Welcome to Middletown, NY – a charming and vibrant destination that seamlessly blends small-town charm with a variety of exciting activities for travelers. Nestled in the picturesque Hudson Valley, Middletown offers a delightful escape for those seeking a perfect blend of history, outdoor adventures, and cultural experiences.

Start your journey by exploring the historic downtown area, where you'll find quaint shops, cozy cafes, and a welcoming atmosphere. Take a stroll along the streets lined with historic architecture, and immerse yourself in the town's rich history. evolution.

For outdoor enthusiasts, Middletown offers a plethora of natural wonders. Head to nearby Highland Lakes State Park for hiking trails, picnicking spots, and serene lakeside views. The region is also home to the beautiful Shawangunk Mountains, providing opportunities for hiking, rock climbing, and birdwatching in a stunning natural setting.
For a bit of family fun, visit the Orange County Fair Speedway, a legendary dirt track that has been entertaining racing enthusiasts for over a century. Experience the thrill of motorsports and enjoy a day at the races.

You can rest easy knowing your stay is covered with $1,500 in “All-Risk” Damage Protection. Although rare, accidental damage from guests does happen. Traditionally, this was managed via a security deposit or vacation rental damage insurance purchased by the guest. Both are cumbersome and often have big limitations in protection.

With “all-risk” protection, all accidental damage from a guest is covered unless specifically excluded such as, but not limited to, normal wear and tear, infestation, or prior damage.
We hope you enjoy your vacation with peace of mind knowing that if an accident happens and damages occur, you are protected under Waivo.

Home Sweet Hudson is a proud member of VRMA, an international Vacation Rental Management Association. Our mission as a professional management company is to foster professionalism, collaboration and growth for short term rentals in our area. We hope you will help us support our mission by abiding by all of our house rules, supporting our local community and being respectful of the home during your time in the beautiful Hudson Valley.

- If you would like to bring a dog, you *must* add it to the reservation under the # of guests section upon booking. One dog is allowed per reservation unless otherwise approved by the host (please send us a message). Sorry, we do not allow cats. Please abide by our pet rules.
- Routinely scheduled maintenance by Home Sweet Hudson team members or lawn care/snow plowing may happen during your stay. This also includes garbage pick up, linen pickup, hot tub service and pool cleanings.
- Parking shall be allowed solely in the designated parking spaces
- Smoking is not permitted anywhere on the premises.
- Weapons are strictly prohibited
- Please adhere to safety instructions for fireplaces, firepits, etc.
- Due to the risk of fire, please do not charge your electric car on the property.
- We do not allow parties or extra guests outside the maximum occupancy allowed on the reservation. We also ask you to follow the good neighbor guidelines and abide by quiet hours after 9 pm.
- Please do not trespass on property boundaries
- Tents, yurts, and other camping equipment are prohibited