Holiday houses in Shepherd

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Top-rated holiday rentals in Shepherd

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Billings

4.91 out of 5 average rating, 100 reviews

Midtown Charmer ~The Original!~Billings

KristiRating, 5 stars1 month ago
My husband and I live in Billings, but needed a place with more bedrooms. Patrice’s home fit the bill. It was a great home for all of us. Patrice was a dream with whom to work. Would certainly recommend this home to others.
Guest favourite

Home in Billings

4.93 out of 5 average rating, 237 reviews

*New* Montana Dreamin’ Entire House

MeghanRating, 5 stars1 month ago
Such a cute place! Feels right at home with a super comfortable bed! Also has a nice walking trail and park right outside. Hosts were great and easy to work work. Thanks again for being so accommodating and having such a great place!
Guest favourite

Home in Billings

4.87 out of 5 average rating, 210 reviews

Hot Tub Escape in Cold Weather Bliss/ Quiet NBHD

KurtisRating, 5 stars1 week ago
I stayed at Tracy’s for a week. The home was very tidy, cozy, and close to really good downtown restaurants. The neighborhood is extremely quiet, and despite being in a Downtown area, it had a hidden in plain sight type of feel. If I’m ever in the Billings area again, I will definitely be staying here.
Guest favourite

Home in Billings

4.94 out of 5 average rating, 16 reviews

Josephine Crossing Retreat

RichardRating, 5 stars3 weeks ago
It was like home away from home. This was close to our son and the grandkids and we had a great time.
Guest favourite

Apartment in Billings

4.93 out of 5 average rating, 142 reviews

Bo's Rusty Relic | Central | Hospital ~7 min

JodyRating, 5 stars2 weeks ago
Jeff was super responsive and friendly. Beds were comfy and the decor made us feel cozy and right at home. Loved the hot tub. It was perfect for relaxing at the end of the day. Would recommend this place to friends and stay again when we are in town. Thanks Jeff and staff. Jody & Erik
Guest favourite

Condo in Billings

4.92 out of 5 average rating, 12 reviews

Rimrock View Vacation Rental, a place with a view.

JudyRating, 5 stars5 months ago
Brent always responded within minutes of contact, he was extremely flexible with our schedules and the place was perfect for the three of us Sisters to spend a week with our Dad who lives in Billings. We look forward to future rentals at this same place!
Guest favourite

Guest suite in Park City

4.87 out of 5 average rating, 702 reviews

Cozy little Cabin in Park city

AlisonRating, 5 stars1 month ago
This cottage was the perfect place to stay! I’m sure it is absolutely beautiful during the summer! I would HIGHLY recommend this place to everyone!!!
Guest favourite

Home in Billings

4.92 out of 5 average rating, 321 reviews

Upscale Townhouse with Patio (Kid Friendly)

MeganRating, 5 stars3 weeks ago
We had a wonderful stay at Jessica’s place during a difficult time as we were in town for a funeral. The house was cozy, clean, and located in a quiet neighborhood, providing a peaceful retreat. The furnishings were comfortable and thoughtfully chosen, making it easy to relax. Jessica ensured everything we needed was available, making our stay stress-free. It was a perfect place to come back to each day, and we truly appreciated the care and comfort provided. Highly recommend!
Guest favourite

Home in Billings

4.95 out of 5 average rating, 64 reviews

Perfect on Pine

ZoeRating, 5 stars1 month ago
Fantastic spot! Will definitely come back again
Guest favourite

Guest suite in Billings

4.94 out of 5 average rating, 374 reviews

*New*Quaint River Retreat:Peaceful Getaway Suite

DustinRating, 5 stars3 days ago
This was absolutely the cozied Airbnb we have ever stayed at, and we honestly did not want to leave!! Everything was very clean, and the communication was excellent. The space is located in a nice neighborhood, and we enjoyed having a coffee shop just down the street. This will certainly be at the top of the list for future visits to Billings!
Guest favourite

Home in Billings

4.94 out of 5 average rating, 98 reviews

Shoppers Central, West End Beauty

JanaRating, 5 stars1 month ago
We stayed at 2906 Canyon Drive over the holidays while visiting family. It is a great little place, perfect for 5 of us to relax and spread out in. We loved having a garage to park our car in and the huge back yard. The whole place felt quite, cozy, and private. The price was also perfect for what we were looking for. It was clean, which is a big plus in the Airbnb world. Eric was always available to check in with and responded promptly when we needed anything. Thank you for letting us stay in your place. When back in Billings, we will definitely return to this spot.
Guest favourite

Home in Billings

4.98 out of 5 average rating, 223 reviews

Beautifully Remodeled 100 Year Old Home Near DT

ScottRating, 5 stars1 month ago
MaKyla's house is exactly as listed. It is very comfortable and a great location. Access was easy and the off street parking is nice. I will definitely stay there next time I'm in Billings. MaKyla is a good communicator and was very responsive.

Popular amenities for Shepherd holiday rentals

Other great holiday rentals in Shepherd

Guest favourite

Home in Billings

4.92 out of 5 average rating, 50 reviews

Peaceful, Country Living. Modern Remodel (Hot Tub)

KimRating, 5 stars1 week ago
Remodeled, tastefully and beautifully with nice furniture and beautiful views. We enjoyed our weekend and being somebody that is from Billings herself. I would recommend it to any of my friends coming to visit. I loved the coffee machine. I used to be a barista and that brought back such fun memories.
Guest favourite

Home in Billings

4.99 out of 5 average rating, 81 reviews

Large Luxury & Private 5BDRM Home W/ Pool

ErinRating, 5 stars1 month ago
Beautiful home, lots of space to spread out, and very quiet and safe neighborhood. We would stay there again.
Guest favourite

Home in Billings

5 out of 5 average rating, 8 reviews

Billings Views

WynetteRating, 5 stars1 month ago
Lots of space, very clean and the decor is fun! My family had an incredible time! Would highly recommend!
Guest favourite

Home in Billings

5 out of 5 average rating, 13 reviews

Billings Getaway

AndreaRating, 5 stars9 months ago
House was close to the soccer fields and was a great stay
Guest favourite

Home in Billings

5 out of 5 average rating, 25 reviews

*NEW* Solar Powered Home, 3Bed 1Bath

dawnRating, 5 stars1 month ago
A cozy home in a quiet and safe location. 3 nice bedrooms with closets and 2 of those with TVs. Good-sized, well stocked kitchen with a table for 6. Very nice laundry room downstairs with daily availability from 4-7pm. We only used the largest bedroom, but found that bed to be comfy with very cozy linens. There's a nice park with 2 blocks. A good walking area. We really enjoyed the house and the neighborhood. We found the price reasonable and worth every penny. Great communication with Madison! Thank you!
Guest favourite

Apartment in Laurel

4.91 out of 5 average rating, 11 reviews

Country studio apartment

CarlosRating, 5 stars4 months ago
breath taking view, very peaceful worth the trip
Guest favourite

Apartment in Billings

4.85 out of 5 average rating, 110 reviews

Bo's 2 bedroom with HOT TUB and washer & dryer.

MichelleRating, 5 stars10 months ago
This was a great little place. Very quiet and peaceful yet not far from businesses and easy to get around town. Nearby park was a hit with the kids.
Guest favourite

Chalet in Billings

5 out of 5 average rating, 23 reviews

Peaceful Billings Chalet

EmmaRating, 5 stars1 month ago
Even better in person! Everything was perfect!

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