Shepherd Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Shepherd holiday rentals

Exterior detail

Quaint Cottage @ Fort Nibbe

Quaint Cottage @ Fort Nibbe
Worden
9.8 out of 10, Exceptional, (16 reviews)
"Very cute and cozy stay!!!"
United States
Sharlys D.
The price is HK$664
HK$1,012 total
includes taxes & fees
13 Feb - 14 Feb
Quaint Cottage @ Fort Nibbe
Interior

Relaxing, cozy and comfortable

Relaxing, cozy and comfortable
Worden
9.8 out of 10, Exceptional, (18 reviews)
"Loved this stay!!! Very cozy and spacious!"
United States
Sharlys D.
The price is HK$598
HK$941 total
includes taxes & fees
5 Feb - 6 Feb
Relaxing, cozy and comfortable
Terrace/patio

*New* Montana Dreamin’ Home

*New* Montana Dreamin’ Home
Billings
9.6 out of 10, Exceptional, (30 reviews)
"We loved it here!! Very clean and inviting! "
United States
amanda b.
The price is HK$949
HK$1,776 total
includes taxes & fees
8 Feb - 9 Feb
*New* Montana Dreamin’ Home
Exterior

Industrial Loft @ Old Pine Retreats

Industrial Loft @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (8 reviews)
"Awesome place with everything you need. Very clean. Highly recommend!"
United States
Matt C.
The price is HK$781
HK$1,727 total
includes taxes & fees
24 Feb - 25 Feb
Industrial Loft @ Old Pine Retreats
Outdoor dining

Farmhouse Cottage @ Old Pine Retreats

Farmhouse Cottage @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (13 reviews)
"So charming and nicely decorated! Wonderful deck areas quiet area. Would definitely recommend and will be back!"
United States
Jessica L.
The price is HK$774
HK$1,719 total
includes taxes & fees
24 Feb - 25 Feb
Farmhouse Cottage @ Old Pine Retreats
Smart TV

Triangular Casa in Billings

Triangular Casa in Billings
Central - Terry
9.6 out of 10, Exceptional, (112 reviews)
"House was super clean! It was perfect for two couples to stay before headed to the airport. "
United States
McKenzie
The price is HK$548
HK$1,141 total
includes taxes & fees
5 Feb - 6 Feb
Triangular Casa in Billings
TV

Custer Cottage / Fenced Yard

Custer Cottage / Fenced Yard
Billings
10.0 out of 10, Exceptional, (21 reviews)
"Perfect place, clean, and had everything you needed. "
United States
Marlenea
The price is HK$1,070
HK$1,966 total
includes taxes & fees
5 Feb - 6 Feb
Custer Cottage / Fenced Yard
Exterior

Restored Vintage Mobile Home on our small Private Ranch

Restored Vintage Mobile Home on our small Private Ranch
Lavina
9.0 out of 10, Wonderful, (8 reviews)
"Our stay was awesome!! 2nd time staying here and will definitely stay here again. "
United States
Kevin J.
The price is HK$625
HK$1,350 total
includes taxes & fees
5 Feb - 6 Feb
Restored Vintage Mobile Home on our small Private Ranch
Terrace/patio

Bo’s Old West Abode with Hot Tub and Sauna

Bo’s Old West Abode with Hot Tub and Sauna
Central - Terry
8.8 out of 10, Excellent, (19 reviews)
"Nice quaint abode, perfect for a little weekend getaway. Very welcoming easy to access and comfortable. Bathroom is a little crammed for larger people. But in all great experience."
United States
Zach S.
Bo’s Old West Abode with Hot Tub and Sauna
Terrace/patio

Boho Bungalow @ Old Pine Retreats

Boho Bungalow @ Old Pine Retreats
Billings
9.8 out of 10, Exceptional, (21 reviews)
"Absolute gem, after 5 days on the road sight seeing this was the perfect spot to relax for a couple days."
United States
Mike W.
The price is HK$697
HK$1,494 total
includes taxes & fees
9 Feb - 10 Feb
Boho Bungalow @ Old Pine Retreats
TV

Bo’s Urban Farm House.

