Best Vacation Homes in Orange County
Cabin
10.0(9 Reviews)
1 Bedroom
1 Bath
6 Guests
1100 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Pet Friendly
US $415/Night
7 Nights - US $2,904
Villa
10.0(11 Reviews)
3 Bedrooms
3 Baths
9 Guests
2497.23 ft²
- Hot Tub
Skiing- Fireplace/Heating
- Balcony/Terrace
US $405/Night
7 Nights - US $2,835
House
4 Bedrooms
3 Baths
12 Guests
- Pet Friendly
Air Conditioner
Internet
Child Friendly
US $182/Night
7 Nights - US $1,273
House
10.0(317 Reviews)
2 Bedrooms
2 Baths
6 Guests
1400 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $570/Night
7 Nights - US $3,991
Apartment
10.0(5 Reviews)
2 Bedrooms
2 Baths
8 Guests
925.69 ft²
- Fireplace/Heating
Breakfast- Pet Friendly
Parking
US $254/Night
7 Nights - US $1,776
House
10.0(156 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
Kitchen- Parking
US $302/Night
7 Nights - US $2,114
House
10.0(72 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $328/Night
7 Nights - US $2,296
Apartment
10.0(56 Reviews)
2 Bedrooms
1 Bath
6 Guests
1250 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $215/Night
7 Nights - US $1,505
Orange County 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
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
US $7,402/Night
7 Nights - US $51,815
Villa
10.0(1 Review)
7 Bedrooms
8 Baths
24 Guests
9279 ft²
Private Pool- Hot Tub
- Spa
- Fireplace/Heating
US $6,899/Night
7 Nights - US $48,296
House
6 Bedrooms
3 Baths
13 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $3,618/Night
7 Nights - US $25,324
New
House
10 Bedrooms
9 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $3,587/Night
7 Nights - US $25,108
Villa
10 Bedrooms
5 Baths
25 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
Pool
US $3,182/Night
7 Nights - US $22,276
House
10.0(12 Reviews)
7 Bedrooms
4 Baths
17 Guests
5000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $2,687/Night
7 Nights - US $18,807
House
10.0(2 Reviews)
6 Bedrooms
6 Baths
14 Guests
6000 ft²
- Private Pool
- Spa
- Fireplace/Heating
- Pool
US $2,637/Night
7 Nights - US $18,461
Orange County Pet Friendly Vacation Rentals
Apartment
10.0(47 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $186/Night
7 Nights - US $1,301
House
10.0(2 Reviews)
6 Bedrooms
5 Baths
16 Guests
5005.22 ft²
Oceanfront- Hot Tub
- Fireplace/Heating
- Ocean View
US $705/Night
7 Nights - US $4,937
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $866/Night
7 Nights - US $6,062
Apartment
10.0(23 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $342/Night
7 Nights - US $2,391
Villa
10.0(2 Reviews)
5 Bedrooms
2 Baths
16 Guests
3100.01 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $1,045/Night
7 Nights - US $7,315
Apartment
10.0(13 Reviews)
1 Bedroom
1 Bath
4 Guests
1 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $193/Night
7 Nights - US $1,354
Apartment
10.0(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $165/Night
7 Nights - US $1,153
Apartment
10.0(7 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $428/Night
7 Nights - US $2,998
Orange County Large Vacation Homes
House
1 Bedroom
1 Bath
20 Guests
3498 ft²
- Spa
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $1,642/Night
7 Nights - US $11,494
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
9149.32 ft²
- Pool
- Pet Friendly
- Parking
- Air Conditioner
US $309/Night
7 Nights - US $2,163
Villa
10.0(8 Reviews)
1 Bedroom
1 Bath
- Kitchen
- Air Conditioner
- Internet
Bedding/Linens
US $197/Night
7 Nights - US $1,379
Bed & Breakfast
1 Bedroom
2 Baths
15 Guests
31215 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
US $1,101/Night
7 Nights - US $7,705
House
10.0(1 Review)
4 Bedrooms
2 Baths
11 Guests
1700.7 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $394/Night
7 Nights - US $2,758
New
House
5 Bedrooms
4 Baths
10 Guests
3640 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $994/Night
7 Nights - US $6,961
House
10.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
3100 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,677/Night
7 Nights - US $11,739
Villa
10.0(81 Reviews)
8 Bedrooms
5 Baths
25 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,595/Night
7 Nights - US $18,165
Why Choose Rent By Owner for your Orange County 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 Orange County
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here can enhance your experience and ensure you find the perfect vacation rentals in Orange County, New York — whether you're seeking vibrant seasonal events or a peaceful retreat during quieter months.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy the region's lush landscapes and milder weather, ideal for outdoor activities and exploring the area’s natural beauty.
