Vacation rentals in Sheridan County

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Top-rated vacation rentals in Sheridan County

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A two-story yellow farmhouse is shown, featuring a central balcony and multiple windows. Surrounding grassland is visible, adding to the rural ambiance. Light clouds are present in the sky, contributing to the serene setting.

Farm stay in Plentywood

4.82 out of 5 average rating, 11 reviews

Farmhouse & Acreage

640 acres of space to roam with solitude and a 4 bedroom home to stay in. This historic farm house was built in 1908 and in our family for 4 generations. The property is all grassland - either pasture or hay, so great habitat for upland game and deer. Dogs are welcome but not allowed past the laundry room/mud room. Hunting access is available through LandTrust website. The well water has a color to it so bring your drinking water! The house is old so it has some quirks to be expected.

Guest favorite

A comfortable living area features a gas fireplace set within a rustic mantel. Two armchairs are positioned near the flickering flames, and a decorative ottoman is placed in front. Natural light enters through the nearby window, enhancing the cozy warmth of the space.

Home in Medicine Lake

4.94 out of 5 average rating, 17 reviews

The Quack Shack, a cozy home in Medicine Lake

The house has been entirely remodeled within the last few years. It features a gas fireplace, 3 bedrooms, 1.5 half baths, laundry, new appliances, new flooring and deck. It's an older home, but updates have been made throughout. It is plenty big and will easily hold 8 people. You will feel very comfortable! Medicine Lake is a tiny town in northeast Montana, known for it's 30,000+ acre refuge. The refuge is home to hundreds of species of birds and is a popular birding and hunting area.

The exterior of a two-story house is observed, featuring a light green facade and a gabled roof. Large windows are present at the front, complemented by a central entryway with a blue door. Minimal landscaping includes low shrubs and a dirt pathway leading to the entrance.

Home in Plentywood

4.7 out of 5 average rating, 33 reviews

3 bedroom, 2 story Craftsman with antique charm

Your family will be close to everything when you stay at this centrally-located place in Sheridan county! It has 3 bedrooms and 1.5 bathrooms. Fully furnished and includes two full sized beds and a queen bed. Dogs are allowed but NOT PAST THE ENTRY. We do have wifi and a TV, so bring your streaming devices! It is a constant work in progress and things may change between guests. Photos may be delayed in regards to updates. The house is over 100 years old and has some old house quirks.

Guest favorite

The exterior of a two-story house is presented, featuring white siding and black shutters. A turquoise door adds a vibrant touch, while flower pots filled with colorful blooms are positioned beside the entrance. A well-maintained lawn enhances the inviting appearance.

Home in Plentywood

4.97 out of 5 average rating, 62 reviews

Hillside Home

A comfortable and relaxing stay featuring a newly remodeled open floor kitchen, dining, and living area, bath and infrared sauna room. Guests have full access on the main level. The two guest bedrooms (queen) and a second full bath are on the second floor and laundry in the basement. Enjoy WiFi throughout the home, an outdoor dog kennel, and a pellet grill on the deck in the back. The house is located just a short drive from many areas of State of Montana public hunting land as well.

The historic school building is set against a vibrant sunset, with hues of orange, purple, and pink filling the sky. The two-story structure, painted white, stands prominently among the open grassy landscape, while rolling hills are visible in the background.

Home in Redstone

4.86 out of 5 average rating, 28 reviews

Historic School Stay

Spend the night in a Historic School Building. One of the classrooms has been converted into a studio apartment. There is a garage with a walk in cooler perfect for processing wild game. The apartment has a full kitchen. Redstone is a very small town with lots of room to roam and wide open spaces. Great for hunters or someone looking for some peace and quiet. We do have wifi and a TV, so bring your streaming devices! The building is old (built 1915) and is a work in progress.

Guest favorite

A living area is seen with a beige couch adorned with decorative pillows. A green upholstered chair is positioned beside a wooden side table topped with a lamp. A ceiling fan with dark blades is visible above, and a large mirror reflects the space.

Farm stay in Plentywood

4.83 out of 5 average rating, 6 reviews

Home on The Range

Enjoy a private country stay on a small working cattle ranch. Just three miles from town, the three bedroom, 2 bath home features a complete kitchen set up, washer and dryer, TV, wifi, AC, patio, firepit, barbeque grill and 10x20x6 dog pen. The most noise you'll hear is from the rooster, but we'll provide a dozen fresh eggs at check in to take the edge off. Just 4 miles from Plentywood, in the heart of NE Montana's pheasant country.

Home in Plentywood

New place to stay

Home on the Hi-Line

Welcome to your Hi-Line Hideaway in Plentywood, Montana! This cozy and casual 3-bedroom, 1.5 bath home is the perfect place to kick back and relax after a day of visiting northeastern Montana. Inside, you’ll find a bright, clean living space with comfy seating, a flat-screen TV, and a bonus game area complete with arcade games, shuffleboard, and retro gaming fun.

Guest favorite

A modern kitchen is equipped with sleek stainless steel appliances, including an oven and refrigerator. White cabinetry and marble countertops create a clean aesthetic. A window is adorned with a sheer curtain, allowing natural light to illuminate the space. Two bar stools are positioned at the counter.

Home in Plentywood

4.92 out of 5 average rating, 24 reviews

Grandma's Place

Our cozy, 2 bedroom home offers a blend of comfort and charm with all the amenities you may need for your stay. Hunters are welcome! If you have dogs, please contact us prior to booking. Dogs may stay in kennels in the garage. We have a small yard that allows for toileting/feeding. Dogs are not allowed in the house for any reason.

Guest favorite

A cozy living area features two leather recliners flanking a rustic trunk. A simple tan sofa sits across from the seating arrangement, with wood-look flooring contributing to the inviting ambiance. A clock is mounted on the wall, complementing the overall decor.

Home in Westby

5 out of 5 average rating, 9 reviews

Almost Stateline

This house located in Westby is in the heart of bird migration with prime observation access within a few minutes. This area is also excellent for upland bird hunting and with the location of the house can be used for either Montana or North Dakota enthusiasts. Westby is a little town with a big heart.

Top guest favorite

A charming exterior of a light-colored house features a distinctive scalloped roofline and a welcoming purple front door. Lush greenery surrounds the building, with flower beds visible along the walkway leading to the entrance.

Home in Plentywood

5 out of 5 average rating, 22 reviews

Northern Nights Cottage

Relax with the whole family at this peaceful place to stay. Northern lights are often brilliant in this area. Hunting pheasants and white tail deer is also quite popular in the fall months. Dogs are allowed only in back room and kennel. No dogs allowed in living quarters on furniture or beds.