Family-friendly holiday rentals in Sheridan

5.0 out of 5 average rating, 135 reviews

A charming two-story home is presented, with a covered front porch and an American flag displayed. A rustic metal sculpture is visible in the foreground, with pebbled landscaping leading to the walkway. Lush green grass surrounds the home, enhancing the welcoming exterior.

Bungalow in Sheridan

Cozy and Charming Bungalow

We welcome you to our charming 2-bedroom home, pleasantly located in the heart of Sheridan, WY. A short 5-minute drive to downtown, M & M Ice Rink, Fairgrounds, and less than 20 minutes to the Equestrian Center. This home has a warm and modern design with newly remodeled kitchen, 2 bedrooms (queen beds), quaint office, newly renovated bathroom, and room for the portable crib (provided). Our favorite spot to hang out is on the patio; fenced, covered, grill, and ample space to lounge and relax.

KitchenIndoor spacesLayout

5.0 out of 5 average rating, 115 reviews

Condo in Sheridan

Chic 3BR Industrial Loft: Main St. w/ Garage

Stay in a gorgeous modern three bedroom condo right on Main Street Sheridan! You’ll be in the heart of downtown with walking accessibility to restaurants, shops, breweries, & historic sites. Sheridan sits at the base of the Big Horn Mountains that offer the best hiking, fly fishing and exploring around. Sheridan/Big Horn is also home to world class polo matches and renowned art museum a short drive away. Skiing within driving distance and events year-round make Sheridan a wonderful destination!

KitchenFamilySkiing

4.92 out of 5 average rating, 124 reviews

Cozy Suite

Tucked away on a quiet street in Sheridan, the Cozy Suite offers a peaceful and comfortable place to land while still being close to everything in town. A plush queen bed and spacious ensuite bathroom make it effortless to unwind after a day of exploring. Natural light pours in through large windows, or pull the blackout curtains for a slower morning and a few extra zzz’s. Step outside to enjoy the patio, a perfect spot for a quiet morning coffee or a relaxed evening under the café lights.

Indoor spacesKitchenSleep quality

4.95 out of 5 average rating, 585 reviews

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

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

Indoor spacesFamilyQuiet

4.95 out of 5 average rating, 227 reviews

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

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. This tiny home will feel spacious with its vaulted ceilings and extra loft space. The tiny home has a queen bed downstairs in a closed off bedroom. Enjoy the loft with one queen bed and a fold out futon, a great place for kids to enjoy the tiny home as the ceiling clearance is very low. A fully equipped kitchenette, and fast Wifi await.

Indoor spacesKitchenGetting around

A modern two-story home featuring a welcoming porch with comfortable seating and a sleek exterior design. Gravel landscaping surrounds the property, complemented by small shrubs and grasses. Large windows invite natural light, while a decorative wooden fence enhances the outdoor space's privacy.

5.0 out of 5 average rating, 311 reviews

Fire Pit Under the Stars |The Wayfarer Bungalow

Centrally located and newly built, this stylish two-bedroom home is perfect for couples, families, or friends. Each bedroom has a queen bed and its own climate control for a personalized stay. Enjoy a cozy night in with a home-cooked meal and movie, or head outside to roast s’mores by the gas fire pit. Luxury linens, heated bathroom floors, and plush towels add a touch of indulgence, while two cruiser bikes are available for exploring town at your own pace.

KitchenFamilyLocation

The kitchen is open to the living area, showcasing modern appliances and a spacious countertop. A dining table with yellow chairs sits in the corner, while light streams in through large windows, enhancing the warm tones of the wooden flooring.

4.97 out of 5 average rating, 103 reviews

Lovely home close to downtown

Welcome to our 2 bedroom, 1 bathroom home. It is a 5 minute walk from downtown or the walking paths. The kitchen is well equipped, and is open to the living room. This open concept is great for chatting while you cook. The backyard has patio furniture and a grill. The bedrooms have black-out curtains and cozy beds. The front door is equipped with a wifi lock for easy anytime access for our guests. Fast wifi internet and Netflix is provided.

