Holiday houses in Shepherd

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Top-rated holiday rentals in Shepherd

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Guest favourite

Tiny home in Billings

4.98 out of 5 average rating, 124 reviews

Boho Bungalow @ Old Pine Retreats

If you can imagine a getaway in a uniquely designed tiny house that is built on 60+ acres of wide open and stunning landscape, then you have captured a glimpse of this rare find. This beautiful tiny house is all yours to enjoy such amenities as a glass garage door that can be opened to experience nature from your kitchen table or a fireplace to cozy up to when the temps are cold. You can enjoy coffee in the morning from your private deck and keep your feet warm in the winter with heated floors.

Guest favourite

Tiny home in Billings

4.95 out of 5 average rating, 149 reviews

Cozy Creekside Cabin Near Billings

Enjoy this beautiful fully furnished cabin just minutes outside the Billings city limits. Check in and then unwind with a walk on the private trails just out your front door. We are located a simple drive to the Metra for concerts and events, Ah-Nei State Recreation Area with ATV, walking, and horse trails, historic Pompey's Pillar, the Yellowstone river with fishing accesses, and Lake Elmo State park. Caretakers reside onsite and also host our four-legged friends through their pet resort.

Guest favourite

Guest suite in Billings

5 out of 5 average rating, 171 reviews

Gail's Guest Suite by MetraPark Arena

CLEAN, COZY spot away from busy traffic streets yet close to the Metra & 10 min from downtown in nice neighborhood. Shared front door only.PLUSH Guest Suite on lower level has private door. Daylight den has beautiful gas fireplace, leather reclining loveseat, microsuede couch & big screen tv. Queen bed has a medium firm Nova foam mattress.Kitchenette has a microwave, small fridge, toaster, coffee pot, coffee, tea and snacks. 1-2 Adults only, must be over 21, non smokers, non vapors, no pets.

Guest favourite

Rental unit in Billings

4.94 out of 5 average rating, 1,167 reviews

Studio type Suite with Own Entrance, Pet Friendly

The Front door is shared leading into the entryway One door leads to the Airbnb Studio in the lower level and the 2nd door leads into the Host’s Space. This provides complete privacy for guests. Located minutes from I-90, Downtown Billings, The Hospital Corridor and Logan Airport. This space is located in the basement of my townhouse. The space has a private bath, King size bed with a memory foam topper and fresh linens. A microwave, mini-fridge/freezer and Keurig coffee maker are provided.

Guest favourite

Rental unit in Billings

4.95 out of 5 average rating, 206 reviews

Billings WestEnd apartment

***CHRISTMAS AND NEW YEAR’S SPECIAL OFFER IN BILLINGS, MT*** Fancy two weeks in our apartment in Billings, MT? That’s plenty of time to discover south central Montana: Red Lodge ski hill, Livingston and Bozeman just two hours away, and lots of places to eat, drink and be merry. 50% discount. Two full weeks just $966. Offer is on a first-come, first served basis. Message me if interested. Located in Billings' WestEnd, with yard, patio, free parking, views over city park, fully fenced lot.

Guest favourite

Home in Billings

4.94 out of 5 average rating, 229 reviews

*New* Montana Dreamin’ Entire House

Our home is an entirely new, single family home. Perfect for 1-4 persons to enjoy a getaway tucked into a family friendly neighborhood with parks and view of the nearby hills. Decked with relaxed vibes and the amenities to make you feel right at home. Professionally decorated and set up with a TV in every room, cookware, in house washer\dryer, Nespresso, breakfast-fixings, a patio that is just waiting for you to enjoy with an afternoon coffee or a nighttime glass of wine. Your choice. ;)

Guest favourite

Tiny home in Billings

4.99 out of 5 average rating, 222 reviews

*NEW BUILD* Mini Mountain View Getaway

Mini Mountain View Retreat is a great weekend get away. Just a short walk to downtown, the hospitals, or a view of the Beartooth Mountains. This tiny home makes for a relaxing stay with everything you need and a peaceful and homey atmosphere. Just because it's tiny doesn't mean it isn't full of all your basic home essentials such as a full kitchen, washer and dryer and luxurious features. This shared property is tucked away in a quiet and peaceful neighborhood.

Guest favourite

Guest suite in Billings

4.98 out of 5 average rating, 203 reviews

Sunsets & City Lights

Sunsets and city lights await in this spacious guest suite that's family friendly & sleeps six. Quick access to I-90/I-94 interchanges. Enjoy the entire lower level with two big bedrooms, a full private bathroom, desk with high speed internet, washer/dryer, continental kitchenette and large open living room with a leather sofa sleeper, comfortable sitting chairs, super sized 65" smart TV, gas fireplace, dining table & walk-out patio to a huge fenced backyard!

Guest favourite

Guest suite in Billings

4.96 out of 5 average rating, 276 reviews

Much More Than a Suite & 2 miles from metra

CLEAN & PLUSH!!! Kitchenette is more than a toaster, fridge micro& coffee in the corner of the living room. It’s an actual wet bar with sink, fridge , toaster,etc. cupboards& table. Living room, leather furniture, fireplace. Your choice… a bedroom with a new Casper mattress or a bedroom with a traditional mattress. If you need both bedrooms, request. Add. Charge. Non smokers/vapors, adults only No one under she 21. NO Hook up’s ! No pets!

Guest favourite

Rental unit in Billings

4.97 out of 5 average rating, 200 reviews

Hospital Corridor Apartment

This special place is close to everything, making it easy to plan your visit. This house was originally built in 1900, then moved to Billings from Broadview in the 1940s. I bought the house in 2004, when my daughter was small, and have lived here ever since. It is a work in progress. Between 2010-13, I had the basement remodeled. I love the yard, and in the summer, I spend a good part of my day outside working in it.

Guest favourite

Home in Billings

4.97 out of 5 average rating, 119 reviews

Broadwater house

Newly remodeled down town home located 2.9 miles from the airport. 6 minutes from Billings Hospitals. 5.3 miles from I-90. Enterprise is located next door for your convenience. NaRa Oriental restaurant, Holliday gas station, and Central High School are all just a short walk away. Easy access to some great spots nearby! This property is located on a busy street, which may result in street noise.

Guest favourite

Home in Billings

5 out of 5 average rating, 140 reviews

Stylish, Homey, & Spacious

Don't pass this one up! This home has everything you need to feel just at home! It is a newer home with high-end appliances and all brand new furniture! Pristine and very clean! Sit on the front patio for morning coffee or an evening glass of wine! Enjoy your privacy in the backyard while sitting around the gas fire pit. You will enjoy your time in Billings even more while staying at this home!