Shepherd Vacation Rentals

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in Shepherd

Our top choices for Shepherd vacation rentals

Rims view pet friendly home
Terrace/patio

Rims view pet friendly home

9.6 out of 10, Exceptional, (45)
"Great place, absolutely recommend!"
$194 nightly
The price is $210
Sep 15 - Sep 16
Total with taxes and fees
Rims view pet friendly home
Come and stay at Emerald Cottage, your mini home away from home.
Fridge, microwave, oven, stovetop

Come and stay at Emerald Cottage, your mini home away from home.

9.0 out of 10, Wonderful, (35)
"Nestled in a quiet, safe neighborhood, this cottage was a perfect weekend spot. It is great for a family of 4. It was well stocked with snacks, laundry, and coffee. Thanks for a nice stay! "
$176 nightly
The price is $190
Sep 9 - Sep 10
Total with taxes and fees
Come and stay at Emerald Cottage, your mini home away from home.
Enjoy the saltwater hot tub and gas fire pit in this 5 bedroom 2.5 bath house
Property grounds

Enjoy the saltwater hot tub and gas fire pit in this 5 bedroom 2.5 bath house

2.0 star property
10.0 out of 10, Exceptional, (17)
"Great Stay in Billings. House has all the amenities. "
$428 nightly
The price is $462
Sep 8 - Sep 9
Total with taxes and fees
Enjoy the saltwater hot tub and gas fire pit in this 5 bedroom 2.5 bath house
Charming Montana Home w/ Grill: 6 Mi to Lake Elmo!
House (2 Bedrooms) | Interior

Charming Montana Home w/ Grill: 6 Mi to Lake Elmo!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great nice place to stay"
Charming Montana Home w/ Grill: 6 Mi to Lake Elmo!
Bo’s Old West Abode with Hot Tub and Sauna
Fridge, microwave, oven, stovetop

Bo’s Old West Abode with Hot Tub and Sauna

8.4 out of 10, Very Good, (15)
"Property as described, easy to find and communication with hosts was prompt. It’s deceiving when you approach from outside but it is as pictured. Decor cleanliness is spot on. We just need a place to rest our heads.. but it was a homey basement set up"
$176 nightly
The price is $190
Sep 2 - Sep 3
Total with taxes and fees
Bo’s Old West Abode with Hot Tub and Sauna
Billings Abode w/ Grill: Walk to Park & Shops
House (3 Bedrooms) | Interior

Billings Abode w/ Grill: Walk to Park & Shops

3.0 star property
10.0 out of 10, Exceptional, (1)
"A very nice aroma inside , very clean bathroom & kitchen"
Billings Abode w/ Grill: Walk to Park & Shops
Quaint sunny cottage that rests in the historical neighborhood of Billings
Terrace/patio

Quaint sunny cottage that rests in the historical neighborhood of Billings

10.0 out of 10, Exceptional, (22)
"Our family loved our stay here! "
$228 nightly
The price is $246
Sep 6 - Sep 7
Total with taxes and fees
Quaint sunny cottage that rests in the historical neighborhood of Billings
Yellowstone Valley Overlook - 10 acres 5 minutes from Billings
Property grounds

Yellowstone Valley Overlook - 10 acres 5 minutes from Billings

10.0 out of 10, Exceptional, (27)
"This house was great for my whole family to stay in during graduation. Would definitely recommend!! "
Yellowstone Valley Overlook - 10 acres 5 minutes from Billings
6 Mi to Zoomontana: Family Home w/ Fenced Yard
House (4 Bedrooms) | Interior

6 Mi to Zoomontana: Family Home w/ Fenced Yard

3.0 star property
6 Mi to Zoomontana: Family Home w/ Fenced Yard
Bo's Rusty Relic Billings |Hot Tub | Rustic decor | Central Billings
Children's area

Bo's Rusty Relic Billings |Hot Tub | Rustic decor | Central Billings

9.8 out of 10, Exceptional, (36)
"Very conveniently located, great service, clean, cute and cozy."
$222 nightly
The price is $240
Sep 1 - Sep 2
Total with taxes and fees
Bo's Rusty Relic Billings |Hot Tub | Rustic decor | Central Billings
Quaint Cottage @ Fort Nibbe
Private kitchen

