Holiday rentals in Shenandoah Valley

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Top-rated holiday rentals in Shenandoah Valley

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Top guest favourite
A cozy interior space features a spacious bed with neutral linens positioned near large stained glass windows. A decorative rug covers the tiled floor, and a comfortable seating area with a light-colored sofa and throw blanket adds warmth. Natural light fills the room.
Guest house in Fiddletown
4.99 out of 5 average rating, 112 reviews

Casita in Wine Country

Take it easy at this unique and tranquil getaway. The hosts live on sight but enjoy sharing their beautiful view from this separate Casita. There is a fun 1 mile hike on the property. Only 5-10 minute drive to local wineries. The quaint town of Plymouth is a 10 minute drive which hosts Taste, a 5 Star restaurant. Black Chasm Caverns is a 30 minute drive as well as Jackson Rancheria Casino. Kirkwood Skiing is an hour drive. We have a Tesla charging station for an additional $20 a night.

Top guest favourite
A comfortable living area features a black leather sectional sofa, paired with a glass coffee table. Natural light enters through a large window, and a door leads to an outdoor space. Soft, neutral tones create a serene atmosphere, complemented by a cozy area rug.
Guest suite in Pioneer
4.99 out of 5 average rating, 267 reviews

Whispering Pines Apartment

The fall colors are spectacular for a hike up scenic Highway 88! Our apartment is located under our main house, with its own keyless private entrance. You'll enjoy a quiet and peaceful setting among tall pines, with wildlife abound. Amador County is rich in gold mining history, and has many charming gold rush towns for you to visit. If your travel journeys include both Yosemite and Lake Tahoe, we are conveniently located between the two ( 2 1/2 hours from Yosemite, and 1 1/2 from Tahoe)

Top guest favourite
A charming front porch is surrounded by vibrant greenery and blooming flowers. The space includes several seating options with two green chairs and a small table. Sunlight filters through the foliage, creating a serene spot for relaxation.
Home in Plymouth
4.98 out of 5 average rating, 561 reviews

Cozy Cottage and Gardens in the Heart of Plymouth

Our historic house is in downtown Plymouth- within 10 minutes to over 50 wineries. Walk to wine tasting and 5-star dining. Our private and tranquil home and gardens await. Relax by our outdoor fireplace, enjoy the outdoor kitchen or just lay low. We are an easy drive to the Bay Area, Lake Tahoe and Yosemite. We are child and business friendly, with high speed internet, scavenger hunts for children and adults, fairy garden tea parties and more. Six guest maximum. No exceptions.

Top guest favourite
A charming casita is situated on a hillside, surrounded by lush greenery. A wooden deck extends from the structure, offering panoramic views of the verdant countryside beneath a gentle morning light. Sunlight filters through the trees, illuminating the natural landscape.
Place to stay in Vallecito
4.91 out of 5 average rating, 310 reviews

The Hideaway

The Hideaway is an enchanting one room casita situated on the outer crest of the property, The Confluence. Wake up to the sunrise with a lush *View* of the natural countryside from your private deck. The Hideaway is accessed by a foot path (200ft) from the Main House. The Private Bathroom is off of the Main House (200ft from room). From the parking area to the room, it is roughly 400ft. There is no kitchen or cooking appliances other than a hot water kettle and a mini-frig.

Guest favourite
A light-filled interior is showcased, featuring a cozy seating area with a brown couch and a small dining table for two. Sliding barn doors create a rustic charm, while a wash basin with vintage fixtures is positioned against the wall. A wooden ladder leads to the loft.
Farm stay in Cool
4.96 out of 5 average rating, 170 reviews

Cozy Tiny House in the Sierra Foothills

This hosted rental is the perfect little getaway in the country. It is located on a mini farm complete with goats, chickens, dogs and a huge garden that you will have access to and is close to ALL the outdoor activities you can think of including hiking, mountain biking, river rafting, hunting and more. We are minutes from world famous trails, 10 minutes from the river, and an hour from the ski slopes. There is just so much to do right outside of our doors!

Top guest favourite
A second-story guesthouse is framed by tall pine trees, blending naturally with the surroundings. The welcoming entrance features a stairway leading to a porch, while a clear path meanders through the landscaped lawn, offering a sense of privacy in a serene setting.
Farm stay in Somerset
5 out of 5 average rating, 210 reviews

Linebarier Vineyards

This is a cute second story guesthouse. Its’s very private, located on our 83+ acre vineyard/ranch. We have a 6 acre working vineyard and commercially growing Zinfandel, Petite Sirah, and Muscat Canelli The guesthouse has recently been up-dated and is light, airy with many up-scale features and amenities. It’s a very private setting with no immediate neighbors. There are approximately 140 wineries within a 25 mile radius of our place.

