Vacation rentals in Saddlestring

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Top-rated vacation rentals in Saddlestring

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Top guest favorite

A white horse grazes peacefully in the lush green pasture, framed by rolling hills and distant mountains. Soft light filters through the clouds, casting gentle rays onto the scene, which is bordered by a wooden fence and trees.

Farm stay in Sheridan

4.99 out of 5 average rating, 184 reviews

Goose Valley Farm, Alpaca Farm under the Big Horns

Idyllic farm setting located below the Big Horn Mountains. Enjoy laying in hammock alley while watching Alpacas graze in the pasture w/ the Mountains as your back drop or read a book and listen to the symphony of birds & the clucks of happy chickens. You’ll feel enveloped by nature & the slow relaxing pace of the farm w/ open access to the farm animals. Enjoy the wide open spaces w/ abundant wildlife, & unobstructed views of the Big Horn Mountains w/ a vast country night sky filled with stars.

Guest favorite

A rustic cottage exterior is visible, featuring wooden shingles and a welcoming sign labeled 'Saint Herman.' Two green chairs are positioned in front, and a natural landscape of trees and grass surrounds the structure, creating an inviting atmosphere.

Home in Sheridan

4.91 out of 5 average rating, 11 reviews

Saint Herman Mini Cottage

The Saint Herman Monastic Cottage offers minimalist, rustic charm, designed for tranquility and simplicity. Nestled along a peaceful stream and backed by wooded land, they provide the perfect escape from modern life. These mini cottages are just steps from the shower and a short walk to the restaurant, where you can enjoy hot meals, good drinks, and a cozy library/study area with a chessboard and pool table (please check hours to see if open). A convenience store is just a short drive or walk.

Top guest favorite

A welcoming guest house is surrounded by tall pine trees, featuring beige siding and a front porch. Nearby, a vintage sheep wagon with a green and white canopy rests on a grassy area, adding a unique element to the tranquil outdoor setting.

Guesthouse in Story

4.98 out of 5 average rating, 205 reviews

The Inn on the River

Relax and enjoy the abundant wildlife at our guest house on North Piney Creek in beautiful Story, WY. This 2nd floor guest house offers 2 bedrooms with adjoining full bath. There is a kitchenette with a dorm size refrigerator, toaster, countertop oven and coffee pot. We have just expanded our AirBNB to include a vintage sheep wagon that accommodates 2 people. There is NO bathroom in the sheep wagon. Bathroom and kitchenette are located in the guesthouse. Only 1 party is accepted nightly.

Top guest favorite

A welcoming living area features a cozy armchair near a wooden table and television. Natural light flows in from large windows adorned with light curtains, highlighting the warm wooden floor and textured area rug that adds depth to the space.

Apartment in Sheridan

4.98 out of 5 average rating, 444 reviews

Stylish 1BR Near Main St |The Troubadour Suite

Experience historic charm in our cozy cottage, nestled in a vibrant, picturesque town. This house is bright and airy with access to everything Sheridan has to offer. With a large living area, full kitchen with local coffee and a queen bed and radiant heat this space is perfect for all your needs. You will be close to great restaurants, shopping and all the area attractions. Enjoy the beautiful outdoors with nearby trails and parks just a few minutes away along with a short walk to downtown!

Guest favorite

A deer stands calmly in a grassy area outside a large window. The view is framed by wooden walls, and natural light illuminates a decorative pottery piece on a nearby surface. Lush greenery is visible in the background.

Home in Story

4.98 out of 5 average rating, 175 reviews

Sadie's Place, Two Bedroom tucked into paradise.

Sadie's Place is a cozy, comfortable two bedroom home located in the heart of Story on a secluded corner of paradise. The house is well equipped to provide a worry free stay. It is a short walk to the local store, library and post office. On the property there is a private walking trail (walking, snow shoeing or cross country skiing), three holes of rustic golf, a beautiful mountain stream and an abundance of opportunities for wild life watching. For relaxation, there is no place better.

Guest favorite

A log cabin is situated under a blue sky with scattered clouds, featuring a welcoming front porch. The porch is furnished with outdoor seating. Lush green grass and decorative boulders enhance the natural landscape, while trees frame the property.

Cabin in Buffalo

4.99 out of 5 average rating, 95 reviews

Bounty of the Bighorns Cabin near Buffalo

Whether you are a history buff looking to explore local battlefields and museums, a group of seasoned hunters in need of a base camp, or just looking to relax and enjoy the tranquil solitude, our cabin will make a great retreat from the hustle and bustle. Minutes from the Bighorn National Forrest, Lake DeSmet and The Bud Love Wildlife Management Area the cabin is conveniently situated near the towns of Buffalo, Big Horn and Sheridan, Wyoming. Access to great hiking, fishing and hunting.

