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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Middletown vacation rentals

Dining

1. Spacious Downtown Owosso Loft

Spacious Downtown Owosso Loft
Owosso
9.8 out of 10, Exceptional, (50 reviews)
"Very clean, accurate pictures and description of unit. We had a great stay and will be back! "
Canada
Michael F.
The price is SAR 394
SAR 771 total
includes taxes & fees
1 Sep - 2 Sep
Spacious Downtown Owosso Loft
Coffee/tea maker, fridge, microwave, electric kettle

2. The Exchange - A Historic Downtown Studio

The Exchange - A Historic Downtown Studio
Owosso
10.0 out of 10, Exceptional, (7 reviews)
"Being in town for a weekend, The Exchange was a perfect place to stay. Very close to town yet far enough away for peace and quiet. The furnishings were very nice and the entire experience was very cozy and comfortable. "
United States
Nathan P.
The price is SAR 436
SAR 511 total
includes taxes & fees
15 Sep - 16 Sep
The Exchange - A Historic Downtown Studio
Exterior detail

3. Historic 2-bedroom condo in Owosso

Historic 2-bedroom condo in Owosso
Owosso
9.8 out of 10, Exceptional, (10 reviews)
"Highly recommend this home! It's located in a prime location, beautifully decorated a d feels like home!"
United States
Daniel S.
The price is SAR 618
SAR 1,026 total
includes taxes & fees
19 Aug - 20 Aug
Historic 2-bedroom condo in Owosso
Coffee/tea maker, fridge, microwave, oven

4. Historic Downtown Owosso Loft

Historic Downtown Owosso Loft
Owosso
9.6 out of 10, Exceptional, (41 reviews)
"It’s a beautiful place, very clean and easy to get into. Very happy with our stay"
United States
Mark
The price is SAR 439
SAR 826 total
includes taxes & fees
18 Aug - 19 Aug
Historic Downtown Owosso Loft
Smart TV

5. Luxurious Downtown Owosso Loft

Luxurious Downtown Owosso Loft
Owosso
9.8 out of 10, Exceptional, (59 reviews)
"Wonderful place to stay. "
United States
Richard
The price is SAR 631
SAR 1,190 total
includes taxes & fees
15 Sep - 16 Sep
Luxurious Downtown Owosso Loft
Terrace/patio

6. Cottage in Bancroft countryside for the perfect relaxing getaway.

Cottage in Bancroft countryside for the perfect relaxing getaway.
Bancroft
10.0 out of 10, Exceptional, (6 reviews)
"The property was absolutely stunning. It was exactly what we were hoping for."
United States
Petra
The price is SAR 394
SAR 469 total
includes taxes & fees
18 Aug - 19 Aug
Cottage in Bancroft countryside for the perfect relaxing getaway.
House (2 Bedrooms) | Interior

7. Pet Friendly: 2 Mi to Downtown Flushing

Pet Friendly: 2 Mi to Downtown Flushing
3.0 star property
Flushing
The price is SAR 469
SAR 1,413 total
includes taxes & fees
19 Aug - 20 Aug
Pet Friendly: 2 Mi to Downtown Flushing
Dining

8. Pet Friendly: 2 Mi to Downtown Flushing

Pet Friendly: 2 Mi to Downtown Flushing
Flushing
9.4 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay and so appreciated all of the amenities along with being pet friendly. The home is beautifully decorated and very comfortable. We would love stay when we visit again. "
United States
Amy C.
Pet Friendly: 2 Mi to Downtown Flushing
Outdoor dining

9. Vintage Main Street Retreat Sleeps 25

Vintage Main Street Retreat Sleeps 25
Ovid
10.0 out of 10, Exceptional, (6 reviews)
"What an great place to stay for an event. We used the kitchen and banquet area for a catered meal of 50 people and the game room up top was a great hang out."
United States
John B.
The price is SAR 2,861
SAR 4,939 total
includes taxes & fees
24 Aug - 25 Aug
Vintage Main Street Retreat Sleeps 25
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

The Comstock Inn and Conference Center

The Comstock Inn and Conference Center

10/10 Excellent
"Great place to stay! Room and bathroom were very clean. The stash was very friendly and helpful. I will definitely start here again"
Lyman 1-night trip
Posted 9 hours ago
The Comstock Inn and Conference Center

Frequently asked questions

Can I find vacation rentals in Middletown?

Yes, we have vacation rentals near popular attractions in Middletown, or you can choose a more secluded option if you'd like a relaxing place to stay.

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

Our historic 140 year old home is a minutes walk to Downtown Flushing: Visitors like this Middletown vacation home rental. It 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 3 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.

What’s there to see and do in Middletown?

While exploring the area, visit family-friendly sights like Steam Railroading Institute, or get outside and enjoy nature at Sleepy Hollow State Park. In the larger area, you’ll find Curwood Castle and Durand Union Station.

What’s a vacation rental in Middletown like?

A vacation rental is a private property you can book for a few weeks or just a few days in Middletown. Vacation rentals offer amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.