Best Vacation Homes in Middletown
Cottage
6.8(11 Reviews)
1 Bedroom
1 Bath
2 Guests
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
US $299/Night
7 Nights - US $2,090
House
8.5(36 Reviews)
2 Bedrooms
2 Baths
4 Guests
156.07 ft²
Air Conditioner
Internet
Child Friendly
Security/Safety
US $67/Night
7 Nights - US $466
US $288/Night
7 Nights - US $2,015
Cottage
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
Parking- Air Conditioner
US $494/Night
7 Nights - US $3,458
Apartment
6.8(82 Reviews)
6 Bedrooms
2 Baths
4 Guests
236.81 ft²
- Fireplace/Heating
Breakfast- Parking
- Air Conditioner
US $214/Night
7 Nights - US $1,496
House
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
Pet Friendly- Air Conditioner
- Internet
US $137/Night
7 Nights - US $960
House
10.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
3100 ft²
Private Pool- Hot Tub
- Fireplace/Heating
Pool
US $1,354/Night
7 Nights - US $9,479
Villa
7 Bedrooms
8 Baths
24 Guests
9279 ft²
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
US $6,907/Night
7 Nights - US $48,352
Middletown Luxury Rentals
Villa
7 Bedrooms
7 Baths
24 Guests
9504.53 ft²
- Hot Tub
- Spa
- Fireplace/Heating
View
US $9,193/Night
7 Nights - US $64,349
House
3 Bedrooms
2 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $473/Night
7 Nights - US $3,308
Hotel
9.0(69 Reviews)
17 Baths
441.32 ft²
- Private Pool
Oceanfront- Fireplace/Heating
- Pool
US $340/Night
7 Nights - US $2,378
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $339/Night
7 Nights - US $2,376
House
10.0(9 Reviews)
4 Bedrooms
1 Bath
8 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $274/Night
7 Nights - US $1,916
Hotel
9.3(45 Reviews)
13 Baths
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $257/Night
7 Nights - US $1,798
Bed & Breakfast
6.0(6 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $237/Night
7 Nights - US $1,659
Hotel
8.8(378 Reviews)
13 Baths
280.69 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $223/Night
7 Nights - US $1,562
Middletown Pet Friendly Vacation Rentals
House
10.0(2 Reviews)
5 Bedrooms
4 Baths
10 Guests
3890 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $479/Night
7 Nights - US $3,353
Hotel
9.0(595 Reviews)
5 Baths
350.9 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $189/Night
7 Nights - US $1,325
Hotel
9.4(1005 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Pet Friendly
US $147/Night
7 Nights - US $1,026
Cottage
9.0(2 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $400/Night
7 Nights - US $2,798
Hotel
9.0(478 Reviews)
1 Bath
301.39 ft²
- Balcony/Terrace
- Breakfast
- Pet Friendly
- Parking
US $190/Night
7 Nights - US $1,330
House
10.0(4 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $291/Night
7 Nights - US $2,034
House
4.6(5 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $200/Night
7 Nights - US $1,400
House
3.5(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $175/Night
7 Nights - US $1,225
Middletown Large Vacation Homes
House
9.4(23 Reviews)
6 Bedrooms
3 Baths
14 Guests
3600 ft²
- Private Pool
Skiing- Fireplace/Heating
- Pool
US $702/Night
7 Nights - US $4,915
House
8.0(4 Reviews)
7 Bedrooms
4 Baths
22 Guests
3600 ft²
- Child Friendly
US $1,190/Night
7 Nights - US $8,330
Why Choose Rent By Owner for your Middletown Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Middletown
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination ensures you can enjoy its local charm at its best, making your stay in Middletown's vacation rentals both enjoyable and memorable.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm weather ideal for outdoor activities and exploring the scenic region.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
Fall (September to November)
Fall offers mild temperatures and vibrant foliage, making it a popular time for visitors seeking picturesque natural beauty in the area.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler temperatures and a peaceful atmosphere, perfect for those looking for tranquility and seasonal charm.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 25°F
Spring (March to May)
Spring sees a gradual warming trend and blossoming scenery, offering a quiet escape before the summer crowds arrive.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Middletown
How to Book Your Middletown Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Middletown
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a garden or patio area to relax and unwind.
- Take advantage of a spacious backyard perfect for outdoor activities or family gatherings.
- Make use of a fire pit or outdoor fireplace to cozy up during cool evenings in the region.
- Utilize an outdoor dining area, ideal for enjoying meals amidst the natural surroundings.
- Partake in recreational activities such as playing on a lawn or sports court if available.
- Benefit from scenic views and peaceful outdoor settings unique to this destination.
- Access outdoor amenities like swimming pools or hot tubs often found in some vacation rentals here.
Top Attractions Around Middletown
What attractions are nearby?
Here, you can explore a variety of outdoor activities and scenic spots that showcase the natural beauty and local charm of the area, offering a perfect backdrop for your memorable stay in this destination.
Family Activities
- Ice Skating at the Ice Time Sports Complex: Enjoy family-friendly ice skating sessions and choose from various skating lessons or public skate times at this popular local ice rink.
- Visiting the Orange County Farmers Market: Explore fresh produce, handcrafted goods, and delicious treats that provide a fun, educational experience for kids and adults alike.
