Holiday rentals in Highwood

4.92 out of 5 average rating, 156 reviews

Home in Fort Benton

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.

4.87 out of 5 average rating, 177 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.

4.84 out of 5 average rating, 32 reviews

Home in Belt

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.

4.83 out of 5 average rating, 306 reviews

Tiny home in Great Falls

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.

4.98 out of 5 average rating, 101 reviews

Charley Pride’s Place Country Music Legend

Our Gorgeous Remodeled 6 BD 2 BA is Clean | Cozy | Spacious with New Salt Water Hot Tub & Massage Chair. Home was built for Country Music Legend Charley Pride. Home is ideal for Families or Groups that want a Cozy 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 Cozy Living Room.

4.99 out of 5 average rating, 109 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.

4.96 out of 5 average rating, 137 reviews

Tent in Raynesford

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!

4.97 out of 5 average rating, 31 reviews

Flat in Fort Benton

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.

4.99 out of 5 average rating, 227 reviews

Little Modern House On The Montana 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.

4.96 out of 5 average rating, 164 reviews

Cabin in Monarch

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.

4.94 out of 5 average rating, 116 reviews

Home in Power

Power Retreat

Small town living with a full house with lots of space and a big yard and private parking that can accommodate a boat or trailer. The house has 3 large bedrooms with lots of space to spread out. Only 20 minutes to Great Falls, 40 minutes to the Rocky Mountain Front and an easy day trip to Glacier National Park. Perfect for a family or hunters looking for a place to set up camp.

Guest suite in Fort Benton

4.89 out of 5 average rating, 80 reviews

Main St. Stay Ft Benton, Small Town Experience

Keep it simple at this peaceful and centrally-located place. Enjoy the comfortable bedrooms, clean and spacious indoor and outdoor relaxation spots while you are visiting the Birth Place of Montana. See the creativity of many Montana Artists and Makers. We don't expect you will spend much time inside as there is so much to do within walking distance!

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Other great holiday rentals in Highwood

4.79 out of 5 average rating, 14 reviews

Prairie Stays

JoshRating, 5 stars1 month ago

I never write reviews. Yet this stay has compelled me to. Keith’s listing at Prairie Stays was above and beyond in every regard. Situated right on a large private pond, the view is inescapably beautiful (I highly recommend watching the sunrise from the sun room from 0530-0800 with a cup of coffee). Keith is a responsive host and made check-in and check-out a breeze. I would highly recommend this local gem to everyone out there looking for a private area with unbeatable views.

4.88 out of 5 average rating, 164 reviews

Home in Fort Benton

Emily's Vacation Cottage cozy 2 bdr

Theresa AnnRating, 5 stars4 days ago

This little cottage was perfect. My husband and I plan to stay there when we visit Fort Benton in the future. It was exceptionally clean, the kitchen was so well stocked with food, as well as anything you may want to cook/serve a meal. Very comfortable beds. So peaceful and quiet and I especially loved seeing deer wondering the neighborhood. Very reasonably priced also.

5 out of 5 average rating, 24 reviews

Home in Highwood

House in the Highwood Mountains

TracyRating, 5 stars1 week ago

Willow's comfortable country home is in a peaceful setting, with the soft musical song of the creek and abundant birdsong. The lilacs around the front porch were in full bloom and filled the air with their sweet, delicate fragrance! It was a treat to sit on the porch, quietly taking it all in. We had everything we needed for a very restful, comfortable stay and would stay again.

5 out of 5 average rating, 17 reviews

Beautiful New Home w/ two Master Suites

BrendaRating, 5 stars4 weeks ago

I totally recommend this place if you are needing a very clean, updated, affordable home to stay at with the best working layout for a family. Jeff was an amazing host. His response time was super quick.

5 out of 5 average rating, 14 reviews

Guest suite in Cascade

Bar Diamond D Ranch Rental

JeremyRating, 5 stars4 weeks ago

Would return ASAP. Great Hospitality, Wonderful Accommodations, Secluded valley experience Must stay when in area. Home away from home

5 out of 5 average rating, 46 reviews

Rivers Edge Cottage!

HeatherRating, 5 stars4 days ago

The house and neighborhood were very beautiful and peaceful. Exploring it made us consider it as a retirement location for the future. We love the fact Cindy allows pups and there was a large, fenced grass backyard for them to hang out in! Cindy was very nice and helpful with recommendations of local places to visit and fish. She is very safety conscious and warned us about the steep riverbank which was a hazard for pets and children. We appreciated that since we thought we could walk right up to it! Will definitely stay again the next time we come to visit family in Great Falls!

Home in Carter

4.58 out of 5 average rating, 12 reviews

The Dodge House

JamesRating, 5 stars6 months ago

Responsive host. Great amenities.