Holiday rentals in Pryor

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Top-rated holiday rentals in Pryor

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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, 452 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.

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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
4.97 out of 5 average rating, 266 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.

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Top guest favourite
The living area features a comfortable brown sofa and a coordinating bench against a wall. A flat-screen TV is mounted above a wooden console with drawers. Decorative wall art and a lamp add warmth to the space, which is illuminated by natural light from a window.
Guest house in Laurel
4.98 out of 5 average rating, 186 reviews

Private Studio Loft

Getaway to our peaceful and centrally-located studio in the heart of Laurel, Montana. Suite Gigi's is an adorable, 100% private, and fully furnished loft atop our detached garage (stairs, no elevator). Suite Gigi's is only 1.5 miles from Main Street with all the fun of downtown USA shopping & amenities. You will have your own keyless entry with private access to one of the garages for secure parking of your vehicle. This property is dog-friendly (max 40 lb) with bbq and outdoor patio seating.

ValueLocationGetting around

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
5.0 out of 5 average rating, 247 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!

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Top guest favourite
A living room features a fully reclining couch facing a wall-mounted TV. Two armchairs provide additional seating beside a console table. Large windows allow natural light to brighten the space, complemented by a soft area rug on the floor.
Home in Billings
4.96 out of 5 average rating, 171 reviews

One Level House With Attached Garage!

✨ Bright, single level home with an attached garage in a quiet, walkable neighborhood ☕ Steps to coffee, treats, parks, trails & a local taproom 📍 Minutes to shopping, dining, hospitals & interstate 🛏 2 bedrooms- each with a private bathroom 🛋 Reclining sofa + cozy living space 🛌 Sealy & Serta beds for a great night’s sleep 🍳 Fully stocked kitchen 🌙 Blackout curtains for rest anytime 🚗 Attached one car garage Perfect for business trips or family getaways—clean, comfortable, and easy.

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Top guest favourite
Home in Billings
5.0 out of 5 average rating, 100 reviews

Billings Cottage

Welcome to The Billings Cottage. A cozy retreat within walking distance to a Coffee Shop and a Pizza/Bar. Designed for comfort and convenience, this charming Montana home is the perfect base for your Big Sky adventures. With 3 Bedrooms & 2 baths. It sleeps up to 6 adults. With an additional child's mattress if needed. Whether you’re here to ski in Red Lodge, explore Yellowstone, visit Cody, Wyoming, Devils Tower or plan a scenic drive to Glacier NP. This home puts you in the heart of it all.

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Top guest favourite
A two-story home features a combination of green and brown siding, accented by warm outdoor lighting. A covered porch with seating invites relaxation. The front yard is landscaped with stone pathways and greenery, providing a welcoming entrance.
Home in Billings
4.9 out of 5 average rating, 151 reviews

New Updates! Spacious 5 BR family home on a park!

Family-friendly! Park front yard/playground back -5 BR 3.5 BA -7beds -use of 2car garage -Central location: 2 minutes from I-90 -Couple minute walk to Yellowstone River and trails to Norm's Island -Master KING bathroom has a 2-person soaking tub, fireplace, smart TV Room darkening blinds/shutters, AC Walk-in closets Living area - smart TV/fireplace Basement rec room with queen futon /smart TV Patio with fire pit and grill Enjoy close access to dining, shopping, restaurants, and recreation!

ValueFamilyCheckout

Top guest favourite
Home in Billings
4.97 out of 5 average rating, 98 reviews

*NEW* Sparkling 1-Level 2-BDRM - Master w/King!

Relax in this NEW 1-level home fresh on the market in 2025. This sparkling clean new construction is peaceful, modern & a perfect home away from home. Enjoy designer furnishings, amazing hybrid-memory foam beds, luxury linens, fully equipped kitchen & double garage in this professionally cleaned & managed property. 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.

LocationFamilyCheckout

Top guest favourite
A single-story house is situated on a grassy lot, featuring a stone-accented side and a covered porch with white chairs. Sunlight gently filters through the trees, creating a serene atmosphere in the surrounding yard.
Home in Joliet
4.87 out of 5 average rating, 134 reviews

Rock Creek Paradise (Near Red Lodge, MT)

Described as "a little piece of heaven," this property is located on Rock Creek in Joliet, MT. Perfect for a family get-away - located 30 minutes from Billings and Red Lodge, MT, offering both city experiences and great outdoor activities. Fish out your back door on Rock Creek-both fly and reel enthusiasts love this creek. Ski in Red Lodge! Watch deer, turkey and other wildlife out your front window! Location is ideal for travel to Yellowstone Park, Custer Battlefield and Cody, WY.

FamilyValueQuiet

Guest favourite
A spacious home with a welcoming facade features a combination of stone and siding. A large driveway leads to the entrance, surrounded by landscaped gardens that include decorative stones and shrubs. Multiple large windows allow natural light to fill the interior.
Home in Billings
4.97 out of 5 average rating, 34 reviews

Family & Fun Oasis.

Bring the entire family to this great place with lots of room for fun. Our 5000+ sq ft home features a distinctive patio with hot tub, game room theatre room, fire experience, grilling and access to pool and minigolf at the adjacent KOA Campground. 5 bedrooms and 5 1/2 bathrooms creates for space while 3 seating areas for connecting to your friends and family. Formal dining room and bar top counters in kitchen for all of our social butterflies. We can't wait to host you.

ValueFamilyHospitality

Top 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.
Guest house in Park City
4.96 out of 5 average rating, 418 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.)

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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, 560 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.

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Popular amenities for Pryor holiday rentals