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Wine Country Old Barn Cottage

Charming, spacious Wine Country Old Barn Cottage by the gentle flowing creek in the back of a working winery/vineyard. Peaceful, serene just minutes from downtown Morgan Hill in the heart of Santa Clara wine trail. A quiet, private, 2 br/2 bath, full kitchen dining room, living room makes this the perfect home away from home. Amenities include luxury king bed, queen bed, wifi, TV, laundry & free parking. (** NO PETS ** if you have a service animal please contact us before booking - thanks )

Luxe Estate w/ Pool | Sleeps 10

Your home base for exploring South Bay wine country. Morgan Hill offers award-winning wineries, farm-to-table dining, and hiking at Coyote Valley and Henry Coe State Park. Just ~20 min to downtown San Jose's theaters, SAP Center, and Santana Row shopping. Close to Gilroy Gardens and perfect for day trips to Santa Cruz beaches. This Mediterranean estate sleeps 10 with a private pool, ideal for family reunions, group getaways, or a relaxing escape from the city while staying connected to it all.

Countryside Container Home

Our family’s custom container tiny home blends minimalist style and natural warmth with all the comforts of home. Inside, you’ll find curated design, tons of sunlight, and a peaceful energy that invites you to slow down and relax. You’ll enjoy a: Raised full sized bed with plush bedding for ultra-comfy nights Intimate lounge with seating and a Smart TV Fully stocked kitchenette Fast WiFi for work or winding down An outdoor fire pit + dining table Private, fenced-in outdoor area with parking

Charming Home in the heart of Downtown Morgan Hill

Kick back and relax in this calm, stylish space, indoors or even outdoors. 🔵 5 minute walk from the up-and-coming Downtown Morgan Hill with its small town accessibility and urban ambiance 🔵 Plethora of restaurants to choose from 🔵 5 Minutes from Highway 101 🔵 Many vineyards and brewery's to choose from 🔵 Nature lovers can bask in the outdoors at Uvas Canyon County Park, Henry W. Coe State Park, amongst others 🔵 Several golf courses nearby 🔵 Enjoy the Coyote Valley Sporting Clay

The Orchard Oasis

With an open floor plan, large kitchen and plenty of outdoor space, this unique home is perfect for you to relax and enjoy. The house is stocked with everything you need. Enjoy the swimming pool, spa, outdoor kitchen, outdoor living room and custom tree house! The home is situated on an active orchard, so depending on the month of your visit, you may be surrounded by gorgeous blossoms, fresh fruit or vibrant fall colors. We hope you enjoy The Orchard Oasis, our little slice of paradise!

STYLISH GUEST HOUSE ON A BEAUTIFUL ESTATE

This Stylish and Private Guest House is located on a 1.2 Acre Estate with beautiful Landscaped Grounds. This Guest House Offers a Private Entrance & Two Private Balconies. This Unit is Fully Furnished & Tastefully Decorated with current trending Styles. This property is on the border of Gilroy and San Martin. Conveniently located near Gilroy Outlets, Restaurants, Costco, Walmart, and Target. This property is centrally located between San Francisco & Monterey. Please request longer stays!

Gorgeous 3-bedroom home, quiet, close to shopping!

Enjoy the Bay Area in your own private, quaint, and comfortable cozy home! Gaze out of your master bedroom window or living room to green grass and Bamboo tree lined backyard with fruit trees and 6' fences. The home is in a safe, quiet, neighborhood, within 2-3 minute drive to Oakridge mall. Conveniently located w/all shopping imaginable within 5 minutes drive. Our inviting full kitchen contains pots, pans, dishes, a Keurig coffee maker, rice cooker, Ninja Air fryer and much more.

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Poolside Wine Country Retreat

Ideally located between downtown Morgan Hill and many local wineries. We’re 35 minutes from SJC airport, 1 hour 15 minutes from SFO airport, and 40 minutes from Levi’s Stadium for Superbowl LX and Soccer World Cup ’26. A short drive to beaches, coastal towns, San Juan Bautista, Pinnacles, and many other parks and attractions. This private and peaceful guest house includes one bedroom with a queen bed, a queen sofa bed, full bathroom, full kitchen, private patio, and a seasonal pool.

‘26 Price Drop: Luxury/Cozy Home Near San Jose

Discover a unique Luxury Escape – far from your average Airbnb. Experience unmatched comfort and tranquility in this serene retreat, located just 20 minutes from vibrant San Jose. To elevate your stay, request our exclusive House Manual in advance, filled with insider tips on must-see attractions, local events, and hidden treasures. Perfectly blending relaxation and convenience, this is your gateway to peace and adventure. Get ready to unwind and explore. Stay refreshed!

Cheerful and bright 4 bedroom 3.5 bath townhouse

This spacious home is perfect for group and family trips. The house is fully furnished with abundantly equipped kitchen and laundry room. This property is located within walking distance of downtown Morgan Hill and driving distance to 60+ wineries. It is conveniently located near Gilroy Outlets, Walmart, Safeway and many restaurants. The property is located 5 minutes away from 101 freeway and CalTrains which gives access to any major cities in the Bay Area.

Morgan Hill Mini Mansion

Perfect family getaway in spacious 4000 sq ft mini mansion. Morgan Hill is a quiet small town 10 mins away from bustling San Jose. Take pictures with horses across the street, go on hiking and biking trails, do water sports on Calero Lake, stroll down downtown Morgan Hill, play pickbleball or enjoy the indoor water park at Centennial Recreation Center, visit wineries or spend some family time at the Gilroy Gardens theme park.

Amazing Country Setting at Cottage Creek Vineyards

Lovely 1000 Sq. ft. Cottage in the heart of wine country. A 400 sq. ft. delightful back patio with fire pit, full kitchen and bathroom makes this the perfect home away from home. Amenities include queen bed, wifi, TV's, fire place, & parking. We are a live winery and have wine tasting two weekends and two Friday evenings a month. We usually have live music, wine tasting is in the same vicinity as the Cottage.