Holiday houses in Middletown

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Top-rated holiday rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 250 reviews

Alexander Valley: Wine Lover and Cycling Paradise

The Finca Guest House is a beautiful modern & private unit, which offers country seclusion just a short hop into Healdsburg. Three private outdoor spaces for your use! Coffee patio, wine patio, goat patio--your choice! World-class biking out the door. Guest House will be thoroughly cleaned per Airbnb guidelines! *This property has farm animals so no outside animals allowed. See Rules and Policies notes Gas grill w/burner is available for outdoor cooking. NO full kitchen. Sonoma Co. TOT#3191N

6–13 Sep

$369 NZD per night

Guest favourite

Cabin in Middletown

4.94 out of 5 average rating, 139 reviews

Cobb Tree House

This comfy cabin is great for a visit to Lake County, a quiet personal retreat, or a well deserved romantic getaway. Turn off from the busy city life. Come for an outdoor adventure or stay in for a quiet and private escape. Sit on the private deck and let the old growth fir wrap you in deep contemplation. Enjoy it's magnificence. SERVICE PETS ARE WELCOME. Please let us know if you are bringing one. There is NO WiFi here. ATT and Verizon personal hot spots work here. We have a TV with DVDs.

26 Feb – 5 Mar

$244 NZD per night

Guest favourite

Guest suite in Windsor

4.98 out of 5 average rating, 361 reviews

Private Entrance Suite in Heart of Wine Country

Situated in an upscale neighborhood, this exquisite guest suite boasts a private entrance on a safe, quiet cul-de-sac in the heart of the wine country. The en-suite is perfect for a romantic getaway, comfortable for an infant or small child, and ideal for the business traveler. We are 5 miles from Healdsburg and 3 from the Sonoma Co. Airport. Three parks within 4 miles encompass over 20 miles of hiking/biking. The Russian River, Redwoods, and Sonoma Coast are only a short, panoramic drive away.

13–20 Aug

$255 NZD per night

Guest favourite

Home in Clearlake

4.97 out of 5 average rating, 317 reviews

Breathtaking Views, Extreme Privacy, and You!

Need to unplug? Burned out? Crave quiet and beauty? Summerset is the cure. Lakehouse on private 3 acres. Exquisite top of the world panoramic water views, magical Mt. Konocti, epic sunsets, and stars. 2B 2Bath, open great room, stocked kitchen. Designed for rest and recharging the soul. Do absolutely nothing...or visit wineries, yoga on the deck, (mats provided) fish, hike, bike, boat. Enhanced cleaning, peaceful surroundings for sound sleeping. Park the car and your cell. Time to reboot.

4–11 Jan

$582 NZD per night

Superhost

Home in Clearlake Oaks

4.89 out of 5 average rating, 245 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 can 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.

12–19 Jul

$234 NZD per night

Guest favourite

Home in Clearlake Oaks

4.96 out of 5 average rating, 156 reviews

Top of the World View of Clear Lake and Mountains

If you’re looking to getaway, This newly updated house, high in the hills surrounding beautiful Clear lake, is the retreat for you! Enjoy panoramic views of the lake and mountains. Very quiet with only one elderly neighbor Relax on a private 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, hike, or fish

2–9 Jun

$282 NZD per night

Guest favourite

Cabin in Loch Lomond

4.91 out of 5 average rating, 234 reviews

Cute Little House in the Pines-Cobb Mt Loch Lomond

Little House in the Pines (Piccola Casa Nei Pini), in Loch Lomond on beautiful Cobb Mountain. Enjoy a relaxing stay in this lovely 2 bdrm/1 bath home. Family activities, great for couples, a solo adventurer, hiking, fishing, golfing, Harbin Hot Springs , Country Shopping , local farms and of course Clearlake the largest natural lake in California is a short distance away. Lake County has adventures waiting for you with its 30 plus wineries many award winning, for your visit. Come explore

5–12 Aug

$301 NZD per night

Guest favourite

Guest suite in Lakeport

4.9 out of 5 average rating, 115 reviews

Private Junior One Bedroom Suite - Sleeps up to 4

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

18–25 Sep

$134 NZD per night

Guest favourite

Guesthouse in Middletown

4.93 out of 5 average rating, 161 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.

19–26 Jun

$215 NZD per night

Guest favourite

Home in Cobb

4.88 out of 5 average rating, 33 reviews

Cobb Mountain Chalet Main House

Relax with the whole family at this peaceful retreat above a forest of whispering pines. After careful consideration, we have made this upper level of our mountain home available for your enjoyment. The upper deck overlooks a dense timberland behind the house and has both gas and charcoal grills. The full kitchen has ample amenities for those who enjoy cooking. The spacious living room boasts a lovely sitting area and a 65 inch Smart TV with WiFi.

13–20 Oct

$206 NZD per night

Guest favourite

Guesthouse in Nice

4.96 out of 5 average rating, 224 reviews

Cottage A (No Cleaning Fee)

Perfect couples getaway with over 30 wineries in Lake County. Caution for tall people. Kitchen area has low ceiling. Approximately 6’3” 150 sf deck with spectacular views of the lake . BBQ and UUNI pizza oven. Lots of wildlife, wild turkeys, deer, rabbits, squirrels, and rare bear and coyote sightings. This unit is completely renovated with new fixtures, electrical, insulated walls and new heating and air conditioning.

25 Jul – 1 Aug

$227 NZD per night

Guest favourite

Guest suite in Cobb

4.93 out of 5 average rating, 316 reviews

Guest Suite in Cobb Mountain Home

Large, sunny guest suite, with separate entrance, full bath, and walk-in closet. Kitchenette: table and chairs, refrigerator, microwave, toaster, dishes, cutlery, and Keurig with coffee, tea etc. Fenced parking. Porch, patio, and bbq. Fast wifi and solid cell service. Forced air house heating + portable heater in the room. Adam Springs Golf Course in the neighborhood, Harbin Hot Springs 20 min, Mt St Helena Trail 30 min.

15–22 Feb

$138 NZD per night