Vacation rentals in Lexington Hills

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Top-rated vacation rentals in Lexington Hills

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Guest favorite
A small rustic cabin is nestled among tall trees, providing a sense of seclusion. Sunlight filters through the canopy, casting dappled shadows across the ground. The cabin features a single window framed by green trim, blending harmoniously with the natural surroundings.
Cabin in Los Gatos
4.89 out of 5 average rating, 478 reviews

The Coach House

The Coach House is located on our mountain top horse and lavender farm. We offer youth summer camps so are set up for fun outdoor adventures and activities. Have fun with our horses, goats, and chickens! You can take a 10 min walk over to Nonno's Restaurant for wine/pizza/BBQ and bacchi ball, or take an 8 min drive into Los Gatos, or 15 min to Santa Cruz for the beach and some of the best restaurants and spas around!. Good for couples, solo adventurers, business travelers, kids, & behaved dogs!

Top guest favorite
A charming green guesthouse is nestled among towering redwood trees. The structure features multiple windows that bring in natural light, enhancing the connection with the surrounding forest. Sunlight filters through the branches, creating a serene outdoor atmosphere.
Cabin in Los Gatos
4.99 out of 5 average rating, 993 reviews

Private Guest-House in the Redwoods

Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

Top guest favorite
A private entrance is visible, leading into the unit. Lush greenery hangs over the door, while a wooden deck offers space for relaxation. Potted plants surround the area, and BBQ grills are positioned near the poolside, enhancing the outdoor ambiance.
Guest suite in Scotts Valley
4.96 out of 5 average rating, 797 reviews

Snug and Cozy between the Skyline and the Sea

Super private, peaceful, and quiet; an excellent place for the traveler who is excited about exploring the Santa Cruz mountains and coast. Completely private In-law unit with extras needed to make it cozy. Snuggled between Scotts Valley, Felton, and Santa Cruz it's near Henry Cowell Redwoods State Park, 1440 Multiversity, and Mount Hermon Conference Center yet less than an hour from Silicon Valley. The Airbnb cleaning handbook is followed making this one of the cleanest places you’ll stay at!

Top guest favorite
A light blue cottage is set amidst lush greenery and towering trees. The exterior features multiple windows, offering views of the surrounding landscape. A narrow pathway leads to the inviting front door, framed by flowering plants, enhancing the tranquil setting.
Guesthouse in Los Gatos
4.96 out of 5 average rating, 106 reviews

Mountain Retreat

Escape to the serene beauty of the Santa Cruz Mountains of Los Gatos! Our charming cottage rental is nestled amidst the towering redwoods, 30mins from Silicon Valley or Santa Cruz, and only 15mins from downtown LG, but feels isolated if you want get away from it all. The cottage features a living room (w/optional murphy bed) & full kitchen/dining area. Amenities like wifi, streaming and washing/dryer available in unit. Bedroom features king size bed and private backyard area. Pet friendly.

Guest favorite
Tall redwoods provide a natural canopy, creating a serene atmosphere with dappled sunlight filtering through the leaves. A forest floor of soft mulch and green undergrowth complements the tranquil setting, inviting exploration and reflection.
Guesthouse in Los Gatos
4.83 out of 5 average rating, 583 reviews

Rustic Cottage, Redwoods, Beaches.

Tiny, quaint Cottage sequestered in a Redwood forest. Outdoor Clawfoot Bathtub with Shower under the Stars overlooking a Spring fed creek ! Mature Pond & Marina with sitting areas with Koi and Turtles ! Solar powered lights come on at night! Lighting at the Cottage is Electric, Solar and Battery powered. Lanterns are provided ! There is a Cell Phone & device Charging Station available. No Kitchen or cooking facilities. Summit Market, four miles away, open 7 days a week, hours are 7am to 7pm.

