Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Guest favorite

A child sits on a rock by the water, focused on fishing with a rod. The calm lake is visible in front, framed by greenery and distant homes. Soft sunlight illuminates the scene, creating a peaceful outdoor setting.

Home in Lakeport

4.99 out of 5 average rating, 110 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

A spacious outdoor deck features comfortable lounge furniture and two large umbrellas providing shade. A hot tub is positioned nearby, offering a relaxing spot. Lush greenery surrounds the space, creating a serene environment for outdoor enjoyment.

Home in Monte Rio

4.75 out of 5 average rating, 20 reviews

Zen by the River-3 bedroom 2 bath hot tub

Spectacular riverfront sanctuary. Enjoy long warm days on the large south facing deck. Several outdoor nooks to enjoy what mother nature has to offer. House is located at the end of a quiet, safe cul-de-sac, with a large open plan living room-kitchen area & a window seat perfect to curl up w/ a good book. A cooks kitchen w/ granite counter tops & upgraded appliances. The house has 3 spacious bedrooms and 2 bathrooms. Imagine a perfect afternoon on the river BBQing & a soak in the hot tub.

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, 330 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

A spacious deck area features a hammock, dining table with chairs, and patio umbrellas. The deck is made of wooden planks and is surrounded by lush greenery, enhancing the outdoor relaxation space. A corner sofa provides additional seating for guests.

Home in Forestville

4.95 out of 5 average rating, 132 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

Superhost

Home in Graton

4.87 out of 5 average rating, 107 reviews

Celia's Garden - Lovely Home, Wonderful Location!

Celia's Garden is a joyful sanctuary - custom built in 2018 and just two blocks from downtown Graton where you’ll find restaurants and wine tasting rooms that exemplify West Sonoma County. This sunny and welcoming property is your home away from home - with an open and well-stocked kitchen and dining room. The living area is comfortable for entertaining and has an eclectic collection of books, DVDs, fanciful records, and kid-friendly activities that fill the bookcases and drawers.

Guest favorite

A spacious living area features a blue sofa adorned with a soft orange throw. A large area rug with intricate patterns anchors the space, while natural light floods in through large windows. A wooden coffee table rests centrally, complemented by decorative items.

Home in Windsor

4.96 out of 5 average rating, 408 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

4.92 out of 5 average rating, 130 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.

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, 218 reviews

Zin & Zen on the River-Hot Tub, Kayaks, Views!

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.