Cool Airbnbs Near San Diego to Book This Winter

Road trip!

valle de guadalupe airbnb
Photo courtesy of Airbnb

After months of sheltering in place, even the most dedicated homebodies are ready for a getaway—but where? Look no further than your own backyard—we’ve got mountain escapes, desert oases and not one, but two legit wine regions waiting for you to explore. We’ve put together a handy list of some of the coolest Airbnbs near San Diego, so pack the car and hit the road. Don’t forget your mask!

catalina cabin
Photo courtesy of Airbnb

A light-filled cabin nestled in the trees

Big Bear Lake
6 guests, $667 per night
Distance from San Diego: ~Two and a half hours
The Cabin on Catalina is a chic, cozy escape that puts you right in the heart of Big Bear, just minutes from the slopes and restaurants, and a doable walk to the ski slope shuttle, but even non-skiers will love it for its gorgeous forest views, fully-stocked kitchen, and lavish free-standing tub in the master bath. There’s also a large yard with a mini-hill for the littles to sled on while the grownups relax in the hot tub.
What guests say: “All I can say is just GO! You will be so happy you did. This property is beautiful and great in design. My family slept well. My husband and I said we felt like we were in a hotel bed. It was gorgeous and we cannot wait to go again.”

treetop cabin
Photo courtesy of Airbnb

Snuggle in a Scandinavian treetop escape

Big Bear
4 guests, $358 per night
Distance from San Diego: ~Two and a half hours
Hit the nearby slopes and hiking trails, then cozy up near the fire while you watch the sunset through soaring, floor-to-ceiling windows in this open-floor plan Scandinavian hideaway. An expansive gourmet kitchen makes whipping up dinner a breeze, a luxurious master bedroom ensures blissful sleep, and sweet touches like heated towel holders leave you feeling extra pampered. Mountain bikes and sleds are available for more outdoor fun. 
What guests say: “Nordik Escape blew our minds. It was truly an oasis—perfect place to bundle up and recharge the batteries. One of our favorite AirBnB experiences ever. Peggy and Christopher are super helpful—tremendous hosts.”

hot tub
Photo courtesy of Airbnb

Soak under starry skies

Yucca Valley
6 guests, $755 per night
Distance from San Diego: ~Two and a half hours
Experience seamless indoor-outdoor living at Ventana Cove, a stunning custom home that boasts enormous LaCantina doors in each of the three bedrooms, opening to the huge interior patio with a hot tub, a lounging area, and a retractable canopy for open air relaxation. Take in spectacular views of the Joshua Tree National Park mountains from the cold dip cowboy tub on the lounge deck, stargaze around the fire pit, or chill in a shaded hammock. Located on two private acres, you’re just minutes from Joshua Tree National Park.
What guests say: “Our four person group (two couples) had an incredible time on this well-appointed property. There are so many lovely things to say. From watching the sunset in the hammocks to the extremely user friendly Sonos speakers. I really felt I didn’t have to worry about a thing and could just relax. It is an experience in itself and I can’t recommend it enough.”

mid-century modern living room
Photo courtesy of Airbnb

Kick back in a mid-century getaway

Palm Springs
6 guests, $340 per night
Distance from San Diego: ~Two and a half hours
From the meticulously restored original 1959 kitchen to the eye-popping splashes of color throughout, you’ll feel like you’ve taken a trip back in time in this stylish mid-century beauty. As an added bonus, pets are allowed and a large park in easy walking distance makes it convenient for dog (or human) outings. Pour a batch of martinis, crank up Sinatra, and sink into the hot tub for the ultimate Palm Springs experience. 
What guests say: “If you need a relaxing getaway in Palm Springs, this is the spot. Amazing pool/hot tub with a fantastic personalized interior design and plenty of space! Can’t recommend Bill and his wonderful spot enough!”

vineyard airbnb
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An artsy enclave in a vineyard

