Orange County Cottage Rentals & Holiday Homes
Find the best cottages in Orange County - We found 42 exact matches
About Orange County Luxury Rental on The Islands Advisors
Searching for cottages to rent near Orange County? The Islands Advisors features more than 42 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Orange County have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. The Islands Advisors’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Orange County.
Are you planning to travel to the lakeside, beach, or mountain area? The Islands Advisors’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
The Islands Advisors boasts of 42 holiday cottages and places to stay in Orange County. The site provides unique Airbnb, VRBO, The Islands Advisors-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Orange County Cottage Rentals
What are the top rated Cottage 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 Cottage Rentals in Orange County:
- Cottage Suites
- Updated Home w/Patio Half Mile to West Point
- Hike & Fish: Outdoor Retreat Near Trails
- Charming 1 BDRM 18th Century post & beam cottage for monthly/extended stay
- 13 miles from West Point Entire Cottage on 1.5 acres 3BR 2BAn
- SIP, STAY & EXPLORE! MINUTES AWAY FROM WINERIES, GREENWOOD LAKE & HIKING TRAILS
- CHARMING BOHO-STYLE COTTAGE IN MIDDLETOWN NY
- Lakeside Haven - Ultimate Relaxation Spot
- Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
- Greenwood Lake Cottage w/ Grill & Lake Access
How much does it cost to rent a cottage in Orange County?
The average cost for a cottage rental in Orange County is $341 per night. Theislandsadvisors has a wide list of great cottages near Orange County that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Orange County that allow pets?
Yes, here are the top cottage rentals in Orange County that allow you to bring your pet:
- A romantic cottage and artist's retreat looking down over an enchanted lake
- Luxury Cottage at Millpond Falls
- Bright Cornwall-on-hudson Vacation Rental!
- Hudson Valley Retreat w/Pool Near Greenwood Lake
See all pet-friendly vacation rentals in Orange County on Theislandsadvisors
Do you have any rental cottages in Orange County that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Orange County to find one that works for you.
Are there quality cottages in Orange County that have indoor swimming pools?
As of 2026, the data from Theislandsadvisors shows that there are Over 42 private swimming pools or cottages with indoor pools in the Orange County area along with other great amenities.