
Vacation rentals in Middletown
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Top-rated vacation rentals in Middletown
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

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!

Sunset Cottage Relax and Enjoy!
Located away from the city lights, this peaceful retreat. We are a mile away from an 18 hole golf course easy access very private. We are also 20 minutes away from Clearlake😊 the biggest lake in California where fishing tournaments are held, our property is very safe to store your boats. We are also surrounded by beautiful wineries . Access to a pool with a beautiful view. 30 -45 minutes away from Napa Valley. Calistoga is a quick drive down the hill.😊 NOTE: we don’t allow any animals in o

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 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

Well House
This comfortable cottage is an awesome place to have some quiet, privacy and fun together. It is surrounded by a privacy fence, from my home. The bedroom area is new, and connected by a porch to an older bathroom and kitchen. You can recline in the double recliner leather love-seat and watch a movie on the flat screen television and walk to the stores and restaurants. Three miles from Harbin Hot Springs, and a 20' drive to Calistoga. All races, folks, and LGBT friendly.

Cozy Private Guest Suite Centrally Located
This recently remodeled guest suite in Santa Rosa’s Junior College neighborhood offers a cozy retreat for 1-2 guests. It features a queen-size bed with a natural latex mattress, Smart TV, WiFi, mini fridge, microwave, Keurig coffee maker, and electric kettle. Relax in the shared garden courtyard with Adirondack chairs, a bistro table, and a propane grill. On-street parking is plentiful, and with a Walk Score of 85, you’re close to shops, dining, and the college.

Lakeview Cottage A (No cleaning fee)
If you’re interested in looking for multiple nights (3plus) 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. This Airbnb requires that if you plan to use the kitchen, you need to leave it the way that you found it, or do not use it. Thank you 👍🏻👨🍳 150 sf deck with spectacular views of the lake. Lots of hummingbirds, wild turkeys, deer, squirrels etc.

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.

Vineyard Loft Very private Incredible views
Imagine yourself waking up to a 360° view of breathtaking rolling vineyards as you sip coffee on your private veranda and plan your day. Hike Mt. Konocti, explore the largest natural lake in California by kayak or speed boat, or enjoy a beautiful day of wine tasting at our local wineries! Whether it's a romantic getaway, honeymoon, girl's night, birthday, anniversary, or just because. Whatever the reason, you definitely want to stay here!

Cozy Cabin in Cobb Mtn near Harbin Hot Springs
This super cute cabin was recently remodeled with all the modern amenities but still has that rustic and cozy charm of a cabin in the woods! It's the perfect getaway for a small group or family. There is lots to explore in the area but also plenty of fun activities provided at the cabin so you don't even have to leave if you don't want to!
Popular amenities for Middletown vacation rentals
Other great vacation rentals in Middletown

Sweetwater Cottage

Middletown nest

Historic Beauty in downtown Middletown

Luxury Cottage in Downtown Calistoga - Accessible

Cozy Mountain Contemplative

Pine Ridge Cabin - Cobb Mountain fun & relaxation

Middletown Woodland Cabin

Overlooking clearlake from the living room
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 € 78 per night before taxes and fees

Verified guest reviews
Over 1,410 verified reviews to help you choose

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!
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