Middletown Holiday Rentals from €77: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Middletown has to offer?

Casa Bella Estate in Wine Country w/ New Pool! : This holiday home rental outside of Middletown is located in a rural location, and has a fireplace, 1 hot tub and a BBQ 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 that you can cook with friends or family.

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Our top choices for Middletown holiday rentals

Garden house with gas fireplace

Middletown

"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...

kelsie i.

includes taxes & fees

20 May - 21 May

Backyard Garden Oasis

Middletown

Jodi

includes taxes & fees

23 May - 24 May

Iron/ironing board, Internet, bed sheets

Stagecoach Cottage quiet efficiency

Middletown

Emerald Lodge quiet efficiency

Middletown

Carol

Tangerine Cottage spacious home

Middletown

The Ranch at Lake Sonoma

Geyserville

Evelyn

includes taxes & fees

13 May - 14 May

Cobb Mountain Chalet Main For

Cobb

Richard D.

includes taxes & fees

17 May - 18 May

2 Hidden Wine Country Gem Upstairs Unit

Scenic Brush Creek

Glen M.

includes taxes & fees

17 May - 18 May

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Top Middletown Hotel Reviews

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

4/10 Poor

"The room was set up awful. To watch tv in bed you had to turn your head sideways making for a long lasting neck pain. No ice in two nearby ice machines. Restaurant morning pastry basket has only one type of pastry. 2 coffees and cinnamon roll=$19!"

The Astro

10/10 Excellent

"The Astro Motel is an absolute gem! The mid-century modern renovation is perfectly executed on the exterior and inside the rooms. The grounds are beautifully designed with lots of citrus, olive trees, grasses and pollinator-friendly plants. A couple of the original motel signs are incorporated into the landscape, too. Our room was sparkling clean...i know this because I spilled something on the floor within minutes of walking in. When I wiped up the spill, the towel had no dirt on it! I loved the simple breakfast of local granola, yogurt, fruit, pastries, coffee and tea. We met other friendly guests in the lounge which is open all day until 10 pm. All the staff was friendly, but a special shout out goes to Betty who took care of us like she was the owner. Don't miss out on the Astro's sister business, restaurant "The Spinster Sisters", which is a short walk away through an alley full of beautiful murals. We ate dinner there in their garden our first night and the experience was 10/10. Don't sleep on their new weekend brunch either! (See what I did there?) We can't wait to return to the Astro Motel!!!"

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

2/10 Terrible

"When I arrived the front desk staff refused to swipe my credit card when the chip wouldn't pick up, she said she wasn't allowed because people had desputed their charges, not sure how that's relevant to how you run it. There were no towels in the room at all and the room smelled like old food"

Hotel La Rose

8/10 Good

"Pros - Beautiful decor/architecture. Convenient walking distance to shops, restaurants and transportation in the historic downtown Railroad district. Very helpful staff. Restaurant/bar conveniently located on site. Free WiFi. Available parking. Cons - Large homeless population in vicinity. Restaurant not affiliated with hotel so no room service availability and closes early. Slow/weak Wifi. Parking is offsite about half a block away and not totally secure. Depending on how you book your reservation, you may have to pay an additional $15.00 per night for parking or you can chance finding a spot on the street for free. Somewhat busy intersection so be prepared for street traffic noise which subsides later in the evening. Overall, Cons aside, we had a nice stay."

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as €77 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday 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 holiday.

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.

Frequently asked questions

Can I find holiday rentals in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Middletown has to offer?

Casa Bella Estate in Wine Country w/ New Pool!: This holiday home rental outside of Middletown is located in a rural location, and has a fireplace, 1 hot tub and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Middletown?

Expedia has 11 holiday 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 Rabbit Hill Preserve.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.

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