Valle de Guadalupe, Baja California, Mexico
6 guests, $388 per night 
Distance from San Diego: ~Under two hours 
An homage to owner Grisel De La Rosa’s family of artists as well as the legendary painter Frida Kahlo, Casa Frida sits adjacent to one of the buzziest tasting room/restaurant parks in the valley. Eclectic mid-century furniture, eye-catching original art and vivid colors abound, while arching French doors and high, blond wood-paneled ceilings keep the rooms airy and bright. Since it’s located close to the tasting room, don’t plan on pin-drop silence at night, especially on weekends, but you’ll probably want to be out there sipping wine anyway. 
What guests say: “The house was absolutely stunning. Artwork on every wall. I also really enjoyed the fire pit and outdoor sound system. We bought a few bottles of wine from the tasting room and drank the night away under the stars. Would highly recommend it and come again!”

hilltop cottage
Photo courtesy of Airbnb

Sip wine in a hilltop cottage

Valle de Guadalupe, Baja California, Mexico
4 guests, $159 per night
Distance from San Diego: ~Under two hours
Enjoy spectacular sunsets and wide open vistas at Terra Monarca in the heart of the Valle de Guadalupe, within walking distance to Corazon de Tierra and Vena Cava and a short drive to wineries, breweries, and top rated restaurants along both the old and new Ruta del Vino. You’ll love returning to this spacious, beautifully adorned home, sipping wine on the wide stone patio and cooking dinner in the brand new, covered outdoor kitchen complete with a Santa Maria grill. 
What guests say: “Zeida was a perfect host. Her home is beautiful, with everything you need for a wonderful and fun stay. The fire pit outside was great, and the zarape blankets were perfect for the chilly night by the fire. We really enjoyed our stay and are planning to stay there again on our next trip. Highly recommend!”

Photo courtesy of Airbnb

Relax in a charming farmhouse

8 guests, $466 per night
Distance from San Diego: One hour, 15 minutes
From the reclaimed barnwood and vaulted ceilings to the wraparound porch and swing, you’ll be utterly charmed by this lovingly restored farmhouse. Situated on an acre of land, it features mountain views from the front and ocean sunsets from the 2nd story deck in the back, weather permitting. Best of all, it’s only three blocks from town, where you’ll find coffee shops, dining, beer and wine tasting, and those famous Julian pies. 
What guests say: “One of the best Airbnb stays we've ever had! The home is absolutely enchanting—the pictures don't do it justice. Decor is impeccable & thoughtful. Had everything we could need for our family of 4. We cooked, played games, watched the sunset from the amazing balcony off the master, watched a meteor shower from the backyard, and just relaxed. It felt like a home away from home. We hope to return someday and cannot recommend this stay more highly.”

fort style house
Photo courtesy of Airbnb

Chill out at a desert destination

Borrego Springs
6 guests, $187 per night
Distance from San Diego: ~Under two hours
Pack the sunscreen and head out to the desert for a break from the daily grind at Borrego Dig, a serene, private getaway on 1.28 acres, with stunning views of Indian Head, Font’s Point, and the Santa Rosa Mountains. Vaulted ceilings and plenty of natural light flood the beautifully decorated rooms, including a large, gourmet kitchen. Spend the day hiking the Ocotillo Forest or golfing at one of Borrego Springs many courses, then chill out under the spectacular canopy of stars—you might even see a meteor shower!
What guests say: “The house was brilliant for a weekend escape. The views were amazing from every window. The house has high ceilings, good circulation and light. We enjoyed playing horseshoes in the back. Jayne was an excellent communicator, very gracious and responsive. I would definitely recommend.”

Photo courtesy of airbnb

A sleek Airstream in the heart of wine country

2 guests, $129 per night
Distance from San Diego: One hour
Perfect for a weekend getaway or a longer stay, Bliss at Serenity Cove is a gorgeous, brand new Flying Cloud Airstream that has all the comforts of home and sits on five acres filled with oak trees and cacti. Spend your days exploring Temecula’s many vineyards and restaurants or zen out in the meditation garden just outside your front door. For the ultimate pampering, book a yoga or meditation class, reiki treatment or massage when you make your reservation (extra charges apply). 
What guests say: “Lena’s place was the perfect spot for our quick weekend getaway. The space was clean and filled with thoughtful touches. The location is great with its close proximity to the local wineries and several great hikes. We’d highly recommend Lena’s property to anyone looking for a quiet, relaxing stay.”

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Mary Beth Abate is a San Diego-based freelance writer by way of Chicago and Los Angeles. Her hobbies include yoga, pickling and fermenting stuff, reading cookbooks and drinking fabulous gin. Keep up with her experiments @MaryBeth_Abate.