Holiday houses in Highwood

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Top-rated holiday rentals in Highwood

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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
4.79 out of 5 average rating, 56 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

Top 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
4.87 out of 5 average rating, 45 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!

Top Guest favourite
Home in Great Falls
4.98 out of 5 average rating, 151 reviews

Charley Pride Place | Hot Tub | Sleeps 13

Home was built for Legendary Country Music Singer Charley Pride. Home is features 6 Bedrooms and 2 Bathrooms as well as a New Salt Water Hot Tub & Massage Chair. Home is ideal for Families or Groups that want a relaxing place to stay while in Great Falls or headed to Glacier Park. The home backs up to a very Large Park with Playground Equipment for the Kids or space for your Dogs to run around and play. Also has a Game Room with a Massage Chair, Basketball Hoop, and 2 Living Rooms .

Top 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
4.92 out of 5 average rating, 219 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
4.85 out of 5 average rating, 41 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 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
4.86 out of 5 average rating, 378 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.

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
4.95 out of 5 average rating, 19 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.

Top Guest favourite
The exterior view features a charming one-story building with a light-colored metal roof. A welcoming back deck is equipped with two wooden chairs, and large windows allow warm light to fill the interior. Steps lead from the deck to the ground level.
Farm stay in Vaughn
5 out of 5 average rating, 16 reviews

Historic Schoolhouse at Big Sky Bison Ranch

Welcome to the newly renovated historic Schoolhouse nestled in the native prairie at Big Sky Bison Ranch, a working regenerative bison operation in the peaceful, private Muddy Creek Valley. The 1,200-acre property is the perfect backdrop for relaxation. Bison, deer, antelope, trout, waterfowl, pheasants, coyotes, badgers, otters, beavers, and the occasional bear call it home. Catch-and-release fly fishing; private bison tours and other ranch experiences are available for an additional fee.

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
4.96 out of 5 average rating, 185 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
Apartment in Great Falls
4.96 out of 5 average rating, 158 reviews

Downtown Snuggery

Who doesn't love to stay in the center of it all? This adorable and snuggly apartment is located in downtown Great Falls on Central Ave! Not to brag, but downtown is really beginning to thrive! From steakhouses, concert venues, toy stores, cocktail bars, dive bars, spas and a darn good diner! Along side the many awesome retailers downtown, we have parades, concerts in the street, farmers markets and so much more! The apartment is just a home away from home!

Top Guest favourite
A grassy area features several deer grazing peacefully, with a prominent butte rising in the background. The expansive sky and rolling fields contribute to the serene landscape, emphasizing the natural beauty of rural Montana.
Home in Geraldine
4.88 out of 5 average rating, 43 reviews

Rural Getaway

Experience a bit of luxury in beautifully rural Central Montana! This walk-out basement includes two large bedrooms, one small bedroom, one bathroom featuring an all tile walk-in shower, fitness room; and living room centered around a gas fireplace which is surrounded by open views of Square Butte and prairie grasslands. Perfect getaway resting-place for any group of hunters or those looking to watch the sunrise in the middle of the last best place.

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, 81 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!

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