Average Temperature Daytime: 75-85°F - Nighttime: 50-60°F
Early Fall (September to October)
This season offers pleasant temperatures and vibrant foliage, providing a picturesque setting that makes your stay even more memorable.
Average Temperature Daytime: 70-80°F - Nighttime: 45-55°F
Off-Season Highlights
Mid Winter (January to February)
The quieter winter months allow for a peaceful retreat amidst the snow-covered landscape, perfect if you prefer solitude and cozy accommodations.
Average Temperature Daytime: 25-35°F - Nighttime: 10-20°F
Late Fall (November to December)
As the region transitions into winter, fewer visitors mean more relaxed experiences and the opportunity to enjoy the holiday season in a charming setting.
Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F
Weekly Weather Forecast for Orange County
How to Book Your Orange County 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 Orange County
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 outdoor seating areas such as patios or decks to relax and take in the scenic views.
- Take advantage of private gardens or landscaped yards for outdoor activities and gatherings.
- Make use of swimming pools or hot tubs that provide a refreshing escape during your stay.
- Benefit from BBQ grills or outdoor cooking stations perfect for summer cookouts.
- Utilize spacious lawns or open spaces suitable for outdoor games and recreational activities.
- Experience fire pits or outdoor fireplaces ideal for cozy evenings with friends and family.
- Explore nearby walking trails or nature paths accessible directly from the property for outdoor adventures.
Top Attractions Around Orange County
What attractions are nearby?
Explore a variety of outdoor activities, cultural attractions, and scenic spots nearby to make the most of your stay in this region’s charming surroundings.
Family Activities
- Spofford Lake: You can enjoy a relaxing day swimming, kayaking, or picnicking by the serene waters of this family-friendly spot in the region.
- The Orange County Fairgrounds: Experience fun-filled events, exhibitions, and carnival rides that make for memorable outings with your loved ones here.
- Harness Racing at Monticello Raceway: Watch exciting harness racing events suitable for all ages, adding a thrilling touch to your family vacation in this destination.
- Historic Downtown Goshen: Stroll through charming streets filled with unique shops and family-friendly eateries, perfect for exploring together during your stay.
Adult Activities
- Hiking at the New York Appalachian Trail: Explore scenic trails that wind through the area's natural beauty, perfect for outdoor enthusiasts seeking an active adventure.
- Visiting Storm King Art Center: Discover impressive outdoor sculptures and contemporary art installations set amidst expansive landscapes in this renowned cultural destination.
- Golfing at local courses: Enjoy a round of golf on well-maintained fairways that offer stunning views and a relaxing atmosphere for adult players.
- Wine tasting tours: Experience regional wines by visiting local wineries and vineyards that showcase the region's burgeoning wine scene.
Other Places to Stay in Orange County, NY
Newburgh
Sparrow Bush
Chester
Monroe
Town of Highlands
Greenwood Lake
Warwick
Highland Falls
Town of Deerpark
Goshen
Middletown
Montgomery
Orange County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of the area’s unique cultural and natural sites to enrich your stay and create memorable experiences.
- Plan Outdoor Activities: Engage in outdoor pursuits like hiking or fishing, which showcase the region’s scenic landscapes and make the most of your visit.
- Discover Culinary Delights: Savor local cuisine at nearby restaurants or markets to get an authentic taste of the area's culinary scene.
- Book Well in Advance: Secure your preferred vacation rentals early to ensure a comfortable stay and enjoy the best properties available here.
