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

Airstream on a Petting Farm

Glamp in this cute, cozy 29' vintage Airstream near Sedona's stunning sights. Perfect for families to unwind - pet friendly farm animals, epic sunsets, starry nights. Sleeps 2 adults on sofa queen bed & 2 kids in bunk beds. Recently redone interior in calm blue/silver tones. Amenities include AC, bathroom, fridge, picnic area with grill & fire pit overlooking sweeping views. Enjoy a taste of ranch life as you explore attractions and make your way to Grand Canyon. Stay includes animal access ❤️.

The Bitty Bungalow

Welcome to The Bitty Bungalow, a charming tiny guest studio, perfect for those seeking cozy simplicity with all the comforts of home. It features a well-supplied mini kitchen, a deluxe redesigned bathroom, and a mini washer and dryer. My grandmother's antique roll-top desk and grandfather's original oil paintings complete the home's rustic look. While ideal for a solo or couple getaway, The Bitty Bungalow sleeps up to 6 guests, allowing families or groups to enjoy a modest retreat in the pines.

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

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

Basecamp 66 - Perfect Location For Your Adventures

Enjoy stunning views & Kaibab National Forest (AZGMU-7) as your backyard at our 2BR house near Bellemont, Arizona. Centrally located between Flagstaff and Williams, near historic Route 66, this quiet, cozy, peaceful and sustainable-building-award-winning cabin is the perfect stay for couples, families, friends and hunters alike. Enjoy modern day comforts with an outdoorsy experience. Wifi has been upgraded and works perfectly! Well stocked to make your stay as comfortable as possible.

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 Sanctuary: Intimate space in vintage church.

The Sanctuary is a self-contained, cozy apartment in a repurposed church. Antique furniture, stained glass windows and chandeliers live among the full bookcases. You can enjoy the steeple library or the cozy bar while on your laptop. A new mini split allows for heat in colder months and AC during warmer months! **Please note that this unit does have stairs to the kitchenette, bathroom and second room and is not accessible for larger walkers and wheelchairs.

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