
Holiday houses in Middletown
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Top-rated holiday rentals in Middletown
Guests agree: these stays are highly rated for location, cleanliness and more.

Velouria - Hot Tub, Woodstove, Redwoods.
Welcome to Velouria, our cabin in the redwoods of northern California. With a cosy loft bedroom in the main house, a romantic wood burning stove, a guest cabin located on the property and an outdoor hot tub, full kitchen surrounded by vaulted redwoods. It has everything to make your forrest retreat perfect. It's close to downtown Guerneville and many beautiful local attractions, nature trails and renown vineyards. It also has a big comfy couch and great Entertainment Center for those rainy days!

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!

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.

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.

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

Studio Cottage on Saffron Farm.
Our open plan cottage studio has lovely views of our walnut orchard, historic barn and fields. Enjoy sunset over the neighboring vineyards from your private deck. We are a mile down the road from a lovely State park, that is if you ever want to leave our tranquil little farm. Also nearby are wineries, hiking trails up a dormant volcano, and California's largest and oldest lake. Our farm is featured in the September 2022 issue of Sunset magazine. Check it out!

Gracianna Winery Vineyard Loft - Farm Stay
Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

Winelight Vineyard Home With Spa
Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

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.

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court
Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

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.
Popular amenities for Middletown holiday rentals
Other great holiday rentals in Middletown

Hottest Property on the Lake! Views Forest Private

Green Valley, Sonoma County at a Working Winery.

Luxury Covered Wagon near Harbin Hot Springs

Downtown Healdsburg Perch

Red-Tail’s Golden Egg l Inspiring Lake & Mtn Views

House and optional cabins near Harbin Hot springs

Wine Country Escape!

Views • Hot Tub + Plunge Pool • 5mi to Calistoga
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 $143 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!
Destinations to explore
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- Six Flags Discovery Kingdom
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- Goat Rock Beach
- Doran Beach
- Safari West
- Johnson's Beach
- Sonoma Coast State Park
- Trione-Annadel State Park
- Armstrong Redwoods State Natural Reserve
- Chateau St. Jean
- University of California - Davis
- Jack London State Historic Park
- V. Sattui Winery
- Charles M. Schulz Museum
- Healdsburg Plaza
- Napa Valley Wine Train Wine Shop
- Sugarloaf Ridge State Park
- VJB Vineyard & Cellars
- Iron Horse Vineyards
- Harbin Hot Springs
- St. Francis Winery and Vineyard
- Francis Ford Coppola Winery
- Salt Point State Park




