Vacation rentals in Middletown

4.85 out of 5 average rating, 27 reviews

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

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!

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.

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).

4.87 out of 5 average rating, 336 reviews

A serene view of the lake is framed by lush green trees. The shoreline is lined with greenery, and hills can be seen in the distance under a clear blue sky. A small decorative feeder hangs from a branch, adding a touch of color.

Home in Clearlake Oaks

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.

4.92 out of 5 average rating, 85 reviews

Two figures are outlined in the steamy water of a pool, surrounded by a serene atmosphere. The steam rises gently, creating a tranquil ambiance. Lush greenery is visible in the background, enhancing the peaceful setting.

Cabin in Cobb

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!

4.94 out of 5 average rating, 126 reviews

Home in Loch Lomond

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.

An outdoor seating area features a table with four metal chairs. A decorative lamp with a floral design casts a warm glow, enhancing the peaceful atmosphere. The background showcases grassy space and trees, creating a natural setting for relaxation.

4.93 out of 5 average rating, 120 reviews

Emerald Lodge

I just updated what was the "Locust Lodge" to the "Emerald Lodge"! Now let's see if this name sticks or I change it to "Lime and Tequila Lodge", and.. still.. open to suggestions. I decided to paint one of the walls green, and upgraded a few other things that I am sure you will appreciate. There is a new memory foam mattress, flat screen TV, desk, table with four chairs, all sorts of new kitchen accoutraments, a gorgeous water color painting from a friend of mine, and lots of love.

4.96 out of 5 average rating, 268 reviews

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

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

4.91 out of 5 average rating, 81 reviews

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

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.

Guesthouse in Kelseyville

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.

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.

4.86 out of 5 average rating, 165 reviews

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

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.

4.97 out of 5 average rating, 74 reviews

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

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.

4.96 out of 5 average rating, 392 reviews

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

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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Other great vacation rentals in Middletown

4.91 out of 5 average rating, 43 reviews

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

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.

5 out of 5 average rating, 13 reviews

A spacious deck features comfortable seating arrangements surrounding a propane fire pit. The lake can be seen in the background, accompanied by distant hills and a colorful twilight sky. Cushions in neutral tones and patterns add to the inviting atmosphere.

Home in Lake County

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

SaranyaRating, 5 stars3 days ago

Hands down the best! We’re still dreaming about this home - it was truly that special. The location was absolutely perfect, with breathtaking views of the lake that we couldn’t get enough of. Every room was so thoughtfully designed, with beautiful decor that made the entire space feel both luxurious and cozy. The kitchen was a dream to cook in, with top-notch appliances and a fully stocked pantry that had everything we needed - plus great coffee and tea. We ended up spending nearly our entire trip at the house because it was just that amazing. The record player added such a lovely, nostalgic touch, and the beds and couches were incredibly comfortable. Every detail was curated with care and it really showed. The host was outstanding - super responsive, even late at night, and went out of their way to make sure we had everything we needed throughout our stay. We’ve stayed at many Airbnbs over the years, and this one is easily at the top of our list. We can't wait to come back!

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.

4.92 out of 5 average rating, 25 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.

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.

5 out of 5 average rating, 9 reviews

Renewal Spring Retreat

AllisonRating, 5 stars3 days ago

Our stay at Courtney’s home was absolutely wonderful! The house has a charming feel, and the bed was very comfortable—if a bit firm (which we prefer) just as another review noted. It’s conveniently located near Harbin as well as local stores and restaurants. The views of the surrounding mountains and the soothing sound of the nearby stream made for a truly peaceful setting. The community has made a gradual recovery since the 2015 fire; remnants of that event are still visible, including some freestanding structures. The neighborhood feels safe, and everyone we met while walking our dogs was warm and welcoming. We recommend staying here!

Private room in Middletown

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.

4.89 out of 5 average rating, 136 reviews

Cool & Compact Studio for Single Person

MartinRating, 5 stars2 weeks 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.

5 out of 5 average rating, 5 reviews

The exterior of a two-story house is presented, featuring a wooden deck with a safety railing and multiple large windows. Surrounding trees provide shade, while autumn leaves cover the ground, suggesting a serene natural setting. A glimpse of solar panels can be seen on the roof.

Chalet in Kelseyville

Discover the Serene Beauty of Cole Ridge Chalet.

AnnaRating, 5 stars2 months ago

We had an amazing stay at this comfortable cabin! It was warm, inviting, and spacious. The fireplace made the living area extra comfy, and the couches were great for lounging. As a dog owner, I loved that it was truly dog-friendly. The back yard was fully fenced and surrounding area was open for privacy. Loved my stay here!

4.91 out of 5 average rating, 11 reviews

A wall-mounted heater is visible, featuring a grid design that reveals glowing red heating elements. The control knob is located at the bottom. The surrounding wall has a simple, neutral finish that complements the heater's functionality within the space.

Apartment in Angwin

Furnished Studio

StephenRating, 5 stars2 weeks ago

Michelle was great, very helpful and responsive throughout my stay. Offered suggestions for breakfast spots and was a great help throughout my stay.