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.

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Top guest favorite
A spacious living area is highlighted by rustic decor, featuring a large leather sectional sofa and a dark wooden coffee table. A recliner is positioned nearby. Three framed prints adorn the wall. A kitchen area with wooden cabinetry is visible in the background.
Home in Middletown
4.98 out of 5 average rating, 131 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).

Guest favorite
A rustic cabin is nestled among tall pine trees, featuring a red exterior and a welcoming American flag mounted on the front. Sturdy stairs lead up to a spacious deck surrounded by lush greenery, providing an inviting retreat.
Cabin in Middletown
4.85 out of 5 average rating, 116 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 favorite
The living area features exposed wooden beams and a cozy stone fireplace at its center. Natural light fills the space through multiple windows, with comfortable seating arranged around the hearth. A warm plaid blanket is draped over a wooden couch, enhancing the cabin's rustic charm.
Cabin in Cobb
4.93 out of 5 average rating, 99 reviews

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!

Superhost
A single-story cottage showcases a welcoming entrance with a stone-accented façade. Large windows allow natural light to illuminate the front porch, while a spacious garage with wooden doors offers convenient vehicle parking.
Guest suite in Hidden Valley Lake
4.92 out of 5 average rating, 113 reviews

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

Guest favorite
A spacious wooden deck features a set of four red Adirondack chairs arranged around a central table. The sun sets in the background, illuminating the surrounding trees and creating a serene outdoor space suitable for relaxation.
Home in Loch Lomond
4.94 out of 5 average rating, 139 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 favorite
A bright interior space features large windows offering views of the lake and mountains. A wooden desk is positioned next to a chair, with a telescope nearby, inviting relaxation and exploration. Natural light fills the room, complemented by neutral-colored furnishings and soft carpet.
Home in Clearlake Oaks
4.97 out of 5 average rating, 315 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 favorite
Guesthouse in Middletown
4.92 out of 5 average rating, 193 reviews

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.

Top guest favorite
A cozy guest suite features a queen-size bed with a textured blanket and decorative pillows. A small desk with a chair and a mini fridge are positioned nearby. Soft lighting and wall art enhance the ambiance, while a ceiling fan provides comfort.
Guest suite in Junior College
4.94 out of 5 average rating, 226 reviews

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.

Guest favorite
A turquoise hummingbird feeder hangs from the ceiling, contrasting with the warm wood railings of the deck. Beyond, the serene lake is visible, reflecting soft pastel hues of the sunset sky. Plants are arranged along the railing, adding greenery to the scene.
Guesthouse in Nice
4.96 out of 5 average rating, 445 reviews

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.

Guest favorite
A charming countryside house is situated under the shade of large oak trees. The exterior features a neutral-coloured façade with multiple windows. A redwood deck leads to the front door, providing a welcoming entryway. The surrounding landscape showcases dry grass and open space.
Guesthouse in Middletown
4.87 out of 5 average rating, 172 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.

Top guest favorite
Loft in Kelseyville
4.97 out of 5 average rating, 137 reviews

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!

Guest favorite
A modern kitchen is seen with stainless steel appliances and a gas range. White cabinetry is paired with a large island, offering additional prep space. Four white chairs surround a glass dining table, while pots and utensils are neatly arranged on the wall.
Cabin in Cobb
4.85 out of 5 average rating, 108 reviews

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

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!

  1. Airbnb
  2. United States
  3. California
  4. Lake County
  5. Middletown