Holiday rentals in Greenfield

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Top-rated holiday rentals in Greenfield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

The exterior of the cottage is presented with a brick patio area surrounded by well-maintained lawn and landscaping. Two wooden chairs are positioned on the patio, set against the backdrop of the cottage's welcoming entrance. A clear blue sky visually enhances the inviting scene.

Home in Salinas

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.

ValueFamilyBathroom

4.91 out of 5 average rating, 320 reviews

Guest favourite

A uniquely designed treehouse is elevated among the trees, showcasing large glass windows and wooden beams. A wooden walkway leads up to the structure, enhancing the connection with the surrounding natural environment.

Treehouse in Aptos

Peaceful Treehouse with Ocean View

Permit 171035 Featured by Sunset Magazine as a “chic escape,” this Peaceful Treehouse-style retreat blends mid-century design with natural materials like wood and stone for a calming, sanctuary feel. Light pours through floor-to-ceiling windows beneath soaring wooden beams, and Japanese-inspired doors add to the architectural charm. Set high in the trees with ocean views, the home offers three elevated decks including one with a hammock. Perfect for relaxing and enjoying the surrounding canopy.

LocationValueGrill

4.91 out of 5 average rating, 613 reviews

Guest favourite

An A-Frame cabin is surrounded by lush greenery, positioned on elevated ground. A stone pathway leads to the entrance, flanked by wooden railings. The cabin features large glass panels on its façade, allowing natural light to flood the interior. A deck with seating overlooks the nature surroundings.

Cabin in Felton

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

FamilyLocationParks

4.96 out of 5 average rating, 190 reviews

Superhost

Home in Greenfield

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🌈

FamilyValueIndoor spaces

4.8 out of 5 average rating, 204 reviews

Top guest favourite

A wooden pathway leads to a charming cabin, positioned among towering coastal redwoods. Lush greenery surrounds the area, with steps ascending to the entrance. The structure features large windows allowing natural light to illuminate the interior, creating a welcoming appearance.

Cabin in Carmel-by-the-Sea

Serene Redwood Retreat w/Modern Comfort

At our Modern cabin nestled among 150 year old redwoods, we invite you to embark on a unique adventure of embracing the outdoors while only minutes from town. Wine tasting in downtown Carmel, World Class Golf at Pebble Beach or Hiking trails of Point Lobos and Big Sur. "Magical", "Amazing", "A True Sanctuary" are just a few words used by our guest to describe their stay with us. Get away and unplug in the stillness and solitude of our Serene Redwood Retreat. Please see property description.

ValueLocationComfort

4.97 out of 5 average rating, 379 reviews

Guest favourite

A scenic view captures the main ranch house set against a backdrop of vibrant autumn foliage and a clear blue sky. The well-maintained grassy area in the foreground leads towards a rustic wooden fence, inviting a sense of outdoor exploration.

Home in King City

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.

LocationValueHeating

4.91 out of 5 average rating, 92 reviews

Guest favourite

The exterior of a mint green bunkhouse is shown, featuring a sloped roof, a welcoming front porch with steps, and multiple large windows allowing natural light. The surrounding area includes trees and a grassy yard, creating a charming rural ambiance.

Ranch in Paicines

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!

FamilyValueTV

4.93 out of 5 average rating, 90 reviews

Top guest favourite

Farm stay in Carmel Valley Village

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).

LocationValuePets

4.99 out of 5 average rating, 585 reviews

Guest favourite

A charming cottage exterior is showcased, featuring a cozy porch area with seating. Large trees provide shade, and well-maintained landscaping surrounds the property. The driveway is spacious and leads to the entrance, while decorative elements reflect a rustic aesthetic.

Cottage in Salinas

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 .

FamilyLocationComfort

4.76 out of 5 average rating, 232 reviews

Guest favourite

An inviting pool area is framed by a spacious deck and lush landscaping, complemented by a covered outdoor kitchen and seating area. Natural light highlights the vibrant red of the home's exterior against a backdrop of rolling hills and greenery.

Home in Carmel Valley Village

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.

LocationFamilyNearby

4.9 out of 5 average rating, 90 reviews

Top guest favourite

Farm stay in Paicines

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.

ValueLocationParking

4.96 out of 5 average rating, 134 reviews

Top guest favourite

A rustic exterior of a ranch-style home is showcased, featuring a combination of wooden and stone elements. Large windows allow natural light to fill the interior, while potted plants add greenery to the entrance. A gravel path leads to the inviting façade.

Cabin in Lake Nacimiento

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!

LocationFamilyAccuracy

4.96 out of 5 average rating, 233 reviews