Shepherd Holiday Rentals

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Holiday Rentals in Shepherd

Come and stay at Emerald Cottage, your mini home away from home.
9.4 out of 10, Exceptional, 6 reviews
"Super clean and well equiped. Quiet neighborhood. Loved the decor and comfort level. Would stay there many times in a heartbeat!"
The price is NZ$469
per night
20 Jun - 21 Jun
Come and stay at Emerald Cottage, your mini home away from home.
Renovated home in vintage neighborhood, close to airport, hospitals, & downtown.
10.0 out of 10, Exceptional, 38 reviews
"Very welcoming, it felt like home the moment we walked in. All the amenities of being at home. Everything was clean, fresh and the property is well maintained. Beautiful, quiet neighborhood. Centrally located giving us easy access to everywhere in Billings. We definitely recommend!"
Renovated home in vintage neighborhood, close to airport, hospitals, & downtown.
Spacious 4-Bedroom Haven in the Heart of Billings: Your Ideal Home Awaits!
9.6 out of 10, Exceptional, 5 reviews
"We rented this house for our Special O team and it was a perfect for our needs. The listing was accurate and perfect for our needs. Thank you!"
The price is NZ$647
per night
10 Jun - 11 Jun
Spacious 4-Bedroom Haven in the Heart of Billings: Your Ideal Home Awaits!
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Downtown 2 bedroom Loft apartment unit 5
10.0 out of 10, Exceptional, 1 review
"Very clean, nice little loft apartment. The bed was super comfy. Everything was great except we had difficulty with the TV and it lacked a good choice of channels. We also didn't think to bring liquid hand soap for the bathroom , so we had to use the dish soap in the kitchen. Very minor inconveniences ,so overall still a 5 star experience, highly recommend over spending money on hotel rooms."
The price is NZ$283
per night
17 Jun - 18 Jun
Downtown 2 bedroom Loft apartment unit 5
Ground level 2 bedroom loft apartment
10.0 out of 10, Exceptional, 2 reviews
"Great location in downtown Billings. Very clean! And convenient parking!"
The price is NZ$283
per night
17 Jun - 18 Jun
Ground level 2 bedroom loft apartment
Beautiful new construction 3-bedroom duplex townhome-
10.0 out of 10, Exceptional, 30 reviews
"I think if a traveler has planned activities in the Heights area, this property is perfect. It's beautiful, new "home" in a nice neighborhood that is currently at the end of the street in which it is quiet and away from the bright lights of the city. Although that being said, it is also located close to shopping and restaurants. Travelling to/from the airport is a breeze. Side note: it was perfect for viewing the Aurora Borealis!"
The price is NZ$558
per night
11 Jun - 12 Jun
Beautiful new construction 3-bedroom duplex townhome-
Modern West-End Haven
9.6 out of 10, Exceptional, 50 reviews
"The property was very nice- clean, comfortable beds, had everything we needed."
The price is NZ$916
per night
10 Jun - 11 Jun
Modern West-End Haven
Cozy one bedroom apartment in a beautiful neighborhood near airport and hospital
9.8 out of 10, Exceptional, 7 reviews
"The apartment is nice and cozy, as well as tucked away. I really enjoyed our stay, and wish we could have stayed longer. Highly recommend."
The price is NZ$209
per night
11 Jun - 12 Jun
Cozy one bedroom apartment in a beautiful neighborhood near airport and hospital
Rustic Modern secluded home minutes from Billings shopping and restaurants
10.0 out of 10, Exceptional, 7 reviews
"You won’t tick the neighbors off in this place…because it’s not in a residential neighborhood! That said, it doesn’t feel weird to be in the quiet industrial park. Very clean, very well stocked with all the basics and close to downtown, retailing, eateries, etc. The only thing that might be different for some parties is there’s just one bath with a shower, and it’s accessed via the master bedroom. Not a big deal for us because we were all friends."
Rustic Modern secluded home minutes from Billings shopping and restaurants
Centrally located, huge shaded patio with hot tub! Entire place to yourself!
10.0 out of 10, Exceptional, 18 reviews
"The heated beds in the basement were helpful when trying to keep the main floor cool! The house is situated within 5 minutes of restaurants, gas, Walmart, and access to the Interstate. Having individual large screen TVs in each of the single bedrooms a plus especially when travelling with younger adults."
The price is NZ$654
per night
9 Jun - 10 Jun
Centrally located, huge shaded patio with hot tub! Entire place to yourself!
Bo’s Central Studio with Washer, Dryer & HOT TUB
10.0 out of 10, Exceptional, 1 review
"Great little place to stay. Super communication! Planning on staying again for our next visit."
Bo’s Central Studio with Washer, Dryer & HOT TUB
Bo’s Bungalow with Hot Tub and Sauna
9.6 out of 10, Exceptional, 4 reviews
"I can't really comment much on this property itself. But I can comment on Bo's hospitality and customer service. You see, there was a no-fault plumbing issue upon our arrival. Bo did everything in his power to make sure we still had a good trip, quickly moving us into another property of his that was right next door to this one. What could have been a headache of a trip turned around to meet and beat our expectations, thanks to Bo being on the ball even though he was out of town. We very much...
The price is NZ$304
per night
9 Jun - 10 Jun
Bo’s Bungalow with Hot Tub and Sauna
Premium Home with Fire Pit-Patio Private Park, Walking Path, Family Neighborhood
10.0 out of 10, Exceptional, 3 reviews
"The house is beautiful, was clean and decorated for Christmas upon arrival. The house has everything you need and the beds were very comfortable. We had a great time and would definitely stay again!"
Premium Home with Fire Pit-Patio Private Park, Walking Path, Family Neighborhood
Rims view pet friendly home
9.0 out of 10, Wonderful, 8 reviews
"Such a nice place to stay. Beautiful comfortable well maintained home. Gorgeous neighbourhood. The outdoor space was so quiet and relaxing. So nicely decorated and welcoming felt like a home away from home."
The price is NZ$368
per night
13 Jun - 14 Jun
Rims view pet friendly home
"The Dugout" in the Bull Mountains...a quaint little getaway!
10.0 out of 10, Exceptional, 28 reviews
"We came home for Christmas and this was a great place to stay. It was clean, quiet and easy to keep warm. Beds were comfortable and the living room was a great place to hang out and relax at night."
The price is NZ$269
per night
29 Jun - 30 Jun
"The Dugout" in the Bull Mountains...a quaint little getaway!
801 North 25 Street · Cozy cottage in the heart of the big city
10.0 out of 10, Exceptional, 2 reviews
"Great little older home -quiet neighborhood ~and is in a great location to downtown businesses, Metro Park etc. Hosts were very responsive too. Thank you!"
801 North 25 Street · Cozy cottage in the heart of the big city
Centrally located 4BR 5 BED; Beautiful backyard
9.6 out of 10, Exceptional, 10 reviews
"Easy to find. Great communication with the owner. Sooooo nice to have a pet friendly home!! Took away the anxiety of trying to find pet sitters or boarding. Our fur babies were super happy with the fully fenced yard! Our human babies enjoyed the tree swing and toys! All in all we very much enjoyed our stay and would highly recommend it!"
Centrally located 4BR 5 BED; Beautiful backyard
720 N 31st · Timelessly restored home - entirely yours to enjoy
720 N 31st · Timelessly restored home - entirely yours to enjoy
Cozy Cabin with Incredible 360 views & Starlink Internet!
10.0 out of 10, Exceptional, 20 reviews
"We came out to pick up our daughter from college. House is amazing with beautiful views. Would definitely book again. Thank you for sharing your home."
The price is NZ$1,057
per night
17 Jun - 18 Jun
Cozy Cabin with Incredible 360 views & Starlink Internet!
Stunning 4 Bedroom Home - Prime Location
9.4 out of 10, Exceptional, 28 reviews
"Great house with a nice backyard and deck"
The price is NZ$658
per night
26 Jun - 27 Jun
Stunning 4 Bedroom Home - Prime Location
Don't see what you're looking for?
See all available properties in Shepherd
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.

