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

Easy Stay House

Enjoy a stylish, yet comfortable experience, that is walking distance to town! This home has a NEW fully equipped kitchen with new quartz counter and new stainless steel appliances. Near by Attractions -Walking distance 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 min Sedona We offer early or late check out for a $25 fee. Please let me know when booking.

Lodestar Loft Farm Experience

Nature, silence, and farm energies subtly nurture, rejuvenate, and inspire visitors at Lodestar Gardens. Beauty abounds and gently infuses us with greater balance; it supports our greater creative potential. If this sounds like church, it kinda is. For the past 25 years our favorite saying is: "chop wood, carry water and laugh a lot." This attitude radiates into all spaces here. You will find the view from the Loft deck breath taking day and night. Musicians and writer find it a creative zone.

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.

Eagle Eye - Private spring fed creek access!

[Mandatory liability waiver signing upon arrival.] This 8-acre haven is not suitable for children under 18 due to the natural terrain, river access, and steep cliffs. NO DOGS (ADA only) Eagle Eye is a cedar sauna converted into a suite, perched atop a limestone cliff overlooking the enchanting creek, offering a unique and immersive experience like no other. With its concave window framing sunrise vistas, guests are treated to a cozy front-row seat to nature's spectacle.. Eagle Eye. 🦅👁️

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.

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!