
Vacation rentals in Middletown
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Top-rated vacation 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!

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!

Quiet, relaxing, home away from home.
Winter time...you can bask in the glow of your fireplace or sit out and gaze at the stars in front of your outdoor fire pit! Spring/summer enjoy colorful gardens and meals picked out of your own backyard....you may cook, or allow me to prep a meal and serve you at your own bistro table. Quiet and peaceful...feels very far away but Kville is just a mile up the road with with numerous wine tasting rooms, restaurants, brewery, shops and LOTS of live music, birding, hiking, fishing, gambling.

Calistoga Tejas Trails
Welcome to Tejas Trails, your country getaway nestled in Calistoga's mountain vistas, just 10 minutes from downtown. This new home (2023) is easy to share with friends or family. Enjoy refreshing mountain sunrises, dinners on the huge deck, watch sunsets sipping wine by the firepit, swing under a large oak tree, and take tranquil walks on the country road. This is the perfect place to leave the hustle and bustle behind, while still minutes from Napa Valley’s finest restaurants and wineries!

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

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.

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!

:|: Samadhi’s Birdhouse
Samadhi’s Birdhouse is a quiet retreat perched atop a tiny peninsula that juts out into the southern portion of Clear Lake reaching toward Mount Konocti [Mountain Woman in Pomo]. Water surrounds you on all sides as birds abound. You’ll see pelicans streaming past; egrets finding their familiar ground; eagles, hawks, and turkey vultures looking down in curiosity. Deer, jackrabbits, and wild turkey graze together while melodic birdsong fills the air.

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

Luxury Covered Wagon near Harbin Hot Springs

Cozy Private Cabin with Views

House and optional cabins near Harbin Hot springs

Redwood Treehouse with Hot Tub

Views • Hot Tub + Plunge Pool • 5mi to Calistoga

Romantic Garden Retreat · Private & Peaceful

Modern Barn Nestled in the Countryside

Wine Country Cottage Escape
Quick stats about vacation rentals in Middletown

Total vacation rentals
Explore 10 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at G$20,920 GYD 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 vacation 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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