Quaint Cottage @ Fort Nibbe

2.0 star property
9.8 out of 10, Exceptional, (11)
"The cottage is awesome, ended up staying 2 extra nights. The cottage is completely furnished. Will highly recommend, and like to come back again."
$115 nightly
The price is $124
Sep 1 - Sep 2
Total with taxes and fees
Quaint Cottage @ Fort Nibbe
Centrally located, huge shaded patio with hot tub! Entire place to yourself!
Outdoor spa tub

Centrally located, huge shaded patio with hot tub! Entire place to yourself!

10.0 out of 10, Exceptional, (45)
"Great place to stay! Hot tub was lovely. House was very clean with anything you need. Easy to find. Great location. Definitely be back in the future. "
$310 nightly
The price is $335
Sep 3 - Sep 4
Total with taxes and fees
Centrally located, huge shaded patio with hot tub! Entire place to yourself!
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (8)
"Very clean, excellent setup and comfortable."
$206 nightly
The price is $222
Sep 4 - Sep 5
Total with taxes and fees
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Bo's Howard Hideaway | Hot Tub | Fenced Yard
Terrace/patio

Bo's Howard Hideaway | Hot Tub | Fenced Yard

9.6 out of 10, Exceptional, (61)
"Loved staying here! It was very cozy and clean and the yard was awesome!"
$273 nightly
The price is $295
Sep 1 - Sep 2
Total with taxes and fees
Bo's Howard Hideaway | Hot Tub | Fenced Yard
Hot Tub + 1,600 sq ft Golf-Course Patio • Game Room & Luxury Living
Outdoor dining

Hot Tub + 1,600 sq ft Golf-Course Patio • Game Room & Luxury Living

4.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful, very family friendly house. Absolutely loved the outdoor living space which is where we spent most of our time when we were home. Manager was very responsive and the little welcoming touches were a nice surprise. Neighborhood is quiet and a great spot to use as a home base. We hope to stay here again next year."
Hot Tub + 1,600 sq ft Golf-Course Patio • Game Room & Luxury Living
Bo’s Urban Farm House.
Property grounds

Bo’s Urban Farm House.

9.4 out of 10, Exceptional, (14)
"As advertised nice little place, clean and everything worked. Neighborhood a little suspect but we had no issues. Would have been nice to get more than 1 roll of toilet paper but otherwise a good stay with our big dog."
Bo’s Urban Farm House.
Montana Mansion: Theater, Gym, Arcade, Billiards
Interior

Montana Mansion: Theater, Gym, Arcade, Billiards

2.0 star property
10.0 out of 10, Exceptional, (8)
"Beautiful home in Billings, MT"
$446 nightly
The price is $482
Sep 3 - Sep 4
Total with taxes and fees
Montana Mansion: Theater, Gym, Arcade, Billiards
Triangular Casa in Billings
Dining

Triangular Casa in Billings

9.6 out of 10, Exceptional, (99)
"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."
$167 nightly
The price is $180
Sep 2 - Sep 3
Total with taxes and fees
Triangular Casa in Billings
Tranquil 5 bedroom home with large deck and yard
Outdoor dining

Tranquil 5 bedroom home with large deck and yard

10.0 out of 10, Exceptional, (42)
"This is a wonderful property, we have stayed here a couple of times and would definitely stay again!"
Tranquil 5 bedroom home with large deck and yard
Wfh-friendly Billings Apt ~ 1 Mi to Downtown!
Apartment (1 Bedroom) | Interior

Wfh-friendly Billings Apt ~ 1 Mi to Downtown!

3.0 star property
8.4 out of 10, Very Good, (5)
"Perfect location and easy everything."
Wfh-friendly Billings Apt ~ 1 Mi to 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shepherd Hotel Reviews

Find out more about Shepherd

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 $124 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

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?

Rims view pet friendly home : This vacation home rental near Shepherd offers a fireplace, a patio, 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 dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.