Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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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, 117 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!

Superhost
A wide window frame showcases a serene view of the lake, bordered by lush green trees. The calm water reflects the surrounding landscape, while rolling hills provide a backdrop, creating a peaceful connection to nature.
Home in Clearlake Oaks
4.86 out of 5 average rating, 354 reviews

Cozy Cottage: Panoramic Lake View, WiFi, Deck

This clean, cozy little getaway sits on a hill overlooking the lake. It boasts panoramic views from almost every room in the house, & if you open the windows at night, you might hear the waves. 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 & BBQ on the deck. Restaurants, coffee, & shopping within easy walking distance.

Top 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, 101 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

Top 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, 141 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
An open living space features a small kitchen area with a refrigerator, microwave, and countertop. A black futon, adorned with an orange plaid throw, complements the coffee table and television area. Natural light filters through a window, illuminating the tile flooring.
Guest suite in Lakeport
4.9 out of 5 average rating, 159 reviews

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

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, 319 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
A view of the lake is framed by tall trees and lush greenery. A white wicker chair sits in the foreground, overlooking a well-maintained lawn that leads to the water. Gentle waves can be seen in the distance beneath a partly cloudy sky.
Guesthouse in Kelseyville
4.88 out of 5 average rating, 293 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.

Top guest favorite
An inviting cottage interior features a spacious bed adorned with a colorful bedspread. A comfortable seating area is visible, while a loft area can be accessed by a wooden ladder. Large glass doors lead to the outdoor deck, offering natural light and views.
Guesthouse in Middletown
4.92 out of 5 average rating, 330 reviews

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.

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, 447 reviews

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. 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.

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!

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 ﺩ.ﺇ331 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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