Shepherd Vacation Rentals

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Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 24 - Oct 26
Next weekend
Oct 31 - Nov 2

Vacation Rentals in Shepherd

Private kitchen
Quaint Cottage @ Fort Nibbe
Quaint Cottage @ Fort Nibbe
2.0 star property
9.8 out of 10, Exceptional, (16)
"The cottage is awesome, ended up staying 2 extra nights. The cottage is completely furnished. Will highly recommend, and like to come back again."
United States
charles
$120 nightly
The price is $130
Oct 25 - Oct 26
Total with taxes and fees
Quaint Cottage @ Fort Nibbe
Fridge, microwave, oven, stovetop
Relaxing, cozy and comfortable
Relaxing, cozy and comfortable
9.8 out of 10, Exceptional, (18)
"This place is a hidden gem. Totally cute and immaculate. We enjoyed sitting on the porch and watching a storm roll in."
United States
Robert
$120 nightly
The price is $130
Oct 25 - Oct 26
Total with taxes and fees
Relaxing, cozy and comfortable
Interior
Cozy cabin - pet friendly
Cozy cabin - pet friendly
$120 nightly
The price is $130
Oct 25 - Oct 26
Total with taxes and fees
Cozy cabin - pet friendly
Dining
Triangular Casa in Billings
Triangular Casa in Billings
9.6 out of 10, Exceptional, (100)
"This property was nicely furnished, clean and well maintained…the beds were comfortable too…also easy to access, thanks. And close to lots of shopping areas. We enjoyed a leisurely breakfast and then went about our day with the knowledge of a comfortable stay at the end of our day."
United States
Laura
$153 nightly
The price is $165
Nov 2 - Nov 3
Total with taxes and fees
Triangular Casa in Billings
Terrace/patio
*New* Montana Dreamin’ Home
*New* Montana Dreamin’ Home
9.6 out of 10, Exceptional, (27)
"Nice little home to stay in! Clean, crisp look."
United States
Melissa S.
$213 nightly
The price is $230
Oct 26 - Oct 27
Total with taxes and fees
*New* Montana Dreamin’ Home
Exterior
Restored Vintage Mobile Home on our small Private Ranch
Restored Vintage Mobile Home on our small Private Ranch
9.0 out of 10, Wonderful, (8)
"Perfect lodging for our trip. Kurt was very responsive and hospitable. We will certainly be back on future trips to the area."
United States
Jake D.
$160 nightly
The price is $173
Oct 25 - Oct 26
Total with taxes and fees
Restored Vintage Mobile Home on our small Private Ranch
Property grounds
Cozy, Stylish 2-Bedroom Retreat in Prime Location – Walk to Shops & Dining!
Cozy, Stylish 2-Bedroom Retreat in Prime Location – Walk to Shops & Dining!
2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything! Just the right size for the 4 of us for the weekend. Close to everywhere we wanted to go and close enough to come home and rest before round 2 of shopping! Send me a text and ill tell you more. Thank you so much for a very memorable weekend in billings that was long overdue!!! We'll defunately stay here again! We will tell all our friend!"
United States
Phyllis J.
$122 nightly
The price is $132
Oct 26 - Oct 27
Total with taxes and fees
Cozy, Stylish 2-Bedroom Retreat in Prime Location – Walk to Shops & Dining!
Fridge, microwave, oven, coffee/tea maker
Barb’s Cozy Home with Office and Covered Parking!
Barb’s Cozy Home with Office and Covered Parking!
2.0 star property
9.6 out of 10, Exceptional, (19)
"Awesome and management. Would gladly stay there again. "
United States
Rodney H.
$197 nightly
The price is $213
Oct 25 - Oct 26
Total with taxes and fees
Barb’s Cozy Home with Office and Covered Parking!
Terrace/patio
Rims view pet friendly home
Rims view pet friendly home
9.6 out of 10, Exceptional, (54)
"Great place "
United States
Frank N.
$188 nightly
The price is $203
Oct 28 - Oct 29
Total with taxes and fees
Rims view pet friendly home
Property grounds
Industrial Loft @ Old Pine Retreats
Industrial Loft @ Old Pine Retreats
10.0 out of 10, Exceptional, (8)
"We had a great time at the Industrial Loft! Beautiful, cozy, and well appointed house situated in a quiet area with beautiful views on the surroundings. We had nice walks from the house and a very pleasant stay. We look forward to coming back!"
United States
Caroline B.
$246 nightly
The price is $259
Nov 4 - Nov 5
Total with taxes and fees
Industrial Loft @ Old Pine Retreats
Fridge, microwave, oven, stovetop