KitchenFamilyQuiet

4.97 out of 5 average rating, 486 reviews

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

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.

KitchenIndoor spacesHospitality

4.95 out of 5 average rating, 508 reviews

Cozy 2BR Getaway | Sleeps 6 | Pets Allowed

Just minutes from downtown Sheridan and historic Main Street, this cozy 2-bed, 1-bath retreat offers an affordable, high-quality stay for up to six guests. Enjoy two queen bedrooms, a sleeper sofa, a fully equipped kitchen, fast WiFi, and a small enclosed yard ideal for your pup. Close to shops, breweries, and the Bighorns, it’s the perfect home base to relax, recharge, and explore everything Sheridan has to offer.

Indoor spacesKitchenAir conditioning

A spacious living area features large windows that fill the room with natural light. The room is designed with industrial elements, including exposed brick walls and a ceiling with metal beams. A comfortable sofa and a round coffee table are positioned on a textured rug, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 158 reviews

Modern Historic Loft | Walk to Breweries & Coffee!

This loft is a brand new renovation of the coolest building in town! Clean, new and a perfect mix of modern amenities with a historic, one of a kind building in the brewery district of Sheridan, WY. It is a ground level loft apartment and the only one of it's kind - no next door neighbors :) The loft is short walk away from Luminous Brewhouse, Black Tooth Brewing and downtown Sheridan. Enjoy your stay!

Indoor spacesFamilyWalkability

4.99 out of 5 average rating, 149 reviews

The guest house features a wooden exterior with a green metal roof, highlighted by large windows on the upper level. A spacious porch with chairs and a table is shown, providing a view of the surrounding landscape and stone landscaping.

Home in Dayton

Our Little Tongue River Guest House

Beautiful location right on the Little Tongue River with river access right outside the back door! Located 1 mile outside Dayton, on the bank of the Little Tongue River at the base of the Big Horn Mountains. The house is surrounded by wildlife and stock, with amazing views in all directions. Hiking and Fishing available on the property as well as in the nearby surrounding area. Close to Sheridan.

Indoor spacesKitchenRiver

4.98 out of 5 average rating, 165 reviews

Loft in Sheridan

Luxe Main St Loft with Rooftop Lounge and Balcony

Welcome to your luxurious, stylish, industrial-chic loft, a stunning retreat nestled within a historic 1892 building in downtown Sheridan. This second-floor apartment has been meticulously renovated to blend its original character with modern comfort. You'll discover an open-concept layout featuring gorgeous hardwood floors, exposed brick walls, and a bright, airy feel.

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Popular amenities for Sheridan family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 228 reviews

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

Goose Valley Farm, Alpaca Farm under the Big Horns

FamilyKitchenWalkability

5.0 out of 5 average rating, 21 reviews

A rooftop patio is furnished with red Adirondack chairs arranged around a modern gas fire feature. The warm glow of the flames contrasts against a sunset backdrop of rolling hills and mountains, set on a wooden deck.

Condo in Sheridan

Blue Line Condo, at the Ice Haus, downtown luxury

KitchenFamilyAmenities

5.0 out of 5 average rating, 3 reviews

Home in Ranchester

The Cottage at Tongue River Canyon

FamilyIndoor spacesWalkability

4.97 out of 5 average rating, 60 reviews

Home in Dayton

Relaxing Mountain view, 5 bdr sleeps 11, 4400 sqft

KitchenIndoor spacesAccuracy

4.8 out of 5 average rating, 79 reviews

Home in Story

Gone Fishin' — Private Hot Tub, Story WY

FamilyIndoor spacesBathroom

4.89 out of 5 average rating, 18 reviews

Barn in Banner

Gone Hunting

FamilyIndoor spacesQuiet

A spacious living area features a light-colored sofa and armchair arranged around a wooden coffee table. Natural light streams through the windows, highlighting the wooden paneling and ceiling beams. An entertainment center with a flat-screen TV is positioned against a wall, creating an inviting space.