Bo’s Urban Farm House.
Central - Terry
9.4 out of 10, Exceptional, (18 reviews)
"This was a great place to stay. "
United States
Christina W.
The price is HK$773
HK$1,696 total
includes taxes & fees
5 Feb - 6 Feb
Bo’s Urban Farm House.
Fridge, microwave, oven, stovetop

Charming 3-bedroom townhome in Billings

Charming 3-bedroom townhome in Billings
Billings
10.0 out of 10, Exceptional, (14 reviews)
"Nice place. As described. "
United States
Russ M.
The price is HK$1,060
HK$2,233 total
includes taxes & fees
9 Feb - 10 Feb
Charming 3-bedroom townhome in Billings
Interior

Rims view pet friendly home

Rims view pet friendly home
Rimrock
9.4 out of 10, Exceptional, (61 reviews)
"Great stay"
United States
Al B.
The price is HK$703
HK$1,561 total
includes taxes & fees
20 Feb - 21 Feb
Rims view pet friendly home
Interior

Townhome • Hospital District • King Bed + Garage

Townhome • Hospital District • King Bed + Garage
Central - Terry
10.0 out of 10, Exceptional, (2 reviews)
"The property was very clean and quiet and very well stocked with plenty of cleaning supplies kitchen utensils and necessities. Very Pet friendly, easy off street parking attached garage. Warm and welcoming."
United States
Carmela H.
The price is HK$766
HK$2,126 total
includes taxes & fees
28 Feb - 1 Mar
Townhome • Hospital District • King Bed + Garage
Terrace/patio

Bo’s Bungalow with Hot Tub and Sauna

Bo’s Bungalow with Hot Tub and Sauna
Central - Terry
9.6 out of 10, Exceptional, (14 reviews)
"Feels like home"
United States
Michael O.
The price is HK$765
HK$1,492 total
includes taxes & fees
5 Feb - 6 Feb
Bo’s Bungalow with Hot Tub and Sauna
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
Central - Terry
10.0 out of 10, Exceptional, (7 reviews)
"Great communication with Jon, checked up on our stay and was very helpful and attentive"
Canada
Anonymous traveller
The price is HK$1,111
HK$2,305 total
includes taxes & fees
5 Feb - 6 Feb
Pet-Friendly 3BR Billings Home with Fenced Yard, Gym Near Hospitals & Downtown
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
Central - Terry
9.8 out of 10, Exceptional, (7 reviews)
"Another great stay in the Den! "
United States
Shayla J.
Bo's Old West Den | Cozy and Comfy | Western Decor | Hot Tub | Off-Street Parking
Fridge, microwave, oven, stovetop

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

Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Billings
9.2 out of 10, Wonderful, (17 reviews)
"Great place to stay while visiting family. The grandkids loved the local park and riding bikes on all the sidewalks! "
United States
JOEL B.
The price is HK$1,160
HK$1,987 total
includes taxes & fees
5 Feb - 6 Feb
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Smart TV, DVD player, video library

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
9.6 out of 10, Exceptional, (5 reviews)
"House was perfect for our group. Beds were comfortable. Communication from property manager was accurate and on point."
United States
Amber R.
The price is HK$1,406
HK$1,713 total
includes taxes & fees
6 Feb - 7 Feb
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
Outdoor dining

Luxury Living Next Door to Hospital

Luxury Living Next Door to Hospital
Downtown Billings
9.8 out of 10, Exceptional, (6 reviews)
"Great little place to stay."
United States
Allison N.
The price is HK$1,031
HK$2,449 total
includes taxes & fees
5 Feb - 6 Feb
Luxury Living Next Door to Hospital
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

DoubleTree by Hilton Hotel Billings

DoubleTree by Hilton Hotel Billings

10/10 Excellent
"Amazing design and feel. Restaurant top notch especially for breakfast. Great to have a full coffee shop connected to lobby. "
Joshua 3-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Billings

Find out more about Shepherd

Search for holiday rentals in Shepherd on Expedia! You can easily find your home rentals, villas, holiday apartments in Shepherd using one of the methods below:

  • View our selection of featured holiday rentals in Shepherd
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  • Enter your travel dates to view the best deals on holiday rentals in Shepherd while they last

Look no further and take a look at our great range of rental properties in Shepherd!

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?

Triangular Casa in Billings: 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. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most 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 wider area, you’ll find Lake Elmo State Park and Heights Buffalo Palace Casino.

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.