Holiday houses in Middletown

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top Guest favourite

Home in Healdsburg

4.95 out of 5 average rating, 464 reviews

Dry Creek Valley Cottage

Enjoy your stay in beautiful Dry Creek Valley, a pastoral rural setting surrounded by vineyards and local wineries, minutes from Healdsburg's historic quaint downtown plaza. The cottage is 480 square feet with big windows, high ceilings and its own private entrance. There is parking right in front. It has kitchen amenities (coffee and tea pot, mini refrigerator, toaster and microwave), living room and bathroom with a mosaic tile shower. Right across the way you can take a lovely walk or run alongside the vineyards or you can rent a bike to explore the beauty of the valley. If you enjoy hiking, seasonal kayaking or canoeing there are opportunities all around us to explore as well. Our property has multiple fruit trees and we will be happy to share whatever bounty is in season when you arrive. The water here is also clean spring fed and very tasty and the sky at night is full of stars! You can enjoy sitting in the front yard which is bordered by a dozen Redwood trees or you can picnic in our big back yard among the fruit trees. We also have 2 female dogs who are quite friendly if you'd like to meet them. We would be happy to welcome you to Sonoma County and insure that your stay here is enjoyable.

Superhost

Home in Middletown

4.8 out of 5 average rating, 15 reviews

Renewal Spring Retreat

Enjoy peace and calm at this brand new, beautifully designed oasis. Surrounded by audible streams of healing water and mighty pines a quick 10-minute drive to Harbin Hot Springs, it's a spot to enjoy year-round. Along with the open living-dining room-kitchen stocked with appliances and a luxurious bath providing the comforts of home and beyond, you’ll have a large wrap-around redwood deck with panoramic valley overlooks and mountain views from every room including the secluded bedroom hideaway.

Guest favourite

Home in Middletown

4.98 out of 5 average rating, 117 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).

Superhost

Cabin in Middletown

4.84 out of 5 average rating, 102 reviews

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!

Guest favourite

Cabin in Calistoga

4.88 out of 5 average rating, 282 reviews

Wine Country Mountain Home

Whole house wine country luxury for 2 in a Private and secluded forested location. Starlink WiFi, Forest at your front door. Clean and Comfortable vintage cabin In the mountains. Mid way between Napa and Sonoma valleys: 7 miles to Calistoga; 10 miles to Santa Rosa. NO cleaning fee at check out. Self-check-in with lock box. Professionally cleaned and sanitized before all check ins. Monthly discounts of 50%, weekly discounts 25% for travelers looking to work from home. Inquire with host.

Guest favourite

Home in Clearlake Oaks

4.93 out of 5 average rating, 100 reviews

Oak Hill Cottage: WiFi, Views

This peaceful cottage sits on an oak dotted hill overlooking the lake and offers sweeping panoramic views from almost every room in the house. 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 & cook a meal in its deluxe kitchen. King size beds in both bedrooms. Restaurants, coffee, & shopping within easy walking distance.

Guest favourite

Cabin in Loch Lomond

4.91 out of 5 average rating, 261 reviews

Cute Little House in the Pines-Cobb Mt Loch Lomond

Little House in the Pines (Piccola Casa Nei Pini), in Loch Lomond on beautiful Cobb Mountain. Enjoy a relaxing stay in this lovely 2 bdrm/1 bath home. Family activities, great for couples, a solo adventurer, hiking, fishing, golfing, Harbin Hot Springs , Country Shopping , local farms and of course Clearlake the largest natural lake in California is a short distance away. Lake County has adventures waiting for you with its 30 plus wineries many award winning, for your visit. Come explore

Guest favourite

Home in Loch Lomond

4.94 out of 5 average rating, 128 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.

Guest favourite

Home in Middletown

4.93 out of 5 average rating, 121 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.

Guest favourite

Home in Clearlake Oaks

4.96 out of 5 average rating, 274 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 favourite

Cabin in Middletown

4.92 out of 5 average rating, 84 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.

Guest favourite

Guesthouse in Middletown

4.86 out of 5 average rating, 166 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.