Vacation rentals in Middletown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middletown

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

A spacious studio guest house is shown, featuring a comfortable queen bed adorned with soft linens. A cozy seating area is present with a plush couch, and a wall-mounted TV is visible. Natural light fills the room through large windows, complemented by wooden beams on the ceiling.

Guesthouse in Healdsburg

4.98 out of 5 average rating, 296 reviews

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

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, 121 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).

Superhost

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, 105 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

A clear blue sky is depicted above a serene lake, with two mountains rising in the background. Sunlight reflects off the water's surface. Leafy branches from nearby trees frame the scene, adding hints of green against the vibrant blue.

Home in Clearlake Oaks

4.93 out of 5 average rating, 105 reviews

Oak Hill Cottage: WiFi, Views

This peaceful cottage sits on an oak dotted hill overlooking the lake and offers sweeping panoramic views from almost every room in the house. It would make a great homebase for adventures fishing, boating, hiking, winetasting, etc. Travel less than one minute by car (5 on foot), & you'll find a park, a public beach, & a free boat launch. Or, you can stay home & cook a meal in its deluxe kitchen. King size beds in both bedrooms. Restaurants, coffee, & shopping within easy walking distance.

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, 129 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, 30 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 vase filled with bright sunflowers, orange lilies, and roses stands at the center of a wooden table. Behind it, a framed watercolor painting featuring sunflowers is displayed on a light gray wall, complementing the green wall to the left. A lamp casts a warm glow in the corner.

Home in Middletown

4.92 out of 5 average rating, 126 reviews

Emerald Lodge

I just updated what was the "Locust Lodge" to the "Emerald Lodge"! Now let's see if this name sticks or I change it to "Lime and Tequila Lodge", and.. still.. open to suggestions. I decided to paint one of the walls green, and upgraded a few other things that I am sure you will appreciate. There is a new memory foam mattress, flat screen TV, desk, table with four chairs, all sorts of new kitchen accoutraments, a gorgeous water color painting from a friend of mine, and lots of love.

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, 285 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

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

4.97 out of 5 average rating, 87 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.

Superhost

A modern kitchen is seen with stainless steel appliances and a gas range. White cabinetry is paired with a large island, offering additional prep space. Four white chairs surround a glass dining table, while pots and utensils are neatly arranged on the wall.

Cabin in Cobb

4.85 out of 5 average rating, 104 reviews

Cozy Cabin in Cobb Mtn near Harbin Hot Springs

This super cute cabin was recently remodeled with all the modern amenities but still has that rustic and cozy charm of a cabin in the woods! It's the perfect getaway for a small group or family. There is lots to explore in the area but also plenty of fun activities provided at the cabin so you don't even have to leave if you don't want to!