Villa in Sheridan

Stunning Sheridan Ranch Villa: Mountain View!

KitchenFamilyAccuracy

4.82 out of 5 average rating, 11 reviews

A spacious outdoor patio is shown, featuring a round table with a blue mosaic centerpiece surrounded by black metal chairs. A hot tub is positioned nearby on wooden decking, while plants and decorative containers add greenery. Soft lighting hangs above the area.

Modern log home 4 blocks from downtown

HospitalityLocation

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 175 reviews

Guesthouse in Ranchester

WYOHANA Studio

FamilyIndoor spacesLayout

A cozy living area is furnished with a dark leather sofa adorned with decorative pillows. Two armchairs complement the seating arrangement. Natural light fills the space through a window dressed with a sheer curtain. A wooden coffee table settles in the center, showcasing various items.

4.87 out of 5 average rating, 114 reviews

1 Bedroom, walking distance to downtown Sheridan.

KitchenFamilyPets

An exterior view of a single-story yellow structure is presented, featuring several windows. A pathway leads to the entrance, bordered by landscaped stones and grass. The surrounding area includes neighboring buildings and utility poles, creating a neighborhood setting.

4.98 out of 5 average rating, 183 reviews

The Hideaway

FamilyKitchenNearby

4.87 out of 5 average rating, 101 reviews

The open living and dining area features a spacious layout with hardwood flooring. A comfortable sofa is positioned near a large window, allowing natural light to illuminate the room. A dining table with multiple chairs is present, complementing the overall inviting atmosphere.

Home in Ranchester

King Bed, Bunks, Hot Shower, Pet-Friendly Home

Indoor spacesFamilyHiking

4.91 out of 5 average rating, 53 reviews

Townhouse in Sheridan

Zen-Den | Sauna + King Bed, Health Oasis-Sleeps 15

KitchenFamilyAccess

An inviting living area features a cozy leather couch and a coffee table, enhancing the modern rustic decor. A flat-screen TV is mounted on the wall, while a faux fireplace adds a warm focal point. Natural light is welcomed through window treatments.

4.96 out of 5 average rating, 77 reviews

Newly Remodeled House close to downtown Sheridan

FamilyIndoor spacesHospitality

A spacious backyard showcases a well-maintained grassy area bordered by trees and shrubs. The greenery provides a tranquil space for relaxation. A patio area and a small structure can be seen in the background, contributing to the inviting outdoor setting.

4.98 out of 5 average rating, 40 reviews

Clean, quiet, private and convienient location.

FamilyIndoor spacesParking

5.0 out of 5 average rating, 21 reviews

Cedar & Sage House | A Calm & Charming Retreat

FamilyIndoor spacesDecor

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 12 reviews

2-Room Camping Cabin w/ A/C | Sleeps 6

FamilyWi-FiBathroom

4.96 out of 5 average rating, 23 reviews

The exterior of a 1905 Victorian apartment building features a gray facade with white trim, large windows, and a welcoming front entryway. A spacious porch is framed by tall trees, while well-maintained landscaping includes vibrant flowers and a neat lawn.

Apartment in Sheridan

Parkside Gardens "Dahlia Suite" Kendrick City Park

KitchenFamilyHospitality

4.94 out of 5 average rating, 16 reviews

Deluxe Cabin Getaway Sheridan KOA

FamilyCleanlinessQuiet

5.0 out of 5 average rating, 3 reviews

Tent in Sheridan

Conestoga Covered Wagon

KitchenFamilyAir conditioning

5.0 out of 5 average rating, 3 reviews

Camping Cabin – Sleeps 4

FamilyLocationSleep quality

5.0 out of 5 average rating, 4 reviews

Deluxe Cabin Retreat|Family-Friendly| Sheridan KOA

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