Vacation rentals in Winona

4.93 out of 5 average rating, 101 reviews

Slow-Living Rural Homestead Retreat

A one-of-a-kind stop on the Mother Road during its 100th year celebration! Built in 1939 (right in the golden era of Route 66 travel), the farmhouse sits on original 66 pavement, with direct access to the historic Walnut Canyon bridge. Guests can literally stand where Dust Bowl migrants, WWII travelers, and 1950s road-trippers drove. Amazing mountain views, a peaceful setting, easy access to Flagstaff, hiking, skiing, and top Northern Arizona attractions. —perfect for unforgettable road trips.

A spacious living area features a comfortable seating arrangement with dark sofas and a wooden coffee table. Natural light streams in through large windows, illuminating the room's warm wood flooring and accents. A dining table can be seen in the background, accompanied by panoramic views.

4.99 out of 5 average rating, 372 reviews

Beautiful Views, Game Room, Hiking Trails

Create wonderful vacation memories with family and friends while enjoying the peace and tranquility of your home away from home. Enjoy beautiful views of the San Francisco peaks while relaxing on the back patio. Explore endless hiking trails a short walking distance from the property. Relax in the central air conditioning on hotter summer days. Prepare family meals in the fully equipped kitchen. Cook on the gas grill outside or visit one of the many fine restaurants in Flagstaff. STR24-0161

4.89 out of 5 average rating, 1166 reviews

An A-frame cabin is surrounded by tall pine trees and vibrant wildflowers, showcasing large front windows that reflect the sky. A wooden deck with steps leads to the entrance, framed by a natural landscape that offers a tranquil setting.

Cabin in Flagstaff

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

4.99 out of 5 average rating, 164 reviews

The image captures a charming Casita set amidst open land, featuring a porch with rocking chairs. Vibrant colors of sunset reflect off the sky, while a large tree stands nearby. A spacious yard is visible, with a storage shed on the right and mountains in the background.

Guesthouse in Flagstaff

Peaks View Casita

Kick back, relax and escape the heat in this modern Casita with breathtaking mountain views on a 2.5 acre fully fenced ranch. Enjoy easy access to this peaceful property centrally located to all Northern Arizona has to offer including Arizona Snowbowl, Downtown Flagstaff, NAU, Bearizona, The North Pole Experience, Grand Canyon, Sedona, National Monuments, hunting, hiking, off-roading and much more! Need more space? Book together with the Lovett Lodge and have the entire property to yourself!

4.99 out of 5 average rating, 330 reviews

A dining table is set on the patio, featuring a vase of fresh flowers, a bottle of red wine, and two wine glasses. The backdrop displays the snow-capped San Francisco Mountains under a clear blue sky, surrounded by open land and a few distant homes.

Apartment in Flagstaff

Amazing Mountain Views! Hiking-Stargazing-Firepit

Luxury guest suite with amazing views of the San Francisco Mountains with direct access to the Coconino National Forest hiking and biking trails and some of the best stargazing in north America! Located 8 minutes from the east side of Flagstaff and 15 minutes to the city, yet conveniently centered between the Grand Canyon, Antelope Canyon, Sedona, Horeshoe Bend, Sunset Crater, Wupatki and Walnut Canyon National Monuments, Meteor Crater, the Petrified National Forest and historic Route 66.

4.99 out of 5 average rating, 276 reviews

A spacious living area features large windows allowing natural light to fill the room. Comfortable seating includes a recliner and a sofa, complemented by a decorative area rug. A ceiling fan and a small TV enhance the cozy atmosphere, while a wood stove adds warmth.

Guesthouse in Flagstaff

Bud & Tracy's Sunset View Guest House

Welcome to your guest house getaway for two. A perfect place to begin your adventures. We have thoughtfully created a clean, cozy home that complements our mountain vibe. The guest house is 100% private with a kitchen equipped with all the comforts of home, a beautiful bathroom with a walk-in glass shower. The space is perfect for relaxing with a glass of wine, drinking cocoa by the gas fireplace, watching the snow fall, or reading a book in the hammock in your private outdoor space.

4.9 out of 5 average rating, 245 reviews

Aspen House - getaway w/mt views and huge backyard

Beautifully remodeled 3 bed/2 bath home on nearly an acre at the base of Mount Elden and the San Francisco Peaks. Enjoy a mountain getaway with all the comforts of home. Aspen House is an ideal launchpad for year-round adventures...the Grand Canyon, Sedona, national monuments, downtown Flagstaff/NAU, skiing, hiking, hunting, mountain biking and more! A variety of sleeping arrangements accommodate various groups, and a keyless entry gives you the freedom to come and go as you please.

4.99 out of 5 average rating, 319 reviews

Flagstaff Forest Retreat • AC + Soaking Tub

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.

A spacious living area is presented with a comfortable sectional sofa and a round coffee table. Kitchen appliances in stainless steel are visible in the background, along with wooden cabinetry. A dining table with x-back chairs can be seen to the left, and natural light enters through the window.

4.98 out of 5 average rating, 157 reviews

New Flagstaff Adventure Getaway

Built in 2023, be one of the first to stay at this brand new adventure-themed home. Walk or bike from the house to the peaceful pines and fresh air of Mt. Elden, Picture Canyon, and the Arizona Trail. Close to downtown Flagstaff, NAU, REI, Snowbowl, sled riding, Continental Country Club, Flagstaff Mall, and historic Route 66. Day trips to the Grand Canyon, Sedona, Lake Powell, Glen Canyon Dam, Petrified Forest, Painted Desert, or Meteor Crater. TPT: 21536670

4.97 out of 5 average rating, 236 reviews

Cabin in Flagstaff

Cheerful Cabin Oasis: Private Yard & Central A/C

Kick back and relax in this calm, stylish space. Our recently fully renovated cabin is nestled on 2 acres and is surrounded by trees including several ponderosa pines. The outdoor space is our oasis where you can enjoy the stone patio, a gas fire pit and hot tub to warm up on those cooler nights. This single level cottage has an open concept layout, three bedrooms and two full bathrooms. A circular driveway allows plenty of parking space for any car size.

A cozy living space features a dark blue accent wall, a comfortable seating area with a sofa and armchair, and a wood-burning stove. Natural light fills the room through large windows with views of the surrounding landscape.

4.94 out of 5 average rating, 232 reviews

Restoration Retreat | Views, Fire Pit & Stargazing

Welcome to Restoration Retreat! This home is the perfect refuge for you to get refreshed, recharged and reconnected. With ample space, thoughtful touches, and a cozy atmosphere makes this home an ideal refuge or base camp for all of your adventures. This is not just a bare bones place to stay, it is a home away from home. It is a place that is inviting and crafted for your comfort and one we know you will make cherished memories in. Welcome home!