Holiday rentals in Greenfield

The Highlands House at Pessagno Winery

The quaint and charming Highlands House is located in the heart of the River Road Wine Trail. The stunning backdrop of the Santa Lucia Highlands and breathtaking views of the Salinas Valley farmland promise an unforgettable getaway. The surrounding vineyard along with the adjacent Pessagno Winery & Tasting Room will complete your wine country experience. Driving proximity to beautiful Carmel / Valley and Monterey with great dining and attractions provides the best Monterey County has to offer.

Value · Location · Walkability

Santa Cruz A-Frame

This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame

Family · Location · Outdoor spaces

Spacious Furnished Home Near Pinnacles Hwy 101

Built in 1954. Mainly original single-family home. Unwind inside private home! Equipped with 1 full size bed, 1 queen size bed, and 1 cal king bed. 1 full bathroom in master bedroom. 1 shared full bathroom. Full size kitchen, living room, and backyard. Greenfield is located in south Salinas Valley. It’s a rural, small town bustling with agricultural. Located two streets from HWY 101, nearby Pinnacles National Park/ 30 mins to Salinas/ 55 mins to Monterey Peninsula/ 1 hour to Paso Robles🌈

Family · Location · Parking

Casey Redtail Ranch

The beautiful Casey Redtail Ranch sits on 100 pristine acres amidst rolling hills and majestic oaks. The tastefully decorated, 5 bedroom ranch house, recently remodeled, is ready for a great friends get away or family gathering! The large kitchen and dining area are perfect for those culinary adventures and fun, family and friends meal times. Nearby wineries, Pinnacles National Park and lakes make it a great launching pad for outdoor fun. There is plenty of parking in the expansive barnyard.

Location · Family · Long stay

The Ranch Retreat, Bunkhouse 3 "The Stall"

Experience a stay like no other in the historic Ranch Retreat bunkhouses from the 1930's on this working cattle ranch in the glorious Gabilan Mountains. Smack dab in the middle of California. Lounge under the Majestic Oaks as you bird watch, paint, write, or hike through the rolling hills where Hammond Livestock Company raise their grass fed cattle. Just down a country road from Mercy Hotsprings, Pinnacles State Park, Panoche Hills Observatory, San Benito Historic Park and so much more!

Location · Family · TV

Beautiful Farm in Carmel Valley

Our 2 bedroom guest house in beautiful Carmel Valley is close to Monterey, Big Sur, Pebble Beach and Carmel by the Sea. Sight see all day and escape to a pastoral setting five minutes from Carmel Valley Village with quaint shops, restaurants and over 20 wine tasting rooms. Visit with our alpacas, horses, giant tortoises, goats, sheep, donkey and more! Wake up to sunshine, fresh air and the donkey braying for breakfast! (Due to the nature of our farm we have a strict "No Pets" policy).

Location · Value · Wifi

Private Carmel Valley Retreat

In the rolling hills of Carmel Valley and hidden between famous vineyards, is our very private, rustic, relaxing country home. The home is perched on 20 acres of Oak trees and Lupine meadows overlooking the Cachagua Valley. Perfect for a family on holiday, weekend getaways, or as a romantic retreat. Use our cottage as a place to recharge or as a home base for exploring local Vineyards, Big Sur, Carmel-By-The-Sea, Monterey and Pebble Beach. Please note: The pool is solar heated only.

Value · Location · Hospitality

Barlocker's Rustling Oaks Ranch - The Cottage

The ranch is close to Monterey Bay Aquarium, California Rodeo Salinas, Pinnacles National Monument, John Steinbeck's Museum and Victorian House, and the Laguna Seca Raceway. The cottage offers two bedrooms, one large full bath including a whirlpool tub, a living room & dining area, full kitchen, and washer/dryer. Pets are welcome upon pre-approval by the onsite manager. Pets cannot be left unattended. There is a pet fee $25 per night can be zelled or paid cash upon arrival .

Location · Value · Sleep quality

Serene Vineyard Chateau with Pool, Hot Tub, BBQ

Disconnect from city life in the heart of Carmel Valley wine country. The Vineyard Chateau sits on 5 creek-front acres with a working Merlot vineyard and countless amenities. Explore 25+ wine tasting rooms in Carmel Valley Village, hike in nearby Ventana Wilderness, or chill & grill by the seasonal saltwater pool (May-Oct). Upgrade with our popular Poolside Wine & Charcuterie Pairing featuring our very own small-batch VINCENT VINES wines. Perfect for a family or two couples.

Location · Family · EV charging

The Telegraph Office Cabin, near Mercy Hotsprings.

Set on the site of an old town from the 1880's, now a working dairy farm, the "Telegraph Office" is a beautiful and comfortable escape to the charm and serenity of the country. The farm offers a unique opportunity to see where the best milk and dairy products are made. The farm enjoys some of the best sunshine in California, best night sky, mountain views, sunrises and sunsets. Relax, commune with the animals, birdwatch, hike, sit by a campfire, or whatever suits you.

Location · Family · Shared spaces

Charming Farmhouse in Carmel Valley

The Briggs Farmhouse is a 1920's 2-story charmer on a secluded ranch in Carmel Valley. A quick drive to Monterey or Carmel - this is a perfect home base to explore the Monterey Peninsula then come back to a relaxing and quiet space with no noise pollution - The perfect countryside getaway. Plan your day of adventure in Big Sur, Monterey, Carmel, or Pebble Beach while sipping on hot cup of coffee in the study, on the porch, or on the balcony overlooking the orchard!

Family · Value · Check-in

Lake Views Hilltop Ranch - 160 Acre Escape

Secluded private hilltop cabin just 5 minutes from the marina, between Lake Nacimiento and Lake San Antonio. Set on 160 lake-view acres—bring your boats! Horses and longhorn cattle graze nearby (and no flies!). This artfully designed 3BR, 2BA ranch home offers sweeping lake, valley, and mountain views. Located on the Wildflower Triathlon route—perfect for cycling, scenic drives to wineries and missions, and epic stargazing. Wildlife sightings possible!

Family · Location · Long stay