
Vacation rentals in Middletown
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Middletown
Guests agree: these stays are highly rated for location, cleanliness, and more.

The Renewal Spring
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.

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).

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!

Lakeview Cottage A (No cleaning fee)
If you’re interested in looking for multiple nights (4+) message me and I’ll make you an offer (Kitchen area) has low ceiling. Approximately 6’3” A reminder, please: kitchens are provided for convenience. Follow kitchen cleaning rules 150 sf deck with spectacular views of the lake. Lots of hummingbirds, wild turkeys, deer, squirrels etc. IMPORTANT: local bookings, please message reason for your stay. Have had issues with parties, etc.. I reserve right to cancel questionable local bookings.

Clean Comfy Cottage Downtown
Our tree shaded studio cottage is one block from the heart of downtown. Stay just a two block walk from Russian River Brewing. This clean and quiet cottage has a full kitchen, a comfortable queen bed. I am happy to customize the space to your needs. I offer soft and firm mattresses. I use cotton blankets so that you can have any weight on your bed that you would like. You are welcome to stack seven or more blankets at a time. I will adjust my cleaning regimen to meet your preferences.

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.

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!

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.

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.

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

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.

Historic Beauty in downtown Middletown
Enjoy a stylish experience at this centrally-located place. Two full bedrooms two full bathrooms plus a loft space with two additional Queen beds and an Office space! Enjoy a beautifully constructed, pergola in the fully fenced yard Walk to town and local shops and restaurants. Minutes from Harbin Hot Springs. Home is completely renovated top to bottom. Furnished by local designer Stellar Homes.
Popular amenities for Middletown vacation rentals
Other great vacation rentals in Middletown

Mountain Nest | Cozy Cobb Getaway | Pet friendly

4 Rock Ranch - Mountain Escape

Lovely older home w/ private rm and bath/tub.

Pine Ridge Cabin - Cobb Mountain fun & relaxation

Cozy Mountain Contemplative

29 West B

Middletown Woodland Cabin

Modern Luxury Suite/Wine Country & Great Outdoors
Quick stats about vacation rentals in Middletown

Total vacation rentals
Explore 10 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at G$20,916 GYD per night before taxes and fees

Verified guest reviews
Over 1,500 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Middletown vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middletown rentals

4.9 Average rating
Middletown stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Northern California Vacation rentals
- San Francisco Bay Area Vacation rentals
- San Francisco Vacation rentals
- Gold Country Vacation rentals
- Central California Vacation rentals
- San Francisco Peninsula Vacation rentals
- San Jose Vacation rentals
- Silicon Valley Vacation rentals
- North Coast Vacation rentals
- Wine Country Vacation rentals
- Oakland Vacation rentals
- South Lake Tahoe Vacation rentals
- Lake Berryessa
- Six Flags Discovery Kingdom
- Jenner Beach
- Safari West
- Goat Rock Beach
- Doran Beach
- Johnson's Beach
- Sonoma Coast State Park
- Trione-Annadel State Park
- Chateau St. Jean
- Jack London State Historic Park
- V. Sattui Winery
- Charles M. Schulz Museum
- Harbin Hot Springs
- University of California - Davis
- Healdsburg Plaza
- Napa Valley Wine Train Wine Shop
- Francis Ford Coppola Winery
- Artesa Vineyards & Winery
- Armstrong Redwoods State Natural Reserve
- Salt Point State Park
- Sonoma State University
- Ledson Winery & Vineyards
- Iron Horse Vineyards