Superhost
An inviting outdoor seating area is arranged around a stone patio, featuring wooden Adirondack chairs. A large wine barrel adds a rustic touch nearby, with string lights overhead providing ambient lighting. The charming cottage, framed by greenery, enhances the warm atmosphere.
Cottage in River Pines
4.83 out of 5 average rating, 151 reviews

Chalet Vigne - 2 bedroom wine country cottage

Incredibly spacious lot just minutes away from several wineries. Outdoor seating and firepit are the perfect place to enjoy time with family and friends. Inside, you'll find a spacious, fully stocked kitchen and welcoming dining table, as well as a comfortable living area with flat screen streaming television and enough seating for everyone. 2 bedrooms (king and queen) that feature incredibly comfortable, high thread count sheets.

Top guest favourite
The exterior of a stone home is framed by lush greenery, featuring a shaded area with bright red awnings and striped lounge chairs. A gravel path leads to the entrance, with wooden shutters adorned on the windows, inviting a casual outdoor atmosphere.
Home in Amador City
4.97 out of 5 average rating, 194 reviews

Historic Stone Home and Charming Retreat Getaway!

Such a magical place of sunlight with a Creekside setting to enjoy the outdoor living. Meander down a paved driveway to your own private stone home, located within walking distance to Amador City, just minutes from the Shenandoah Valley wine region and Sutter Creek along historic Highway 49, California's Gold Country. Amador City is California's smallest incorporated city, with a population of just under 200 residents.

Top guest favourite
A wooden outdoor deck surrounded by lush greenery features a propane grill and seating options. A solar panel is positioned on the cabin, while nearby colorful flowers enhance the natural setting. The area offers a peaceful retreat amidst the trees.
Guest suite in Wilseyville
4.95 out of 5 average rating, 279 reviews

Sierra Foothills River Retreat

Enjoy a private guest suite on the Mokelumne river with no cleaning fees and a hassle free stay. Fall asleep to the sound of the river. Sit on 1 of 3 decks to enjoy the scenic views and watch the wildlife. Walk in the river, go fishing, pan for gold. The lower deck on the river has a hammock & 2 person swing. Visit Silver lake, Kirkwood, Big Trees Nat. Park or Lake Tahoe. Go wine tasting, antiquing or hiking.

Top guest favourite
An open living area features a cozy sofa, a dining table with black chairs, and a decorative area rug. A wall-mounted air conditioning unit is visible, along with a bed partially made in the corner, allowing for a relaxed and functional space.
Flat in Pioneer
4.96 out of 5 average rating, 106 reviews

Sanctuary in the Pines

45 minutes away from Kirkwood Sky Resort as well as, the mountains, lakes, hiking, and fishing of the Sierra Nevada mountains. Easy access to Highway 88. Close to Silver Lake, Cables Lake, Salt Springs Reservoir, Bear River Reservoir, and fishing at Tiger Creek. El Dorado National Forest minutes away. Quiet location in the pines close to outdoor activities.

Top guest favourite
An inviting entrance is framed by a lush arch of greenery. A brick pathway meanders through the garden, bordered by colorful plants and decorative pots. The pathway leads toward a cozy cottage, concealed by the foliage.
Guest house in Fiddletown
4.96 out of 5 average rating, 154 reviews

Fiddletown Cottage

Comfortable 350sf guest suite in a safe, quiet neighborhood in the Northern California Sierra Foothill community of Fiddletown. Fiddletown is in the heart of the Shenandoah Valley wine country and just minutes away from 30 + wineries and tasting rooms. The cottage is located 60 miles from Kirkwood resort and approximately 80 miles to South Lake Tahoe.

Top guest favourite
Two vintage clawfoot tubs are positioned on a wooden deck, facing a scenic vineyard landscape. A small table with two potted plants sits between the tubs, with rolling hills and a cloudy sky in the background.
Farm stay in Sutter Creek
4.98 out of 5 average rating, 228 reviews

Stay on a Private Vineyard & Winery

Escape to your own private vineyard and winery in the heart of California wine country. This romantic one-bedroom Carriage House offers vineyard views, rustic charm, and total privacy. Enjoy sunset soaks in outdoor clawfoot tubs and explore on-site wine experiences like barrel tastings, vineyard walks, and safari tours—all steps from your door.

Popular amenities for Shenandoah Valley holiday rentals