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Holiday rentals in Shepherd

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Top-rated holiday rentals in Shepherd

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

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Flat in Billings

4.81 out of 5 average rating, 447 reviews

Bo’s Old West Abode with Hot Tub and Sauna

Spacious two bedroom, 1 bath basement apartment with full kitchen (stove, fridge/freezer, microwave, toaster, utensils, silverware, etc. The living room has a nice free-standing gas fireplace, which makes the apartment very cozy. There is also a TV with an Amazon Firestick, allowing guests access to Netflix, Hulu, YouTube, etc. Each bedroom has a comfortable queen sized bed, dresser, and electric fireplace for added comfort and ambiance. There is also access to a full-sized washer and dryer.

Guest favourite

Home in Billings

4.94 out of 5 average rating, 234 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

Home in Billings

4.86 out of 5 average rating, 202 reviews

Hot Tub Escape in Cold Weather Bliss/ Quiet NBHD

Located just one block from Downtown is this stylish, central home with everything you could need for a comfortable stay just minutes from all the action. The home features bright, sun-filled living with a fully equipped kitchen, 3 generous bedrooms, a modern bathroom & a leafy backyard oasis with a hot tub and a huge playground. Stay within walking distance to delicious restaurants, breweries and the happening Pub Station and just a short drive to Yellowstone River and many hiking trails.

Guest favourite

Flat in Billings

5 out of 5 average rating, 5 reviews

Charming Getaway at cozy 2206

Discover charm in our one-bedroom, one-bath apartment nestled in the heart of downtown. Embrace the energy of the city while enjoying the comfort of a cozy retreat. Recently updated with new furniture. Perfect for solo travelers or couples seeking an authentic urban experience. Our apartment provides a welcoming haven for guests to explore the city's eclectic offerings. With easy access to cafes, nightlife, and cultural landmarks, your stay at our cozy apt. promises a memorable adventure.

Guest favourite

Home in Billings

4.93 out of 5 average rating, 15 reviews

Josephine Crossing Retreat

You will love my new, modern townhome in the best location for convenience, quiet, cleanliness and comfort. 2 BR with 2 ATTACHED baths perfect for business travelers, temporary housing or the solo adventurer. Located 2 blocks from the Yellowstone river with walking trails, X- country ski trails and parks. 2 minutes to the interstate, 8 minutes to downtown brewpubs, restaurants and stores, 15 minutes to the airport, 5 mi from both hospitals, and only 45 minutes to Red Lodge ski mountain.

Guest favourite

Home in Billings

4.84 out of 5 average rating, 104 reviews

Modern West-End Haven

Discover a cozy 4-bedroom retreat in Billings, MT! Just minutes from Rimrock Mall, Rocky Mountain College, and ZooMontana, this home is ideal for your adventures. Relax with smart TV entertainment, cook in the fully stocked kitchen, or grill outside. Enjoy WiFi, in-unit laundry, and 4 bathrooms with linens, towels, and bath essentials. With AC and heating, you're set for any season. Perfect for work or leisure, this inviting home offers all you need for a memorable Billings stay!

Guest favourite

Flat in Billings

4.93 out of 5 average rating, 139 reviews

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

We welcome you to the Rusty Relic. This unique Montana retreat includes a beautiful 2 bedroom 1 bath top floor unit of a duplex. This space has that classic old-time feel with gorgeous, well-preserved hardwood flooring and the arched entrances will guide you from one room to the next. The Relic overlooks a backyard that is landscaped for your enjoyment and relaxation which includes a new hot tub (note this shared between multiple rental units).

Guest favourite

Apartment in Billings

4.92 out of 5 average rating, 12 reviews

Rimrock View Vacation Rental, a place with a view.

Large top level unit with views of a water way off a covered deck, abundant with wildlife and spacious living area for dining, cooking and relaxing smart t.v. room to relax in. Lake Hills public golf course is 10 minutes away, the medical corridor, downtown and the universities are a short 5 minutes away and the First Interstate is even closer, you can walk there along the Yellowstone Bike Trail and on to the r

Guest favourite

Guest suite in Park City

4.87 out of 5 average rating, 701 reviews

Cozy little Cabin in Park city

Cutest little cozy and comfortable cabin in town. It has it's own deck With a beautiful view of flower gardens and a koi pond. The flooring and decoration are very country. This is right off the interstate. Quiet little town. 7 minutes from Laurel, 20 minutes from Billings. TV with access to Netflix. This doesn't have a kitchen but there is a microwave and mini fridge.

Guest favourite

Home in Billings

4.92 out of 5 average rating, 316 reviews

Upscale Townhouse with Patio (Kid Friendly)

Brand new and professionally decorated. You will want to move in, I promise! Located in a beautiful new development (Annafeld) close to everything. Good coffee, plush beds, blackout curtain + smart TVs in every room, perfect patio to read or hang out + a grill! We even include some fun books and toys (not pictured) for the kids.

Guest favourite

Guest suite in Billings

4.94 out of 5 average rating, 369 reviews

*New*Quaint River Retreat:Peaceful Getaway Suite

This river retreat is a great getaway with a full kitchen and living area making it ideal to stay in while also having the perfect location to go out. Amenities include a 55 inch Smart TV, a comfortable living room, full kitchen, Pac n Play, Keurig.

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Popular amenities for Shepherd holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Shepherd

Guest favourite

Home in Billings

4.92 out of 5 average rating, 48 reviews

Peaceful, Country Living. Modern Remodel (Hot Tub)

Guest favourite

Home in Billings

4.99 out of 5 average rating, 80 reviews

Large Luxury & Private 5BDRM Home W/ Pool

Guest favourite

Home in Billings

5 out of 5 average rating, 13 reviews

Billings Getaway

Guest favourite

Home in Billings

5 out of 5 average rating, 23 reviews

*NEW* Solar Powered Home, 3Bed 1Bath

Guest favourite

Flat in Laurel

4.91 out of 5 average rating, 11 reviews

Country studio apartment

Guest favourite

Home in Billings

4.93 out of 5 average rating, 42 reviews

Cozy home away from home

Guest favourite

Guest house in Billings

4.98 out of 5 average rating, 87 reviews

Private modern loft in country setting.

Guest favourite

Flat in Billings

4.85 out of 5 average rating, 110 reviews

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

Destinations to explore