Holiday houses in Pryor

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Top-rated holiday rentals in Pryor

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Top Guest favourite
The cottage's exterior is framed by natural logs and stones, highlighting large glass windows that extend along the structure. Located in a grassy area, the building creates a seamless connection to the surrounding landscape under a clear blue sky.
Cottage in Roberts
5 out of 5 average rating, 42 reviews

Glass Cottage Overlooking Beartooth Mountain Range

This spectacular, exquisite cottage is the perfect getaway spot for those looking for secluded privacy with a million dollar view! Perched atop a hill overlooking the Beartooth Mountain Range, the Glass Cottage lives up to its name! Breathtaking views of the picturesque mountains can be seen from every room in this luxurious log cottage through the large, glass windows. On beautiful days, you can open up all the sliding glass doors to have the full Montana experience with the fresh mountain air!

Top Guest favourite
A rustic log cabin is set amidst lush greenery, featuring a welcoming front porch supported by sturdy wooden beams. Nearby, a stone patio is complemented by picnic tables, inviting outdoor gatherings. The surrounding landscape includes trees and well-maintained grass, creating a serene setting.
Cabin in Roberts
4.99 out of 5 average rating, 145 reviews

Private Luxury Log Cabin near Red Lodge, MT

Private luxury one (queen) bedroom log cabin with a queen sofa bed, full bathroom (shower), radiant floor heat, ceiling fans, beautiful rustic furnishings, and a kitchenette. This beautiful cabin sits on 10 pristine acres that border Rock Creek (prime fly fishing) and Red Lodge ski mountain is only minutes away. Enjoy camping and hiking in the summer and drive over the scenic Beartooth Pass to get to Yellowstone Nat'l Park. This truly is a one-of-a-kind location to spend with friends & family!!

Top Guest favourite
The exterior of the barn is shown, featuring a unique curved roof and a combination of wood and stone materials. The entrance is highlighted by a large wooden door and adorned with the word 'THE BARN.' Surrounding fencing and agricultural elements complement the rustic setting.
Barn in Lovell
4.99 out of 5 average rating, 424 reviews

The Loft of the old barn at the Rafter JB

The barn, where the loft is, was moved from Cody where it was the old feed store. Cozy space. Sit by the pond and relax or walk around the landscaped property visiting with the animals. We are in a quiet neighborhood, but close to town to enjoy the restaurants and little shops that line main street. Only 20 minutes to the Bighorn Mountains, enjoy beautiful scenery, hiking or picnicing or a guided trail ride. Yellowtail Reservoir offers fishing and hunting opportunities only minutes away.

Top Guest favourite
A single-story house is set against a clear blue sky, surrounded by lush green grass. Several trees with budding foliage are visible in the yard, creating a serene landscape. A driveway leads to the house, with outbuildings located nearby.
Cottage in Joliet
4.96 out of 5 average rating, 250 reviews

Peaceful Country Cottage - Gateway to Yellowstone

Farmlands surround you in this peaceful valley. Your house overlooks farm fields down to the Clarks Fork of the Yellowstone River. 2 min South of the Rockvale Junction (Highway intersect of the 212 and the 310). 1 Hour North of Cody, WY, 35 min from Red Lodge, MT. Take a scenic drive over Beartooth Pass into Yellowstone Park. Your house is a 2 bedroom, 1 bathroom. 2 min from the Edgar Bar & Steakhouse. 8 min away in Joliet is a local grocery store, Blackbrew Coffee, and Jane Dough's Pizza.

Top Guest favourite
Two horses stand in a fenced pasture in front of a rustic cabin. The cabin, made of wood, features a welcoming porch and large windows. The surrounding area is open, with green grass and a clear blue sky overhead, creating a serene ranch atmosphere.
Cabin in Lovell
5 out of 5 average rating, 242 reviews

The Bunkhouse/Private cabin/all amenities

Completely private cabin. Located 5 mi east of Lovell, Wy. Family-friendly activities in the Big Horn Mountains, Pryor Mountains and the Big Horn Canyon National Recreation area. Yellowstone Park and Cody are close enough to enjoy. You’ll love our place! Our horses, the solitude, beautiful views of the mountains, old west charm coupled with all the modern conveniences. It's just what you would expect in Wyoming!. Excellent for couples, solo adventurers, and business travelers. Kids welcome!

Guest favourite
A cozy dining area features a round wooden table with four chairs, set against a backdrop of nature-themed artwork. A small fireplace adds warmth, while a nearby seating area is furnished with a comfortable sofa and a flat-screen television mounted on the wall.
Cabin in Powell
4.91 out of 5 average rating, 112 reviews

Country Chic Cabin

This country chic cabin offers comfortable stay with all the necessary and modern amenities. The space is professionally decorated and designed for comfort and relaxing getaway from hustle and bustle of city. It encompasses western and country art décor to coincide with surroundings. Cabin is 800sqft and sits on 24 acres surrounded by farm land with 360 view of mountain ranges. It is located 1 mile from town and short drive to Cody Wyoming. Long term stays are possible, send message.

