Holiday houses in Middletown

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Top-rated holiday rentals in Middletown

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Guest favourite
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, 129 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 favourite
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, 112 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!

Top Guest favourite
The entrance features a wooden deck with steps leading up to a door, surrounded by lush greenery. Decorative metal accents and potted plants add character, while wooden double doors below exhibit rustic charm. The overall setting is inviting and blends harmoniously with the natural surroundings.
Cabin in Calistoga
4.89 out of 5 average rating, 289 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
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, 112 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 favourite
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
4.93 out of 5 average rating, 138 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
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 favourite
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
4.96 out of 5 average rating, 313 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
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, 291 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 favourite
The interior of the cottage features a spacious sleeping area with a king-sized bed, a soft sofa, and a leather love seat. A large window allows natural light, with curtains providing a touch of color. Nearby, a guitar and a small entertaining space can be seen.
Cottage in Middletown
4.98 out of 5 average rating, 150 reviews

Garden house with gas fireplace

Beautiful new cottage with lots of light, swing, and gas fireplace. Large open space with private deck looking out at Mt St. Helena. In the evening, turn on the outdoor string lights and relax on the swing under the huge oak tree before sinking into the memory foam king size bed. In the morning there is pour over coffee and robes so you can sit outside and sip your coffee. Perfect place to stay for a while, or have a romantic weekend.

Guest favourite
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 favourite
A compact kitchen area is complemented by shelving adorned with decorative items. A cozy sofa is positioned beside a small table, while a staircase leads to a sleeping loft above. Natural light filters in through multiple windows, brightening the inviting space.
Tiny home in Middletown
4.87 out of 5 average rating, 102 reviews

Blue Door Cottage

Stylish and cozy tiny house at the base of the beautiful Mayacama mountain range. A country side oasis nestled 20 minutes away from Calistoga in Napa Valley, 10 minutes away from Harbin Hot Springs, 2 minutes away from Twin Pine Casino, and a short drive away from 30 Lake County wineries. 1 queen size bed, a sofa, 1 bath, kitchenette, and gorgeous views is the perfect setting for a couples getaway.

Top Guest favourite
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, 442 reviews

Lakeview Cottage A (No cleaning fee)

(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.

Popular amenities for Middletown holiday rentals

Quick stats about holiday rentals in Middletown

  • Total holiday rentals

    Explore 10 holiday rentals in Middletown

  • Nightly prices starting at

    Middletown holiday rentals start at $138 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,410 verified reviews to help you choose

  • Wi-Fi availability

    10 of Middletown holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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  3. California
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  5. Middletown