Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Top guest favorite

Large windows offer views of lush greenery and the river outside, allowing natural light to fill the space. A comfortable seating area includes a television and is accompanied by a wooden deck with seating, blending indoor and outdoor living.

Home in Guerneville

4.98 out of 5 average rating, 217 reviews

Zin & Zen April Promo - Hot Tub, Kayaks, Views!

PROMOTION VALID UNTIL APRIL 30, 2025: Book any two nights and get 3rd night (Sunday to Thursday) free. Holidays excluded. Charming two-story riverfront cottage with wood-burning stove in Sonoma wine country with hot tub, kayaks, bicycles, private dock, outdoor shower, propane BBQ grill, and fire-pit area. Wine tasting, hiking, golf and ocean beaches nearby! Movies, games, and books for all ages. Serene views from inside the house, or from the brick-paver patio and upper and lower decks.

Guest favorite

An inviting outdoor deck offers comfortable seating with accent pillows in bright orange and teal. A shaded umbrella stands near a dining area overlooking the tranquil waters, while a gas heater provides warmth. Scenic views of the lake and distant mountains are prominently featured.

Home in Lakeport

4.99 out of 5 average rating, 108 reviews

Lakefront | King Bed | Private dock |SUPs & Kayaks

Escap'Inn presents The Lake. Imagine spending time lounging on the deck with a glass of wine from one of the nearby wineries as you enjoy the tranquil waters below. Or perhaps you prefer going out for an afternoon hike before taking a dip in the hot tub under starlit skies. This beautiful lakefront home is perfect for anyone looking to soak up the sun, take in breathtaking scenes, enjoy award-winning wineries and do it all while experiencing all of the comforts of home. With its own private dock

Superhost

An outdoor deck features a wooden floor and two blue lounge chairs facing a serene view of the lake through surrounding trees. A small grill is positioned nearby, inviting opportunities for outdoor meals.

Home in Clearlake Oaks

4.87 out of 5 average rating, 326 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.

Guest favorite

Home in Forestville

4.95 out of 5 average rating, 131 reviews

Hilltop Haven 🌅 view & hot tub

Relax with the whole family at this peaceful place to stay on a quiet hilltop. This is a quaint 2 bedroom, 1 bath with a queen bed in one bedroom and bunk (twin over full) in the second bedroom. Relax in the hot tub or in the hammock on the backyard deck with a peaceful nature view or hang inside the cozy abode and make use of the fully-stocked kitchen. we have a limit of 4 overnight guests and 2 vehicles per Sonoma County permit rules. For more pictures on IG @hilltop_haven_vacation

Top guest favorite

A spacious wrap-around deck is presented, featuring a large wooden dining table surrounded by six chairs. A lounge chair rests nearby, with the scenic backdrop of trees and the river visible through the railing. Natural light filters through the foliage, creating a serene atmosphere.

Cottage in Monte Rio

5 out of 5 average rating, 220 reviews

Riverfront Remodel | Hot Tub | Stunning Views

This stunning remodeled riverfront property is the perfect place for your Russian River getaway. You can truly unwind in the comforts of the house and the beauty of the surroundings. With a modern rustic feel, the house exudes charm, sophistication and an ease for luxurious riverfront relaxation. Just minutes from the Sonoma coast, the Russian River Wine Country, and the Alister MacKenzie Golf Course. Your vacation in wonderland awaits! (Sorry, no pets of any kind allowed)

Guest favorite

Home in Guerneville

4.95 out of 5 average rating, 177 reviews

Celebrate~Bar~Kayaks~ Kids~Hot tub~Redwoods~

Looking for the ultimate chill spot? We've got you covered! Our place is the perfect mix of zen and zest, nestled just 3 miles from Armstrong Woods and a hop, skip, and a jump from the Russian River. Grab our kayaks and paddle your worries away, or make a splash with memories that stick. Party in the backyard with an outdoor shower and hot tub that scream 'fun in the sun', and when hunger strikes, our chef's kitchen is your gourmet playground. Book local, stay loco!

Guest favorite

A cozy living room is furnished with a comfortable leather armchair and a decorative coffee table, centered around a romantic fireplace. A flat-screen TV sits on a stand, while French doors lead to an adjacent room, allowing natural light to fill the space.

Home in Windsor

4.96 out of 5 average rating, 407 reviews

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.

Guest favorite

A view of a cozy redwood deck is framed by an open doorway, featuring two white chairs positioned around a small table. The area is adorned with string lights, and greenery is visible in the background, highlighting the tranquil outdoor setting.

Guesthouse in Middletown

4.86 out of 5 average rating, 163 reviews

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.

Guest favorite

A serene view of a winding river bordered by lush greenery and dense trees. The gently flowing water reflects the surrounding landscape. A sandy bank can be seen along the river's edge, complemented by patches of grass and shrubs in the foreground.

Home in Guerneville

4.94 out of 5 average rating, 190 reviews

Escape to Guernevilla, sunniest spot on the river!

Adventure awaits at Vacation Beach! Guernevilla is our happy place and pretty sure it'll become yours too. This charming family- and dog-friendly home offers everything you need to kick back and relax, including a chef's kitchen, outdoor dining, a front porch that overlooks an enclosed patio courtyard and a fully fenced and private backyard with 4-person hot tub. Two different beaches with river access are both just a short 5-7 minute walk away.

Guest favorite

A wooden deck is positioned near a gently flowing creek, surrounded by lush greenery. Two wooden chairs and a small table invite relaxation, with natural stone borders framing the area. Trees provide a serene backdrop, enhancing the peaceful setting.

Cottage in Santa Rosa

4.91 out of 5 average rating, 128 reviews

Mins from Napa, Sonoma, spas. Cozy home w/ Hot tub

* Hot Tub to relax in, nestled among the redwoods * 3 bdrms + 1 pull-out sofa bed, sleeps 8 * 10 mins to spas in Calistoga * Wineries (5-10 mins), St. Helena(22 mins) * Gorgeous views of a gurgling creek * Backyard deck + grill * For familiies, kid friendly - pack n play, kid utensils, 5 mins to Safari West Note: accurate guest count required to honor county rules. Extra fees will be charged if more guests at check-in.