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Shepherd Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Shepherd vacation rentals

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

1. 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)
"Perfect for a family of 6, comfy and clean. Far enough outside of Billings but not to far. "
United States
Dustin
$164 nightly
The price is $177
Oct 28 - Oct 29
Total with taxes and fees
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
A modern kitchen with a bar area, wooden cabinets, and a dining set.

2. Custer Cottage / Fenced Yard

Custer Cottage / Fenced Yard
Midtown
9.8 out of 10, Exceptional, (40 reviews)
"This was a great centrally located home in Billings!"
United States
Jill
$294 nightly
The price is $318
Oct 25 - Oct 26
Total with taxes and fees
Custer Cottage / Fenced Yard
A living room with a grey sofa, a television on a wooden stand, a ceiling fan, and a large window with curtains.

3. Triangular Casa in Billings

Triangular Casa in Billings
Central - Terry
9.6 out of 10, Exceptional, (135 reviews)
"Nice location. Good space."
United States
Michael
$161 nightly
The price is $174
Oct 26 - Oct 27
Total with taxes and fees
Triangular Casa in Billings
A living room with a fireplace, two large windows, a blue couch, a beige sofa, and a coffee table.

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

The Lakehouse: Pool, Theater, Game Room, Lakefront
Billings Heights
9.8 out of 10, Exceptional, (17 reviews)
"Great house / great location "
United States
maggie g.
$393 nightly
The price is $424
Oct 27 - Oct 28
Total with taxes and fees
The Lakehouse: Pool, Theater, Game Room, Lakefront
A dining table with white bowls and a vase of white flowers, surrounded by wooden chairs.

5. Pet Friendly, Fenced Backyard with Washer and Dryer

Pet Friendly, Fenced Backyard with Washer and Dryer
Central - Terry
9.4 out of 10, Exceptional, (29 reviews)
"We stayed in town for a couple months and the place was great!"
United States
Ben W.
$261 nightly
The price is $282
Oct 25 - Oct 26
Total with taxes and fees
Pet Friendly, Fenced Backyard with Washer and Dryer
A hot tub under a wooden pergola with a white house in the background.

6. Pet Friendly with Hot Tub and Sauna

Pet Friendly with Hot Tub and Sauna
Central - Terry
9.6 out of 10, Exceptional, (41 reviews)
"Was a great home"
United States
Dan W.
$280 nightly
The price is $303
Oct 25 - Oct 26
Total with taxes and fees
Pet Friendly with Hot Tub and Sauna
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, (31 reviews)
"Very clean and nice house. Very close by to the major stores and great places to eat."
United States
Justin D.
$223 nightly
The price is $241
Oct 25 - Oct 26
Total with taxes and fees
Pet Friendly 2BR Home w/ fenced backyard
A dining table with two white bowls on plates, a vase with white tulips, and a wall-mounted decorative piece.

8. Bo’s 3BR Retreat • Hot Tub • Sauna • Den Suite

Bo’s 3BR Retreat • Hot Tub • Sauna • Den Suite
Central - Terry
10.0 out of 10, Exceptional, (2 reviews)
"It was just a quick trip for us but it was nice to have a place to stay all together. We enjoyed the hot tub and sauna. "
United States
Jennifer A.
$278 nightly
The price is $300
Oct 25 - Oct 26
Total with taxes and fees
Bo’s 3BR Retreat • Hot Tub • Sauna • Den Suite
A compact kitchen with a built-in stove, a refrigerator, and a wooden countertop.

9. 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, (28 reviews)
"Property was clean & well appointed. Host was welcoming and communicative. Nice yard. Great location!"
United States
Mildred
$225 nightly
The price is $243
Oct 24 - Oct 25
Total with taxes and fees
Quaint sunny cottage that rests in the historical neighborhood of Billings
A deck with wicker furniture, a table, and a lantern.

10. Farmhouse Cottage @ Old Pine Retreats

Farmhouse Cottage @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (24 reviews)
"Will definitely be my go to for when traveling to Billings. Everything was perfect for us."
United States
Travis W.
$241 nightly
The price is $254
Nov 17 - Nov 18
Total with taxes and fees
Farmhouse Cottage @ Old Pine Retreats
A hot tub with a built-in seat and steps, surrounded by a fence and greenery.

11. Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood

Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood
Central - Terry
9.6 out of 10, Exceptional, (82 reviews)
"The house was in a convenient location and was just what we where looking for to escape the heat and thunderstorms on our road trip."
United States
Matt P.
$268 nightly
The price is $290
Oct 25 - Oct 26
Total with taxes and fees
Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood
A modern building with multiple windows and a balcony.

12. 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.
$246 nightly
The price is $259
Nov 17 - Nov 18
Total with taxes and fees
Industrial Loft @ Old Pine Retreats
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.

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

Bo’s Urban Farm House | 2bed | 1 bath | Large Yard
Central - Terry
9.0 out of 10, Wonderful, (27 reviews)
"This was a great place to stay. "
United States
Christina W.
$220 nightly
The price is $237
Oct 25 - Oct 26
Total with taxes and fees
Bo’s Urban Farm House | 2bed | 1 bath | Large Yard
A bedroom with a large bed, a dark door, a wall-mounted mirror, and a large floral painting.

14. Luxury Living Next Door to Hospital

Luxury Living Next Door to Hospital
Downtown Billings
10.0 out of 10, Exceptional, (15 reviews)
"Great place to stay, very clean."
United States
Orson J.
$323 nightly
The price is $337
Oct 24 - Oct 25
Total with taxes and fees
Luxury Living Next Door to Hospital
A modern kitchen with a central island, pendant lighting, and a view to the dining area.

15. 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, (42 reviews)
"Great stay!"
United States
Logan H.
$201 nightly
The price is $217
Nov 2 - Nov 3
Total with taxes and fees
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
A covered porch with a grill, outdoor seating, and a number sign.

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

Cozy 2 bedroom cabin! Country charm with comfort and scenery!
Ballantine
10.0 out of 10, Exceptional, (3 reviews)
"The cabin was an excellent place to stay on our trip. It was clean and comfortable. The setting was beautiful. The price was great. We were very happy with our stay."
United States
Christy
$158 nightly
The price is $171
Nov 2 - Nov 3
Total with taxes and fees
Cozy 2 bedroom cabin! Country charm with comfort and scenery!
A cozy living room with a large window, a plant, a lamp, and a leather couch.

17. Pet Friendly, Private HOT TUB & Fenced Backyard

Pet Friendly, Private HOT TUB & Fenced Backyard
Central - Terry
9.2 out of 10, Wonderful, (38 reviews)
"This place is awesome, and ever comfortable. The down stairs shower was amazing, probably one of the better places I stayed at."
United States
Louis
$287 nightly
The price is $310
Oct 25 - Oct 26
Total with taxes and fees
Pet Friendly, Private HOT TUB & Fenced Backyard
A gym with wooden walls, a treadmill, dumbbells, and a bench.

18. 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
9.6 out of 10, Exceptional, (31 reviews)
"The rental was perfect for us. Location is central to everything you need. "
United States
Mike B.
$303 nightly
The price is $327
Oct 26 - Oct 27
Total with taxes and fees
Bo`s Heart of Central Billings Green Retreat w/ Hot Tub | near park | Game Room | Office
A spacious living room with leather sofas, a wooden coffee table, and a large window offering a view of the outdoors.

19. Privates Home with Views • Near Med & Airport/DT Two King beds and 2 Queen Beds

Privates Home with Views • Near Med & Airport/DT Two King beds and 2 Queen Beds
Rimrock
10.0 out of 10, Exceptional, (15 reviews)
"Everything was great"
United States
Ryan A.
$440 nightly
The price is $475
Oct 26 - Oct 27
Total with taxes and fees
Privates Home with Views • Near Med & Airport/DT Two King beds and 2 Queen Beds
A modern living room with a grey sofa, a wooden coffee table, and a TV mounted on the wall.

20. 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.
$280 nightly
The price is $303
Oct 26 - Oct 27
Total with taxes and fees
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

Howard Johnson by Wyndham Billings

Howard Johnson by Wyndham Billings

8/10 Good
"It was good"
Nicholas 1-night trip
Posted 10 hours ago
Howard Johnson by Wyndham Billings

Find out more about Shepherd

Everything you need to know about Shepherd vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherd vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shepherd vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shepherd vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shepherd. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shepherd in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shepherd rentals

At Expedia, we put the best Shepherd vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shepherd rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shepherd vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shepherd. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.