Transportation Options
- Orange County Transit Authority: This regional bus service offers convenient transportation across the area, making it easy for you to explore local attractions from your vacation rental.
- Amtrak Station in Harriman: For travel beyond the region, the Amtrak station provides reliable rail connections to major cities, perfect for day trips or extended journeys.
- Local Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available here, providing flexible transportation directly to your desired destinations.
- Car Rental Companies: Several car rental agencies operate nearby, giving you the freedom to explore the region at your own pace during your stay.
Local Customs Options
- Apple Picking Tradition: Embrace the local custom of apple picking, a beloved activity during the fall season that allows you to experience the region’s rich agricultural heritage firsthand.
- Farmers' Markets: Visiting farmers’ markets is a common practice here, offering fresh, locally grown produce and crafts that reflect the area's vibrant community spirit.
- Historical Preservation: Respect for historical sites and traditions is prevalent, providing an authentic glimpse into the region’s past through well-preserved landmarks and local events.
- Community Festivals: Participating in seasonal festivals and outdoor events is a cherished custom, where locals celebrate their culture and natural surroundings with lively gatherings.
Orange County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Orange County?
There are a lot of options in Orange County. If you plan on staying in the Orange County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Orange County:
- Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
- Waterfall Cottage - Romantic Luxury Escape - nearby hiking, wineries and skiing
- Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC
- Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
- Cozy Cottage minutes to West Point
- Colonial-Style 'Warwick Retreat' - 1 Hour to NYC!
- Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
- Stay in the heart of Greenwood Lake minutes away from the lake
- Lakefront Home 3200 Sq' - 5 Queen Beds + Twin
- Cosy lakefront cottage in Hudson Valley
2. How many vacation rentals have private pools in Orange County?
There are 88 vacation rentals with private pools near Orange County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Orange County are best for families?
If you are looking for a family-friendly vacation home in Orange County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Orange County:
4. How many Rentbyowner vacation rentals are available in Orange County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 909 in the Orange County 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 Orange County.
5. What is the cancellation policy for vacation rentals in Orange County, NY?
Cancellation policies vary depending on the individual property listing. To understand the specific terms, please review the cancellation section of the listing or contact the property owner directly before booking.
6. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning fees, security deposits, or service charges may apply and are detailed within each property listing. Be sure to check the listing details or ask the owner for clarification before confirming your reservation.
7. How do I find the most suitable vacation rental in Orange County that fits my needs?
To find the ideal property, filter your search based on your preferred dates, size, amenities, and budget. Read the property descriptions carefully, including reviews, to ensure it meets your expectations.
8. What should I know about checking in and out of vacation rentals in this region?
Check-in and check-out procedures are specified in each listing. You can often coordinate these times with the owner beforehand. Clear communication ensures a smooth arrival and departure experience.
9. How do I contact the property owner if I have questions about my stay in Orange County?
Contact information for the owner is typically available through the booking platform. Use the messaging system provided to ask any questions or clarify details prior to your stay.
Orange County Top Rated Vacation Rentals
House
10.0(43 Reviews)
4 Bedrooms
2 Baths
11 Guests
3500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $962/Night
7 Nights - US $6,734
House
10.0(26 Reviews)
5 Bedrooms
3 Baths
10 Guests
4596 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $829/Night
7 Nights - US $5,805
House
10.0(24 Reviews)
6 Bedrooms
2 Baths
12 Guests
3300 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,113/Night
7 Nights - US $7,789
House
10.0(19 Reviews)
10 Bedrooms
5 Baths
25 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,606/Night
7 Nights - US $18,245
Villa
10.0(19 Reviews)
4 Bedrooms
3 Baths
8 Guests
4150 ft²
- Private Pool
- Spa
- Skiing
- Fireplace/Heating
US $1,349/Night
7 Nights - US $9,443
Ski Chalet
10.0(13 Reviews)
5 Bedrooms
5 Baths
10 Guests
6600 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,449/Night
7 Nights - US $10,142
House
10.0(13 Reviews)
3 Bedrooms
2 Baths
10 Guests
1700 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $1,006/Night
7 Nights - US $7,042
House
10.0(10 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,306/Night
7 Nights - US $9,145
