We all need a staycation or a trip to a different city from time to time. Whether you’re a San Josean feeling a little cooped up or a visitor looking for a special Teal Town experience, picking the perfect home away from home is crucial.
We went looking for unique lodgings around town that showcase that “Capital of Silicon Valley” spirit. So choose your ideal digs, pack your bags, and get ready for a memorable getaway.
Rooms with a view
Airstream with gorgeous views of Silicon Valley | San Jose foothills
A sleek, vintage, view from above with some staggering vistas. With a kitchen, a full-size bed, and a surprisingly spacious living room + flatscreen TV, it’ll be like sleeping in the sky.
- $162 a night
- 1 BD | 1 BA
- Free parking, central air conditioning, private patio, WiFi.
Casita with balcony overlooking Willow Glen | Willow Glen
A classic, cozy little casita in the heart of the hustle and bustle. The massive balcony offers a comfortable outdoor space to view scenic downtown Willow Glen.
- $234 a night
- 2 BD | 2 BA
- Outdoor space, barbecue grill, air conditioning, proximity to downtown.
Peaceful villa overlooking the city | East San Jose
When you want to get away in style — the spacious 6-bedroom, 9 bath palm tree-lined villa offers a gorgeous hot tub + pool combo overlooking the South Bay.
- $951 a night
- 6 BD | 6 BA
- Gigantic space, patio, pool, fire pit, outdoor furniture.
Hideaways with history
The Hensley House | Hensley
Step into the 1890s with the historic Queen Anne-style accommodations in this Victorian flashback — gorgeous architecture + luxury trim right in the heart of downtown San Jose.
- $850 a night
- 6 BD | 10 BA
- Luxury experience, piano, unique architecture, proximity to downtown.
Former mayor’s mansion | Newhall
Once a part of the San Jose Mayor’s Mansion, this beautiful Victorian with unique furnishings is close to all of the downtown action along the Alameda.
- $148 a night
- 3 BD | 2 BA
- Pet friendly, private entrance, WiFi, and proximity to downtown.
The Hayes Mansion | Hayes
Now a part of the Curio Collection by Hilton, the Hayes Mansion’s opulence highlights San Jose’s heritage with modern accommodations.
- $264-$586 a night
- 1 BD | 1 BA
- Quiet neighborhood, unique accommodations.
Hotel De Anza | Downtown
From the penthouse to the lobby, step back into San Jose’s jazz-era with high tech amenities mere steps from downtown’s San Pedro Square.
- $154-$214 a night
- 1 BD | 1 BA
- Pet friendly, free WiFi, fitness center, on-site restaurant, downtown access.
Farm charm
Ranch living with city views | Clayton North
Work from home in style. This gorgeous retreat exemplifies the natural beauty of the San Jose foothills with nearby farms and incredible views of the South Bay.
- $92 a night
- 1 BD | 1 BA
- Pet friendly, free washer + dryer, indoor fireplace, WiFi.
Retreat casita | Calero County Park
Trade in the hustle and bustle of the city for the quiet of the countryside. This is a pet-friendly home away from home on the range.
- $126 a night
- 1 BD | 1 BA
- Pet friendly, indoor fireplace, WiFi.
Calaveras Creek Ranch | East Foothills
A peaceful, remote hideaway for when you truly want to go off-grid. Ditch your phone + computer and relax with simple pasture past-times. Note: pets are not allowed, so you’ll want to leave your furry friends at home.
- $390 a night
- 4 BD | 2 BA
- Indoor fireplace, remote, off-grid.
Country Gem | Clayton North
Modern luxury meets farmhouse living at this massive mountain-top space near Mount Hamilton. Your furry friends will enjoy the expansive patio + greenhouse while you take in the sights and sounds of the surrounding countryside.
- $2,239 a night
- 4 BD | 2.5 BA
- Pet friendly, EV charger, WiFi, free washer + dryer, indoor fireplace, game consoles, exercise equipment.
Modern chic
Modern guesthouse | Buena Vista
If you want to feel connected, try this newly-renovated guesthouse decked out with high-tech wizardry. Smart lights, blinds, and bathroom allows you complete control of the space with the push of a button.
- $159 a night
- 1 BD | 1 BA
- High-speed WiFi, free washer + dryer, Alexa compatible.
The Seahorse | Willow Glen
This award-winning space features a swimming pool + spa shaped like a seahorse, open concept floor plan, and a bathroom floor made out of pennies. The kids will enjoy the cabinets of toys + games while you admire the Swan and Flamingo-inspired bedrooms.
- $545 a night
- 3 BD | 2.5 BA
- Private pool + hot tub, High-speed WiFi, piano, themed rooms.
Cabin fever
Treehouse | East Foothills
It’s a childhood dream come true in this lofty space atop three sycamore trees. With two queen beds (one of which is hexagonal), and a spacious patio, you’ll be living the high-life with a fantastic view of the South Bay. Note: due to the nature of the space, accessibility is extremely limited.
- $381 a night
- 2 BD | 1 BA
- WiFi, air conditioning + heating, unique architecture.
Fig Tree Cabin | Northside
A private, backyard, DIY cabin featuring a mini-golf course, tiki hut, sauna, and a hot tub. This hideaway is definitely a hole in one.
- $171 a night
- 1 BD | 1 BA
- WiFi, hot tub, mini golf, tiki hut.
Sanctuary | Sierra Azul Open Space Preserve
Combining rustic decor with steampunk art, this hideaway under the trees is near multiple hiking trails and features a Japanese wooden soaking tub.
- $308 a night
- 1 BD | 1 BA
- WiFi, pool, hot tub, hiking trails.
