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Shepherd Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Shepherd vacation rentals

Room

1. Quaint Charm at 2210: Your Idyllic Retreat!

Quaint Charm at 2210: Your Idyllic Retreat!
Downtown Billings
9.6 out of 10, Exceptional, (8 reviews)
"Great place super close to everything. My wife and I walked everywhere we went. The place was awesome and the AC kept us cool in the heat."
Canada
Jacob W.
$154 nightly
The price is $166
Aug 24 - Aug 25
Total with taxes and fees
Quaint Charm at 2210: Your Idyllic Retreat!
Exterior

2. Chic Urban Escape: Stay at 2202! Pet Friendly

Chic Urban Escape: Stay at 2202! Pet Friendly
Downtown Billings
10.0 out of 10, Exceptional, (1 review)
"It was a very great place to stay will stay again. Very cute and charming the host was amazing"
United States
Megan G.
$129 nightly
The price is $139
Aug 24 - Aug 25
Total with taxes and fees
Chic Urban Escape: Stay at 2202! Pet Friendly
Living area

3. Triangular Casa in Billings

Triangular Casa in Billings
Central - Terry
9.6 out of 10, Exceptional, (129 reviews)
"The place was good for what we needed for a quick stop over."
United States
Robert
$184 nightly
The price is $199
Aug 23 - Aug 24
Total with taxes and fees
Triangular Casa in Billings
Outdoor dining

4. Farmhouse Cottage @ Old Pine Retreats

Farmhouse Cottage @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (19 reviews)
"So charming and nicely decorated! Wonderful deck areas quiet area. Would definitely recommend and will be back!"
United States
Jessica L.
$268 nightly
The price is $283
Sep 15 - Sep 16
Total with taxes and fees
Farmhouse Cottage @ Old Pine Retreats
Interior

5. 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, (24 reviews)
"Great place!"
United States
Julie C.
$130 nightly
The price is $141
Aug 24 - Aug 25
Total with taxes and fees
A clean, comfortable space just off the interstate with easy parking.
Living area

6. 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
10.0 out of 10, Exceptional, (13 reviews)
"Perfect for a family of 6, comfy and clean. Far enough outside of Billings but not to far. "
United States
Dustin
$191 nightly
The price is $207
Sep 1 - Sep 2
Total with taxes and fees
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
Exterior

7. Industrial Loft @ Old Pine Retreats

Industrial Loft @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (13 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.
$270 nightly
The price is $285
Sep 22 - Sep 23
Total with taxes and fees
Industrial Loft @ Old Pine Retreats
Terrace/patio

8. Boho Bungalow @ Old Pine Retreats

Boho Bungalow @ Old Pine Retreats
Billings
9.8 out of 10, Exceptional, (32 reviews)
"Everything about this place was perfect! They also have a fabulous area for group meetings!!! Make this your next stay"
United Kingdom
Melanie W.
$232 nightly
The price is $245
Aug 25 - Aug 26
Total with taxes and fees
Boho Bungalow @ Old Pine Retreats
Exterior

9. Parkhill Bungalow • Pioneer Park

Parkhill Bungalow • Pioneer Park
Midtown
9.6 out of 10, Exceptional, (5 reviews)
"Veey nice property "
United Kingdom
Juli L.
$285 nightly
The price is $308
Aug 24 - Aug 25
Total with taxes and fees
Parkhill Bungalow • Pioneer Park
Living area

10. Private 1BR Guesthouse Retreat

Private 1BR Guesthouse Retreat
Central - Terry
9.8 out of 10, Exceptional, (20 reviews)
"It was a nice place to relax and enjoy some time alone"
United States
nasheena
$192 nightly
The price is $207
Aug 23 - Aug 24
Total with taxes and fees
Private 1BR Guesthouse Retreat
Exterior

11. Pet Friendly 2BR Home w/ fenced backyard

Pet Friendly 2BR Home w/ fenced backyard
Central - Terry
9.2 out of 10, Wonderful, (27 reviews)
"Great value for the price on a quick trip to Billings."
United States
Tim K.
$215 nightly
The price is $233
Aug 25 - Aug 26
Total with taxes and fees
Pet Friendly 2BR Home w/ fenced backyard
Interior

12. Townhome • Hospital District • King Bed + Garage

Townhome • Hospital District • King Bed + Garage
Central - Terry
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful home and close to downtown so that was a bonus! "
United States
Chandale F.
$312 nightly
The price is $337
Sep 8 - Sep 9
Total with taxes and fees
Townhome • Hospital District • King Bed + Garage
Living area

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

Bo’s Urban Farm House | 2bed | 1 bath | Large Yard
Central - Terry
9.2 out of 10, Wonderful, (22 reviews)
"This was a great place to stay. "
United States
Christina W.
$207 nightly
The price is $224
Aug 23 - Aug 24
Total with taxes and fees
Bo’s Urban Farm House | 2bed | 1 bath | Large Yard
Terrace/patio

14. Pet Friendly with Hot Tub and Sauna

Pet Friendly with Hot Tub and Sauna
Central - Terry
9.6 out of 10, Exceptional, (35 reviews)
"Bed & pillows were super comfortable! Had amazing coffee and all the necessities. Great hostess and great fast response! "
United States
Brandi T.
$260 nightly
The price is $281
Aug 26 - Aug 27
Total with taxes and fees
Pet Friendly with Hot Tub and Sauna
Private kitchen

15. 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, (25 reviews)
"Property was clean & well appointed. Host was welcoming and communicative. Nice yard. Great location!"
United States
Mildred
$217 nightly
The price is $235
Aug 23 - Aug 24
Total with taxes and fees
Quaint sunny cottage that rests in the historical neighborhood of Billings
Private kitchen

16. 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, (34 reviews)
"Great stay!"
United States
Logan H.
$203 nightly
The price is $219
Aug 23 - Aug 24
Total with taxes and fees
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Living area

17. Custer Cottage / Fenced Yard

Custer Cottage / Fenced Yard
Midtown
10.0 out of 10, Exceptional, (32 reviews)
"It was a great experience will definitely want to stay there again when we come back "
United States
Chris R.
$273 nightly
The price is $295
Aug 24 - Aug 25
Total with taxes and fees
Custer Cottage / Fenced Yard
Pool

18. 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.
$411 nightly
The price is $443
Sep 8 - Sep 9
Total with taxes and fees
The Lakehouse: Pool, Theater, Game Room, Lakefront
Living area

19. Pet Friendly, Private HOT TUB & Fenced Backyard

Pet Friendly, Private HOT TUB & Fenced Backyard
Central - Terry
9.6 out of 10, Exceptional, (31 reviews)
"We had a great stay, the house was exactly what we needed and very hospitable "
United States
STEPHEN L.
$261 nightly
The price is $282
Aug 24 - Aug 25
Total with taxes and fees
Pet Friendly, Private HOT TUB & Fenced Backyard
Private kitchen

20. Modern townhome minutes from Billings' best shopping, family friendly community!

Modern townhome minutes from Billings' best shopping, family friendly community!
Billings
10.0 out of 10, Exceptional, (41 reviews)
"Quick overnight stay that was convenient for our plans and comfortable for our family "
United States
Jasmine D.
$224 nightly
The price is $242
Aug 31 - Sep 1
Total with taxes and fees
Modern townhome minutes from Billings' best shopping, family friendly community!
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

Billings Hotel and Convention Center

Billings Hotel and Convention Center

8/10 Good
"Comfortable beds. Seem like room was renovated."
Matthew 3-night trip
Posted 12 hours ago
Billings Hotel and Convention Center

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?

Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood: This vacation home rental near Shepherd offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.