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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Guest favorite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 249 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

Sep 25 – Oct 2

G$39,385 GYD per night

Superhost

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.

Dec 2 – 9

G$25,928 GYD per night

Guest favorite

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.

Aug 21 – 28

G$70,005 GYD per night

Superhost

Home in Clearlake Oaks

4.89 out of 5 average rating, 244 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.

Jul 10 – 17

G$25,581 GYD per night

Guest favorite

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

Jun 1 – 8

G$33,087 GYD per night

Guest favorite

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

May 4 – 11

G$34,902 GYD per night

Guest favorite

Guest suite in Lakeport

4.9 out of 5 average rating, 114 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

Oct 2 – 9

G$15,910 GYD per night

Guest favorite

Guesthouse in Sebastopol

4.96 out of 5 average rating, 300 reviews

Arbor View

Bright one-room studio cottage with queen bed, bathroom and kitchenette. City of Sebastopol Business License #1610 Private entrance. Windows overlook the kiwi arbor and gardens. Skylights. Quiet and private, yet right in the heart of town on Sebastopol's famous "sculpture street." Walk to restaurants, movie theater, The Barlow, Sebastopol Center for the Arts, town plaza with Sunday Farmer's Market, library, Ives Park (public swimming pool). Bike path is nearby. Bike to wineries.

Jul 7 – 14

G$25,328 GYD per night

Guest favorite

Guesthouse in Middletown

4.93 out of 5 average rating, 160 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.

Dec 7 – 14

G$21,565 GYD per night

Guest favorite

Guesthouse in Nice

4.96 out of 5 average rating, 222 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.

Nov 4 – 11

G$27,354 GYD per night

Guest favorite

Guest suite in Cobb

4.93 out of 5 average rating, 315 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.

Jul 14 – 21

G$16,217 GYD per night

Guest favorite

Cabin in Lake County

4.97 out of 5 average rating, 272 reviews

Rural 1 Acre Lakefront Location With Private Beach

This charming modern cabin is on one acre in a secluded location surrounded by beautiful oaks. The deck offers spectacular views of Clear Lake and your private beach is just steps away. It is a great place to enjoy nature and recharge. More than 40 wineries are only a short drive away. Early check-in and late check-out are usually available.

Oct 5 – 12

G$38,477 GYD per night