Family-friendly vacation 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

Cabin by the Pond

Make some memories at this unique and family-friendly place. Cute, cozy picturesque cabin with wood burning stove, queen bedroom downstairs and upstairs loft that sleeps 6 and has large TV Also available, to accommodate large families is an annex that sleeps 3 Not only will you enjoy the cabin, deck with great views, and bbq but be my guest to explore 40 acres which includes 2 ponds (kayaks and paddleboats), petroglyphs, waterfall, orchard and beautiful vistas especially at sunset and sunrise.

“Ranch House” Welcome Long Term w/discount

Enjoy this cozy, well decorated 1000 sq ft ranch house Built in 1948 this home (The Jones Ranch) was surrounded by grazing land and now is located in the heart of Holbrook. Walking distance to shopping, historical walking tour, Rt 66, dog park, great eateries, movie theater, historical museum and nice play park. You can make this your base for visiting the Petrified Forest, Grand Canyon, Navajo Reservation, Meteor Crater, Canyon de Chey, Hubbel Trading Post, Sedona Red Rock Country 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

• 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 2 twin beds. Established, quiet neighborhood. 2 car covered carport & street parking. Convenient to restaurants and grocery store.

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

Route 66 Bungalow

Beautiful historic home in downtown Holbrook on the historic Route 66. This modern yet comfortable bungalow is for you! Built in 1915, this home features 2 bedroom/1 bath, living room, formal dining room and a fully stocked kitchen. The kitchen features a coffee bar with a deluxe espresso and latte maker. Our home is pet friendly with a fenced in yard for your pets to run around. Can’t find the dates you need? Check out our other property in Holbrook! airbnb.com/h/highdesertcottage

Vintage 50s cabin has a deck, yard, and privacy.

Stay in a rural, cozy cabin just 30 minutes south of Route 66. The Petrified Forest as well as local lakes, streams, and the White Mountains are just a short drive away. Situated amongst pine trees, this private, single-level guesthouse for 2 (plus 1 infant) offers comfort, privacy, and a taste of nature. Your 30-pound or less, well-behaved dog is welcome and will enjoy a fenced yard. A microwave, frig, Keurig, toaster oven, and outdoor griddle are provided for your convenience.

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