Shepherd Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Shepherd vacation 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 ￥13,470
￥20,538 total
includes taxes & fees
Jan 24 - Jan 25
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 ￥12,123
￥19,083 total
includes taxes & fees
Jan 24 - Jan 25
Relaxing, cozy and comfortable
Exterior

Quiet 2BR w/ Backyard, Cozy Home and Covered Parking

Quiet 2BR w/ Backyard, Cozy Home and Covered Parking
Central - Terry
9.4 out of 10, Exceptional, (21 reviews)
"Great value for the price on a quick trip to Billings."
United States
Tim K.
The price is ￥14,205
￥31,777 total
includes taxes & fees
Jan 24 - Jan 25
Quiet 2BR w/ Backyard, Cozy Home and Covered Parking
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 ￥15,693
￥33,897 total
includes taxes & fees
Jan 24 - Jan 25
Bo’s Urban Farm House.
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.
Billings
8.8 out of 10, Excellent, (44 reviews)
"Great cozy place that is close to a alot to do "
United States
James B.
The price is ￥10,301
￥26,528 total
includes taxes & fees
Jan 24 - Jan 25
Come and stay at Emerald Cottage, your mini home away from home.
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)
"Great place and responsive owner. Love the hot tub."
United States
c h.
The price is ￥15,055
￥29,780 total
includes taxes & fees
Jan 24 - Jan 25
Bo’s Old West Abode with Hot Tub and Sauna
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 ￥10,649
￥37,687 total
includes taxes & fees
Jan 30 - Jan 31
Townhome • Hospital District • King Bed + Garage
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 ￥15,982
￥34,838 total
includes taxes & fees
Feb 10 - Feb 11
Industrial Loft @ Old Pine Retreats
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 ￥19,254
￥36,026 total
includes taxes & fees
Jan 25 - Jan 26
*New* Montana Dreamin’ Home
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.
The price is ￥14,143
￥28,111 total
includes taxes & fees
Jan 24 - Jan 25
Bo's Old West Den | Cozy and Comfy | Western Decor | Hot Tub | Off-Street Parking
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 ￥15,700
￥34,534 total
includes taxes & fees
Feb 10 - Feb 11
Farmhouse Cottage @ Old Pine Retreats
TV

Custer Cottage / Fenced Yard

Custer Cottage / Fenced Yard
Billings
9.8 out of 10, Exceptional, (20 reviews)
"Perfect place, clean, and had everything you needed. "
United States
Marlenea
The price is ￥26,940
￥46,210 total
includes taxes & fees
Jan 24 - Jan 25
Custer Cottage / Fenced Yard
Sport court

Bo’s 3BR Retreat • Hot Tub • Sauna • Den Suite

Bo’s 3BR Retreat • Hot Tub • Sauna • Den Suite
Central - Terry
10.0 out of 10, Exceptional, (1 review)
"It was just a quick trip for us but it was nice to have a place to stay all together. We enjoyed the hot tub and sauna. "
United States
Jennifer A.
Bo’s 3BR Retreat • Hot Tub • Sauna • Den Suite
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 ￥9,984
￥21,907 total
includes taxes & fees
Feb 1 - Feb 2
Triangular Casa in 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 ￥28,525
￥34,743 total
includes taxes & fees
Jan 24 - Jan 25
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
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 ￥12,678
￥27,384 total
includes taxes & fees
Jan 24 - Jan 25
Restored Vintage Mobile Home on our small Private Ranch
Dining

Bo’s White House with Fenced Yard

Bo’s White House with Fenced Yard
Central - Terry
9.6 out of 10, Exceptional, (24 reviews)
"Clean, convenient and perfect for our family!"
United States
Mindy J.
The price is ￥19,424
￥43,057 total
includes taxes & fees
Jan 24 - Jan 25
Bo’s White House with Fenced Yard
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 ￥22,677
￥39,209 total
includes taxes & fees
Jan 24 - Jan 25
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful 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 ￥14,262
￥31,833 total
includes taxes & fees
Jan 25 - Jan 26
Rims view pet friendly home
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 ￥15,506
￥30,267 total
includes taxes & fees
Jan 24 - Jan 25
Bo’s Bungalow with Hot Tub and Sauna
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
"Yes"
Robert 1-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:

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

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?

Enjoy the hot tub and gas fire pit in this 5 bedroom 2.5 bath house: This vacation home rental near Shepherd offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

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.