Book Holiday Homes in Shepherd

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Featured Holiday Homes in Shepherd

Cozy, Stylish 2-Bedroom Retreat in Prime Location – Walk to Shops & Dining!

Cozy, Stylish 2-Bedroom Retreat in Prime Location – Walk to Shops & Dining!

2 out of 5
Billings MT
Stay at this holiday home in Billings. Enjoy laundry facilities and air conditioning. Popular attractions Jackpot Casino and Rimrock Mall are located ...
Opens in a new windowCozy, Stylish 2-Bedroom Retreat in Prime Location – Walk to Shops & Dining!
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings

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

Billings MT
Stay at this holiday home in Billings. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Magic City Casino and Lucky ...
Opens in a new windowCharming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Bo’s White House with Fenced Yard

Bo’s White House with Fenced Yard

Billings MT
The price is NZ$436 per night from 12 Feb to 13 Feb
NZ$436
12 Feb - 13 Feb
includes taxes & fees
Stay at this holiday home in Billings. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Nickels Casino and Maverick Casino are located ...
Opens in a new windowBo’s White House with Fenced Yard
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Triangular Casa in Billings

Triangular Casa in Billings

Billings MT
The price is NZ$241 per night from 16 Feb to 17 Feb
NZ$241
16 Feb - 17 Feb
includes taxes & fees
Stay at this holiday home in Billings. Enjoy breakfast (surcharge), a garden and laundry facilities. Popular attractions Nickels Casino and Palms Grand Casino ...
Opens in a new windowTriangular Casa in Billings
Barb’s Cozy Home with Office and Covered Parking!

Barb’s Cozy Home with Office and Covered Parking!

2 out of 5
Billings MT
Stay at this holiday home in Billings. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Maverick Casino and Bullwackers Lounge and Casino ...
Opens in a new windowBarb’s Cozy Home with Office and Covered Parking!
Peaceful Cul-De-Sac Home, 1 Min. Drive To Zoo MT!

Peaceful Cul-De-Sac Home, 1 Min. Drive To Zoo MT!

Billings MT
Stay at this family-friendly holiday home in Billings. Enjoy free Wi-Fi, a water park and a garden. Popular attractions ZooMontana and Reef Indoor Water Park ...
Opens in a new windowPeaceful Cul-De-Sac Home, 1 Min. Drive To Zoo MT!
Centrally located 4Bedroom, 5 BEDs & 2Bath; Beautiful backyard

Centrally located 4Bedroom, 5 BEDs & 2Bath; Beautiful backyard

Billings MT
Stay at this family-friendly holiday home in Billings. Enjoy free Wi-Fi, a water park and a garden. Popular attractions Bullwackers Lounge and Casino and Maverick ...
Opens in a new windowCentrally located 4Bedroom, 5 BEDs & 2Bath; Beautiful backyard
Bo’s Urban Farm House.

Bo’s Urban Farm House.

Billings MT
The price is NZ$359 per night from 12 Feb to 13 Feb
NZ$359
12 Feb - 13 Feb
includes taxes & fees
Stay at this holiday home in Billings. Enjoy air conditioning. Popular attractions Nickels Casino and Maverick Casino are located nearby.
Opens in a new windowBo’s Urban Farm House.
The Lakehouse: Pool, Theater, Game Room, Lakefront

The Lakehouse: Pool, Theater, Game Room, Lakefront

Billings MT
The price is NZ$650 per night from 17 Feb to 18 Feb
NZ$650
17 Feb - 18 Feb
includes taxes & fees
Stay at this family-friendly holiday home in Billings. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Northwest Trailhead and Lake Elmo State ...
Opens in a new windowThe Lakehouse: Pool, Theater, Game Room, Lakefront
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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.

Shepherd Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Shepherd vacation homes are the perfect way for you to wing it.

Holiday houses in Shepherd let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Shepherd in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Shepherd adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Shepherd with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Shepherd vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Shepherd Holiday Homes essential information

Accommodation
118 Holiday Homes
Lowest Price
NZ$187
Highest Price
NZ$650
Popular accommodation
Cozy, Stylish 2-Bedroom Retreat in Prime Location – Walk to Shops & Dining!, Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings, Bo’s White House with Fenced Yard, Triangular Casa in Billings, Barb’s Cozy Home with Office and Covered Parking!, Peaceful Cul-De-Sac Home, 1 Min. Drive To Zoo MT!, Centrally located 4Bedroom, 5 BEDs & 2Bath; Beautiful backyard, Bo’s Urban Farm House., The Lakehouse: Pool, Theater, Game Room, Lakefront

Top trending hotels in Shepherd

Hyatt Place Billings

Hyatt Place Billings

3 out of 5
705 Henry Chapple Street Billings MT
Fully refundableReserve now, pay when you stay
The price is NZ$187 per night from 15 Feb to 16 Feb
NZ$187
15 Feb - 16 Feb
includes taxes & fees
Stay at this hotel in Billings. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Casino Mardi Gras West and Dotty's Casino are located ...
Opens in a new windowHyatt Place Billings
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
1223 Mullowney Ln Billings MT
Fully refundableReserve now, pay when you stay
Stay at this 3-star hotel in Billings. Enjoy free Wi-Fi, free parking and a casino. Our guests praise the pool and the helpful staff in their reviews. Popular ...
Opens in a new windowBillings Hotel and Convention Center
Northern Hotel

Northern Hotel

4 out of 5
19 North Broadway Billings MT
Fully refundableReserve now, pay when you stay
The price is NZ$380 per night from 20 Feb to 21 Feb
NZ$380
20 Feb - 21 Feb
includes taxes & fees
Stay at this business-friendly hotel in Billings. Enjoy free Wi-Fi, free parking and 2 restaurants. Our guests praise the restaurant and the bar in their reviews. ...
Opens in a new windowNorthern Hotel
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La Quinta Inn & Suites by Wyndham Billings

La Quinta Inn & Suites by Wyndham Billings

3 out of 5
5720 S Frontage Rd Billings MT
Fully refundableReserve now, pay when you stay
The price is NZ$214 per night from 15 Feb to 16 Feb
NZ$214
15 Feb - 16 Feb
includes taxes & fees
Stay at this business-friendly hotel in Billings. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Billings
Don't see what you're looking for?
See all available properties in Shepherd
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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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^Subject to availability and chosen travel dates.