Shepherd Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Shepherd holiday rentals

Exterior detail

Cottage in Worden

Quaint Cottage @ Fort Nibbe
9.8 out of 10, Exceptional, (16 reviews)
"Very cute and cozy stay!!!"
United States
Sharlys D.
Quaint Cottage @ Fort Nibbe
Interior

Holiday Home in Worden

Relaxing, cozy and comfortable
9.8 out of 10, Exceptional, (18 reviews)
"Great place!"
United States
Julie C.
The price is HK$666
HK$1,015 total
includes taxes & fees
6 Apr - 7 Apr
Relaxing, cozy and comfortable
Terrace/patio

Holiday Home in Central - Terry

Bo’s Bungalow with Hot Tub and Sauna
9.6 out of 10, Exceptional, (15 reviews)
"Feels like home"
United States
Michael O.
The price is HK$766
HK$1,513 total
includes taxes & fees
23 Mar - 24 Mar
Bo’s Bungalow with Hot Tub and Sauna
Smart TV, fireplace

Mobile Home in Central - Terry

Bo`s Private 1BR Guesthouse Retreat | Hot Tub • Sauna • Gym
10.0 out of 10, Exceptional, (15 reviews)
"Great location in Billings. Adorable home, tiny but much better than hotel options. "
United States
Melani V.
The price is HK$807
HK$1,430 total
includes taxes & fees
23 Mar - 24 Mar
Bo`s Private 1BR Guesthouse Retreat | Hot Tub • Sauna • Gym
Terrace/patio

Apartment in Central - Terry

Bo’s Old West Abode with Hot Tub and Sauna
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.
The price is HK$744
HK$1,472 total
includes taxes & fees
23 Mar - 24 Mar
Bo’s Old West Abode with Hot Tub and Sauna
Terrace/patio

Cottage in Billings

*New* Montana Dreamin’ Home
9.6 out of 10, Exceptional, (30 reviews)
"We loved it here!! Very clean and inviting! "
United States
amanda b.
The price is HK$1,057
HK$1,937 total
includes taxes & fees
5 Apr - 6 Apr
*New* Montana Dreamin’ Home
Exterior

Holiday Home in Billings

Industrial Loft @ Old Pine Retreats
10.0 out of 10, Exceptional, (9 reviews)
"Awesome place with everything you need. Very clean. Highly recommend!"
United States
Matt C.
The price is HK$1,028
HK$2,030 total
includes taxes & fees
23 Mar - 24 Mar
Industrial Loft @ Old Pine Retreats
Interior

Cottage in Rimrock

Rims view pet friendly home
9.4 out of 10, Exceptional, (70 reviews)
"Host was very quick to respond to messages, the third time we have stayed here and it always good!"
United States
Tonya B.
The price is HK$705
HK$1,590 total
includes taxes & fees
23 Mar - 24 Mar
Rims view pet friendly home
TV

Cottage in Billings

Custer Cottage / Fenced Yard
10.0 out of 10, Exceptional, (22 reviews)
"Perfect place, clean, and had everything you needed. "
United States
Marlenea
The price is HK$1,230
HK$2,174 total
includes taxes & fees
23 Mar - 24 Mar
Custer Cottage / Fenced Yard
Outdoor dining

Holiday Home in Billings

Farmhouse Cottage @ Old Pine Retreats
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$987
HK$1,977 total
includes taxes & fees
30 Mar - 31 Mar
Farmhouse Cottage @ Old Pine Retreats
Smart TV, DVD player, video library

Holiday Home in Billings

Lovely 4-bedroom house in Lockwood with large yard and covered patio!
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$1,410
HK$1,743 total
includes taxes & fees
3 Apr - 4 Apr
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
Smart TV

Holiday Home in Central - Terry

Triangular Casa in Billings
9.6 out of 10, Exceptional, (115 reviews)
"Wonderful little home! Warm and cozy and super centrally located. "
United States
Lauren J.
The price is HK$585
HK$1,182 total
includes taxes & fees
30 Mar - 31 Mar
Triangular Casa in Billings
Outdoor spa tub

Holiday Home in Central - Terry

Rustic Cottage Cozy & Charming
9.4 out of 10, Exceptional, (69 reviews)
"Only stayed one night, beds were comfortable, fenced in yard great for dog."
United States
jon b.
The price is HK$1,009
HK$1,977 total
includes taxes & fees
23 Mar - 24 Mar
Rustic Cottage Cozy & Charming
Fridge, microwave, oven, stovetop

Holiday Home in Billings

Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
9.2 out of 10, Wonderful, (17 reviews)
"Beautiful place!!! Host was wonderful and I would LOVE to stay there again in the future!!"
United States
Laura
The price is HK$1,057
HK$1,878 total
includes taxes & fees
22 Apr - 23 Apr
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Terrace/patio

Holiday Home in Billings

Boho Bungalow @ Old Pine Retreats
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$946
HK$1,807 total
includes taxes & fees
29 Mar - 30 Mar
Boho Bungalow @ Old Pine Retreats
TV

Holiday Home in Billings

Big Sky Retreat
10.0 out of 10, Exceptional, (18 reviews)
"Host was very helpful with information about the house, closest grocery store and what we would need. "
United States
Carla W.
Big Sky Retreat
Outdoor dining

Apartment in Downtown Billings

Luxury Living Next Door to Hospital
9.8 out of 10, Exceptional, (6 reviews)
"Great little place to stay."
United States
Allison N.
The price is HK$1,120
HK$2,554 total
includes taxes & fees
9 Apr - 10 Apr
Luxury Living Next Door to Hospital
Exterior

Holiday Home in Central - Terry

Quiet 2BR w/ Backyard, Cozy Home and Covered Parking
9.4 out of 10, Exceptional, (22 reviews)
"Great value for the price on a quick trip to Billings."
United States
Tim K.
The price is HK$766
HK$1,665 total
includes taxes & fees
30 Mar - 31 Mar
Quiet 2BR w/ Backyard, Cozy Home and Covered Parking
Property grounds

Holiday Home in West End

Enjoy the hot tub and gas fire pit in this 5 bedroom 2.5 bath house
10.0 out of 10, Exceptional, (28 reviews)
"Beautiful place to stay. Host went above and beyond. Would definitely love to stay here again."
United States
Rachel L.
Enjoy the hot tub and gas fire pit in this 5 bedroom 2.5 bath house
Interior

Holiday Home in Central - Terry

Townhome • Hospital District • King Bed + Garage
10.0 out of 10, Exceptional, (3 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$666
HK$2,030 total
includes taxes & fees
20 Apr - 21 Apr
Townhome • Hospital District • King Bed + Garage
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

Boothill Inn And Suites

Boothill Inn And Suites

10/10 Excellent
"Clean, comfortable beds, pool/hot tubs excellent. Staff were awesome "
Sue 2-night trip
Posted 3 hours ago
Boothill Inn And Suites

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
  • Use the map to find apartments and other holiday homes in the Shepherd neighbourhood you prefer
  • 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 First Interstate Arena at 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.