Holiday houses in Middletown

Adorable Cottage - Walking distance to downtown

Comfortable Studio Cottage with full kitchen & bathroom, plus a Queen Bed & a Futon. Conveniently located in downtown Middletown, and just a short drive to Harbin Hot Springs, this modern cottage is perfect for your visit to south Lake County! Set behind a main house, this cottage has a private entrance with its own courtyard patio. Inside is a full kitchen, dining area, living room, office work space, sleeping area, full bathroom, Roku TV, Wi-Fi & all the conveniences of home! Cute & cozy!

The Renewal Spring

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.

Cozy Lakefront Retreat - Private Trails & Beach

A bright historic farmhouse overlooking Clear Lake, with a private lakefront cove and access to a second shared beach & dock. Scenic views, private trails, and generous indoor and outdoor gathering areas are ideal for unwinding together. Enjoy meals on the covered veranda, cook in the well-stocked kitchen, bathe in the outdoor spa, play in the game room, or gather by the fire pit after sunset. Wineries, farm stands, shops, and hiking nearby make great outings for couples, families, and friends.

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!

Little Falling Water - Mid-Mod Masterpiece

We invite you to experience the exceptional mid-century modern style and mountain tranquility of Little Falling Water. Set beside a waterfall and built literally over a stream, this architecturally significant residence completed in 1961 was inspired by Frank Lloyd Wright's iconic home of the same name. Walls of glass frame treetop views and the soothing sounds of cascading water surround you on all sides. Decorated with taste, curated for your comfort, close to fine wineries, come enjoy!

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!

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.

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!

Eagle's Nest Treehouse Farm Stay

Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

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.

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.

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.