Holiday rentals in Pony

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Top-rated holiday rentals in Pony

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Top guest favourite
Farm stay in Manhattan
4.99 out of 5 average rating, 174 reviews

Sunrise Silo - Luxury silo near Bozeman, Montana.

Newly constructed, 675 sq ft Sunrise Silo sleeps 4, with a queen bed in the loft and a main floor pull-out sleeper sofa. Sunrise Silo is a unique example of how rustic charm pairs perfectly with modern amenities and an indulgent experience. The stunning, unobstructed views of the Bridger Mountains and surrounding Gallatin Valley will ensure this becomes your favorite Montana vacation destination. Enjoy a rural setting while having easy access to adventure and entertainment opportunities.

Guest favourite
A rustic cabin is displayed with a reddish-brown wooden exterior under a cloudy sky. A gravel path leads to the entrance, flanked by cut logs and stone stumps. Nearby, an open area of grass offers a spacious view of the surrounding landscape.
Cabin in Twin Bridges
4.93 out of 5 average rating, 150 reviews

2-bedroom Cabin in the Heart of the Ruby Valley

Bring your family for a vacation and enjoy some fishing in one of our Blue Ribbon trout streams including the Big Hole and Beaverhead Rivers less than a mile away… or maybe track down that monster bull this fall ... or come for a winter getaway and take a snow excursion in Yellowstone Park.... or just enjoy the peaceful views from our property and relax... the options are endless. This cabin has a full kitchen with dinnerware and utensils, full bathroom with full tub/shower and oil stove heat.

Top guest favourite
Apartment in Big Sky
4.98 out of 5 average rating, 191 reviews

Golf Course & MTN Views, walk to Town Center

Tucked along the Big Sky Golf Course with unobstructed views of Lone Mountain, this is the kind of place you can settle into right away. Mornings start slow with coffee on the patio before heading into town, exploring nearby trails, or making the drive to Yellowstone. We’ve stocked the space the way we’d want it: a fully equipped kitchen, thoughtful extras, and comfortable spaces to unwind after a full day. It’s an easy, low-key home base for experiencing Big Sky without overcomplicating it.

Guest favourite
Yurt in Bozeman
5 out of 5 average rating, 218 reviews

WILD+WANDER Luxury Yurt near Bozeman, Montana

Get away from it all when you stay under the stars at Wild+Wander. This light-filled, 30 ft yurt has all the comforts of home while escaping from the everyday. A perfect couples' retreat, this yurt features a full kitchen, bedroom and bath, hot tub, stove, and charm that you can't find anywhere else. Nestled in the hills, the yurt sits on 5 acres of panoramic mountain views. Protected from the noise and lights of town, yet only 20 minutes from main street, this property is a hidden sanctuary.

Top guest favourite
Cottage in Cardwell
4.94 out of 5 average rating, 180 reviews

The Ranch Cottage Hideaway with Sauna!

This three bedroom three bath cottage is part of a Montana working ranch that sits where the original homesteaders once staked their claim. Nestled along the South Boulder River this location is a great jumping off point for all your Southwest Montana adventures. Relax in your own private sauna with the beautiful backdrop of the Tobacco Root Mountains. Only two hours from Yellowstone National Park, minutes away from Lewis and Clark Caverns, and 75 feet from your new favorite fishing hole.

Guest favourite
Tiny home in Whitehall
4.95 out of 5 average rating, 147 reviews

Tiny house and RV hook-up in Big Sky Country

Keep it simple at this rural, peaceful and centrally-located place. The house is located between an abundance of mature trees providing a "tucked-in" feeling. There is ample parking and a large grassy area great for outdoor activities. A full hook-up camp spot is available for an additional fee. The location is close to the Town of Whitehall, the Jefferson River, Lewis and Clark Caverns, Copper K Barn wedding venue, Ringing Rocks, and numerous ATV, horseback, and hiking trails.

