Discover Your Ideal Merchants Square Vacation Rentals in Ossining, New York for an Unforgettable Stay
Discover Your Perfect Merchants Square Vacation Homes
Best Vacation Homes in Merchants Square
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- