Vacation rentals in Highwood

Charley Pride Place • Hot Tub • Family Retreat

Home was built for Legendary Country Music Signer 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 .

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.

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.

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.

The Dodge House

Built in the early 1900's, the home has some natural floor sloping, part of historic charm, and completely safe. There are 3 steps to go up from the back door with a hand rail. Located in a small community close to a lot of nice places to visit and site see. 5 miles from the Missouri River. Surrounded by flowering hedges and a nice flower garden. Off street parking. Fenced yard with a gate to close to keep your dog safe. Surrounded by agriculture fields, cows, deer, antelope, and birds.

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!

Cozy movie theater basement near downtown!

Enjoy a unique and cozy stay at this stylish shared duplex. Located within walking distance of downtown Great Falls, you'll have easy access to local restaurants, shops, and attractions. Perfect for a fun getaway or a peaceful retreat, this space offers the perfect balance of entertainment and comfort. Whether you're watching a film in the private theater, working out in the gym, or sipping beer from the tap, this home has everything you need for a memorable stay.

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!

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.

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.

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.

Buffalo Jump Retreat - Extended Stay

Our spacious and centrally-located home is ready for you and your large group! With five bedrooms, two bathrooms, two living rooms, fenced yard, and a large kitchen, the Buffalo Jump is the perfect place for your group to spread out and relax.