Top Guest favourite
Home in Billings
4.96 out of 5 average rating, 76 reviews

*BRAND NEW* Sparkling 1-Level 2-BDRM King!

We invite you to relax in this brand NEW 1-level home. Fresh on the market in 2025, this sparkling clean new construction, stylish, peaceful, modern cottage is a perfect home while you're away from home. Enjoy designer furnishings, amazing hybrid-memory foam beds, luxury linens, fully equipped kitchen & double garage. Conveniently located in a charming neighborhood with parks, playground, coffee shop & pub within walking, 10 minutes to downtown or 5-10 minutes to west-end shopping & dining.

Guest favourite
An organized space is shown, featuring a comfortable sleeping area with a queen-sized bed covered in soft linens. A modern bathroom area with dark tiles is partially visible, along with a sleek fridge in the corner. Large windows allow natural light to fill the room.
Guesthouse in Billings
4.92 out of 5 average rating, 123 reviews

The Modern Midtown Tiny

Welcome to our charming, centrally located Tiny Home, just minutes from downtown Billings, both hospitals, and the airport. This modern space features high ceilings, large windows that fill the home with natural light, and a queen-size bed that promises a restful night’s sleep. Enjoy the convenience of a fridge, oven/stove, and a new full-size washer and dryer. With stunning tile work and heated bathroom floors, we’ve created a space where you can truly relax and feel at home.

Guest favourite
A cozy sleeping area features a quilt adorned with wildlife motifs, complemented by decorative pillows. Warm wood paneling creates an inviting space, accompanied by soft lighting from mounted sconces. A framed nature-themed artwork enhances the rustic charm of the room.
Guesthouse in Park City
4.96 out of 5 average rating, 393 reviews

NEW Charming Little Cottage in Park City, Mt

Brand New! Super cute little cottage tucked away in the back yard with a contemporary farmhouse/rustic charm to it. Located right off I-90. Less than 10 minutes from Laurel ( which has Walmart, fast food, grocery store, restaurants). 25 minutes from Billings and 20 minutes to Columbus. Private entrance. Perfect for the traveling worker, couple or solo adventure. Wifi is available with a smart TV so you can watch your shows on your favorite apps (Netflix, HuLu, ect.)

Top Guest favourite
A single-story tiny home is shown with a welcoming green door and a front porch featuring a bench. Light-colored siding is complemented by large windows that offer views of the surrounding landscape, consisting of gentle hills and trees.
Tiny home in Billings
4.97 out of 5 average rating, 335 reviews

*NEW BUILD* Mini Mountain View Getaway

Mini Mountain View Retreat is a great weekend get away. Just a short walk to downtown, the hospitals, or a view of the Beartooth Mountains. This tiny home makes for a relaxing stay with everything you need and a peaceful and homey atmosphere. Just because it's tiny doesn't mean it isn't full of all your basic home essentials such as a full kitchen, washer and dryer and luxurious features. This shared property is tucked away in a quiet and peaceful neighborhood.

Top Guest favourite
The exterior of the house is presented, showcasing a blend of natural wood and modern materials. Large windows reflect sunlight, while a spacious deck extends from the structure, surrounded by trees and open sky.
Tiny home in Billings
4.98 out of 5 average rating, 169 reviews

Industrial Loft@Old Pine Retreat

Here is your opportunity to experience a remote getaway just minutes away from downtown Billings. This beautiful, vintage-industrial themed house has features that include a 21 foot high ceiling in the living room, a gas fireplace, a loft master bedroom and a second bedroom, large bathrooms on both levels and a private deck. If this isn't enough, the views and remote space that you will get to experience will be enough to take your breath away!

Guest favourite
A cozy living area features a large TV mounted on the wall and a contemporary clock. A gray sofa is complemented by a bright yellow throw blanket and decorative cushions. A wooden table with black chairs and a plant adds to the comfortable ambiance.
Townhouse in Billings
4.93 out of 5 average rating, 148 reviews

Updated Home | Hot Tub | Parking for Trailers

🏠 Welcome to our newly remodeled retreat! Located in central Billings close to everything. 🚚 We offer extra parking for trucks AND + trailers! 📺 Enjoy seamless entertainment with smart TVs in every room along with WiFi. You'll have a charging station for all your devices! 🛏️ The beds are super comfy! ⭐️ With brand new furnishings, enjoy comfort and modernity in our professionally decorated space. Pristine and very clean!

Popular amenities for Pryor holiday rentals

  1. Airbnb
  2. United States
  3. Montana
  4. Big Horn County
  5. Pryor