Vacation rentals in Middletown

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middletown

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

Guest favourite

Guesthouse in Healdsburg

4.98 out of 5 average rating, 246 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. 2 – 9

$298 CAD per night
Superhost

Cabin in Middletown

4.93 out of 5 average rating, 138 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.

Jan. 30 – Feb. 6

$196 CAD per night
Guest favourite

Home in Clearlake

4.97 out of 5 average rating, 316 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.

Apr. 15 – 22

$438 CAD per night

Popular amenities for Middletown vacation rentals

Stay near Middletown's top sights

Cowpoke Cafe14 locals recommend
La Parrilla Mexican Grill15 locals recommend
Buddha Thai Kitchen23 locals recommend
Rosales Market6 locals recommend
Mount St Helena Brewing Company6 locals recommend
Su Garden Restaurant4 locals recommend

Other great vacation rentals in Middletown

Guest favourite

Guest suite in Lakeport

4.9 out of 5 average rating, 112 reviews

Private Junior One Bedroom Suite - Sleeps up to 4

Jul. 3 – 10

$104 CAD per night
Guest favourite

Home in Kelseyville

4.86 out of 5 average rating, 100 reviews

Clearlake Riviera Jewel! Cozy, Comfortable & Clean

Jul. 1 – 8

$167 CAD per night
Superhost

Cottage in Middletown

4.78 out of 5 average rating, 23 reviews

Straw bale farmhouse in Middletown

Nov. 26 – Dec. 3

$173 CAD per night
Guest favourite

Home in Cobb

4.88 out of 5 average rating, 32 reviews

Cobb Mountain Chalet Main House

Nov. 28 – Dec. 5

$174 CAD per night
Guest favourite

Cottage in Middletown

4.79 out of 5 average rating, 19 reviews

Adorable Cottage - Walking distance to downtown

Apr. 16 – 23

$195 CAD per night
Superhost

Cabin in Middletown

4.83 out of 5 average rating, 71 reviews

Cozy PET-FRIENDLY 1 bd cabin w/ indoor fireplace

Apr. 4 – 11

$186 CAD per night
Guest favourite

Guesthouse in Cobb

5.0 out of 5 average rating, 20 reviews

Cozy Guesthouse with Deck and Mountain Views!

Jul. 9 – 16

$169 CAD per night
Superhost

Cabin in Cobb

4.85 out of 5 average rating, 34 reviews

Cozy vintage cabin w fireplace + deck in the woods

Apr. 22 – 29

$216 CAD per night
Superhost

Tiny homes in Middletown

4.89 out of 5 average rating, 47 reviews

Blue Door Cottage

Oct. 5 – 12

$254 CAD per night
Guest favourite

Home in Middletown

5.0 out of 5 average rating, 83 reviews

Western Mine Retreat near wine country

Jun. 25 – Jul. 2

$348 CAD per night
Superhost

Cabin in Cobb

4.91 out of 5 average rating, 23 reviews

Creekside Zen Writer's Cabin & Tearoom, library

Apr. 15 – 22

$189 CAD per night
Guest favourite

Cabin in Cobb

5.0 out of 5 average rating, 26 reviews

Little Falling Water - Mid-Mod Masterpiece

Sep. 22 – 29

$302 CAD per night

Quick stats about vacation rentals in Middletown

Total rentals

10 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

10 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

920 reviews

Nightly prices starting at

$95 CAD before taxes and fees

Destinations to explore

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