Holiday Rentals in Shepherd

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Our top choices for Shepherd holiday rentals

2.0 star property
9.8 out of 10, Exceptional, (16 reviews)
"Very cute and cozy stay!!!"
United States
Sharlys D.
The price is €116
includes taxes & fees
19 Jan - 20 Jan
Quaint Cottage @ Fort Nibbe

Holiday Home in Worden

Relaxing, cozy and comfortable
9.8 out of 10, Exceptional, (18 reviews)
"Loved this stay!!! Very cozy and spacious!"
United States
Sharlys D.
The price is €108
includes taxes & fees
19 Jan - 20 Jan
Relaxing, cozy and comfortable
9.6 out of 10, Exceptional, (30 reviews)
"Great location, cozy and clean."
United States
Laura R.
The price is €200
includes taxes & fees
20 Jan - 21 Jan
*New* Montana Dreamin’ Home
10.0 out of 10, Exceptional, (12 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 €201
includes taxes & fees
18 Feb - 19 Feb
Farmhouse Cottage @ Old Pine Retreats

Holiday Home in Central - Terry

Triangular Casa in Billings
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 €126
includes taxes & fees
26 Jan - 27 Jan
Triangular Casa in Billings
2.0 star property
9.4 out of 10, Exceptional, (21 reviews)
"Great value for the price on a quick trip to Billings."
United States
Tim K.
Quiet 2BR w/ Backyard, Cozy Home and Covered Parking

Holiday Home in Billings

Industrial Loft @ Old Pine Retreats
10.0 out of 10, Exceptional, (8 reviews)
"Stayed at the house with my 75 yr old parents. We loved the decor as every room was perfectly put together for convivence, comfort and charm. The kitchen was fully stocked and well organized to find exactly anything we needed. We loved the tranquility of the deck. Beds were very comfortable. Showers were spacious, towels were so soft. Thank you for sharing this amazing space with us."
United States
Adrienne L.
The price is €193
includes taxes & fees
10 Feb - 11 Feb
Industrial Loft @ Old Pine Retreats

Holiday Home in Billings

Boho Bungalow @ Old Pine Retreats
9.6 out of 10, Exceptional, (20 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 €167
includes taxes & fees
21 Jan - 22 Jan
Boho Bungalow @ Old Pine Retreats

Holiday Home in Rimrock

Rims view pet friendly home
9.4 out of 10, Exceptional, (61 reviews)
"It was a great stay and in a good neighborhood! "
United States
Kaylen L.
The price is €176
includes taxes & fees
25 Jan - 26 Jan
Rims view pet friendly home

Holiday Home in Central - Terry

Bo’s Urban Farm House.
9.4 out of 10, Exceptional, (18 reviews)
"This was a great place to stay. "
United States
Christina W.
Bo’s Urban Farm House.
8.8 out of 10, Excellent, (19 reviews)
"Great place and responsive owner. Love the hot tub."
United States
c h.
The price is €166
includes taxes & fees
19 Jan - 20 Jan
Bo’s Old West Abode with Hot Tub and Sauna
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 €151
includes taxes & fees
21 Jan - 22 Jan
Come and stay at Emerald Cottage, your mini home away from home.

Holiday Home in Central - Terry

Bo’s Bungalow with Hot Tub and Sauna
9.6 out of 10, Exceptional, (14 reviews)
"Feels like home"
United States
Michael O.
The price is €169
includes taxes & fees
19 Jan - 20 Jan
Bo’s Bungalow with Hot Tub and Sauna
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
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 €153
includes taxes & fees
21 Jan - 22 Jan
Restored Vintage Mobile Home on our small Private Ranch
2.0 star property
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 €211
includes taxes & fees
30 Jan - 31 Jan
Townhome • Hospital District • King Bed + Garage

Cottage in Billings

Custer Cottage / Fenced Yard
9.8 out of 10, Exceptional, (20 reviews)
"Perfect place, clean, and had everything you needed. "
United States
Marlenea
The price is €256
includes taxes & fees
19 Jan - 20 Jan
Custer Cottage / Fenced Yard
9.8 out of 10, Exceptional, (6 reviews)
"Had a great time! Great central location to all our adventures and excursions. Plenty of activities on the property too."
United States
Pauline M.
The price is €325
includes taxes & fees
19 Jan - 20 Jan
The Lakehouse: Pool, Theater, Game Room, Lakefront
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 €187
includes taxes & fees
20 Jan - 21 Jan
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful 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 €190
includes taxes & fees
19 Jan - 20 Jan
Lovely 4-bedroom house in Lockwood with large yard and covered patio!
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

Find out more about Shepherd

Everything you need to know about Shepherd holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shepherd holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shepherd holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shepherd holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shepherd. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shepherd holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shepherd holiday rentals we have selected for you start as low as €116 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shepherd rentals

At Expedia, we put the best Shepherd holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shepherd rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shepherd holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shepherd. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Enjoy the hot tub and gas fire pit in this 5 bedroom 2.5 bath house: This holiday home rental outside of Shepherd offers a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 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 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.