Family-friendly holiday rentals in Helena

Cheerful 1 Bedroom Luxurious Suite w/Hot Tub!

The Lillie Pad Awaits Your Arrival... Come home to your Ultimate, Mountaintop Luxury Glamping-Suite w/ brand new hot tub - Majestic Mile High Ranch beauty at its best! Total seclusion with world class views of the rocky mountain front and continental divide, only minutes from Montana's Capital. Meticulously handcrafted in the center of the CanyonRidge Ranch, which borders the immense Helena National Forest & lush mountain meadows... Makes the Lillie Pad a truly one-of-a-kind experience and stay!

Historic Montana Home Moments from Downtown Helena

A piece of Helena’s history meets modern living! Quiet, historic two-bedroom house in prime historic Westside location! Located a short walking distance from endless hiking & cross-country skiing trails for the adventurous nature lovers! Also just a short walk to downtown Helena's best dining, entertainment & shopping! Smart TV with xbox in living room, smart TV in each bedroom. Well stocked kitchen, coffee, tea, cream, sugar variety. Two covered porches, private backyard, propane grill & more!

Oro Forest hideout, minutes to town

Escape to a peaceful, retreat tucked into the National Forest, just 10 minutes from Downtown Helena. This spacious home sleeps 10 and offers a true Montana experience—wildlife, trees, mountain air—without sacrificing convenience. Perfect for family vacations, holidays, work trips, anyone wanting nature with easy access to town. Enjoy the yard for kids to play, hot tub April through October, Trager smoker and huge kitchen. Have a larger group? Book the guest house too! --> airbnb.com/h/oronestmt

Cozy Mid-Century Guest Suite

A recently remodeled mid-century guest suite in the heart of Helena. The suite features zero step entry, a queen size bed, closet space, high quality bedding, microwave, mini fridge, coffee pot, AC, and natural light throughout. A comfy, wide couch with bedding can be used in the living room for an extra bed. Brand new shower and replaced flooring in every room. Easy access to I-15, a quick drive to downtown Helena which is full of microbreweries, eateries and shopping, and close to the Capitol.

The Trail House

Centrally located and within walking distance to Helena's Historic Downtown, Carroll College, parks, and some of the finest dining, this 1 bedroom, 1 bath duplex unit is the perfect stay. Newly furnished with everything your stay will desire. On street parking, self check in, shared laundry facility on premise, workspace with wifi, and air conditioning. Kitchen fully stocked with dishwasher for a comfortable stay while away from home. We hope you enjoy your stay with us at our vacation rental!

Hilltop House

Situated at the base of Mount Helena, in the mansion district, Hilltop House features a beautifully landscaped exterior introducing you to a well kept upstairs apartment with plenty of charm. A comfortable 1 bed/1 bath has a relaxing living room with gas fireplace and walkout balcony , a cute kitchen, bathroom with a claw foot tub/shower and lots of light. The close proximity to our historic downtown and walking /biking trails allows visitors the opportunity to experience the Helena we love.

Cozy, charming basement on the west side

Welcome to our bright, happy basement apartment where you'll find the perfect blend of cozy comfort and underground allure! We are located on Helena’s west side. Centrally located to downtown, Spring Meadow lake, Broadwater hot springs, and hiking and biking trails. Our spacious basement apartment boasts all the essentials for an unforgettable stay! The kitchen and bath are equipped with all the amenities you need. The decor is comfortable with just a little twist of humor and good spirit

Silver Creek Accessible Studio

Enjoy a bright and welcoming accessible studio suite just 10 minutes from Helena’s city limits. This thoughtfully designed space features a full kitchen and an extra spacious, wheelchair-friendly bathroom with a roll-in shower—large enough to comfortably accommodate a caregiver and a shower chair. Whether you're visiting for business or relaxation, this cozy retreat offers both comfort and convenience in a peaceful setting.

The Hideaway at Creekside Meadows-Hobbit House

Nestled in the foothills of the Elkhorn Mountains you’ll find our charming earth home. Clean Scandinavian style decor allows the magnificent construction of this home to shine. A few unique features include 4 full sized built in sleeping nooks each with their own lights and electrical outlets, a secret door to a hidden private bedroom, and a shower you enter through a ‘tree trunk’ with almost 13ft ceilings!

Entire Apartment with Guest-Favorite Bed

Bright, newly renovated private apartment with stunning Mount Helena views. This stylish retreat comfortably fits 3 guests and features a dedicated workspace with fiber internet, a full kitchen, and vintage decor. Enjoy views of Mount Helena, a fully stocked coffee bar, and cozy queen bed. Perfect for a relaxing getaway or remote work. Beds: Queen in the bedroom and a twin cot in the living room.

Cloudview Private Retreat

With views of the mountains in all four directions, this south central apartment with parking and a separate entrance is located next to Helena's trail system. Quiet and privacy are key attractions to the comfortable, newly constructed space above our garage. Enjoy the south deck facing Mt Ascension equipped with lounge chairs and a table., and soon a pergola for shad and more privacy.

Heart of Helena

Enjoy the best that Helena has to offer within walking distance. There are great restaurants, breweries and trails all within a couple of blocks. Comfortable, quiet, economical, clean basement studio apartment. Lots of sleeping arrangements and well equipped kitchen and private bathroom.