Middletown Vacation Rentals from $110: Search Short-Term Rentals

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

Storybook Cottage : This vacation home rental outside of Middletown offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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Our top choices for Middletown vacation rentals

#24 Serenity A Lakefront Cottage Retreat

Middletown

Rodrigo C.

$341 nightly

Aug 5 - Aug 6

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

“3BR Home Near Wesleyan & Downtown Middletown

Washington Street Historic District

Jousette C.

$339 nightly

Jul 31 - Aug 1

Total with taxes and fees

3 BR Apartment Near Wesleyan 202

Washington Street Historic District

Douglas M.

$357 nightly

Jul 31 - Aug 1

Total with taxes and fees

2BR Apartment Near Wesleyan 102

Washington Street Historic District

DANIEL M.

$264 nightly

Aug 1 - Aug 2

Total with taxes and fees

Family Stays: Middletown, CT

Middletown

Trisha T.

$247 nightly

Aug 10 - Aug 11

Total with taxes and fees

3 BR Apartment Near Wesleyan 201

Washington Street Historic District

Rebecca P.

$352 nightly

Aug 11 - Aug 12

Total with taxes and fees

#29 - Modern 5 Bedroom/2 Bath

Middletown

Gail R.

$477 nightly

Aug 11 - Aug 12

Total with taxes and fees

Private Apt in Middletown-Wesleyan 101

Washington Street Historic District

Kristoph

$284 nightly

Aug 6 - Aug 7

Total with taxes and fees

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Top Middletown Hotel Reviews

Omni New Haven Hotel at Yale

10/10 Excellent

"Loved the hotel which is located in downtown New Haven. Extremely walkable area, with lots of great restaurants and bars. Hotel and staff were lovely. Would absolutely stay here again."

Motel 6 Wethersfield, CT - Hartford

8/10 Good

"Our room was clean but had a baked in smoke odor. The room was quite small, the desk chair cheap and hard, and the usable desk space was insufficient. The fridge and microwave were a plus. The bathroom was okay but lacked shelf space. No shampoo was provided. Neighbors were rather noisy."

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 $110 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.

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Frequently asked questions

Are there vacation rentals in Middletown?

Yes, you can find vacation rentals in Middletown close to Van Vleck Observatory, or you can choose a more remote option if you want a relaxing stay. Middletown is known for its entertainment choices and festivals. Make sure you have time to check out the basketball games and university setting during your trip.

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

Storybook Cottage: This vacation home rental outside of Middletown offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 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?

With 10 Expedia vacation rentals, you're sure to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Family-friendly attractions include Van Vleck Observatory and Kidcity Children's Museum, whereas General Mansfield House and Connecticut River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Wadsworth Mansion and Middletown Nature Gardens.

What’s a vacation rental in Middletown like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Middletown. Vacation rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.

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