Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Middletown vacation rentals

Porch

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 ￥27,472
￥30,631 total
includes taxes & fees
Feb 26 - Feb 27
Backyard Garden Oasis
Property grounds

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 ￥18,093
￥37,370 total
includes taxes & fees
Mar 17 - Mar 18
Garden house with gas fireplace
TV

Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
The price is ￥16,237
￥35,146 total
includes taxes & fees
Mar 16 - Mar 17
Emerald Lodge quiet efficiency
Terrace/patio

Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
The price is ￥19,639
￥44,731 total
includes taxes & fees
Feb 25 - Feb 26
Tangerine Cottage spacious home
Front of property

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
10.0 out of 10, Exceptional, (2 reviews)
"Nice camping spot "
United States
Evelyn
The price is ￥9,186
￥10,472 total
includes taxes & fees
Feb 25 - Feb 26
The Ranch at Lake Sonoma
Microwave, oven, stovetop

Cozy 2-bedroom home in amazing Clearlake with AC, WiFi,

Cozy 2-bedroom home in amazing Clearlake with AC, WiFi,
Clearlake
10.0 out of 10, Exceptional, (1 review)
"Everything was comfortable and the kitchen was relatively well stocked and easy to use!"
United States
Patricia
The price is ￥27,139
￥30,232 total
includes taxes & fees
Feb 25 - Feb 26
Cozy 2-bedroom home in amazing Clearlake with AC, WiFi,
Property grounds

Cozy RV Oasis 5 Min to Adventist Health and Redbud Park Clearlake

Cozy RV Oasis 5 Min to Adventist Health and Redbud Park Clearlake
Clearlake
The price is ￥15,309
￥23,041 total
includes taxes & fees
Mar 8 - Mar 9
Cozy RV Oasis 5 Min to Adventist Health and Redbud Park Clearlake
Apartment, 1 Bedroom (Sonoma Stonehouse in Boutique Hotel) | Free WiFi

Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
The price is ￥14,653
￥42,055 total
includes taxes & fees
Feb 25 - Feb 26
Sonoma Stonehouse, Wine Country Vibes
Exterior

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 ￥41,753
￥64,485 total
includes taxes & fees
Feb 26 - Feb 27
Guinda's Finest Nature Get-Away!
Living area

Lake house bungalow!

Lake house bungalow!
Clearlake Oaks
9.4 out of 10, Exceptional, (3 reviews)
"Love the location and owner is really helpful..will definitely keep this property in my favorite when i come back to clear lake"
United States
Oohhse D.
The price is ￥18,510
￥46,191 total
includes taxes & fees
Mar 1 - Mar 2
Lake house bungalow!
Interior

Cozy Cottage: Panoramic Lake Views, WiFi, Deck

Cozy Cottage: Panoramic Lake Views, WiFi, Deck
Clearlake Oaks
8.6 out of 10, Excellent, (8 reviews)
"Beautiful view and comfy beds. "
United States
Elizabeth P.
The price is ￥23,196
￥34,794 total
includes taxes & fees
Mar 6 - Mar 7
Cozy Cottage: Panoramic Lake Views, WiFi, Deck
Outdoor dining

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (25 reviews)
"Wonderful spot! Clean, quiet, great, shower and lovely deck. "
United States
Chloe K.
The price is ￥8,907
￥23,369 total
includes taxes & fees
Feb 25 - Feb 26
Cobb Mountain Chalet King Size Suite
House (2 Bedrooms) | Interior

Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
Clearlake
The price is ￥22,268
￥41,740 total
includes taxes & fees
Mar 1 - Mar 2
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Exterior

Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga
Calistoga
9.6 out of 10, Exceptional, (33 reviews)
"Great getaway for a couple"
United States
David G.
The price is ￥42,526
￥58,248 total
includes taxes & fees
Feb 25 - Feb 26
Escape to Wine County in your independant Cottage in Downtown Calistoga
Property grounds

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 ￥20,598
￥30,493 total
includes taxes & fees
Feb 25 - Feb 26
Bungalow on the lake
Exterior

Escape to Wine Country in your independant Cottage in Downtown Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (2 reviews)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
United States
Ronny
The price is ￥42,639
￥57,783 total
includes taxes & fees
Feb 25 - Feb 26
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Property grounds

Lake front unit #6 right by the water

Lake front unit #6 right by the water
Clearlake
8.4 out of 10, Very Good, (22 reviews)
"Maureen was very accommodating "
United States
JOSH
The price is ￥9,046
￥18,965 total
includes taxes & fees
Feb 28 - Mar 1
Lake front unit #6 right by the water
Interior

Overlooking Clearlake From The Living Room

Overlooking Clearlake From The Living Room
Clearlake
9.0 out of 10, Wonderful, (42 reviews)
"Host was great. They worked around my stay even though a large tree needed to be cut down. Plenty of wild ducks etc.."
United States
randy h.
The price is ￥12,247
￥24,513 total
includes taxes & fees
Feb 25 - Feb 26
Overlooking Clearlake From The Living Room
Lake

Clear Lake Cottages & Marina

Clear Lake Cottages & Marina
2.5 star property
Clearlake
9.0 out of 10, Wonderful, (330 reviews)
"Great stay!"
United States
Andrey and Irina
The price is ￥20,580
￥22,947 total
includes taxes & fees
Feb 25 - Feb 26
Clear Lake Cottages & Marina
Exterior

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is ￥29,227
￥72,876 total
includes taxes & fees
Mar 5 - Mar 6
Charming King Cottage
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.
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Top Middletown Hotel Reviews

Rancho Caymus Inn

Rancho Caymus Inn

10/10 Excellent
"Friendly and knowledgeable staff, great location and charming set up, nice facility and good size rooms make it a perfect stay in the wine country. "
Marietta 1-night trip
Posted 1 day ago
Rancho Caymus Inn

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middletown!

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?

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021: This vacation home rental near Middletown is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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 Langtry Estate and Vineyards.

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.