Middletown Holiday Rentals, New York: Private House Rentals

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Middletown

Pet friendly

Pool

Apartment

Hot tub

Spa

Family friendly

Condo

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Middletown hotels

A breakfast area with a counter displaying hard-boiled eggs, a bowl of green apples, and various pastries.

A modern hotel with a prominent 'tru by Hilton' sign, a covered entrance, and a well-lit facade.

A modern lounge area with seating, tables, and hanging chairs.

A modern reception area with a curved wooden counter, seating area with colorful cushions, and pendant lighting.

1. Tru by Hilton Middletown

Middletown

Rebecca

2.103.861 ₫

2.485.186 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.

A gym with treadmills, a weight bench, and various exercise equipment.

A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

A vending machine area with two beverage dispensers and a snack shelf stocked with various products.

2. La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

Marvin

2.819.661 ₫

3.330.725 ₫ total

includes taxes & fees

10 Nov - 11 Nov

A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

An indoor swimming pool with lounge chairs and a stone wall.

A Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.

A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

3. Sleep Inn & Suites Middletown - Goshen

Middletown

Mark

2.621.403 ₫

3.096.531 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A landscaped outdoor area with a fire feature, seating, and a pathway.

A Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.

A modern hotel lobby with a seating area, large windows, and a television screen.

A modern bar area with a curved counter, bar stools, and a television screen.

4. Courtyard by Marriott Middletown Goshen

Middletown

marc

2.621.403 ₫

3.096.531 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.

A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.

A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.

An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.

5. Holiday Inn Express & Suites Middletown - Goshen by IHG

Middletown

Mignonne

2.954.424 ₫

3.489.913 ₫ total

includes taxes & fees

11 Nov - 12 Nov

A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

A gym with exercise equipment, treadmills, and weight machines.

A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.

A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

6. Hampton Inn by Hilton Middletown

Middletown

Myung

2.180.831 ₫

2.576.106 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.

A modern restaurant with a central island, multiple tables, and chairs.

A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.

A multi-story hotel building with a prominent 'HOME 2' sign, featuring a modern design with brick and beige facades, and a parking lot in front.

7. Home2 Suites by Hilton Middletown

Middletown

Carl

4.163.405 ₫

5.008.727 ₫ total

includes taxes & fees

27 Oct - 28 Oct

An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.

An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.

A spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.

A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.

8. Residence Inn by Marriott Middletown Goshen

Middletown

jubert cruz

4.872.208 ₫

5.755.295 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.

A modern living room with a large TV, comfortable seating, and a patterned rug.

A swimming pool with four lounge chairs and a metal ladder.

9. Candlewood Suites Middletown Goshen by IHG

Middletown

Antonio

2.850.760 ₫

3.367.461 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A multi-story hotel with a central courtyard, large windows, and a parking lot.

A modern hotel lobby with a reception desk, seating area, and a fireplace.

A modern dining area with long tables and chairs, a bar area with a TV, and a kitchen in the background.

A hotel room with a bed, a desk, a chair, a wardrobe, and a bathroom mirror.

10. Microtel Inn & Suites by Wyndham Middletown

Middletown

2.467.203 ₫

2.914.383 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a bed, two bedside tables with lamps, a wall-mounted telephone, and a large black and white windmill painting.

A Super 8 motel sign with a parking lot and a building in the background.

A reception area with a counter, a clock, a no cash refunds sign, and a fire alarm.

A lobby with a red sofa, two lamps, a coffee table with flowers, and a wall art piece.

11. Super 8 by Wyndham Middletown

Middletown

Katelynn

1.828.374 ₫

2.159.840 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

A modern kitchen with a built-in microwave, a stainless steel refrigerator, and a wooden floor leading to a bedroom with a bed and a window.

A modern kitchen with a microwave, double sink, and a dining area with a TV and a plant.

A modern kitchen with stainless steel appliances, a dining area with a geometric rug, and a dark door with a number.

12. Columbus Suites

Middletown

Jose

2.565.684 ₫

4.808.066 ₫ total

includes taxes & fees

15 Oct - 16 Oct

A modern bedroom with a four-poster bed, a desk, and a chair.

A staircase with a black handrail and a fire alarm on the wall.

A kitchen with a stainless steel sink, a coffee maker, a bottle of hand soap, a paper towel dispenser, and a microwave.

A room with a grey armchair, a small round table with a black top and gold legs, and a white pedestal lamp.

13. Columbus Hotel

Middletown

Joseph

3.783.736 ₫

6.185.989 ₫ total

includes taxes & fees

15 Oct - 16 Oct

A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

A spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee table.

An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

A modern restaurant with a long counter, wooden chairs, and pendant lighting.

14. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Aeron

3.343.164 ₫

4.116.268 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel with a central entrance pavilion, a flag, and a landscaped garden.

A modern hotel lobby with a large map mural, seating areas, and a reception desk.

A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.

A boat ride with passengers holding binoculars, surrounded by water and themed structures.

15. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

WARREN

2.695.264 ₫

3.318.543 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A hotel room with a large bed, a desk, a chair, a desk lamp, a wall-mounted TV, and a window with curtains.

A hotel entrance with stone pillars, a covered walkway, and a bench.

A modern hotel lobby with seating areas, a bar, and a television screen.

A modern hotel room with a flat-screen TV, a fireplace, a desk with a computer, and comfortable seating.

16. Sleep Inn & Suites Monroe - Woodbury

Monroe

Maureen

2.915.550 ₫

3.298.217 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A brick exterior with outdoor seating, tables covered with white tablecloths, and brick walls.

A hotel room with a large bed, a desk, a chair, and a TV.

A cozy lounge area with green and blue upholstered chairs, marble tables, and a fireplace.

A lobby with green and blue upholstered chairs, a Christmas tree, and a bar area with red bar stools.

17. The Orange Inn Boutique Hotel

Goshen

DENISE

6.200.403 ₫

7.634.247 ₫ total

includes taxes & fees

15 Oct - 16 Oct

A large, two-story house with a wrap-around porch and multiple chimneys.

A spacious living room with a large sectional sofa, a wooden floor, and large windows offering views of the outdoors.

A spacious living room with a large sectional sofa, a fireplace, and a chandelier.

A spacious dining area with a large table and chairs, surrounded by large windows offering views of a residential neighborhood.

18. Parkway House Goshen Family-Friendly Bed & Breakfast

Goshen

Aakif

5.971.046 ₫

7.351.851 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A lobby with a fireplace, seating area, and a reception desk.

A hotel room with a large bed, a sofa, a desk, and a bathroom.

An outdoor patio with brick flooring, round tables, and blue umbrellas.

A snack and beverage display in a store with various snacks, drinks, and a 'Welcome to Harriman Woodbury' sign.

19. Hampton Inn Harriman Woodbury

Central Valley

John

3.061.975 ₫

3.770.057 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with colorful umbrellas and lounge chairs.

A restaurant with multiple dining tables and chairs, a central counter with a chef figure, and colorful hanging lights.

A bar area with a long counter, multiple hanging lights, and a variety of bottles.

A colorful play area with a check-in counter and a mascot.

20. LEGOLAND Hotel NEW York

Goshen

Kylaia

1.980.086 ₫

5.733.019 ₫ total

includes taxes & fees

25 Oct - 26 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Middletown attractions

A large Ferris wheel against a sunset sky.

Orange County Fairgrounds

8.0/10 (87 reviews)

This historic fairgrounds combines a century-old county fair with thrilling dirt track racing. Enjoy carnival rides during the July fair or catch heart-pounding motorsport action at the legendary speedway.

See properties

A lake surrounded by dense vegetation and a hill with a house in the background.

Highland Lakes State Park

8.0/10 (43 reviews)

Discover 3,115 acres of pristine wilderness with informal trails winding through forests and around lakes. Bring supplies for horseback riding, fishing, or hiking in this peaceful, undeveloped natural retreat.

See properties

Highland Lake

10.0/10 (3 reviews)

Explore 3,000 acres of pristine wilderness at this undeveloped sanctuary for outdoor enthusiasts. Hike forest trails, cast a line in serene lakes, or ride horseback with a permit through untouched nature.

See properties

Orange County Fair Speedway

8.4/10 (119 reviews)

America's oldest continuously operating dirt track, Orange County Fair Speedway has thrilled racing fans since 1919. Experience the roar of engines and excitement of dirt track racing at this historic motorsport venue.

See properties

Galleria at Crystal Run

8.6/10 (200 reviews)

The Galleria at Crystal Run offers over 100 stores and entertainment venues in the heart of Middletown. Explore premium retailers like Macy's or catch a film at the cinema for a complete shopping experience.

See properties

Paramount Theatre

7.8/10 (96 reviews)

This 1929 theatre boasts Carnegie Hall-like acoustics, hosting diverse performances in its intimate 1,100-seat venue. Experience cultural richness through concerts, films, or shows in this historic Middletown gem.

See properties

Orange County Community College

Enjoy the student vibe at Orange County Community College during your stay in Middletown. While in this family-friendly area, you can savour the top-notch restaurants.

