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.

Guest favourite

Home in Billings

4.91 out of 5 average rating, 100 reviews

Midtown Charmer ~The Original!~Billings

Last Best Place Home Base! Nearly 100 5 STAR REVIEWS!! Mid-century modern charm with exceptional amenities! Beautiful 3000 sq. ft. home with oversized living and dining space, 3 bedrooms, full bath and laundry on main floor. Well-appointed quaint kitchen is loaded with essentials. Lower level has a cozy, oversized family room, two bedrooms, 3/4 bath. Relax on the enchanting 20’ x 40’ deck shaded by a magnificent 70-foot maple tree. A lengthy, accommodating driveway provides off-street parking.

Guest favourite

Home in Billings

4.93 out of 5 average rating, 237 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

4.87 out of 5 average rating, 210 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

Home in Billings

4.94 out of 5 average rating, 16 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

Flat in Billings

4.93 out of 5 average rating, 142 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, 702 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, 321 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

Home in Billings

4.95 out of 5 average rating, 64 reviews

Perfect on Pine

Discover the perfect retreat in downtown Billings, Montana! Our delightful 3-bedroom VRBO welcomes you with open arms to a cozy neighborhood adorned with charming 1940s architecture. As you step inside, you'll find a meticulously designed home, blending modern amenities with retro charm.

Guest favourite

Guest suite in Billings

4.94 out of 5 average rating, 374 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.

Guest favourite

Home in Billings

4.94 out of 5 average rating, 98 reviews

Shoppers Central, West End Beauty

The whole group will enjoy easy access to everything from this centrally located place. Walmart, Target, Rimrock Mall as well as hardware stores, groceries, fast food and restaurants are all within a quick 5 minute drive.

Guest favourite

Home in Billings

4.98 out of 5 average rating, 223 reviews

Beautifully Remodeled 100 Year Old Home Near DT

•Beautiful historic home, centrally located near downtown Billings and 5 minutes from I-90 •Recently remodeled to add all the modern comforts •Family-friendly, single-level •Cozy, yet open and spacious