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Compare 105 Vacation Homes in Shepherd with updated reviews, rates, and availability.

"Nicely appointed, great size rooms, spacious shared space. Location is great too - located in a quiet neighborhood and easy access to the main road."

Living room, gas fireplace, tv, and rustic decor

"We stayed 2 nights and loved it. House was clean, well maintained and perfectly decorated to give it that “homey” feeling that is missing in a lot of VRBO homes. The pet friendly lawn is well groomed and fenced nicely. My service animal loved it. We will definitely book here again next time we come to Billings. "

"Everything was great. We will be back!!"

SAR 856 total

includes taxes & fees

30 Nov - 1 Dec

"Nice home in nice neighborhood. Great for talking walks."

"The property was nice, in a quite neighborhood. The home brought back memories of my childhood as it was a similar floor plan."

SAR 1,577 total

includes taxes & fees

24 Nov - 25 Nov

"We booked this home for the trip to celebrate our daughter's wedding at Camelot Ranch. It was close to the venue and large enough for family and friends. The owners allows us to hoat the rehearsal dinner there as well. It was clean and a beautiful home and had everything we needed during our stay. "

"Plenty of space. Nice shower. Everything we needed was accessible. "

"Awesome home with big, fenced back yard. The communication from the host was the best I’ve ever had. Very accommodating and going out of her way to assist. Very clean, close to the airport, would 100% stay here again. "

SAR 1,160 total

includes taxes & fees

1 Dec - 2 Dec

"The stay was good. Housekeeping could have been a bit better, but it wasn't horrible."

SAR 1,529 total

includes taxes & fees

10 Dec - 11 Dec

"There are few things that I might recommend; like a direction page for the remote control and how to work tv. also the way to use the retro microwave would be helpful. "

"Close to downtown and some day trips we took"

SAR 1,082 total

includes taxes & fees

23 Nov - 24 Nov

"The hosts were great and everything made sense for check out and check in. Highly recommend any rental here! "

"We stopped here on our way to Glacier for a quick one night break. House had everything we needed and more. Great location. Was very clean and had all the amenities plus some. Would definitely recommend. "

SAR 1,346 total

includes taxes & fees

1 Dec - 2 Dec

"Very convenient and lovely older home. Need to guard your parking spot though! lol"

"Exactly what we were hoping for particularly with out 2 dogs."

SAR 1,257 total

includes taxes & fees

24 Nov - 25 Nov

"The house was very simple but decent. Very comfortable beds! Kitchen had minimal dishes. Very convenient to the Metra which is where we were headed each day so that was great. We also messed up our dates and ended being late to leave and the owner was very kind about it, allowing us some extra time to pack up and rush out. Overall this was a decent place to stay."

"This is exactly what I was hoping for a quiet neighborhood walking distance to downtown and an easy drive to the metro … I was blessed to spend time in a comfortable home with my young adult children ..I will look for this place every time I visit Billings"

SAR 827 total

includes taxes & fees

23 Nov - 24 Nov

Billings Vacation Rental | 3BR | 2BA | 2,012 Sq Ft | Steps Required to Enter

"Mostly a great stay. Comfortable for our toddler grandson. The backyard was nice. Thankful to have brought our pet. Host was super responsive and helpful. Great location. The arrangement looked different than in the pictures. The second bedroom wasn't shown. There is a foos ball table in the living room that is really in the way and more furniture which made for a cramped space. Wish there had been a full/queen size bed somewhere. "

Billings Vacation Rental | 2BR | 1BA | Stairs Required for Entry | 1,000 Sq Ft

"This was such a cute and cozy home and worked great for our stay during our sons wedding "

"Everything about the unit itself is great. Super clean, well stocked, etc. I would stay again if what I'm about to to type was no longer present. The problem is there's some sort of full on 24 hour a day construction operation not even 100 yards away. Every few minutes is thunderous banging as large rocks are dropped into a metal trailer that shakes the whole place. Beeping from construction vehicles reversing and engine noise all night as well. Needless to say, no one slept and my dog was...

SAR 405 total

includes taxes & fees

25 Nov - 26 Nov