Holiday houses in Middletown

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Top-rated holiday rentals in Middletown

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Top Guest favourite
A large, covered deck extends from the building, surrounded by trees and adorned with soft lighting. Fallen leaves cover the ground, contributing to the rustic atmosphere. The structure features warm-colored walls and multiple entry points, inviting guests to explore the spacious retreat.
Home in Middletown
4.99 out of 5 average rating, 136 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 favourite
Cabin in Middletown
4.85 out of 5 average rating, 124 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!

Top Guest favourite
The exterior of the cottage is presented, showcasing a charming, light-colored façade. Potted plants line the walkway, while a small seating area with black chairs is visible nearby. Lush greenery surrounds the property, creating a tranquil environment.
Guesthouse in Santa Rosa
4.89 out of 5 average rating, 1,203 reviews

Clean Comfy Cottage Downtown

Our tree shaded studio cottage is one block from the heart of downtown. Stay just a two block walk from Russian River Brewing. This clean and quiet cottage has a full kitchen, a comfortable queen bed. I am happy to customize the space to your needs. I offer soft and firm mattresses. I use cotton blankets so that you can have any weight on your bed that you would like. You are welcome to stack seven or more blankets at a time. I will adjust my cleaning regimen to meet your preferences.

Guest favourite
A comfortable swinging chair is positioned on a wooden deck, offering views of the lake and surrounding trees. Sunlight filters through the branches, creating a serene outdoor space for relaxation.
Home in Clearlake Oaks
4.94 out of 5 average rating, 140 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.

Top Guest favourite
Cabin in Cobb
4.94 out of 5 average rating, 113 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 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, 143 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 favourite
A spacious private deck is seen with views overlooking the rolling hills and valleys. Comfortable green lounge chairs are positioned for relaxation. The deck features wooden railing and steps leading down, while a doorway connects to the guest suite.
Guest suite in Santa Rosa
4.96 out of 5 average rating, 364 reviews

Wikiup lookout retreat

We self-developed our rural property as a secluded retreat with dog-friendly gardens. To share our creation with you, we designed a private 2nd-floor guest suite (ok to bring your good dogs). Your suite includes secure parking, private entrance, deck, kitchen, dining, living, 3 beds (queen, double, twin), one bath & a fenced back yard. We are on a country road near Healdsburg, Windsor, Russian River, Sebastopol, Santa Rosa, Calistoga, Sonoma & Napa valleys, wineries & beaches.

Top Guest favourite
Home in Middletown
4.93 out of 5 average rating, 149 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.

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, 342 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
Cabin in Cobb
4.96 out of 5 average rating, 108 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.

Guest favourite
Guesthouse in Healdsburg
4.97 out of 5 average rating, 234 reviews

Healdsburg Contemporary Cottage With Lush Backyard Patio

Your private Healdsburg retreat—just a 4-minute walk to downtown wine tasting rooms, restaurants, shops, and the Farmers Market. This stylish guest cottage offers parking in front of a private entry, garden with al fresco dining, BBQ, lounge area, and a fully equipped Pilates studio. Designed with international contemporary art and thoughtful touches, it’s perfect for a weekend escape or a longer stay while house hunting.

Top Guest favourite
Farm stay in Geyserville
4.99 out of 5 average rating, 163 reviews

Country Barn in Downtown Geyserville

Linger over coffee on your quaint patio amongst 6 acres downtown in sweet Geyserville. An industrial loft vibe with wine country bones—the "barn" is a modern/rustic country-correct cottage. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Property rental supports Farm Sanctuary on site of rescue goats, horses, and one heifer named Francis.

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 $142 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, Wifi 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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