Family-friendly holiday rentals in Winslow

The Birds Nest on Route 66

Holbrook is a charming town in the heart of Route 66. My family has lived here our whole lives and love our town. We have a two story home with with a birds eye view of Holbrook and The historic Wigwam Hotel that was the inspiration for the Cozy Cone Motel in Disney’s Cars movie. The downstairs is for our guests and is comfortable, cozy and clean. We are 20 minutes to a four hour drive to The Painted Desert, Petrified Forest, Grand Canyon, Four Corners National Monument, Sedona and much more

Wright Hill Cabin: Backing Kaibab Forest w/ Access

The Wright Hill Cabin is located in the small, rural community of Parks, Arizona - 20 minutes West of Flagstaff and 15 minutes East of Williams. Situated just within the tree line, the cabin sits on the edge of beautiful Government Prairie which provides unobstructed views of the San Francisco Peaks while providing the beautiful scenery and wildlife of the vast Ponderosa Pine Forest. The quiet community of Parks provides easy access to Grand Canyon National Park, Snowbowl, Bearizona and more!

A-frame Mountain View Cabin in the National Forest

@AFrameFlagstaff is a tiny house A-Frame on 1.5 acres in the National Forest. Featured in American Eagle Outfitters worldwide campaign. Dog friendly. AC. Epic glamping and stargazing. 10 min to historic downtown/Route 66. 15 min to Walnut Canyon, Sunset Crater, Wupatki National Parks, NAU, AZ Snowbowl. 30 min to Meteor Crater and Sedona. 90 min to GRAND CANYON, Horseshoe Bend, Antelope Canyon, and Petrified Forest. 2.5hrs to Monument Valley. Our listing "Tiny Mountain View Sauna Cabin" nearby

Sleep under the Stars near Sedona!

Gaze at a million stars, comet showers, or the full moon in this magical Dome, just 25mins from Sedona. Sleep under the stars on a comfy bed right in the Dome, or in nearby "Garden Shed". Relax in the patios surrounding this hidden desert paradise. Access nearby trails & ruins. Less than 2-mile hike to breathtaking views of the confluence of the Verde River & Oak Creek. Five miles to Cottonwood, gas & shops. Close to vineyards, & so much more! No chores at check-out! Just enjoy your vacation!

• Holbrook Hub •

Great jumping off point for adventure in and around NE Arizona or just a good night’s rest. 20 miles from Petrified Forest. 1 mile from two I-40 exits. Newly remodeled home featuring southwestern flair with a Route 66 themed room. Stocked kitchen, coffee/tea area, spacious living/dining room, and family room. Three bedrooms with queen beds and another with a twin beds. Established, quiet neighborhood. 2 car covered carport & street parking. Convenient to restaurants and grocery store.

The Hidden Sedona Gem - A Private Cliffside Escape

Wake up to hot air balloons over Sedona’s red rocks. Greet friendly goats, gather fresh eggs, or unwind by the fire pit under a blanket of stars. The Gem is a private 2-acre cliffside retreat with panoramic views over Dry Creek—just 10 minutes from Sedona’s most iconic trails. Pets always stay free with access to a private, fully fenced yard. Starlink Wi-Fi, Roku TV, full kitchen, washer/dryer, and trailer parking. Loved by 600+ guests and consistently rated among Sedona’s top stays.

Route 66 Retreat w/Tesla Charger

We are 25 mins from the PF National Park ✅ Whether you're visiting or passing through, our updated home will ensure your stay is comfortable. - King suite w/ split floor plan - Tankless water heater - Lvl 2 Tesla Charger (43~mph) - Parking for 3 cars on the driveway & gravel w/ trailer parking - Brand new high end Washer & Dryer - Coffee bar w/ coffee pods, flavorings, teas, & snacks. - Fast wifi - Fully equipped kitchen - Black out curtains in all rooms Enjoy your stay in Northern AZ

Cabana at the Pond

7 sided Cabana, screened windows (no glass, no heat) bamboo shades, sleeps 2+1 pet cozily, overlooks beach+pond. Door locks from inside only. Lots of Wildlife. Well trained pets only, no barkers!. Private bath below via outdoor bridge +steps. Outdoor kitchen corner nook privately yours, Dining areas may be shared w/others. 2.5 miles to town. Close to urban trails +Little America. quiet time 10pm-8am. pet fee$25. Open May-Oct. see also ' GUESTHOUSE NEAR THE POND' listing #14698421.

Winslow Stay

Newly renovated kitchen comes fully equipped with quartz counter tops and new stainless steel appliances. Coffee machine is kcup. Family room has smart tv for relaxation and enjoyment. Our home is pup friendly with a fully fenced yard and nice patio space. Near by Attractions -2 min drive to standing on the corner, down town, and La Posada -3 miles to Clear Creek -10 min drive Painted Desert -10 min drive Homolovi Ruins -60 min petrified Forest -45 min Flagstaff -60

The Family Size Chicken Coop

This spacious home is in a rural community perfect for the whole family. It features plenty of off-street parking with the ability to accommodate trucks and trailers. The kitchen is fully stocked for your use, though we recommend coming with your groceries as the nearest store is 10 minutes away. The Chicken Coop is conveniently located off I-40/Route 66 allowing for travel to the Petrified Forest/Painted Desert, Meteor Crater, the Grand Canyon, Flagstaff, and more!

Cozy Forest Retreat • AC + Near Trails

Escape to our private 40-acre ranch near Flagstaff! This fully renovated 2-bed, 2-bath retreat comfortably sleeps 4 and features two king beds, central AC, a gas fireplace, and stunning forest views. Perfect for couples or small families seeking a peaceful getaway with direct access to the Arizona Trail and national forest, yet only a short drive from town. Enjoy cool mountain air, rare privacy, star-filled nights, and the quiet beauty of a working ranch setting.

Railway Stop - Stay in a piece of History

Built in 1940, close to the train station. This historic building was first built and used as a Chicken restaurant to feed the hungry passengers traveling through one of the busiest train junctions in the west. Being right on old Route 66 this building changed it's face from restaurant to barber shop, Boot and leather repair shop, hair salon and now a place you can bring your family to stay and experience the railway through America