Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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A serene landscape is displayed, featuring a light-colored house nestled among lush greenery. Towering trees and distant mountains provide a calming backdrop, while patches of grass and small rocks are visible in the foreground, suggesting a peaceful natural setting.

Home in Middletown

4.83 out of 5 average rating, 24 reviews

Renewal Spring Retreat

Enjoy peace and calm at this brand new, beautifully designed oasis. Surrounded by audible streams of healing water and mighty pines a quick 10-minute drive to Harbin Hot Springs, it's a spot to enjoy year-round. Along with the open living-dining room-kitchen stocked with appliances and a luxurious bath providing the comforts of home and beyond, you’ll have a large wrap-around redwood deck with panoramic valley overlooks and mountain views from every room including the secluded bedroom hideaway.

Guest favorite

A spacious living area is highlighted by rustic decor, featuring a large leather sectional sofa and a dark wooden coffee table. A recliner is positioned nearby. Three framed prints adorn the wall. A kitchen area with wooden cabinetry is visible in the background.

Home in Middletown

4.98 out of 5 average rating, 125 reviews

Western Mine Retreat near wine country

This private vacation retreat is located just 20 minutes from Calistoga in Middletown, CA. Decorated in a rustic mining-theme after the historic area, this large living space is enhanced by a 60'x15' covered deck with relaxing views of the woods and a pond just down the hill. Amenities include high speed WiFi, a large smart television, and game tables. Nearby attractions include wine tasting, hot springs resorts, quaint downtown Middletown, and the Twin Pines Casino (just down the street).

Guest favorite

A rustic cabin is nestled among tall pine trees, featuring a red exterior and a welcoming American flag mounted on the front. Sturdy stairs lead up to a spacious deck surrounded by lush greenery, providing an inviting retreat.

Cabin in Middletown

4.85 out of 5 average rating, 109 reviews

Cozy PET-FRIENDLY 1 bd cabin w/ indoor fireplace

Welcome to Castlewood Cabin in the beautiful Whispering Pines community on Cobb Mountain. Wrapped in a forest of pine trees, this rustic, refinished cabin offers one bedroom and one bathroom as well as a fold out sofa in the living room. With room for up to 5 guests this cabin is the ideal spot for a romantic couples getaway, a family road trip or even a small group of friends. Come enjoy all that Lake County has to offer - hiking, biking, boating, fishing, wineries, casinos Harbin and more!

Guest favorite

The living area features exposed wooden beams and a cozy stone fireplace at its center. Natural light fills the space through multiple windows, with comfortable seating arranged around the hearth. A warm plaid blanket is draped over a wooden couch, enhancing the cabin's rustic charm.

Cabin in Cobb

4.93 out of 5 average rating, 94 reviews

Cozy vintage cabin with fireplace near hot spring

Our rustic wood cabin is nestled among pine trees in the little village of Cobb Mountain, close to Harbin hot springs, Clear Lake, and just north of Napa valley wine country. Enjoy being surrounded by forest while you relax in the hammock or bbq on the deck. Step back in time in the vaulted wood rooms, warm fireplace, modern amenities including A/C and comfy bedding. A short walk to the swimming pool, little stream, general store and cafe. A perfect romantic getaway, or for the whole family!

Guest favorite

A spacious canvas yurt is lit softly from within, showcasing a warm ambiance as dusk approaches. The structure is surrounded by lush greenery and an expansive view of rolling hills, creating an inviting outdoor retreat in nature.

Yurt in Hidden Valley Lake

4.81 out of 5 average rating, 48 reviews

Magical, serene yurt near Harbin Hot Springs

✨ Serene camping retreat in a high end Stout canvas yurt with HEATED mattress pad o 5 acre organic farm in Lake County's rustic "undiscovered wine country" near Harbin Hot Springs -- on spectacular 360 degree View property.✨ Reconnect with nature, your partner and the cosmos in the Bohemian Belle - a beautifully decorated and furnished handcrafted 250 square foot 9 foot high yurt. Whether you're seeking a healing retreat or inspiration, this space is designed for peace and rejeuvenation.

Guest favorite

A spacious wooden deck features a set of four red Adirondack chairs arranged around a central table. The sun sets in the background, illuminating the surrounding trees and creating a serene outdoor space suitable for relaxation.

Home in Loch Lomond

4.94 out of 5 average rating, 136 reviews

Cozy Mountain Retreat | Peaceful with Scenic Views

Get away from it all and enjoy the peace and quiet of Loch Lomond. Relax on the deck surrounded by oaks, grill your favorite meals, and unwind in comfort. The kitchen is fully stocked for cooking, and there’s a small gym area for yoga or stretching. Each room has a comfy queen bed and mini-split A/C and heating. Kick back in the spacious TV room with a wet bar and a desk for remote work, plus fast WiFi to stay connected. Perfect for a peaceful retreat, remote work, or a mountain adventure.

Top guest favorite

Home in Middletown

5 out of 5 average rating, 34 reviews

Casa Loco

Experience tranquility at Casa Loco, a serene retreat on 20 picturesque acres in Piner Valley. Perfect for families, this home is a short drive to Middletown, Harbin Hot Springs (10 min), and numerous local wineries. Enjoy bird watching, scenic views, and watch for the luxurious Lotusland resort and Coore & Crenshaw golf course. Explore nearby attractions like the Guenoc/Langtry Farms Winery, Calpine Geothermal Visitor Center, and stunning hiking trails. Book now for a peaceful getaway!

Guest favorite

A bright interior space features large windows offering views of the lake and mountains. A wooden desk is positioned next to a chair, with a telescope nearby, inviting relaxation and exploration. Natural light fills the room, complemented by neutral-colored furnishings and soft carpet.

Home in Clearlake Oaks

4.96 out of 5 average rating, 302 reviews

Top of the World View of Clear Lake and Mountains

If you’re looking to getaway, this home high in the hills surrounding beautiful Clear lake, is the retreat for you! Enjoy panoramic views of the lake and mountains. Very quiet, the perfect stop between the redwood trees and the Bay Area Relax on the deck shaded by mature oak trees and watch the osprey’s gliding below you or use the house as a jumping off point. Mendocino National Forest, just 20 minutes away, offers endless possibilities: mountain bike and explore the local trails

Guest favorite

A vibrant red cabin with a classic front door is framed by greenery. A small deck is featured at the entrance, showcasing a table and two chairs. A grill is positioned nearby, contributing to the outdoor dining space.

Cabin in Middletown

4.91 out of 5 average rating, 87 reviews

Sawdust Trails Cabin 4 near wine country

Take it easy at this unique and tranquil getaway. This studio Cabin includes a queen bed (sleeps 2). Located on 90 private acres (previously a 1940's resort) has a seasonal running creek, hiking trails, and a pond with fishing. Located within walking distance to Twin Pines Casino. 5 min to downtown, restaurants, shopping. 20 min drive to Calistoga, near Clear Lake, Harbin Hot Springs, and several wineries. Cabin is 1 of 5 cabins, 3 of which are available through Airbnb.

Guest favorite

A charming countryside house is situated under the shade of large oak trees. The exterior features a neutral-coloured façade with multiple windows. A redwood deck leads to the front door, providing a welcoming entryway. The surrounding landscape showcases dry grass and open space.

Guesthouse in Middletown

4.86 out of 5 average rating, 170 reviews

Countryside Cottage

Escape to our charming countryside oasis near the beautiful Mayacama mountain range. This small, comfortable house offers the perfect getaway just a short drive from the renowned Harbin Hot Springs. Located only 2 minutes from Twin Pine Casino. Whether you're planning a romantic couples getaway, a memorable family vacation, or a fun-filled trip with friends, our cozy haven provides the ideal setting. Book your escape now and experience the countryside.

Top guest favorite

The interior of the cottage features a spacious sleeping area with a king-sized bed, a soft sofa, and a leather love seat. A large window allows natural light, with curtains providing a touch of color. Nearby, a guitar and a small entertaining space can be seen.

Cottage in Middletown

4.98 out of 5 average rating, 142 reviews

Garden house with gas fireplace

Beautiful new cottage with lots of light, swing, and gas fireplace. Large open space with private deck looking out at Mt St. Helena. In the evening, turn on the outdoor string lights and relax on the swing under the huge oak tree before sinking into the memory foam king size bed. In the morning there is pour over coffee and robes so you can sit outside and sip your coffee. Perfect place to stay for a while, or have a romantic weekend.

Guest favorite

A modern kitchen and dining area feature a large wooden table surrounded by black chairs. The kitchen is equipped with stainless steel appliances and sleek cabinetry. Natural light floods the space through large windows, highlighting the wood-beamed ceiling and minimalist decor.

Cabin in Cobb

4.96 out of 5 average rating, 96 reviews

Wrenwood Cabin | Modern Mtn Home

Welcome to our newly renovated modern farmhouse cabin, nestled on a private acre surrounded by majestic 200-foot Douglas Firs. Enjoy the seasonal creek that graces the backyard during the wet season, providing a tranquil retreat. Perfect for a peaceful escape or productive remote work, our cabin features high-speed internet and modern amenities. Explore Cobb Mountain’s hiking, biking, and swimming adventures, all just a short distance away.