Top guest favorite
The cottage exterior features a charming design with a slate stone patio and a round dining table with two chairs. Glass double doors provide access, and large windows offer views of the surrounding greenery. The roof is intricately shaped, complementing the natural setting.
Guesthouse in Monte Sereno
4.98 out of 5 average rating, 449 reviews

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

Guest favorite
A bright living area features light wooden flooring and white walls. Two rattan chairs are arranged around a small table in front of a decorative fireplace, while a modern TV sits on a console nearby. Natural light streams through two sets of double doors leading outside.
Guest suite in Los Gatos
4.83 out of 5 average rating, 130 reviews

Bright Garden Suite in Silicon Valley

This sun-soaked suite has a private entrance and access to a beautiful garden patio, complete with night-time ambiance and a fireplace. The big bay window provides a view into the lush fruit, flower, and vegetable garden right outside. The comfy bed and beautiful old-town neighborhood add to the warm, homey feel. The suite is tucked away from the busiest parts of the city, perfect for a hub in the middle of NorCal's best attractions: SF, Carmel, Pebble Beach, Monterey, Santa Cruz, and more.

Top guest favorite
Rows of grapevines stretch across the hillside, with traces of autumn colors visible on the leaves. A picturesque blend of green and gold foliage contrasts against the muted earth tones of the ground, while distant trees and hills are lightly shrouded by morning mist.
Farm stay in Felton
4.95 out of 5 average rating, 136 reviews

Vineyard Retreat with Expansive Mountain View

Vineyard retreat in Santa Cruz Mountains with expansive hilltop views. Situated off the beaten path between Los Gatos & Felton. The perfect place to disconnect, unwind & relax in a rural mountain setting. Our vineyard is 100% natural, no chemicals, pesticides or additives, from the soil to your cup. Please enjoy meandering the rows, soaking in the views and being in nature. Watch the marine layer recede in the morning & enjoy stargazing at night. Pricing is the same for 1-4 guests.

Top guest favorite
A colorful tiny home is seen surrounded by tall redwood trees. The exterior showcases vibrant blue and yellow walls, contrasted by natural wood planters filled with greenery. Sunlight filters through the trees, enhancing the inviting outdoor space.
Tiny home in Boulder Creek
4.96 out of 5 average rating, 209 reviews

Custom Cabin Retreat in the Redwoods

This retreat offers guests a unique experience of living in a well designed, minimalist space while having all one really needs. From the nautically-inspired curved ceiling w/ skylights to the custom redwood trim, this cozy retreat will inspire. Relax on the private deck with the fire pit, walk to the river or enjoy the local trails thru the towering redwoods. Santa Cruz beaches are just 35 min away, 25 min to Big Basin and Henry Cowell, and 35 min to fine dining in Saratoga.

Top guest favorite
A spacious sleeping area is highlighted by a large bed featuring white bedding. Two windows allow natural light to fill the room, offering views of greenery. A small table with two stools is positioned near the windows, and modern lighting fixtures complement the overall design.
Guesthouse in Scotts Valley
4.92 out of 5 average rating, 191 reviews

The Hen House Haven

Welcome to The Hen House Haven, a charming retreat where comfort meets modern amenities. Enjoy fresh eggs from our ten friendly hens, though egg availability may vary, especially in winter. Located near the Santa Cruz Beach Boardwalk, Henry Cowell Redwoods, and scenic hiking trails, our cozy studio is perfect for a relaxing getaway or adventure-filled stay. Embrace the serenity and warmth of staying with us, and make yourself at home. We can't wait to host you!

Top guest favorite
The exterior view showcases a contemporary guest house with a tiled roof, set beside a pool. Large glass doors provide access to the living area, surrounded by well-maintained landscaping featuring various plants and trees. The pool area contributes to the serene outdoor environment.
Guesthouse in Monte Sereno
4.91 out of 5 average rating, 225 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

Superhost
A round dining table is set for four, featuring red placemats and white dinnerware. Glasses are positioned beside each plate, and stylish utensils are arranged on either side. The wooden chairs are designed with a light finish, complementing the warm tones of the table.
Guest suite in Los Gatos
4.85 out of 5 average rating, 238 reviews

Mountain Gem - $1M VIEW

We are offering a 1-bedroom apartment on the lower level of a 2-unit house. It is located in a very beautiful place and has a huge balcony with a million-dollar view of the Santa Cruz mountains. Close by 17 highway, which can take you to Los Gatos in 10 minutes, and Santa Cruz - in 20. Great for Bay Area business travelers. Ideal for Santa Cruz beach vacationers. 15 minutes to gorgeous nearby wineries. Got everything one needs for a super stay.

Popular amenities for Lexington Hills vacation rentals