- Exploring the Hudsonville Nature Preserve: Discover scenic nature trails, wildlife viewing opportunities, and peaceful picnic spots perfect for a day out in the region's natural beauty.
- Participating in Community Events at the Middletown Community Center: Attend seasonal festivals, craft workshops, and recreational activities designed to entertain families visiting this area.
Adult Activities
- Wine Tasting Tours: Embark on wine tasting tours at local vineyards, offering you a refined experience in the scenic landscapes of this region.
- Golfing Experiences: Play a round of golf at nearby courses known for their challenging layouts and picturesque settings within this destination.
- Historic Site Visits: Discover the rich history by visiting preserved historic sites that tell the story of this area's past.
Other Places to Stay in Middletown, NY
Howells
Orange County Fair Speedway
Paramount Theatre
Mechanicstown
Orange County Fairgrounds
Orange Regional Medical Center
Scotchtown
Galleria at Crystal Run
Washington Heights
Wallkill
Middletown Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Festivals: Take advantage of community celebrations and happenings to immerse yourself in the area's culture during your stay.
- Discover Nearby Outdoor Activities: Utilize your vacation rentals as a base for exploring outdoor pursuits like hiking, biking, or scenic drives around here.
- Plan Flexible Itineraries: Keep your schedule adaptable to enjoy unplanned discoveries and hidden gems that make your trip unique.
- Connect with Local Cuisine: Sample regional flavors at local eateries or prepare homemade meals using fresh ingredients from nearby markets to enhance your experience.
Transportation Options
- Bus Services: Convenient bus routes connect this area with nearby cities and regional destinations, making public transportation an accessible option for exploring here.
- Regional Airport: The closest major airport provides easy access for travelers arriving from different parts of the country or internationally, ensuring seamless connectivity to here.
- Taxi and Rideshare Services: Reliable taxi companies and rideshare options such as Uber and Lyft offer flexible transportation within the region, ideal for short trips or last-minute needs.
- Car Rentals: Local car rental agencies enable you to explore the surrounding area at your own pace, giving you freedom to visit attractions beyond here.
Local Customs Options
- Local Craftsmanship: You can observe the region’s rich craftsmanship through handcrafted goods and artisan markets that reflect the area's cultural heritage.
- Seasonal Festivals: Participating in seasonal festivals offers a glimpse into local traditions, making your stay here more immersive and memorable.
- Traditional Cuisine: Enjoying regional cuisine allows you to savor authentic flavors that have been passed down through generations in this destination.
- Community Celebrations: Engaging in community events provides an authentic experience of the area's hospitality and vibrant social customs.
Middletown Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Middletown?
There are a lot of options in Middletown. If you plan on staying in the Middletown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Middletown:
- Quaint country house nestled in the woods
- Casa Manzara: Mountain Top Views, Pool + Hot Tub by Red Cottage
- La Quinta Inn & Suites by Wyndham Middletown-Goshen
- Residence Inn by Marriott Middletown Goshen
- Candlewood Suites Middletown - Goshen by IHG
- Candlewood Suites Middletown Goshen by IHG
- Home2 Suites by Hilton Middletown
- La Quinta Inn & Suites by Wyndham Middletown-Goshen
- Tru By Hilton Middletown
- Residence Inn Middletown Goshen
2. Which vacation homes in Middletown are best for families?
If you are looking for a family-friendly vacation home in Middletown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Middletown:
3. How many Rentbyowner vacation rentals are available in Middletown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 67 in the Middletown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Middletown.
4. What is the cancellation policy for vacation rentals in Middletown, NY?
Cancellation policies vary depending on the property listing. It’s important to review the specific rental’s cancellation terms before booking and contact the host directly if you have any questions.
5. How do I find available dates and secure a reservation in Middletown's vacation rentals?
You can easily check availability and book your stay by entering your desired dates on the listing page. For further assistance, reach out to the property owner directly through the messaging platform.
6. Are there any additional fees or deposits required for staying in vacation rentals here?
Additional fees or deposits are detailed within each listing and may include cleaning fees or security deposits. Please review the property details carefully and contact the host if you need clarification before confirming your reservation.
7. What amenities are typically included in vacation rentals in this region?
Most properties offer essential amenities such as Wi-Fi, parking, and kitchen facilities. Exact features are listed on each property page, so be sure to read the description thoroughly or ask the owner about specific requirements.
8. How close are these vacation rentals to local attractions and transportation options?
Many rentals are conveniently located near key points of interest and transportation hubs within the area. Details about proximity to attractions and transit are included in each listing to help you plan your visit effectively.
Middletown Top Rated Vacation Rentals
Hotel
9.4(322 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $222/Night
7 Nights - US $1,554
Hotel
9.0(768 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $209/Night
7 Nights - US $1,462
Hotel
8.8(705 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $150/Night
7 Nights - US $1,050
Hotel
8.6(1005 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $118/Night
7 Nights - US $829
Hotel
8.4(1003 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $109/Night
7 Nights - US $766
Hotel
8.4(119 Reviews)
1 Bath
441.32 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $190/Night
7 Nights - US $1,331
Hotel
7.9(244 Reviews)
1 Bath
279.86 ft²
- Oceanfront
- Fireplace/Heating
- Pool
Ocean View
US $162/Night
7 Nights - US $1,132
Hotel
7.3(197 Reviews)
7 Baths
345.98 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $192/Night
7 Nights - US $1,343
