Holiday rentals in Pryor

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Top-rated holiday rentals in Pryor

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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, 244 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
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, 448 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
Cabin in Roberts
4.98 out of 5 average rating, 312 reviews

Renovated Historic Cabin w/ Hot Tub Near Red Lodge

*Pls see other listing for winter bookings ! Only sleeps 2 in winter. Nestled in the town of Roberts, a short drive from Red Lodge, Kodow Kabin is a perfect retreat for a getaway. While the exterior is log, the inside is renovated & beautifully decorated. The cabin is 1 bed/1 bath for 2 guests w/ detached bunkhouse (may-Oct) for 2 more guests! The kitchen has a farmhouse sink, and cabinetry made from the siding that covered the logs. Use the private deck to BBQ or hot tub soak under the stars

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, 265 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
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, 180 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.

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!

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.

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, 417 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, 359 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
A bright living area features large windows allowing natural light to fill the space. Comfortable seating is provided by two chairs alongside a wooden table. A television is mounted on the wall, while a small dining table sits nearby, adorned with a centerpiece of flowers.
Home in Billings
4.98 out of 5 average rating, 129 reviews

Garden Hideaway (HOT TUB!)

With craft coffee & a greenhouse downstairs, a private hot tub, & comfy memory foam mattresses, this is the best stay in Billings. Quiet & centrally located, this large & sunny one-of-a-kind home sleeps up to 8, with a clean and relaxing space to chill. Wake to fresh flowers, play ping pong, read about plants and trees, or wander the on-site greenhouse & garden, art gallery, and shop for local artisan crafts.

Guest favourite
Home in Billings
4.95 out of 5 average rating, 283 reviews

Broadwater house

Newly remodeled 2 bedroom down town home located 2.9 miles from the airport. 6 minutes from Billings Hospitals. 5.3 miles from I-90. Enterprise is located next door for your convenience. NaRa Oriental restaurant, Holliday gas station, and Central High School are all just a short walk away. Easy access to some great spots nearby! This property is located on a busy street, which may result in street noise.

Top guest favourite
A modern single-story home is set against a clear blue sky, featuring a welcoming front porch with seating. Lush green grass surrounds the home, with a neatly manicured pathway leading to the entrance. A fenced yard enhances the sense of privacy.
Home in Billings
5.0 out of 5 average rating, 233 reviews

Stylish, Homey, & Spacious

Don't pass this one up! This home has everything you need to feel just at home! It is a newer home with high-end appliances and all brand new furniture! Pristine and very clean! Sit on the front patio for morning coffee or an evening glass of wine! Enjoy your privacy in the backyard while sitting around the gas fire pit. You will enjoy your time in Billings even more while staying at this home!

Popular amenities for Pryor holiday rentals