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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Property grounds
Backyard Garden Oasis

Backyard Garden Oasis

3.0 star property
Middletown
9.6 out of 10, Exceptional, (51)
"Greta was an amazing host, which made for a restful couple of days. Enjoyed the homemade goodies each morning"
United States
les
$194 nightly
The price is $216
Nov 9 - Nov 10
Total with taxes and fees
Backyard Garden Oasis
Outdoor dining
Garden house with gas fireplace

Garden house with gas fireplace

Middletown
10.0 out of 10, Exceptional, (1)
"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.
$203 nightly
The price is $223
Nov 10 - Nov 11
Total with taxes and fees
Garden house with gas fireplace
Fridge, microwave, oven, stovetop
Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency

Middletown
10.0 out of 10, Exceptional, (1)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
$197 nightly
The price is $217
Nov 9 - Nov 10
Total with taxes and fees
Emerald Lodge quiet efficiency
Terrace/patio
Riverbed House with hot tub

Riverbed House with hot tub

Middletown
10.0 out of 10, Exceptional, (1)
"I am on a non-profit board with 4 people on it. We needed to get our annual planning for 2025-26 done quickly and the best way to do that was to get away from our day-to-day lives and location.Linda's home is lovely, extremely comfortable and has ideal amenities and is a perfect balance between quiet and easily accessible.We had a great visit! Got a ton accomplished while having a great time. We truly felt relaxed even though we were busy nearly the whole time!Thank you so much for making us...
United States
Patricia B.
$432 nightly
The price is $476
Nov 19 - Nov 20
Total with taxes and fees
Riverbed House with hot tub
Property grounds
Tangerine Cottage spacious home

Tangerine Cottage spacious home

Middletown
$268 nightly
The price is $295
Nov 10 - Nov 11
Total with taxes and fees
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, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
United States
Tamara
$79 nightly
The price is $90
Nov 9 - Nov 10
Total with taxes and fees
The Ranch at Lake Sonoma
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
$202 nightly
The price is $222
Nov 12 - Nov 13
Total with taxes and fees
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Property grounds
Overlooking Clearlake From The Living Room

Overlooking Clearlake From The Living Room

Clearlake
8.8 out of 10, Excellent, (38)
"awesome place! right on the water"
United States
Asha S.
$141 nightly
The price is $149
Nov 9 - Nov 10
Total with taxes and fees
Overlooking Clearlake From The Living Room
Meeting facility
Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center

3.5 star property
Kelseyville
8.6 out of 10, Excellent, (27)
"Everything was great ... except the people staying next door in the cabin to me intruded in my space. This had nothing to do with the property though just rude bad manner people. The property folks were amazing about communicating. The site is very nice and the new cabins are terrific."
United States
Lisa
$244 nightly
The price is $272
Nov 9 - Nov 10
Total with taxes and fees
Mandala Springs Wellness Retreat Center
Studio | Exterior
Rouge Cobb Mountain Hotel - Cabin 3

Rouge Cobb Mountain Hotel - Cabin 3

3.0 star property
Cobb
$192 nightly
The price is $215
Nov 12 - Nov 13
Total with taxes and fees
Rouge Cobb Mountain Hotel - Cabin 3
Exterior detail
Cobb Mountain Chalet Main For

Cobb Mountain Chalet Main For

Cobb
9.6 out of 10, Exceptional, (14)
"Just what we needed while visiting our family."
United States
Jason O.
$176 nightly
The price is $193
Nov 10 - Nov 11
Total with taxes and fees
Cobb Mountain Chalet Main For
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, (20)
"amazing! "
United States
Stetson D.
$117 nightly
The price is $123
Nov 9 - Nov 10
Total with taxes and fees
Lake front unit #6 right by the water
View from property
Clear Lake Cottages & Marina

Clear Lake Cottages & Marina

2.5 star property
Clearlake
9.0 out of 10, Wonderful, (323)
"Nice spot on the lake"
United States
Shawn
$153 nightly
The price is $171
Dec 7 - Dec 8
Total with taxes and fees
Clear Lake Cottages & Marina
Terrace/patio
Lakeside Retreat with Private Boat Ramp by RedAwning

Lakeside Retreat with Private Boat Ramp by RedAwning

2.0 star property
Clearlake
9.0 out of 10, Wonderful, (6)
"The ramp at the house was great we had 3 boats and we're able to close the gate and keep everything secure. The store across the street is very convenient. The house is very comfy and nice. Though be aware of any valuables parked on the street outside of the gate. "
United States
Hunter K.
$444 nightly
The price is $491
Nov 9 - Nov 10
Total with taxes and fees
Lakeside Retreat with Private Boat Ramp by RedAwning
Dining
Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage

Calistoga
9.8 out of 10, Exceptional, (49)
"Nice location and space was very comfortable"
United States
Tracy T.
$365 nightly
The price is $438
Nov 17 - Nov 18
Total with taxes and fees
Comfort and Style in Our Queen Cottage
Terrace/patio
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, (28)
"We were extremely pleased with the location and overall condition of the property! We will definitely look for this property the next time we are visiting Napa Valley!"
United States
Mike C.
$340 nightly
The price is $408
Nov 9 - Nov 10
Total with taxes and fees
Escape to Wine County in your independant Cottage in Downtown Calistoga
Fridge, microwave, oven, stovetop
Guinda's Finest Nature Get-Away!

Guinda's Finest Nature Get-Away!

Guinda
10.0 out of 10, Exceptional, (7)
"The property was adequate for our bachelor weekend, it was close to Yocha De Golf Course and the Cache Creek casino. We had a great time."
United States
Jen J.
$417 nightly
The price is $417
Nov 10 - Nov 11
Total with taxes and fees
Guinda's Finest Nature Get-Away!
Property grounds
Bungalow on the lake

Bungalow on the lake

Clearlake
7.6 out of 10, Good, (7)
"although "clean" the house smelled of mildew, many windows had no screens, making the airing out process more difficult. Water heater closet seemed to be the main origin of odor. We enjoyed the pier at sunset and sunrise, beautiful views of the lake and surrounding hills. No outside chairs or umbrella, Gopher holes and tall weeds made getting to the pier an adventure."
United States
Juliet d.
$184 nightly
The price is $198
Nov 12 - Nov 13
Total with taxes and fees
Bungalow on the lake
Terrace/patio
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)
"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
$342 nightly
The price is $410
Nov 11 - Nov 12
Total with taxes and fees
Escape to Wine Country in your independant Cottage in Downtown Calistoga
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

Hyatt Regency Sonoma Wine Country

Hyatt Regency Sonoma Wine Country

10/10 Excellent
"Rooms were comfortable and clean"
Anne 3-night trip
Posted 2 days ago
Hyatt Regency Sonoma Wine Country

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Casa Bella Estate in Wine Country w/ New Pool!: This vacation home rental near Middletown is located in a rural location and has a fireplace, a hot tub, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Middletown?

Expedia has 12 vacation rentals for your stay in Middletown.

What can I see and do in Middletown?

Explore the area and family-friendly sights such as Calistoga Spit N' Cycle, 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 Beaver Creek 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.