Holiday houses in Highwood

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Top-rated holiday rentals in Highwood

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

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Guest favourite

An aerial view captures the updated farmhouse nestled by a serene lake surrounded by greenery. The expansive fields extend towards the distant mountains, creating a scenic backdrop under a cloudy sky. The rustic charm of the property is complemented by the natural landscape.

Home in Great Falls

4.82 out of 5 average rating, 50 reviews

Prairie Stays

The Prairie stay is located just 15 minutes east of Great Falls. With gorgeous views of the Highwood Mountains which often reflect off the lake. Welcome to ours and now your little slice of Heaven. This updated farm house is located on a working wheat farm. While you may see the tractors out in the field the house is secluded and quiet. The perfect place to kick back and relax. This single level 3 Bedroom 2 Bath house will sleep eleven and is a great spot for couples, families, and bigger groups

Guest favourite

A living room is presented with a light-colored sofa positioned near a wooden coffee table and a decorative rug. A stone fireplace serves as a focal point, complemented by a nature-themed artwork above. Natural light enters through two windows, enhancing the space's comfort.

Home in Fort Benton

4.84 out of 5 average rating, 37 reviews

The Cute Craftsman at 1502

Your family will be close to everything when you stay at this centrally-located, historical home! Complete with four bedrooms and a living room, this house is perfect for enjoying all that Fort Benton has to offer. The location is only a couple blocks away from the beautiful Missouri river and restaurants and coffee shops! Please note that this is an adorable but older home with steep stairs! The safety and enjoyment of our guests is important and we want you to love the house as much as we do!

Guest favourite

A quaint home with a blue metal roof is surrounded by lush green grass and trees. The entrance features a covered porch supported by wooden beams, while large windows allow natural light to enter. A stone accent wall complements the rustic design.

Home in Fort Benton

4.91 out of 5 average rating, 205 reviews

Little Blue Cabin

Welcome to our cozy Montana escape—nestled in the heart of downtown Fort Benton! LBC is just steps away from the beautiful Missouri River, restaurants, bars, and museums. This newly remodeled home blends modern comfort with a rustic MT touch—perfect for a romantic getaway or a weekend fishing with buddies. We love our pets too, so your furry companions are more than welcome! Just be sure to add them on your reservation as we have a one-time pet fee to help us keep the place fresh for everyone.

Guest favourite

A compact tiny home is displayed, featuring a sleek metal exterior with a light gray finish. Two windows allow natural light to enter, while a wooden entryway steps lead to the front door. Additional utilities are seen beside the structure.

Home in Belt

4.84 out of 5 average rating, 38 reviews

Belt Butte Street Tiny homes

Enjoy a stylish experience at this centrally-located place. This tiny home has so much to offer while you stay in the quaint little town of Belt Montana. Centrally located in Montana for all sorts of recreational opportunities or just come for an evening at the historic theater and enjoy a show and dine in at the Harvest Moon all within walking distance. Skiing, snowmobiling, Hiking, fishing, hunting or just relaxing as your traveling through to one of the national parks Montana has to offer.

Top Guest favourite

A hot tub is set on a private deck, illuminated by soft blue lights. The bubbling water creates a soothing ambiance, inviting relaxation. A railing surrounds the area, providing safety and a view of the surrounding landscape at night.

Home in Great Falls

4.96 out of 5 average rating, 127 reviews

Cozy Charmer Cottage - Soak and Relax w/ King Beds

Charming 4BR home is the perfect for families or groups. Relaxing Private Backyard with a Hot Tub & Tree Swing for the little ones. Enjoy grilling out & spending time with family under the Big Montana Sky. A short 2 min walk to a very Large Park and Jaycee Swimming Pool to enjoy on Hot Summer Afternoons. Jaycee Park includes a Basketball Court, Pickleball Courts, & large playground. A Few Mins from Restaurants, Grocery Stores & Shopping. Make lasting memories on your Montana Adventure!

Guest favourite

A charming private guest house is presented, featuring a light blue exterior and a welcoming front deck. Sturdy wooden steps lead up to the entrance, while vibrant pink flowers are positioned beside the pathway. Lush green grass surrounds the building, under a clear blue sky.

Tiny home in Great Falls

4.85 out of 5 average rating, 366 reviews

Shed with a Bed

Private guest house in a highly desirable neighborhood. The entire guest house to your self with a self check-in, accommodating, studio-like outbuilding. Great place to rest and have a hot shower while fulfilling your agenda in Great Falls. Hot tub available for use for an additional $25 fee per stay. Guest house is in a fenced backyard with privacy, cleanliness, and safety. Equipped with a T.V, Wifi, a mini fridge with refreshments & some snacks, microwave, & an outdoor grassy hangout venue.

