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Shepherd Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Shepherd holiday rentals

Smart TV, DVD player, video library

1. 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
10.0 out of 10, Exceptional, (14 reviews)
"Perfect for a family of 6, comfy and clean. Far enough outside of Billings but not to far. "
United States
Dustin
The price is HK$1,404
HK$1,736 total
includes taxes & fees
10 Sept - 11 Sept
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
Outdoor dining

2. Farmhouse Cottage @ Old Pine Retreats

Farmhouse Cottage @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (19 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$1,169
HK$2,200 total
includes taxes & fees
29 Sept - 30 Sept
Farmhouse Cottage @ Old Pine Retreats
Exterior

3. Industrial Loft @ Old Pine Retreats

Industrial Loft @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (13 reviews)
"We loved this place! It was very clean and the hot tub was kept clean as well. I definitely will stay here again for our next Billings weekends"
United States
Nicholas M.
The price is HK$1,276
HK$2,332 total
includes taxes & fees
24 Sept - 25 Sept
Industrial Loft @ Old Pine Retreats
Terrace/patio

4. Boho Bungalow @ Old Pine Retreats

Boho Bungalow @ Old Pine Retreats
Billings
9.8 out of 10, Exceptional, (32 reviews)
"Everything about this place was perfect! They also have a fabulous area for group meetings!!! Make this your next stay"
United Kingdom
Melanie W.
The price is HK$1,045
HK$1,915 total
includes taxes & fees
29 Sept - 30 Sept
Boho Bungalow @ Old Pine Retreats
Outdoor pool

5. The Lakehouse: Pool, Theater, Game Room, Lakefront

The Lakehouse: Pool, Theater, Game Room, Lakefront
Billings Heights
9.8 out of 10, Exceptional, (17 reviews)
"Great house / great location "
United States
maggie g.
The price is HK$1,311
HK$3,447 total
includes taxes & fees
8 Sept - 9 Sept
The Lakehouse: Pool, Theater, Game Room, Lakefront
Outdoor dining

6. Luxury Living Next Door to Hospital

Luxury Living Next Door to Hospital
Downtown Billings
10.0 out of 10, Exceptional, (14 reviews)
"Great place to stay, very clean."
United States
Orson J.
The price is HK$1,293
HK$2,859 total
includes taxes & fees
8 Sept - 9 Sept
Luxury Living Next Door to Hospital
TV

7. Big Sky Retreat

Big Sky Retreat
Midtown
9.6 out of 10, Exceptional, (24 reviews)
"It was great place to stay. "
United States
Stacy S.
The price is HK$1,681
HK$3,416 total
includes taxes & fees
7 Sept - 8 Sept
Big Sky Retreat
Smart TV

8. Triangular Casa in Billings

Triangular Casa in Billings
Central - Terry
9.6 out of 10, Exceptional, (131 reviews)
"The place was good for what we needed for a quick stop over."
United States
Robert
The price is HK$790
HK$1,547 total
includes taxes & fees
1 Sept - 2 Sept
Triangular Casa in Billings
TV

9. Bo’s Urban Farm House | 2bed | 1 bath | Large Yard

Bo’s Urban Farm House | 2bed | 1 bath | Large Yard
Central - Terry
9.2 out of 10, Wonderful, (22 reviews)
"This was a great place to stay. "
United States
Christina W.
The price is HK$1,050
HK$2,066 total
includes taxes & fees
30 Aug - 31 Aug
Bo’s Urban Farm House | 2bed | 1 bath | Large Yard
Outdoor spa tub

10. Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood

Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood
Central - Terry
9.6 out of 10, Exceptional, (78 reviews)
"Appreciated the easy check-in, hot tub, and comfortable beds."
United States
Chad B.
The price is HK$1,203
HK$2,349 total
includes taxes & fees
31 Aug - 1 Sept
Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood
Exterior

11. Pet Friendly 2BR Home w/ fenced backyard

Pet Friendly 2BR Home w/ fenced backyard
Central - Terry
9.4 out of 10, Exceptional, (29 reviews)
"Great value for the price on a quick trip to Billings."
United States
Tim K.
The price is HK$912
HK$1,857 total
includes taxes & fees
30 Aug - 31 Aug
Pet Friendly 2BR Home w/ fenced backyard
Dining

