Holiday houses in Pryor

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Top-rated holiday rentals in Pryor

Guests agree: these stays are highly rated for location, cleanliness and more.

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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
A modern tiny house is depicted with its natural wood exterior, featuring a welcoming covered entrance. A wooden deck extends into the landscape, adorned with outdoor seating and surrounded by trees, creating an inviting connection to nature.
Tiny home in Billings
4.99 out of 5 average rating, 232 reviews

Boho Bungalow @ Old Pine Retreats

If you can imagine a getaway in a uniquely designed tiny house that is built on 60+ acres of wide open and stunning landscape, then you have captured a glimpse of this rare find. This beautiful tiny house is all yours to enjoy such amenities as a glass garage door that can be opened to experience nature from your kitchen table or a fireplace to cozy up to when the temps are cold. You can enjoy coffee in the morning from your private deck and keep your feet warm in the winter with heated floors.

Top Guest favourite
A rustic cabin entrance is framed by wooden beams, showcasing a cozy porch with two chairs and a barbecue grill. Potted flowers add a touch of color at the base, while a gravel path leads to the door, inviting visitors to explore the surrounding nature.
Tiny home in Billings
4.96 out of 5 average rating, 283 reviews

Cozy Creekside Cabin Near Billings

Enjoy this beautiful fully furnished cabin just minutes outside the Billings city limits. Check in and then unwind with a walk on the private trails just out your front door. We are located a simple drive to the Metra for concerts and events, Ah-Nei State Recreation Area with ATV, walking, and horse trails, historic Pompey's Pillar, the Yellowstone river with fishing accesses, and Lake Elmo State park. Caretakers reside onsite and also host our four-legged friends through their pet resort.

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
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
Home in Billings
4.92 out of 5 average rating, 278 reviews

Cozy Retreat - Walk to Downtown, Shops & Breweries

Colorful comfort meets Montana charm — your cozy downtown escape🌿 This cozy and colorful home is the perfect retreat after a day of exploring. Whether you’re visiting for work, family, medical visits, or city events, you’ll love the convenience of our central location 🏙️🍴☕️🏔️🍻 • Downtown Billings – 2 min • Hospitals – 7 min • Billings Airport – 8 min • MetraPark Arena – 7 min • Yellowstone River – 5 min • Starbucks – 6 min • Lake Elmo – 15 min This home is the perfect home base

Guest favourite
A winding road curves gently alongside a rugged rocky formation, with greenery lining the base. Tall trees and vibrant foliage contrast against the stone, while a clear blue sky overhead enhances the picturesque landscape.
Apartment in Red Lodge
4.94 out of 5 average rating, 757 reviews

Secluded Rock Creek Apartment

Fully furnished apartment with complete kitchen and a great view up Rock Creek Canyon. This is a very private apartment separate from main house. Bathroom has toilet, shower and sink...private from the rest of the apartment. Property is directly on Rock Creek and includes WiFi and smart TV. Only 5 miles from Red Lodge. Queen bed in bedroom and the couch in living room is a queen hide-a-bed. My neighbor's bedroom is only 40 feet away, so I will not accept any loud motorcycles.

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.

Guest favourite
The living area features a modern sofa with neutral upholstery, complemented by a cozy throw. Two artwork pieces are displayed on the wall. A wooden coffee table sits in front of the sofa, accompanied by a floor lamp and a decorative plant in the corner.
Home in Billings
4.9 out of 5 average rating, 541 reviews

Montana Modern Home

This is a family-friendly home. We made sure to include all of our favorite touches that we look for when we travel. 1) Great Sleep! We got brand-new Tuft & Needle mattresses, comfy pillows, luxurious bedding, and darkening shades. 2) Amazing Coffee. We got you a Nespresso and a Keurig with K Cups. We will provide a few options, but bring your favs if you have them! 3) Professionally Decorated. We think you will love all the Montana Modern special touches.

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