Holiday houses in Middletown

4.92 out of 5 average rating, 149 reviews

Cabin in Middletown

Cobb Tree House

This comfy cabin is great for a visit to Lake County, a quiet personal retreat, or a well deserved romantic getaway. Turn off from the busy city life. Come for an outdoor adventure or stay in for a quiet and private escape. Sit on the private deck and let the old growth fir wrap you in deep contemplation. Enjoy its magnificence and. SERVICE PETS are allowed. Please let us know if you are bringing one. There is NO WiFi here. ATT and Verizon personal hot spots work here. We have a TV with DVDs.

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).

4.94 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, 149 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

4.96 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.

4.91 out of 5 average rating, 314 reviews

Guesthouse in Middletown

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.

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.

4.97 out of 5 average rating, 73 reviews

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.

4.93 out of 5 average rating, 41 reviews

Home in Cobb

Spacious Retreat with Mountain Views!

Spacious one bedroom with enormous great room and plenty of windows to take in the trees and surrounding views. The view-side deck runs the length of the house and is accessible from every room, providing fabulous views of Cobb Mountain! The kitchen is large and well equipped! "Amazing Home!" and "Absolutely stunning" are quotes from the home's prior 5 star Airbnb listing under our then-manager. See those reviews in our photos section.

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Other great holiday rentals in Middletown

4.74 out of 5 average rating, 938 reviews

Hotel room in Calistoga

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

MirandaRating, 5 stars3 days 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!

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.

4.96 out of 5 average rating, 24 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.

Yurt in Hidden Valley Lake

4.8 out of 5 average rating, 45 reviews

Magical yurt above Lake County wine country.

DawnRating, 5 stars2 weeks ago

Fun getaway, great hosts, and beautiful location. We’re also a big fan of their new dog named Jury.

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.

5 out of 5 average rating, 5 reviews

Chalet in Kelseyville

Discover the Serene Beauty of Cole Ridge Chalet.

AnnaRating, 5 stars1 month 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!