Middletown Cottages

Q: Why book your cottage in Middletown with Expedia?

We think a getaway should be a walk in the park, so if you're seeking cottages in Middletown at a competitive rate, Expedia has got your back. Keep costs down and select an inexpensive option far from the downtown buzz, or splurge on a 5-star cottage to spoil your loved ones.

Q: How can I find cheap cottages in Middletown?

With Expedia's useful filter tool, sourcing cheap cottages in Middletown is a cinch. To discover accommodation that'll make your wallet smile, narrow down your search by budget, amenities and star rating.

Q: What is there to do in Middletown near my cottage?

If you'd like to see the sights of Middletown, be sure to visit Orange County Fair Speedway . It's a hit among visitors and locals alike.

A lake surrounded by autumn-colored trees reflecting on the water.

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Our top choices for Middletown cottages

A rustic cabin with a stone exterior, wooden deck, and a small porch.

1. Hello Small Stone

Middletown

John H.

HK$2,968 total

includes taxes & fees

2 Oct - 3 Oct

A grey sectional sofa with patterned cushions, a round wooden coffee table with a green plant, and a window with a view of trees.

2. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen

Jessica C.

HK$2,296 total

includes taxes & fees

4 Oct - 5 Oct

A wooden deck with a barbecue grill and a trash can.

3. Hike & Fish: Outdoor Retreat Near Trails

Westbrookville

HK$2,696 total

includes taxes & fees

5 Oct - 6 Oct

A small cabin with a porch, surrounded by dense forest and a clear night sky with a visible moon.

4. Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Bloomingburg

Stephen H.

HK$1,694 total

includes taxes & fees

5 Oct - 6 Oct

A house with a view of a bridge and mountains.

5. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery

Jasmine

HK$2,595 total

includes taxes & fees

6 Oct - 7 Oct

A cottage with a wooden deck, a porch, and a staircase leading to the entrance.

6. Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Kerhonkson

Anthony M.

HK$1,890 total

includes taxes & fees

6 Oct - 7 Oct

An outdoor dining area with tables and chairs, surrounded by greenery and a view of the landscape.

7. Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Vernon Township

Cherlyn I.

HK$3,749 total

includes taxes & fees

5 Oct - 6 Oct

8. Cozy Cottage w/ Hot Tub! — Family Friendly

Mongaup Valley

yisroel k.

HK$3,127 total

includes taxes & fees

6 Oct - 7 Oct

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Top Middletown Hotel Reviews

Holiday Inn Express & Suites Middletown - Goshen by IHG

10/10 Excellent

"Breakfast was the best I ever had for a free breakfast"

Resorts World Catskills Casino

10/10 Excellent

"Very well run property, All the staff was well trained and pleasant, Large modern and clean room with nice views. My wife is a Celiac and requires gluten free food. The Bistro was our only option, however they handled the GF needs very well, They offer GF bread and rolls, so my wife was able to have a nice burger with a GF side and also a Pastrami Reuben sandwich. Breakfast omelets were great. Ariel in the Bistro was a gem, but so was Clara and all the other servers. The other restaurants on the property might offer GF food but they are not listed on their menus :<"

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