12. Pet Friendly, Fenced Backyard with Washer and Dryer

Pet Friendly, Fenced Backyard with Washer and Dryer
Central - Terry
9.6 out of 10, Exceptional, (27 reviews)
"We stayed in town for a couple months and the place was great!"
United States
Ben W.
The price is HK$912
HK$2,086 total
includes taxes & fees
30 Aug - 31 Aug
Pet Friendly, Fenced Backyard with Washer and Dryer
TV

13. Custer Cottage / Fenced Yard

Custer Cottage / Fenced Yard
Midtown
10.0 out of 10, Exceptional, (33 reviews)
"It was a great experience will definitely want to stay there again when we come back "
United States
Chris R.
The price is HK$1,333
HK$2,303 total
includes taxes & fees
20 Sept - 21 Sept
Custer Cottage / Fenced Yard
Smart TV, fireplace

14. Private 1BR Guesthouse Retreat

Private 1BR Guesthouse Retreat
Central - Terry
9.8 out of 10, Exceptional, (20 reviews)
"It was a nice place to relax and enjoy some time alone"
United States
nasheena
The price is HK$807
HK$1,625 total
includes taxes & fees
30 Aug - 31 Aug
Private 1BR Guesthouse Retreat
Interior

15. Steps to Hospital and MSU-B| Renovated Hospital Retreat

Steps to Hospital and MSU-B| Renovated Hospital Retreat
Downtown Billings
9.8 out of 10, Exceptional, (8 reviews)
"Very close to medical facilities, clean and new."
United States
Danielle T.
The price is HK$1,293
HK$2,859 total
includes taxes & fees
30 Aug - 31 Aug
Steps to Hospital and MSU-B| Renovated Hospital Retreat
Coffee/tea maker, fridge, microwave, oven

16. Quaint sunny cottage that rests in the historical neighborhood of Billings

Quaint sunny cottage that rests in the historical neighborhood of Billings
North Elevation Historic District
10.0 out of 10, Exceptional, (26 reviews)
"Property was clean & well appointed. Host was welcoming and communicative. Nice yard. Great location!"
United States
Mildred
The price is HK$974
HK$1,932 total
includes taxes & fees
31 Aug - 1 Sept
Quaint sunny cottage that rests in the historical neighborhood of Billings
Interior

17. Townhome • Hospital District • King Bed + Garage

Townhome • Hospital District • King Bed + Garage
Central - Terry
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful home and close to downtown so that was a bonus! "
United States
Chandale F.
The price is HK$923
HK$2,444 total
includes taxes & fees
30 Aug - 31 Aug
Townhome • Hospital District • King Bed + Garage
Exterior

18. Pet Friendly 2BR near hospitals, downtown, & airport

Pet Friendly 2BR near hospitals, downtown, & airport
North Elevation Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Great spot. Super close to everything in Billings. The hosts are great and VERY responsive to any questions or concerns you have. Thanks for the great stay!"
United States
Melanie S.
Pet Friendly 2BR near hospitals, downtown, & airport
Interior

19. A clean, comfortable space just off the interstate with easy parking.

A clean, comfortable space just off the interstate with easy parking.
Worden
9.8 out of 10, Exceptional, (25 reviews)
"Great place!"
United States
Julie C.
The price is HK$748
HK$1,104 total
includes taxes & fees
30 Aug - 31 Aug
A clean, comfortable space just off the interstate with easy parking.
Smart TV

20. Privates Home with Views • Near Med & Airport/DT Two King beds and 2 Queen Beds

Privates Home with Views • Near Med & Airport/DT Two King beds and 2 Queen Beds
Rimrock
10.0 out of 10, Exceptional, (12 reviews)
"Everything was great"
United States
Ryan A.
The price is HK$1,709
HK$3,657 total
includes taxes & fees
2 Sept - 3 Sept
Privates Home with Views • Near Med & Airport/DT Two King beds and 2 Queen Beds
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

Hyatt Place Billings

Hyatt Place Billings

10/10 Excellent
"The hotel facilities were excellent. Friendly staff, clean rooms, pool and fitness areas were top notch. Only complaint was the breakfast. The room and set up was excellent. However, the food was mediocre at best. Except for the food, excellent place to stay!"
Bruce 1-night trip
Posted less than an hour ago
Hyatt Place 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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  • 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?

Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood: This holiday home rental outside of Shepherd offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.