Holiday rentals in Glendive

5 out of 5 average rating, 34 reviews

Western Ranch Getaway

Experience the spirit of the West in this beautifully renovated 3-bedroom home nestled in the heart of Glendive, Montana but away from all the hustle & bustle. Surrounded by sweeping views of the Badlands and Big Sky horizons, this spacious retreat blends modern comfort with rustic charm. Perfect for families, hunters, road-trippers, or anyone looking to soak in the quiet beauty of Eastern Montana. Minutes from Makoshika State Park and downtown Glendive, your basecamp for adventure starts here!

4.95 out of 5 average rating, 61 reviews

*New* tiny house 1 mile from Makoshika State Park

This cabin//tiny house (12’ x 33’) is located only 1 mile from the base of Makoshika State Park. Located in a small RV park. Amenities include: Microwave, Refrigerator, Keurig; k-cups, Hot water kettle, tea, Clothing Steamer, Shower with an on-demand water heater, smart TV, Netflix, Free Wi-Fi, Free parking, and porch. Pull-out couch that sleeps 2 and 2 twin mattresses in the loft. 📣As of 7/11/25: Brown leather couch is temporarily out of order so new pull-out couch provided is white cloth.

5 out of 5 average rating, 25 reviews

Farm stay in Kinsey

Cowboy Country Bunkhouse/Guesthouse Modern, Quiet

Take it easy at this unique, quiet, tranquil getaway, just a short drive from Miles City, Cow Capitol of the world! You'll pass by several active farm and ranches on your drive and have horses right out your back door. The Yellowstone River is close by for boating or fishing. Bunkhouse - Brand new one queen bed bunkhouse, just finished! Parking - Gated gravel drive with parking space next to the bunkhouse. Plug-ins available. Plenty of room for trailers or campers. Safe and secure site

4.94 out of 5 average rating, 31 reviews

Home in Wibaux

Badlands Bunkhouse

This unique property is within walking distance of everything in the small town of Wibaux, including restaurants, a brewery, town swimming pool, parks, horseshoe pits, and basketball courts, but also central to Makoshika State Park (30 miles west) and Medicine Rocks State Park (67 miles south). A 32 mile drive east, puts you in Medora, ND, a great little town with an old west feel, home of the Bully Pulpit Golf Course, Medora Musical, and Pitchfork Fondue as well as many other attractions.

4.87 out of 5 average rating, 282 reviews

Flat in Glendive

Cap Rock

This unique and cozy apartment is located in a newly remodeled home located in a nice quiet residential neighborhood close to the heart of downtown Glendive but near parks and hospital. The apartment is on the second floor and has two entrances, one through the open front lobby and up the stairs 12 stairs up, plus 3 to the right). The kitchen is stocked with pots and pans for cooking and coffee and juice. Come enjoy Montana and relax in the comfort of this unique and warm living space.

4.98 out of 5 average rating, 102 reviews

Cottage in Miles City

Historic Cottage Charm!

Clover Cottage is a cozy retreat that lives large in spite of its compact size. Featuring two bedrooms and two baths, plus two sofa beds, this cute charmer can sleep 7-8. Built in 1925, this sweet home away from home is chock full of character with many original details, but it's been remodeled from top to bottom with modern living in mind. You'll love the cheerful front porch and central location, and will appreciate the comfy beds, tasteful furnishings, and useful amenities.

Place to stay in Miles City

4.94 out of 5 average rating, 151 reviews

Historic Montana Theater-Movie Themed Apartment

Discover this charming 800 sq ft apartment nestled within the Historic Montana Theatre, located in the vibrant heart of downtown Miles City! Immerse yourself in its original 1936 charm, lovingly preserved yet enhanced with modern updates for your comfort. With a cozy bedroom featuring a king bed and a spacious living room adorned with comfortable couches, this delightful abode can comfortably accommodate up to 4 guests, ensuring a memorable stay in this historic setting.

4.94 out of 5 average rating, 178 reviews

Quaint home near Yellowstone River

Small, one story pet-free, smoke-free home available for rent. This house contains 3 bedrooms, 1 bath, kitchen, living area, and laundry. Two bedrooms feature queen size beds while the third offers a twin trundle bed. It is clean and updated with central air and heat. Wi-fi available as well as an outdoor patio with grill enclosed by a privacy fence. Keurig available, bring your favorite K-cups. Parking includes on street parking and one off-street parking space.

4.92 out of 5 average rating, 107 reviews

Comfy with views of the badlands

This location borders Makoshika State Park. You'll enjoy views of the badlands right outside your windows. This park offers a variety of activities, from hiking, disc golf, guided dinosaur adventures, and other events throughout the summer months. You will also be close to the downtown area, where boutique shopping, coffee shops, and bars are located. The Yellowstone River is also right there, offering trails and agate & hunting. We also welcome hunters to the area.

Superhost

Bungalow in Terry

4.72 out of 5 average rating, 18 reviews

Tin-Can Cabin

Internet provided. The Tin-Can Cabin is on private property, with plenty of parking. The cabin is quant, peaceful, with new interior. Warm & cozy for a peaceful retreat after a day of hunting, fishing, sightseeing or rock exploring. Nestle up and take personal time at this tranquil and unique get-away. The Cabin is with-in five blocks of down-town, with social events & sites to visit. Keeping it simple while making memories.