Top guest favorite

A rustic log cabin is surrounded by lush green grass and large trees. The porch features a railing, while the cabin's wooden exterior blends naturally with the outdoor environment. The structure is designed to provide a cozy retreat with easy access to the surrounding landscape.

Cabin in Banner

4.95 out of 5 average rating, 512 reviews

Our Little Slice of Heaven 🐶 Pet Friendly

Quiet and Relaxing 1,000 sq ft Cabin with gorgeous view will make you feel like you're in Heaven. 10 miles (16km) outside of Sheridan Wy on Hwy 14, easy access off I-90, with a beautiful drive. This is the perfect get away for you to unplug. Those crisp Wyoming winter days, relax by the stove with a cup of hot coco . Cabin stays cool in summer if you open windows at night and close up in the morning. Pets welcome after approval & $20 pet fee. Must be pet & child friendly. Starlink WIFI

Top guest favorite

The cabin features a large wrap-around porch supported by rustic wooden posts. A set of outdoor seating frames the entrance, with steps leading to the front door. Lush greenery surrounds the cabin, enhancing the connection to nature.

Guesthouse in Story

4.97 out of 5 average rating, 113 reviews

Creekside Cabin at Story Brooke Lodge

Come relax at a cozy cabin along Piney Creek with a large wrap around porch. Open your windows to listen to the water running by all night with fresh cool air. The cabin features a queen size bed and a pull out couch. Kitchenette includes a sink, Keurig, toaster oven, microwave, hot plate, and mini fridge. The cabin features a gas fireplace, a covered porch with skylights and also has a glass dining table with four chairs. This cabin has cable TV that is also a smart TV and wifi.

Top guest favorite

A panoramic view of a canyon features steep rocky cliffs and lush greenery below. The sky is bright with fluffy clouds, and the landscape showcases rolling hills and distant mountain ranges. Natural rock formations create a dramatic backdrop, highlighting the area’s rugged beauty.

Cabin in Ten Sleep

4.95 out of 5 average rating, 110 reviews

The Bunkhouse

The Bunkhouse- Experience the wonder of Wyoming and the charm of TenSleep. Nestled at the base of Powder River Pass, TenSleep is the place to explore, fish, hunt, climb, hike, snowmachine, ski, ride and play! Meadowlark ski area is 20 miles up the canyon, on the far side of Meadowlark lake. The canyon is wild and majestic, the mountains immense. TenSleep is known for its outdoor adventures and impressive climbing opportunities! Come and join in the fun!

Guest favorite

The exterior of a tiny home features a deep blue facade with natural wood trim and a covered porch. A welcoming white door is framed by a large window, while a sign indicating 'PARK HERE' is placed on the porch. The yard is gravel-covered, with planters decorating the entrance.

Tiny home in Sheridan

4.96 out of 5 average rating, 136 reviews

Holloway Hideaway Tiny Home

Welcome to your cozy tiny home retreat minutes from downtown Sheridan, WY. This charming tiny home is the perfect blend of rustic comfort and style. Visit historic downtown Sheridan and enjoy a day of shopping or visit one of the many local western museums. Spend an evening out to one of our local breweries and enjoy some local talent. Take a day rip enjoying the mountains only 20 minutes from the Holloway Hideaway front door.

Top guest favorite

A lush green yard is visible, featuring several blue spruce trees and a winding creek. A garden area is enclosed by a fence, while a modern home sits in the background. Additional trees and open fields add to the scenic landscape.

Guesthouse in Sheridan

4.97 out of 5 average rating, 434 reviews

Big Horn Getaway

The bedroom is in the loft above a working ceramics studio. The bathroom is on the main floor with one flight of stairs. We are located about two miles from the base of the Bighorn Mountains with a beautiful view and lots of privacy. It is a perfect getaway for two people who can handle the stairs. The space is not suitable for children under 18 or pets. We are unable to accommodate service dogs due to host's allergies.

Top guest favorite

A rustic wooden home is surrounded by a grassy area, showcasing a welcoming front porch with seating. Bright blue skies and lush green trees create a serene backdrop, while distant hills add to the natural setting.

Farm stay in Buffalo

4.98 out of 5 average rating, 82 reviews

Entire Home-Private Guest Ranch

Stay in your own private, western-styled home surrounded by a mile of pristine creek. Get a taste of the Wyoming lifestyle with a family-friendly stay on a breathtaking ranch. Beautiful view of the Bighorn Mountains. Swim and fish the creek, feed the chickens and much more! Perfect retreat to unplug, unwind, and enjoy God’s beautiful creation. Due to the loft, we can't host families with children under 5 years old.