Lodging Image

Middletown Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Middletown vacation rentals

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is CA $292
CA $326 total
includes taxes & fees
Jul 3 - Jul 4
Backyard Garden Oasis

Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (3 reviews)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
The price is CA $165
CA $312 total
includes taxes & fees
Jun 30 - Jul 1
Emerald Lodge quiet efficiency

Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (1 review)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
United States
kelsie i.
The price is CA $148
CA $295 total
includes taxes & fees
Jun 21 - Jun 22
Garden house with gas fireplace

Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
The price is CA $211
CA $416 total
includes taxes & fees
Jun 22 - Jun 23
Tangerine Cottage spacious home

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.4 out of 10, Exceptional, (3 reviews)
"Nice camping spot "
United States
Evelyn
The price is CA $111
CA $126 total
includes taxes & fees
Jul 14 - Jul 15
The Ranch at Lake Sonoma

Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (112 reviews)
"Nice location to go and have a good time in the family "
United States
Ismelda Cortez
The price is CA $167
CA $190 total
includes taxes & fees
Jun 17 - Jun 18
Wildhaven Sonoma Glamping

Russian River RV Campground

Russian River RV Campground
1.5 star property
Cloverdale
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time in the cabin. It was well stocked, had a nice layout, and was bigger than expected. The bunk bed are creatively placed and reminiscent of a cubby hole. The property is undergoing upgrades to the public restrooms so it will be even better soon. "
United States
Samantha
The price is CA $266
CA $303 total
includes taxes & fees
Jun 18 - Jun 19
Russian River RV Campground

Suites On Main

Suites On Main
2.0 star property
Kelseyville
The price is CA $273
CA $402 total
includes taxes & fees
Jun 24 - Jun 25
Suites On Main

Clear Lake Living! Pet-friendly Gem w/ Fenced Yard

Clear Lake Living! Pet-friendly Gem w/ Fenced Yard
3.0 star property
Lakeport
Clear Lake Living! Pet-friendly Gem w/ Fenced Yard

Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
8.0 out of 10, Very good, (1 review)
"Muy bonito diseño interior en ambos la recepción y el cuarto."
Mexico
Tara
The price is CA $353
CA $612 total
includes taxes & fees
Jul 7 - Jul 8
Sonoma Stonehouse, Wine Country Vibes

Rainbow Lodge

Rainbow Lodge
2.0 star property
Lakeport
4.4 out of 10, (17 reviews)
"Friendly manager at check in, quiet location, conveniently located. Room was adequately "
United States
Daniel
The price is CA $103
CA $136 total
includes taxes & fees
Jun 17 - Jun 18
Rainbow Lodge

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.4 out of 10, Exceptional, (27 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is CA $102
CA $251 total
includes taxes & fees
Jun 17 - Jun 18
Cobb Mountain Chalet King Size Suite

Bungalow on the lake

Bungalow on the lake
Clearlake
7.8 out of 10, Good, (8 reviews)
"Great little cottage for a good price. "
United States
Danielle C.
The price is CA $191
CA $287 total
includes taxes & fees
Jun 22 - Jun 23
Bungalow on the lake

Rouge Cobb Mountain Hotel - Cabin 4

Rouge Cobb Mountain Hotel - Cabin 4
2.0 star property
Cobb
10.0 out of 10, Exceptional, (1 review)
The price is CA $188
CA $380 total
includes taxes & fees
Jun 22 - Jun 23
Rouge Cobb Mountain Hotel - Cabin 4

Lake front unit #6 right by the water

Lake front unit #6 right by the water
Clearlake
8.4 out of 10, Very good, (27 reviews)
"Great place"
United States
Eddie F.
The price is CA $86
CA $176 total
includes taxes & fees
Jun 23 - Jun 24
Lake front unit #6 right by the water

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is CA $178
CA $398 total
includes taxes & fees
Jun 17 - Jun 18
2 Hidden Wine Country Gem Upstairs Unit

Guinda's Finest Nature Get-Away!

Guinda's Finest Nature Get-Away!
Guinda
9.8 out of 10, Exceptional, (8 reviews)
"Wonderful location, beautiful view."
United States
George M K.
The price is CA $378
CA $589 total
includes taxes & fees
Jun 17 - Jun 18
Guinda's Finest Nature Get-Away!

Overlooking Clearlake From The Living Room

Overlooking Clearlake From The Living Room
Clearlake
9.0 out of 10, Wonderful, (42 reviews)
"Maureen was lovely and the sunset and sunrise were beautiful!"
United States
Steven W.
The price is CA $98
CA $208 total
includes taxes & fees
Jun 22 - Jun 23
Overlooking Clearlake From The Living Room

Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
Clearlake
4.0 out of 10, (1 review)
"If it weren’t for the kindness of the host, who accommodated us for an early check-in and late checkout, I would’ve given this zero stars. It’s totally rundown, looks like it hasn’t been power washed in 20 years, as soon as you walk up it smells like mold. The listing doesn’t tell you that it’s on a main street. The inside has rotting walls with actual holes, you can smell the mold and in one of the bedrooms it smelled so toxic like cat urine and chemicals - no one could sleep in there. The...
United States
Jennifer
The price is CA $201
CA $378 total
includes taxes & fees
Jun 17 - Jun 18
Watefront Getaway w/ Mtn Views & Dock in Clearlake

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.8 out of 10, Exceptional, (40 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is CA $404
CA $555 total
includes taxes & fees
Jun 22 - Jun 23
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Find out more about Middletown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Middletown?

Yes, we offer vacation rentals close to top attractions in Middletown, or you can go with a secluded option if you'd like a relaxing place to stay. Middletown is known for its hot springs and wineries. Make sure you have time to check out the spas and casinos during your trip.

What are some of the best vacation rentals that Middletown has to offer?

Lakefront Home Private Boat Ramp, Clear Lake: You might like this vacation home rental near Middletown. It has laundry facilities and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, an oven, and a coffee maker.

How many vacation rentals are there in Middletown?

Expedia has 11 vacation rentals for your stay in Middletown.

What can I see and do in Middletown?

Explore the area and family-friendly sights such as SingleThread Farm at Dry Creek, or get out into nature at a spot like Boggs Mountain Demonstration State Forest. Other places in town to visit include Twin Pine Casino and Robert Louis Stevenson State Park.

What are vacation rentals like in Middletown?

Vacation rentals are private properties you can stay in for several days or longer in Middletown. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.