Other types of properties in Shepherd you may be interested in

Kelly Inn Billings Montana
2.5 star property
8.2 out of 10, Very good, 1,290 reviews
"Very nice."
The price is NZ$216
per night
9 Jun - 10 Jun
Kelly Inn Billings Montana
La Quinta Inn & Suites by Wyndham Billings
2.5 star property
9.0 out of 10, Wonderful, 1,017 reviews
"Our one night stay was very pleasant. Nice appearance in this hotel including hallways and rooms. Plenty of choices at breakfast. The service was good at all levels. "
The price is NZ$267
per night
16 Jun - 17 Jun
La Quinta Inn & Suites by Wyndham Billings
Hilltop Inn by Riversage
3.0 star property
9.0 out of 10, Wonderful, 1,315 reviews
"Nice clean confortable room. Free popcorn and cookies at check in."
The price is NZ$211
per night
10 Jun - 11 Jun
Hilltop Inn by Riversage
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Shepherd holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Shepherd. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Shepherd. Seeing all the best attractions is bound to make you fall in love with Shepherd. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Shepherd short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Shepherd?

Yes, there are holiday rentals close to the most popular sights in Shepherd, or you can select a more secluded option if you're looking for a relaxing stay.

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

Beautiful new construction 3-bedroom duplex townhome-: This holiday home rental outside of Shepherd offers a patio, a garden and air conditioning 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 that 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 wider area, you’ll find Lake Elmo State Park and MetraPark.

What are holiday rentals like in Shepherd?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shepherd. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for families.

Recent reviews of Shepherd properties
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