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Shepherd Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Shepherd vacation 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
9.8 out of 10, Exceptional, (15 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 AED 549
AED 672 total
includes taxes & fees
30 Sep - 1 Oct
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, (21 reviews)
"Will definitely be my go to for when traveling to Billings. Everything was perfect for us."
United States
Travis W.
The price is AED 501
AED 969 total
includes taxes & fees
20 Oct - 21 Oct
Farmhouse Cottage @ Old Pine Retreats
Exterior

3. Industrial Loft @ Old Pine Retreats

Industrial Loft @ Old Pine Retreats
Billings
10.0 out of 10, Exceptional, (15 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.
Industrial Loft @ Old Pine Retreats
Smart TV

4. Triangular Casa in Billings

Triangular Casa in Billings
Central - Terry
9.6 out of 10, Exceptional, (133 reviews)
"Nice location. Good space."
United States
Michael
The price is AED 257
AED 595 total
includes taxes & fees
12 Oct - 13 Oct
Triangular Casa in Billings
Interior

5. 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, (26 reviews)
"Great place!"
United States
Julie C.
The price is AED 350
AED 517 total
includes taxes & fees
26 Sep - 27 Sep
A clean, comfortable space just off the interstate with easy parking.
Exterior

6. Parkhill Bungalow • Pioneer Park

Parkhill Bungalow • Pioneer Park
Midtown
9.8 out of 10, Exceptional, (6 reviews)
"Veey nice property "
United Kingdom
Juli L.
The price is AED 364
AED 1,115 total
includes taxes & fees
23 Sep - 24 Sep
Parkhill Bungalow • Pioneer Park
Terrace/patio

7. Cozy Bungalow w/Hot Tub and Sauna

Cozy Bungalow w/Hot Tub and Sauna
Central - Terry
9.6 out of 10, Exceptional, (20 reviews)
"Host reached out on took good care of us."
United States
Greg I.
Cozy Bungalow w/Hot Tub and Sauna
Exterior

8. Pet Friendly 2BR Home w/ fenced backyard

Pet Friendly 2BR Home w/ fenced backyard
Central - Terry
9.4 out of 10, Exceptional, (30 reviews)
"Great value for the price on a quick trip to Billings."
United States
Tim K.
Pet Friendly 2BR Home w/ fenced backyard
TV

9. Big Sky Retreat

Big Sky Retreat
Midtown
9.4 out of 10, Exceptional, (25 reviews)
"It was great place to stay. "
United States
Stacy S.
The price is AED 400
AED 1,138 total
includes taxes & fees
23 Sep - 24 Sep
Big Sky Retreat
Exterior

10. Beautiful 3-bedroom house with hot tub in beautiful Billings

Beautiful 3-bedroom house with hot tub in beautiful Billings
Billings
The price is AED 423
AED 1,056 total
includes taxes & fees
23 Oct - 24 Oct
Beautiful 3-bedroom house with hot tub in beautiful Billings
Coffee/tea maker, fridge, microwave, oven

11. Montana Gathering House: Fire Pit, BBQ, HUGE Yard

Montana Gathering House: Fire Pit, BBQ, HUGE Yard
Midtown
10.0 out of 10, Exceptional, (1 review)
"Decent place to stay while on the road. Worked well for our family with kids."
United States
Stefan L.
The price is AED 291
AED 1,266 total
includes taxes & fees
23 Sep - 24 Sep
Montana Gathering House: Fire Pit, BBQ, HUGE Yard
Terrace/patio

12. Boho Bungalow @ Old Pine Retreats

Boho Bungalow @ Old Pine Retreats
Billings
9.8 out of 10, Exceptional, (33 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 AED 490
AED 901 total
includes taxes & fees
1 Oct - 2 Oct
Boho Bungalow @ Old Pine Retreats
TV

13. 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, (24 reviews)
"This was a great place to stay. "
United States
Christina W.
The price is AED 408
AED 853 total
includes taxes & fees
29 Sep - 30 Sep
Bo’s Urban Farm House | 2bed | 1 bath | Large Yard
Smart TV, fireplace

14. Private 1BR Guesthouse Retreat

Private 1BR Guesthouse Retreat
Central - Terry
10.0 out of 10, Exceptional, (22 reviews)
"It was a nice place to relax and enjoy some time alone"
United States
nasheena
Private 1BR Guesthouse Retreat
Outdoor spa tub

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

Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood
Central - Terry
9.6 out of 10, Exceptional, (81 reviews)
"Appreciated the easy check-in, hot tub, and comfortable beds."
United States
Chad B.
The price is AED 488
AED 1,019 total
includes taxes & fees
23 Sep - 24 Sep
Hot Tub | Pets | Fenced Yard | Quiet Neighboorhood
Smart TV, video games, offices

16. Bo’s 2BR Eclectic + Antique-Modern Pet Friendly w/ Big Yard

Bo’s 2BR Eclectic + Antique-Modern Pet Friendly w/ Big Yard
North Elevation Historic District
10.0 out of 10, Exceptional, (18 reviews)
"This is a lovely house, well appointed and in a great Billings, MT neighborhood. My dog loved it, too. Correspondence with our host was seamless. We had a great stay."
United States
Sidney M.
Bo’s 2BR Eclectic + Antique-Modern Pet Friendly w/ Big Yard
Coffee/tea maker, fridge, microwave, oven

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

Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Billings
9.6 out of 10, Exceptional, (38 reviews)
"Great stay!"
United States
Logan H.
The price is AED 430
AED 793 total
includes taxes & fees
23 Sep - 24 Sep
Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings
Exterior

18. Mocha Haven King Bed Quiet Walkable To Parks, Coffee, Yellowstone River

Mocha Haven King Bed Quiet Walkable To Parks, Coffee, Yellowstone River
Billings
10.0 out of 10, Exceptional, (5 reviews)
"Brand new and clean, quiet neighborhood."
United States
Elaina
The price is AED 354
AED 699 total
includes taxes & fees
23 Sep - 24 Sep
Mocha Haven King Bed Quiet Walkable To Parks, Coffee, Yellowstone River
Outdoor pool

19. 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 AED 743
AED 1,811 total
includes taxes & fees
6 Oct - 7 Oct
The Lakehouse: Pool, Theater, Game Room, Lakefront
Smart TV, fireplace

20. Pet Friendly, Private HOT TUB & Fenced Backyard

Pet Friendly, Private HOT TUB & Fenced Backyard
Central - Terry
9.4 out of 10, Exceptional, (35 reviews)
"This place is awesome, and ever comfortable. The down stairs shower was amazing, probably one of the better places I stayed at."
United States
Louis
The price is AED 537
AED 1,021 total
includes taxes & fees
23 Sep - 24 Sep
Pet Friendly, Private HOT TUB & Fenced Backyard
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

FairBridge Inn Express Billings Airport

FairBridge Inn Express Billings Airport

10/10 Excellent
"Pleasantly surprised on the service and how clean the room was. Service was excellent"
Valerie 1-night trip
Posted less than an hour ago
FairBridge Inn Express Billings Airport

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?

Charming 2-bedroom townhome with WiFi, AC/Heat in delightful Billings: This vacation home rental near 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 the hot tub 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 Four Dances Recreation Area, or get outside and enjoy nature at Yellowstone River. In the larger area, you’ll find Lake Elmo State Park and First Interstate Arena at 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.