Holiday houses in Middletown

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Top-rated holiday rentals in Middletown

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Guest favourite
A private entrance is featured, with a gray cottage set among trees. The entrance is framed by wood and metal fencing, leading to a small patio area containing two white chairs and a round table. Sunlight illuminates the outdoor space.
Cottage in Middletown
4.89 out of 5 average rating, 38 reviews

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!

Guest favourite
Home in Middletown
5 out of 5 average rating, 11 reviews

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.

Top Guest favourite
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
4.99 out of 5 average rating, 135 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).

Top Guest favourite
A warm living space features wooden paneling and natural light from large windows. A comfortable chair sits beside a small wooden table, and a piano is positioned nearby. Decorative plants hang from the ceiling, complemented by a cozy fireplace and a bookshelf in the background.
Home in Forestville
4.96 out of 5 average rating, 298 reviews

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.

Guest favourite
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, 123 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!

Superhost
A wide window frame showcases a serene view of the lake, bordered by lush green trees. The calm water reflects the surrounding landscape, while rolling hills provide a backdrop, creating a peaceful connection to nature.
Home in Clearlake Oaks
4.86 out of 5 average rating, 364 reviews

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.

Top Guest favourite
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
4.94 out of 5 average rating, 112 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!

Top Guest favourite
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
4.97 out of 5 average rating, 337 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

Top Guest favourite
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, 169 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.

Superhost
The open living space features large windows revealing mountain views. A comfortable seating area is present along with a dining table and a well-equipped kitchen. Light wooden flooring enhances the inviting atmosphere, complemented by neutral wall colors and tasteful decorations.
Guesthouse in Cobb
4.85 out of 5 average rating, 41 reviews

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!

Top Guest favourite
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, 105 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.

Top Guest favourite
A spacious living area is illuminated by natural light from large windows. Plush sofas are arranged around a coffee table, while a fireplace adds warmth. A wall-mounted TV is positioned for easy viewing. A sliding door leads to an outdoor space with seating.
Home in Santa Rosa
4.94 out of 5 average rating, 281 reviews

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

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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