Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Superhost

A private entrance is visible, leading to a charming courtyard patio adorned with gravel. Two white chairs are positioned beside a small potted plant. The exterior walls of the cottage are green, contrasted by wooden and corrugated metal fencing, all framed by trees and blue sky.

Cottage in Middletown

4.85 out of 5 average rating, 27 reviews

Adorable Cottage - Walking distance to downtown

Comfortable Studio Cottage with full kitchen & bathroom, plus a Queen Bed & a Futon. Conveniently located in downtown Middletown, and just a short drive to Harbin Hot Springs, this modern cottage is perfect for your visit to south Lake County! Set behind a main house, this cottage has a private entrance with its own courtyard patio. Inside is a full kitchen, dining area, living room, office work space, sleeping area, full bathroom, Roku TV, Wi-Fi & all the conveniences of home! Cute & cozy!

Guest favorite

A view of a rustic retreat surrounded by trees adorned with autumn leaves. The ground is covered in fallen leaves, with a grassy area visible in the background. A wooden deck attached to the house overlooks the natural landscape.

Home in Middletown

4.98 out of 5 average rating, 116 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 favorite

Home in Loch Lomond

4.94 out of 5 average rating, 126 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 favorite

An open living space features a small kitchen area with a refrigerator, microwave, and countertop. A black futon, adorned with an orange plaid throw, complements the coffee table and television area. Natural light filters through a window, illuminating the tile flooring.

Guest suite in Lakeport

4.91 out of 5 average rating, 149 reviews

One Bedroom-Sleeps 3 adults or 2 adults/2 children

1. Junior One Bedroom - Entire Space 2. Bedroom (queen) w/En Suite Bathroom and Shower 3. Small Futon for 2 Kids or 1 Adult (2 adults OK please notify) 4. Private Parking for Two Vehicles (covered parking available upon request) 5. TV Wifi Netflix 6. Workspace/Desk 7. Full Size Frig 8. Microwave and NuWave Stove tops, elec skillet & wok 9. Bedding, Towels, Sheets, Soap, Shampoo 10. BBQ 11. 4 Blocks to Lake, 3 Blocks Restaurants 12. 5 Miles to Hospital / 2 Blocks to Courthouse

Guest favorite

A bright living area features large windows that frame views of the lake and surrounding trees. The space includes leather seating, a coffee table, and a dining area that opens to the balcony. Natural light illuminates the room, enhancing its spacious feel.

Home in Clearlake Oaks

4.96 out of 5 average rating, 267 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

Guest favorite

A serene outdoor area features a small pond surrounded by lush greenery and gentle slopes. A bench is positioned nearby, inviting peaceful moments amidst nature. The setting is complemented by mature trees providing shade and a sense of tranquility.

Cabin in Middletown

4.91 out of 5 average rating, 81 reviews

Sawdust Trails Cabin 4 near wine country

Take it easy at this unique and tranquil getaway. This studio Cabin includes a queen bed (sleeps 2). Located on 90 private acres (previously a 1940's resort) has a seasonal running creek, hiking trails, and a pond with fishing. Located within walking distance to Twin Pines Casino. 5 min to downtown, restaurants, shopping. 20 min drive to Calistoga, near Clear Lake, Harbin Hot Springs, and several wineries. Cabin is 1 of 5 cabins, 3 of which are available through Airbnb.

Superhost

Two wicker chairs with patterned cushions are positioned beside a small table, creating a cozy outdoor seating area. A flower box adorned with vibrant flowers complements the setting, while greenery provides a natural backdrop.

Guesthouse in Kelseyville

4.88 out of 5 average rating, 281 reviews

Cottage on lakeside property.

This is a cozy guestroom attached to the garage on our stunning half-acre lakefront, tree-studded property. The bedroom (double bed) and bath are quite small (not room for much luggage), but perfect for a few nights stay. We have two chairs and a little table set up right outside, and there are other relaxing spots. Check-in time is normally 3:00, but can be earlier with prior approval. We also rent out our house on occasion. They are 2 separate places non attached.

Top guest favorite

Guesthouse in Middletown

4.91 out of 5 average rating, 312 reviews

Love Shack

Come stay in the good vibes of the Love Shack. Built for one of my sons and his sweet love to escape his mother's hearing range.... It was built to be inviting to snuggle up in and enjoy. The cottage is comfortable and charming with a newly added bathroom and kitchen area. The back deck faces the morning sun, where you can sit and drink your morning, coffee . Walking distance to shops and restaurants in Middletown. All folks, races, LGBT friendly.

Guest favorite

A laundry area is visible, featuring a white washing machine and a white dryer side by side. A bottle of laundry detergent is placed on top of the washing machine. The wood cabinetry above adds functional storage space.

Guesthouse in Middletown

4.86 out of 5 average rating, 165 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.

Top guest favorite

A modern farmhouse cabin is nestled amid tall trees, covered in a blanket of fresh snow. Soft, warm light glows from the cabin’s windows, creating a cozy contrast against the cool, blue ambiance of the surrounding forest.

Cabin in Cobb

4.97 out of 5 average rating, 73 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 favorite

A clean, modern bathroom features a compact toilet set against a neutral grey wall. White wainscoting enhances the space, complemented by a window allowing natural light to enter. The space is well-maintained and designed for comfort.

Cabin in Cobb

4.87 out of 5 average rating, 95 reviews

Cozy Cabin in Cobb Mtn near Harbin Hot Springs

This super cute cabin was recently remodeled with all the modern amenities but still has that rustic and cozy charm of a cabin in the woods! It's the perfect getaway for a small group or family. There is lots to explore in the area but also plenty of fun activities provided at the cabin so you don't even have to leave if you don't want to!