Top guest favourite
The exterior of the duplex showcases a brown wooden façade with crisp white trim. A covered entry features a white door marked with a letter 'B'. Nearby, a decorative pot filled with colorful flowers adds a welcoming touch to the pathway.
Cottage in Whitehall
4.94 out of 5 average rating, 385 reviews

Unique Tiny Cottage w/ loft ~ 3 min to I-90

This 280 sq. ft. tiny house has a comfortable bedroom and beautiful, tall ceilings. A vertical ladder goes to a small, carpeted loft with a twin mattress on the floor. The queen bed in the main bedroom has a soft mattress. Most people think it's luxurious and cozy. Those who need a firm mattress might not want to choose this cottage. The interstate is just a few minutes away. The small kitchen has a sink, microwave, a one burner stove, small frig, dishes and utensils.

Top guest favourite
Cabin in Dillon
4.93 out of 5 average rating, 452 reviews

Alturas 1 - 1BR Modern Cabin, Big Beautiful Views

This is a beautiful cabin with modern touches, clean lines, and spectacular mountain views via massive windows. The cabin takes its name from one of the peaks you'll see right out your window, Alturas 1 (Our 2 BR cabin is named for the next peak to the north... Alturas 2. Alturas 1 is a 1 BR cabin with a convertible sofa in the front room to accommodate up to 3 guests. **(PET OWNERS, please read pet section in the "the space" section.**

Top guest favourite
A wooden sign marked 'River Stone Cabin' is affixed to a tree in a lush green yard. The cabin structure is visible in the background, surrounded by tall trees and mountainous terrain under clear blue skies.
Cabin in Cardwell
4.97 out of 5 average rating, 274 reviews

River Stone Cabin

The River Stone Cabin is a modern Montana cabin with internet access that sits next to the South Boulder River. The Cabin is comfortable and warm with bright spaces for friends and family. The location is rural with many guests seeing a variety of wildlife. We are pet friendly with a fee. The Cabin can serve as a convenient base for visiting parks and local attractions or simply as a great place of sanctuary to relax and unplug.

Top guest favourite
A rustic kitchen features wood-paneled walls and a long dining table with four wooden chairs. Large windows offer expansive views of the surrounding landscape, while a modern stove and stainless-steel appliances are neatly arranged along one wall.
Tiny home in Whitehall
4.97 out of 5 average rating, 110 reviews

Luxury Solar Powered Tiny Cabin-Full Kitchen-Sauna

Stay in our Gala Cabin on a WORKING (formerly Amish) farm in rural southwest Montana—complete with access to a wood-fired barrel sauna. This is a true farm experience—rustic, grounded, and one-of-a-kind. The cabin is off-grid (solar), so power is limited at times. Expect open land, animals, and the rhythms of farm life (including guardian dogs at night). Located 17 minutes south of I-90 near hot springs and hiking.

Top guest favourite
A hot tub is positioned on a wooden deck, providing a view of the expansive snowy landscape. The seating area includes a single, classic Adirondack chair nearby, with a rustic wooden structure framing the scene. Rolling hills and trees are visible in the distance.
Farm stay in Dillon
4.94 out of 5 average rating, 377 reviews

Ranch Retreat at the base of the Pioneer Mountains

Come experience life on an authentic ranch in beautiful southwestern Montana! Just 30 minutes outside the charming town of Dillon, stay in a quiet and remote cabin at the base of the Pioneer Mountains, with the Beaverhead National Forest right outside your back door. Located 5 miles from Birch Creek for fishing and hiking enthusiasts. We have cattle, horses and donkeys that you can see right from the front porch.

Top guest favourite
The bright-red caboose is positioned on a grassy area, showcasing its vintage exterior. A series of windows and a cupola can be seen on top, while the iconic railroad logo is displayed on the side. The clear blue sky complements the colorful structure.
Tiny home in Pony
4.93 out of 5 average rating, 27 reviews

Red Caboose in Pony

Inside this restored 1968 bright-red Northern Pacific caboose, located on the eastern edge of Montana’s Tobacco Root Mountains, you’ll find a cozy living space for up to 4 people, a full bathroom, kitchenette, one full-sized bed, one full-sized fold-out couch, and a loft. This caboose sits on original 1889 Statehood railroad tracks, on a 3 acre property in Pony, Montana.

Popular amenities for Pony holiday rentals

  1. Airbnb
  2. United States
  3. Montana
  4. Madison County
  5. Pony