Bo’s Bungalow with Hot Tub and Sauna
Bo’s Bungalow with Hot Tub and Sauna
9.6 out of 10, Exceptional, (12)
"Was perfect for our 2 day stay in Billings!"
United States
Tiffany G.
$175 nightly
The price is $189
Oct 26 - Oct 27
Total with taxes and fees
Bo’s Bungalow with Hot Tub and Sauna
TV, fireplace, books
Farmhouse Cottage @ Old Pine Retreats, Farmhouse Cottage @ Old Pine Retreats
Farmhouse Cottage @ Old Pine Retreats, Farmhouse Cottage @ Old Pine Retreats
10.0 out of 10, Exceptional, (12)
"Place was wonderful. It was clean had everything needed and amazing views. Hosts were kind enough to let us check in a little early and were very kind. "
United States
Emma C.
$245 nightly
The price is $258
Nov 5 - Nov 6
Total with taxes and fees
Farmhouse Cottage @ Old Pine Retreats, Farmhouse Cottage @ Old Pine Retreats
Private kitchen
Big Sky Retreat
Big Sky Retreat
10.0 out of 10, Exceptional, (14)
"Nice central location. Super comfy beds and nice updates in the house."
United States
Blake S.
$360 nightly
The price is $389
Nov 5 - Nov 6
Total with taxes and fees
Big Sky Retreat
Children's area
Bo's Old West Den | Cozy and Comfy | Western Decor | Hot Tub | Off-Street Parking
Bo's Old West Den | Cozy and Comfy | Western Decor | Hot Tub | Off-Street Parking
9.8 out of 10, Exceptional, (7)
"Another great stay in the Den! "
United States
Shayla J.
$168 nightly
The price is $182
Oct 27 - Oct 28
Total with taxes and fees
Bo's Old West Den | Cozy and Comfy | Western Decor | Hot Tub | Off-Street Parking
Fridge, microwave, oven, stovetop
Come and stay at Emerald Cottage, your mini home away from home.
Come and stay at Emerald Cottage, your mini home away from home.
9.0 out of 10, Wonderful, (39)
"Owners were very responsive. Neighorhood super quiet. Easy to get to places."
United States
Carl T.
$178 nightly
The price is $192
Nov 10 - Nov 11
Total with taxes and fees
Come and stay at Emerald Cottage, your mini home away from home.
Fridge, microwave, oven, stovetop
Bo’s Old West Abode with Hot Tub and Sauna
Bo’s Old West Abode with Hot Tub and Sauna
8.4 out of 10, Very Good, (16)
"Great place and responsive owner. Love the hot tub."
United States
c h.
$175 nightly
The price is $189
Oct 25 - Oct 26
Total with taxes and fees
Bo’s Old West Abode with Hot Tub and Sauna
TV, fireplace
Boho Bungalow @ Old Pine Retreats
Boho Bungalow @ Old Pine Retreats
9.6 out of 10, Exceptional, (20)
"Absolute dream. Such a great getaway experience. "
United States
April
$206 nightly
The price is $217
Oct 27 - Oct 28
Total with taxes and fees
Boho Bungalow @ Old Pine Retreats
Private kitchen
Custer Cottage / Fenced Yard
Custer Cottage / Fenced Yard
9.8 out of 10, Exceptional, (15)
"It was a great place to spend the night on my way west."
United States
JT H.
$254 nightly
The price is $274
Nov 2 - Nov 3
Total with taxes and fees
Custer Cottage / Fenced Yard
Smart TV, table tennis, books
The Lakehouse: Pool, Theater, Game Room, Lakefront
The Lakehouse: Pool, Theater, Game Room, Lakefront
9.6 out of 10, Exceptional, (5)
"It's nice "
United States
Brayden E.
$375 nightly
The price is $405
Oct 26 - Oct 27
Total with taxes and fees
The Lakehouse: Pool, Theater, Game Room, Lakefront
Exterior
Pet-Friendly 3BR Billings Home with Fenced Yard, Gym Near Hospitals & Downtown
Pet-Friendly 3BR Billings Home with Fenced Yard, Gym Near Hospitals & Downtown
10.0 out of 10, Exceptional, (6)
"Great communication with Jon, checked up on our stay and was very helpful and attentive"
Canada
Anonymous traveler
$250 nightly
The price is $270
Nov 18 - Nov 19
Total with taxes and fees
Pet-Friendly 3BR Billings Home with Fenced Yard, Gym Near Hospitals & Downtown
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

Dude Rancher Lodge

Dude Rancher Lodge

10/10 Excellent
"Older facility but clean and cozy. Very convenient to restaurants and bars. Nice staff. "
Collette 1-night trip
Posted 2 days ago
Dude Rancher Lodge

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 $165 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?

Triangular Casa in 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 selection of games 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 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.