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Vacation rentals in Winslow

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Top-rated vacation rentals in Winslow

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious living area is highlighted by a red pool table, positioned in the foreground. Two ceiling fans are visible, along with comfortable seating arrangements behind the table. Directly ahead, a large television is mounted on the wall, while glass doors open to a private patio.
Guest suite in Holbrook
4.95 out of 5 average rating, 861 reviews

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

Top guest favorite
The two-story black structure is set among tall pine trees, with large windows allowing natural light to illuminate the exterior. A paved driveway leads to the entrance, while outdoor stairs connect the upper and lower levels. Soft lighting highlights the building’s contemporary design.
Guesthouse in Flagstaff
4.89 out of 5 average rating, 166 reviews

Mountain Town Retreat

Enjoy this peaceful retreat with views of a mature forest and the San Francisco Peaks! Deer and elk graze across the ravine outside your bedroom window, and hummingbirds drink nectar from the abundant wildflowers. This is a really special spot! Still, our home sits inside Flagstaff, with all its amenities: cafes, roasteries, beer gardens, and breweries. Snow Bowl, Sedona, and the GC are not too far from us, along with many other day trip hikes and destinations. We love this place! Come join us!

Top guest favorite
A single-story home with a black exterior and a brown shingled roof is set within a gravel yard. Large windows allow natural light to fill the interior. A light blue front door adds a pop of color. A fenced perimeter features a sign indicating private property.
Home in Winslow
4.94 out of 5 average rating, 221 reviews

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.

Top guest favorite
A framed Route 66-themed artwork is displayed, featuring a vintage car, a bright red truck, a dinosaur, and southwestern motifs. The design incorporates iconic imagery such as a sunset, maps, and teepees, all set against a backdrop that symbolizes travel and adventure.
Home in Holbrook
4.9 out of 5 average rating, 221 reviews

• 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.

Guest favorite
A cozy living area is highlighted by a large wall-mounted television and a comfortable hanging chair. Light wooden flooring is complemented by soft neutral tones in the decor. A ceiling fan adds a modern touch, while plants and subtle storage enhance the inviting space.
Home in Holbrook
4.99 out of 5 average rating, 137 reviews

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

Top guest favorite
A cozy studio apartment is highlighted by wooden beams and a spacious layout. A luxury queen-sized bed, adorned with patterned bedding, is complemented by a gray couch that converts into a full bed. A flat-screen TV is mounted on the wall opposite the couch.
Guest suite in Snowflake
4.95 out of 5 average rating, 702 reviews

Meadowlark Cottage apartment, private entrance

Beautiful studio apartment. Private entrance makes coming and going easy. Beautiful front porch to rest and relax. New luxury queen sized bed, couch that makes into a full bed. Smart TV. Full Kitchen. Studio Apt. is on lower level. Washer & dryer in bathroom. Close to Flagstaff and Pinetop for skiing and hiking. Close to Petrified Forest & other national parks. Cooler in the summer than average temperatures for Arizona, and mild winter. Lovely, quiet, quaint neighborhood.

Top guest favorite
Guesthouse in Taylor
4.99 out of 5 average rating, 366 reviews

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.

Top guest favorite
A light gray sofa is positioned against a white wall, accompanied by two yellow pillows. Above the sofa, a colorful floral painting adds a touch of vibrancy. A plush area rug and a storage cabinet are visible nearby, contributing to the cozy ambiance of the living area.
Home in Snowflake
4.96 out of 5 average rating, 166 reviews

Cheerful 2 bedroom cottage on quiet street

This is a cozy little 2 bedroom cottage on a quiet street located in the heart of Snowflake. It has been recently remodeled and has a new feel. It has a small peaceful back yard with a covered porch and a small fire pit. Because of it's location it is great for walks around town and a close drive to shopping. Please be aware that smoking, vaping, drugs or alcohol or animals are not allowed on the property. If this is a problem, please seek other accommodations.

Superhost
Two wooden chairs with blue cushions are positioned on a concrete patio in front of the tiny home. A screen door provides access, and a light fixture is mounted on the exterior wall. The area is surrounded by natural landscape and a wooden fence.
Tiny home in Taylor
4.85 out of 5 average rating, 123 reviews

Tiny Home in Arizona White Mountains!

PERFECT QUIET SPACE FOR TRAVELERS! Located on a 17-acre property with an expansive view for miles. The guest tiny home is located on a homestead where you may hear the clucking of chickens or the oinking of pigs depending on the season. You will have privacy as you walk through the gate into a secluded fenced in yard. The rental is designed for the minimalist in mind while providing all the necessities to enjoy a vacation or quiet space to work.

Superhost
The living area features a large blue sectional sofa and a stylish orange couch, arranged around a decorative area rug. A flat-screen TV is mounted on the wall, and two framed artwork pieces are displayed. Natural light enters through a nearby window.
Place to stay in Holbrook
4.85 out of 5 average rating, 476 reviews

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

Top guest favorite
A spacious wooden deck is surrounded by trees, providing a serene outdoor space. Several rustic chairs and a round table are arranged on the polished wooden floor, inviting relaxation. A railing made of logs adds to the natural aesthetic of the setting.
Cabin in Payson
4.98 out of 5 average rating, 130 reviews

Cozy Cabin in Payson

Location, Location, Location! Beautiful cabin retreat overlooking the East Verde River. At the base of the Mogollon Rim in Rim Trail. Surrounded by tall pines and the Tonto National Forest. Endless hiking on the nearby Highline or Arizona Trails. Abundant quad/side-by-side and mountain bike trails. Fishing a few feet from the property. Knotty pine interior, pine cabinets, fir wood flooring, large sleeping loft and fully fenced.

Top guest favorite
The Great Room showcases a long dining table surrounded by ornate chairs, under a wooden ceiling with exposed beams. A decorative mantle is adorned with art and a fan. The room features a piano, a vibrant rug, and lamps providing soft illumination.
Place to stay in Winslow
4.94 out of 5 average rating, 284 reviews

The Haven: Incomparable space in a vintage church

The Haven is a unique apartment in a cozy, repurposed church in the heart of Winslow. Its soaring wooden arches and adobe walls help deliver that getaway feeling you've been needing. The space sleeps 5 comfortably with 1 on a huge Victorian sofa. The Sanctuary, the Haven, and the Idyll may be rented together sleeping up to 10 in the three conjoined spaces subject to availability of all three separate units.

Popular amenities for Winslow vacation rentals

When is the best time to visit Winslow?

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Avg. price$108$107$112$109$115$113$110$101$102$114$104$99
Avg. temp36°F41°F48°F55°F64°F74°F79°F77°F70°F57°F45°F35°F

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Winslow?

    Winslow has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there vacation rentals with a dedicated workspace in Winslow?

    Yes! Work meets play with ease at over 10 vacation rentals in Winslow featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winslow?

    Four-legged friends are welcome in Winslow. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Winslow have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Winslow. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winslow have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Winslow. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winslow have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Winslow. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winslow have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Winslow. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Winslow?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Winslow

  • Total vacation rentals

    Explore 40 vacation rentals in Winslow

  • Nightly prices starting at

    Winslow vacation rentals start at $50 per night before taxes and fees

  • Verified guest reviews

    Over 1,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Winslow vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winslow rentals

  • 4.9 Average rating

    Winslow stays are highly rated by guests—averaging 4.9 out of 5!

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