10/10 Excellent

Find out more about Shepherd

Frequently Asked Questions

Can I find a vacation rental in Shepherd?

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

What can I see and do in Shepherd?

What are vacation rentals like in Shepherd?