Top guest favorite

A deck offers panoramic views of the lake, framed by trees and distant hills. Sunlight reflects off the water, creating a serene atmosphere. The structure features wooden railings and a partially shaded area, enhancing the space for relaxing outdoors.

Guesthouse in Nice

4.96 out of 5 average rating, 389 reviews

Lakeview Cottage A (No cleaning fee)

$15 of your cost goes directly to the county of Lake For taxes. I don’t charge a cleaning fee to keep the prices down. (Kitchen area) has low ceiling. Approximately 6’3” 150 sf deck with spectacular views of the lake. Lots of hummingbirds, wild turkeys, deer, squirrels etc. There is a futon in the living room with Linens available

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Popular amenities for Middletown vacation rentals

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Middletown

Superhost

A close-up of a sandwich featuring layers of corned beef, sauerkraut, and melted cheese, served on whole grain bread. A small side salad of mixed greens is presented alongside, with a glass of amber beer blurred in the background.

Hotel room in Calistoga

4.74 out of 5 average rating, 938 reviews

A Room with a Brew: Stay at a Microbrewery in Napa

MirandaRating, 5 stars1 day ago

Such a cute place! It was very comfortable, in a very cute, and walkable town, not far from Napa winery’s. The staff was very kind and friendly. The food at the restaurant was great. Definitely a good stay!

Top guest favorite

Yurt in Monte Rio

5 out of 5 average rating, 9 reviews

Tiny House + Yurt Nature Retreat

BenjaminRating, 5 stars3 days ago

I enjoyed my stay at this incredibly peaceful and relaxing property. Christy is an incredible host who is very responsive, thoughtful, and committed to ensuring that everything I needed was cared for. I have never stayed in such a unique property, which is the embodiment of indoor/outdoor living. There are also plenty of amazing activities to do around the area. I enjoyed hiking the Islands in the Sky Vista Loop (just down the street from the property), as well as visiting Goat Rock Beach and spending time in the nearby small town of Duncan Mills. The only thing of note from my stay is that I encountered a few banana slugs on the property. While they are completely harmless and I never encountered them indoors, they do tend to hang around on the path from the Yurt to the house and can be a bit shocking upon first sight. However all in all, this is an amazing place and I would highly recommend it for those looking to escape and connect with nature.

Guest favorite

A wooden deck surrounds a newly installed cedarwood hot tub, situated amidst lush greenery and autumn foliage. The serene creek and forest landscape provide a tranquil setting, with vibrant leaves reflecting in the water. Natural wooden elements are featured in the design.

Cabin in Cobb

4.91 out of 5 average rating, 43 reviews

Creekside Zen Writer's Cabin, Hottub, Tearoom

EdnaRating, 5 stars1 month ago

Great views and private. The hot tub was so relaxing and felt like luxury in the middle of nature. The neighbor has some friendly goats that added to the experience. Host was very accommodating and even provided access to his own place so we could get more towels. Would definitely stay again.

Guest favorite

A serene landscape features a gently flowing creek surrounded by lush greenery. Tall trees provide shade, with sunlight filtering through the leaves. Smooth stones are visible along the water's edge, contributing to the tranquil natural setting.

Home in Middletown

4.96 out of 5 average rating, 24 reviews

Middletown nest

SylviaRating, 5 stars2 months ago

The house was big, beautiful, and so peaceful. All you hear are the birds and the creek outside, very private. Big balconies to accommodate a comfortable group hang out. Big kitchen. Loved it and would stay again.

Guest favorite

A spacious redwood deck is highlighted, featuring lounge chairs and a dining table with an umbrella for shade. Lush greenery surrounds the deck, and tall trees create a serene backdrop, enhancing the natural setting and inviting relaxation.

Home in Middletown

5 out of 5 average rating, 8 reviews

Renewal Spring Retreat

ChrisRating, 5 stars5 days ago

Very beautiful home, wonderful view of the trees. Loved all the amenities offered and the instruments as well!

Guest favorite

A compact kitchen space is equipped with a microwave and toaster oven on a wall-mounted shelf. A wooden counter features a cutting board, a small vase with a flower, and a teapot beside a decorative box. Wall art is displayed above the counter.

Private room in Middletown

4.89 out of 5 average rating, 136 reviews

Cool & Compact Studio for Single Person

MartinRating, 5 stars1 week ago

I stayed for a couple of nights to attend a nearby workshop. This house is tucked away in cool forest area, and was very comfortable. I slept well here. There is a small refrigerator for food which was very convenient.

Guest favorite

Dome in Hidden Valley Lake

4.88 out of 5 average rating, 16 reviews

Luxury Stargazing Yurt With Skylights, Pano View!

MaryRating, 5 stars1 month ago

We had a wonderful stay at Gisele’s beautiful tent. It was spacious, private, and incredibly relaxing. It truly felt like being immersed in nature, but with all the comforts—like a hot shower, easy access to a regular toilet (non compostable), and a grill perfect for cooking up delicious meals. Gisele was a fantastic host, sharing interesting facts about the Hidden Valley Lake area and offering great recommendations for things to do. She also generously gave us fresh vegetables from her organic garden, which we really appreciated. Bruce introduced us to their new chicks—we even got to hold them—and the two free-roaming chickens on the property were so entertaining to watch as they enjoyed their “chicken spa day” and laid eggs.

Guest favorite