See properties

Learn more about Middletown

Just an hour from NYC, this historic Hudson Valley town offers scenic hikes along the Heritage Trail and apple picking at local orchards. Explore the interactive exhibits at the National Soaring Museum, then catch a performance at the beautifully restored Paramount Theatre built in 1930.

See all hotels in Middletown

Top Middletown Hotel Reviews

Courtyard by Marriott Middletown Goshen

10/10 Excellent

"Stayed for a wedding. Terrible weather, but my room was large, clean, warm, comfortable. Lots of space and nice light on 4th floor looking at foliage. Big bathroom, coffee bar, fridge - convenient. Really perfect and used the whirlpool in the morning. Maybe some extra sugars for the coffee bar but just comfy, nice staff, very pleasant."

The Kartrite Resort & Indoor Waterpark

10/10 Excellent

"We love the Kartrite and go every year. It’s clean, fun and always good food!"

Resorts World Catskills Casino

10/10 Excellent

"Great place to stay"

Hampton Inn by Hilton Middletown

10/10 Excellent

"Room was clean, bed was comfortable."

The Thayer Hotel at West Point

10/10 Excellent

"Amazing Place absolutely wonderful place to stay"

Holiday Inn Express & Suites Middletown - Goshen by IHG

10/10 Excellent

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

More cheap stays in Middletown

Ramada by Wyndham Newburgh/West Point

1289 Route 300 Newburgh NY

1.656.032 ₫

1.956.658 ₫ total

19 Oct - 20 Oct

includes taxes & fees

4.8/10 (1,001 reviews)

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

915 Union Ave New Windsor NY

2.308.856 ₫

2.726.881 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Sleep Inn & Suites Middletown - Goshen

3491 Route 6 Middletown NY

2.621.403 ₫

3.096.531 ₫ total

8 Nov - 9 Nov

includes taxes & fees

Holiday Inn Express Hotel & Suites Chester by IHG

2 Bryle Place Chester NY

2.695.264 ₫

3.318.543 ₫ total

18 Oct - 19 Oct

includes taxes & fees

8.6/10 Excellent! (1,004 reviews)

Overlook Lodge at Bear Mountain

55 Hessian Drive Bear Mountain NY

3.008.848 ₫

3.554.202 ₫ total

4 Nov - 5 Nov

includes taxes & fees

8.4/10 Very good! (1,012 reviews)

Comfort Suites Central Valley - Woodbury

100 Estrada Road Central Valley NY

3.056.533 ₫

3.763.521 ₫ total

26 Oct - 27 Oct

includes taxes & fees

Hotels in Middletown with star rating

Frequently asked questions

What's the seasonal weather in Middletown?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Middletown are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

Explore a world of travel with Expedia

Book Hotels in Middletown on Expedia.com

Find hotels in Middletown, NY from 1.956.658 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Middletown

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Middletown hotels

1. Tru by Hilton Middletown

2. La Quinta Inn & Suites by Wyndham Middletown-Goshen

3. Sleep Inn & Suites Middletown - Goshen

4. Courtyard by Marriott Middletown Goshen

5. Holiday Inn Express & Suites Middletown - Goshen by IHG

6. Hampton Inn by Hilton Middletown

7. Home2 Suites by Hilton Middletown

8. Residence Inn by Marriott Middletown Goshen

9. Candlewood Suites Middletown Goshen by IHG

10. Microtel Inn & Suites by Wyndham Middletown

11. Super 8 by Wyndham Middletown

12. Columbus Suites

13. Columbus Hotel

14. Fairfield Inn & Suites by Marriott Goshen Middletown

15. Holiday Inn Express Hotel & Suites Chester by IHG

16. Sleep Inn & Suites Monroe - Woodbury

17. The Orange Inn Boutique Hotel

18. Parkway House Goshen Family-Friendly Bed & Breakfast

19. Hampton Inn Harriman Woodbury

20. LEGOLAND Hotel NEW York

Stay near popular Middletown attractions

Orange County Fairgrounds

Highland Lakes State Park

Highland Lake

Orange County Fair Speedway

Galleria at Crystal Run

Paramount Theatre

Orange County Community College

Learn more about Middletown

Top Middletown Hotel Reviews

Courtyard by Marriott Middletown Goshen

The Kartrite Resort & Indoor Waterpark

Resorts World Catskills Casino

Hampton Inn by Hilton Middletown

The Thayer Hotel at West Point

Holiday Inn Express & Suites Middletown - Goshen by IHG

More cheap stays in Middletown

Ramada by Wyndham Newburgh/West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Sleep Inn & Suites Middletown - Goshen

Holiday Inn Express Hotel & Suites Chester by IHG

Overlook Lodge at Bear Mountain

Comfort Suites Central Valley - Woodbury

Hotels in Middletown with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app