
Holiday houses in Middletown
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Top-rated holiday rentals in Middletown
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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.

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).

Forest Cozy Home
My house in Forestville is a walk to the river (Steelhead County Beach), near endless wineries, canoe rentals, gorgeous Sonoma coast beaches, Santa Rosa airport, a bicycle trail through West County with bike rentals in downtown Forestville offering immediate access to the trail, and a very well-stocked little grocery store a 5-minute walk down the hill. Lovely back roads take you to Healdsburg to the north or Sebastopol to the south. My dog & I stay in a basement studio when guests are here.

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!

Cozy Cottage: Panoramic Lake View, WiFi, Deck
This clean, cozy little getaway sits on a hill overlooking the lake. It boasts panoramic views from almost every room in the house, & if you open the windows at night, you might hear the waves. 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 & BBQ on the deck. Restaurants, coffee, & shopping within easy walking distance.

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!

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

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.

Guesthouse with Deck and Mountain Views!
From the gorgeous kitchen to the charming bath, a lot of thought has gone into the guest's experience! With amazing views of Cobb Mountain and Mount Saint Helena, this studio offers a peaceful place from which to explore the area. The deck is very large. The comfortable seating are is a great place to relax or watch tv. The kitchen is well stocked with all the dishes, cookware and small appliances needed for cooking. Extended stays are welcome!

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.

Russian River Valley Brew-cation Home
Welcome to the Russian River Brewhouse! Where modern comfort meets rustic charm, and the good beer vibes flow as freely as the wine. Enjoy up-to-date appliances and amenities paired with cozy wrought-iron framed beds wrapped in warm, inviting blankets. This home is your home, offering the ideal balance of relaxation and adventure. Step inside, unwind, and get ready to explore all the wonders wine country has to offer.
Popular amenities for Middletown holiday rentals
Other great holiday rentals in Middletown

Branch + Boulder

Mountain Nest | Cozy Cobb Getaway | Pet friendly

4 Rock Ranch - Mountain Escape

Discover the Serene Beauty of Cole Ridge Chalet.

Lovely older home w/ private rm and bath/tub.

Pine Ridge Cabin - Cobb Mountain fun & relaxation

Cozy Mountain Contemplative

29 West B
Quick stats about holiday rentals in Middletown

Total holiday rentals
Explore 10 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at $145 AUD per night before taxes and fees

Verified guest reviews
Over 1,500 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Middletown holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Middletown rentals

4.9 Average rating
Middletown stays are highly rated by guests—averaging 4.9 out of 5!
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