Vacation rentals in Shepherd

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Top-rated vacation rentals in Shepherd

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

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Guest favorite

A living area features a brown sofa with a decorative pillow and a leather recliner, accompanied by a side table. Natural light illuminates the space through large windows, showcasing a view of the landscaped front yard. Hardwood flooring extends throughout the room.

Apartment in Billings

4.93 out of 5 average rating, 143 reviews

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

TaylorRating, 5 stars3 days ago

Jeffs home was perfect for us for our quick weekend trip to Billing’s. The location was perfect being close to downtown and easy to get around for shopping. Very quiet and peaceful neighbourhood. Hot tub was a great added bonus! Jeff was great to communicate with and responded quickly. Will definitely be back!!

Guest favorite

The interior space features a warm color palette with hardwood flooring. A kitchen area with wooden cabinetry is visible, accompanied by a dining space with a table and chairs. A colorful painting of a cow adorns the wall, while hooks for coats are mounted beside the entryway.

Condo in Billings

4.92 out of 5 average rating, 12 reviews

Rimrock View Vacation Rental, a place with a view.

JudyRating, 5 stars6 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 favorite

A comfortable living area is showcased with a light brown sofa adorned with throw pillows. A flat-screen TV is mounted on the wall above a dark sideboard. Soft curtains frame the windows, and a small side table and chair complete the inviting space.

Home in Billings

4.92 out of 5 average rating, 324 reviews

Upscale Townhouse with Patio (Kid Friendly)

ClintRating, 5 stars3 weeks ago

This was a super easy stay! Easy to find, nice new construction neighborhood close enough to the place I needed to frequent during the weekend that I had no issues at all finding anything that was needed. Everything in the facility was perfectly clean and ready for us to enjoy our stay. I didn't have to contact Jessica for anything as her instructions were very clear and easy to follow. Would highly recommend this as a place to consider for your trip!

Guest favorite

A light-filled living area features a modern gray sofa paired with a circular wood coffee table. A cozy armchair and a textured rug complement the space, while a world map artwork is displayed on the wall. Large windows provide natural light, enhancing the inviting ambiance.

Guest suite in Billings

4.94 out of 5 average rating, 377 reviews

*New*Quaint River Retreat:Peaceful Getaway Suite

BethAnnRating, 5 stars3 days ago

We absolutely enjoyed this space. It was small and cozy, just what we needed for a weekend away. It was quiet & peaceful, the only noise we heard was the garage door opening a few times, which is understandable since the space is above the garage.

Guest favorite

A welcoming living room features a large brown sectional sofa positioned near a window with sheer curtains. A flat-screen TV is mounted on the wall opposite a patterned area rug. A table and floor lamp add to the relaxed atmosphere.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Shepherd vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Shepherd

Guest favorite

A spacious kitchen features modern stainless steel appliances and a large island with a marbled countertop. Pendant lights hang above, illuminating the ample cabinet space. A comfortable living area is visible in the background, complemented by large windows framing the surrounding landscape.

Home in Billings

4.92 out of 5 average rating, 50 reviews

Peaceful, Country Living. Modern Remodel (Hot Tub)

KimRating, 5 stars1 month 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 favorite

The exterior of a spacious two-level home is depicted, featuring a clear blue heated pool surrounded by a deck with lounge chairs. Lush greenery and flowering plants frame the area, while large windows enhance natural light. A stone wall adds texture to the scene.

Home in Billings

4.99 out of 5 average rating, 84 reviews

Large Luxury & Private 5BDRM Home W/ Pool

ChrisRating, 5 stars2 weeks ago

It was a really great experience overall. great place great host. We will definitely come back to this host and place.

Guest favorite

An outdoor dining area features a large table surrounded by six black chairs, with a fire table at its center. A hanging pod chair is visible nearby, and views of the landscape can be seen through expansive windows. The space is accented by subtle autumn decorations.

Home in Billings

4.91 out of 5 average rating, 11 reviews

Billings Views

HollyRating, 5 stars1 month ago

The house looks just like the photos. Our grandkids enjoyed coming over and visiting and playing games. The driveway is very steep but was clean and clear of snow and ice. The main living area is upstairs. There was a lot of room and it was very comfortable. It was also nice to have 2 bathrooms. One on each level. There are tv's in all of the bedrooms and the livingroom. We would stay here again.

Guest favorite

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 favorite

Apartment in Laurel

4.91 out of 5 average rating, 11 reviews

Country studio apartment

CarlosRating, 5 stars5 months ago

breath taking view, very peaceful worth the trip

Guest favorite

Apartment in Billings

4.86 out of 5 average rating, 111 reviews

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

MichelleRating, 5 stars11 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 favorite

A single-story house is situated on a grassy lot, featuring a stone-accented side and a covered porch with white chairs. Sunlight gently filters through the trees, creating a serene atmosphere in the surrounding yard.

Home in Joliet

4.85 out of 5 average rating, 109 reviews

Rock Creek Paradise (Near Red Lodge, MT)

SherriRating, 5 stars3 months ago

A charming private getaway. Walkable distance to the grocery store, church, coffee, etc. Peaceful setting, creek sounds, wildlife, and a cozy home. Excellent communication and timely assistance. Will stay here again.

Guest favorite