Holiday rentals in Middletown

4.85 out of 5 average rating, 27 reviews

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!

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).

4.85 out of 5 average rating, 98 reviews

Cabin in Middletown

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!

4.99 out of 5 average rating, 76 reviews

Cabin in Cobb

Little Falling Water - Mid-Mod Masterpiece

We invite you to experience the exceptional mid-century modern style and mountain tranquility of Little Falling Water. Set beside a waterfall and built literally over a stream, this architecturally significant residence completed in 1961 was inspired by Frank Lloyd Wright's iconic home of the same name. Walls of glass frame treetop views and the soothing sounds of cascading water surround you on all sides. Decorated with taste, curated for your comfort, close to fine wineries, come enjoy!

4.92 out of 5 average rating, 85 reviews

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.

Top guest favourite

5 out of 5 average rating, 23 reviews

Casa Loco

Experience tranquility at Casa Loco, a serene retreat on 20 picturesque acres in Piner Valley. Perfect for families, this home is a short drive to Middletown, Harbin Hot Springs (10 min), and numerous local wineries. Enjoy bird watching, scenic views, and watch for the luxurious Lotusland resort and Coore & Crenshaw golf course. Explore nearby attractions like the Guenoc/Langtry Farms Winery, Calpine Geothermal Visitor Center, and stunning hiking trails. Book now for a peaceful getaway!

4.92 out of 5 average rating, 119 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

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

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.

Guest house 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.

Guest house 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.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Middletown holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Middletown

4.74 out of 5 average rating, 941 reviews

Hotel room in Calistoga

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

EllaRating, 5 starstoday

Had a really great stay here. Was a perfect, convenient location with a clean, comfortable atmosphere and comfortable bed. Will definitely be staying again!

4.91 out of 5 average rating, 43 reviews

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.

Private room in Guerneville

4.95 out of 5 average rating, 238 reviews

Sweetwater Cottage

JudyRating, 5 stars2 weeks ago

Very clean welcoming cottage. Quiet beautiful surroundings. Brendan checked to make sure I was comfortable and had filtered water and coffee.

Top guest favourite

Home in Lake County

5 out of 5 average rating, 14 reviews

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

SaranyaRating, 5 stars4 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!

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.

Private room in Middletown

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.

Top guest favourite

Chalet in Kelseyville

5 out of 5 average rating, 5 reviews

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!