Holiday houses 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

Home in Middletown

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, 337 reviews

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

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.

4.91 out of 5 average rating, 150 reviews

Guest suite in Lakeport

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

4.92 out of 5 average rating, 119 reviews

Home in Middletown

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.

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.

4.86 out of 5 average rating, 165 reviews

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.

4.87 out of 5 average rating, 38 reviews

Guesthouse in Cobb

Guesthouse with Deck and Mountain Views!

From the gorgeous kitchen to the charming bath, a lot of thought has gone into the guest's experience! With amazing views of Cobb Mountain and Mount Saint Helena, this studio offers a peaceful place from which to explore the area. The deck is very large. The comfortable seating are is a great place to relax or watch tv. The kitchen is well stocked with all the dishes, cookware and small appliances needed for cooking. Extended stays are welcome!

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Other great holiday rentals in Middletown

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.

5 out of 5 average rating, 14 reviews

Home in Lake County

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

SaranyaRating, 5 stars1 week 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

Home in Middletown

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.

5 out of 5 average rating, 14 reviews

Apartment in Forestville

Enchanting Russian River Retreat

BrendanRating, 5 stars1 week ago

My wife and I enjoyed an absolutely delightful 4-night visit. Perfect place for a quiet, peaceful home base from which to enjoy all that the Russian River area has to offer. Kathy and Mike are very thoughtful and generous hosts. Their care and attention to detail to ensure their guests have everything they need to have as comfortable and enjoyable a stay as possible was evident throughout our visit. Highly recommended!

Private room in Santa Rosa

4.89 out of 5 average rating, 253 reviews

Casa Giovanna

ErinRating, 5 stars3 weeks ago

This is the second time I have stayed at Diane's. The unit is on a quiet street with easy parking and access to main roads. I sometimes travel by myself to Santa Rosa to visit family and it's nice to have an affordable space that also feel safe and secure. Diane is friendly, responsive, and offers a comfortable and clean spot to stay!

Private room in Middletown

4.88 out of 5 average rating, 137 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

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!