Top Guest favourite

A comfortable living area features two plaid armchairs facing a central coffee table. A large flat-screen television is positioned on a wooden stand across from a decorative fireplace, framed by stone and adorned with various decor pieces. Natural light enters through window treatments.

Home in Great Falls

5 out of 5 average rating, 16 reviews

Copper Roost

Discover tranquility at the Copper Roost, a retreat 4 1/2 miles from Great Falls. Main level in a charming house, 3 bedrooms, 2 baths. Enjoy scenic views that were that Native Americans camped and buffalo roamed. Relax and whip up something special from owners fresh eggs (upon request) from their friendly backyard chickens. Unwind on the peaceful decks with freshly roasted local Morning Light Coffee. Ideal for a restful escape or as a base for exploring the surrounding areas of Montana.

Guest favourite

Home in Cascade

4.93 out of 5 average rating, 15 reviews

Pivot House:Mountain View and Short Walk to River.

Unplug, relax, and reconnect with nature at this peaceful retreat just minutes from Cascade. Enjoy sweeping views of open fields and the Adel Mountains, or open the garage door for breezy indoor-outdoor living. Just 1/4 mile from your private river access—downriver from the Cascade take-out—you’ll rarely see another soul. With no TV, it’s the perfect place to unwind, paddle, picnic, and stargaze. Want to enjoy some of the city? You are only 25 min. from Great Falls or 50 min. to Helena.

Top Guest favourite

A custom-built canvas tent is showcased against a clear blue sky, featuring a spacious covered porch supported by wooden beams. Two Adirondack chairs are positioned on the porch, and firewood is neatly stacked underneath. Surrounding trees and rocky terrain create a natural atmosphere.

Tent in Raynesford

4.97 out of 5 average rating, 181 reviews

Unique Canvas Tent with Amazing Mountain Views!

Room to Relax! No fees here! We understand how it feels to search for the a high quality place to stay on your trip. Like you, we are frustrated by the struggle to find affordable high quality places to stay. Nobody should have to experience low quality accommodations. Book with us and your family will thank you! You’ll be able to stay in a high quality place that your family will remember for years to come. Come experience high quality off grid glamping in Montana!

Top Guest favourite

The exterior of a unique round house is showcased, featuring a metal roof and large windows. The house is elevated on a grassy hill, surrounded by open fields. A balcony extends from the structure, overlooking the landscape under a vibrant sky at sunset.

Home in Vaughn

4.98 out of 5 average rating, 86 reviews

Roosters & Reels

Nestled on the shore of a peaceful and private set of fishing ponds sits this award winning home. The 235 acre property is the perfect backdrop for relaxation. Brown Trout, Rainbow Trout, waterfowl, pheasants, and deer call this property in the Big Sky State home. This rental allows for catch and release fishing at your leisure. Pheasant hunting opportunity available for additional fee. Please communicate your desire to hunt and/or fish in your correspondence with the host(s).

Guest favourite

A small cabin with a vibrant blue exterior is set against a snow-dusted landscape. A wooden deck leads to the entrance, with colorful skis displayed in a vertical fence in the foreground. Surrounding trees and mountains are partially visible, enhancing the rustic charm.

Home in Neihart

4.95 out of 5 average rating, 44 reviews

Montana Mountain Cabin on Highway 89

The Little Belt Mountains are truly a Montana hidden gem and Neihart, MT is dead center of this magical place! There are endless amounts of outdoor recreational opportunities within minutes from The Montana Mountain Cabin. Seeking amazing powder at Showdown? Hunting big game? We welcome anyone and everyone to stay. Neihart is small, but has everything you need during your stay. Bob's Bar is the local bar and restaurant, and the Inconvenience Store has a bit of everything.

Top Guest favourite

A charming single-story home is set back from the sidewalk, surrounded by greenery and colorful flowerpots. A pathway leads to the front entrance, flanked by a small porch. The yard is well-maintained, featuring a grassy area and a wooden fence in the background.

Home in Fort Benton

4.96 out of 5 average rating, 76 reviews

Spacious 4-Bedroom Home

Please come and enjoy our spacious 4 -bedroom home in beautiful Fort Benton, MT. Our home is located on a quiet street only 2 blocks from the beautiful Missouri River and walking distance to downtown shopping and restaurants. Perfect space for a larger group, comfortably accommodating 8. We have 1 king, 2 queens, and 2 twin beds. Large kitchen, 2 living rooms, and a great backyard patio with BBQ. You will love our home and Fort Benton!