Holiday rentals 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
4.81 out of 5 average rating, 32 reviews

Prairie Stays

The Prairie stay is located just 15 minutes from 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 cozy living area is adorned with log beams and rustic decor. A comfortable sofa is positioned opposite a gas fireplace. Natural light streams through a window draped in curtains, and a wooden dining table is set nearby, featuring a decorative welcome sign.
Home in Great Falls
4.99 out of 5 average rating, 101 reviews

Hangin' Heart Ranch Guest House W/Western Sunsets

Enjoy stunning sunrises and sunsets at Hangin’ Heart Ranch, nestled in the peaceful countryside west of Great Falls—10 to 15 min. from town. This cozy, one-of-a-kind home sleeps 2 adults (*possibly up to 4) and features high-speed internet, a small workspace, HD TV, well-equipped kitchen, and front-load washer/dryer. Best of all, soak under a star-filled sky in the hot tub right outside your door. *Need space for an extra guest or two? Let us know—we may be able to offer a pull-out sofa bed.

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, 174 reviews

Little Blue Cabin

Quaint home in the middle of historic downtown Fort Benton. Parks, museums, bars, and restaurants all within walking distance. Only a few blocks from the Missouri River and the beautiful river walk. Newly remodeled home with a rustic Montana touch. Great place for a couple getaway or some friends traveling for a fishing trip. We love our pets too so we want you to travel with yours! But pets can also be messy. So be sure to add your pet onto your reservation as we do charge a one time pet fee.

Guest favourite
A spacious living area features a large sectional sofa with yellow accent pillows and a cozy throw. Natural light enters through an adjacent archway, highlighting a textured wall art piece. A wooden coffee table complements the décor, while a ceiling fan overhead adds to the comfort.
Home in Great Falls
4.86 out of 5 average rating, 199 reviews

Where the Buffalo Roam

Come stay where the buffalo roam. This Charlie Russell era home is stylishly updated and sleeps up to six in 3 bedrooms - 2 queens and 2 twins. Centrally located between the airport and Malmstrom AFB, it is walking distance from the heart of downtown and only minutes from the Charles M. Russell Museum, Paris Gibson Square and the Lewis and Clark Interpretive Center. Pets are welcome with a fully fenced (but shared) yard. Enjoy this fantastic home to immerse yourself in the best of Great Falls.

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
4.85 out of 5 average rating, 335 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
The updated kitchen features modern appliances, including a stainless steel refrigerator and a dishwasher. A large marble kitchen counter allows for food preparation, while the open layout provides views of the adjoining dining and living areas, enhanced by natural light from multiple windows.
Home in Great Falls
4.98 out of 5 average rating, 124 reviews

3rd Ave. North Bungalow

This charming century- old bungalow is the perfect location to enjoy all that Great Falls has to offer. Centrally located with mature tree lined sidewalks, it is just a short walk to the C.M. Russell Museum and a quick drive to downtown restaurants and bars. The home has been recently renovated to provide modern features while also thoughtfully preserving its original character. There are two well appointed bedrooms with additional sleeping in the living room and one central bathroom.

Guest favourite
The studio features a comfortable bed with a cozy throw blanket, accompanied by a chair and a small kitchenette area. A bathroom is visible in the background, and shelves display decorative items. Natural light enters through multiple windows, creating a bright atmosphere.
Tiny home in Great Falls
4.96 out of 5 average rating, 54 reviews

Stylish She Shed

Enjoy a romantic night in by the fireplace in this stylish studio home! This tiny gem has everything you need for a private, cozy, getaway! Mini Kitchenette, full bathroom with a rain shower head, an extendable table for eating/working, Wi-Fi, and a ROKU tv. Come experience the tiny life and make memories in our stylish she shed! Central/East end of town located, with quick access to the base, Giant Springs park, both hospitals, the college and a straight shot to downtown Great Falls.

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, 155 reviews

Canvas Tent with Amazing Mountain Views and WIFI!

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
A charming entrance features two wooden chairs positioned on a stone pathway, inviting guests to relax. Potted flowers hang from the overhang, while a pair of double doors with large windows welcomes visitors into the cottage. The surroundings are well-maintained and enhance the outdoor appeal.
Flat in Fort Benton
4.97 out of 5 average rating, 39 reviews

Garden Cottage

Retreat to this quiet cottage after a day spent floating the Missouri or exploring Fort Benton's shops and museums. Set in a walkable neighborhood full of kids and dogs, this studio apartment offers privacy and comfort in easy walking distance to downtown and the river. Your host lives on the property in a separate craftsman home, surrounded by gardens, abundant in summer and fall with flowers and edibles. Two friendly dogs and a cat share the yard.

Top guest favourite
A modern cottage exterior is shown, featuring a sloped roof and a mix of blue and beige siding. Two comfortable chairs are positioned on the patio, inviting relaxation. Large windows allow natural light to flood the interior, offering a view of the surrounding open prairie.
Cabin in Great Falls
4.99 out of 5 average rating, 248 reviews

$99 Sept/Oct Little Modern House On The Prairie

Retreat to a Beautiful New Modern Cottage in the Country. 5 min. to city. High speed internet. NETFLIX & YOUTUBE TV. 2 acres of peaceful serenity. Enjoy the wildlife as you relax watching the sunset from your own private patio. Close to Missouri river fishing access . 1 Hour to World Famous Blue Ribbon fishing . Plenty of Outdoor activities in Montana. 50 amp EV charge area. Need your own charger. Be prepared for a Quiet Stay!! Sorry No Pets.

Top guest favourite
A spacious backyard is depicted, featuring a swing set and fire pit surrounded by lush green grass. The cabin is visible in the background, complemented by tall trees that provide shade and privacy. Clear blue skies create a peaceful outdoor setting.
Cabin in Monarch
4.96 out of 5 average rating, 187 reviews

Sun Mountain Cabin

Our Cabin is located just outside of Monarch, Montana. You will find many activities to do in the area such as hunt, hike, ski, 4 wheel, raft, kayak, and fish are just a small list of the possibilities that await you. It's also the perfect getaway as cell service is very limited. Our cabin is perfect for couples, solo adventures and your furry friends, however there is a hide a bed couch that folds out if you need extra sleeping room.

Guest favourite
A single-story house features a light-colored exterior with a welcoming front door and a small covered porch. A well-maintained lawn surrounds the home, complemented by flowering plants near the entrance. A garage is visible on one side of the structure.
Home in Fort Benton
4.88 out of 5 average rating, 174 reviews

Emily's Vacation Cottage cozy 2 bdr

A comfortable and relaxing furnished house located in historic Fort Benton, Montana. Accommodations for up to 6 people, with 2 bedrooms, kitchen, full bath, laundry room, and backyard space with outdoor furniture. Off street parking. Restaurants, shopping, museums and the historic levee and downtown district are a walk away. Your comfort is our goal. Pet fee apply per pet, per night. Only 2 dogs allowed. No cats allowed.

Popular amenities for Highwood holiday rentals

  1. Airbnb
  2. United States
  3. Montana
  4. Chouteau County
  5. Highwood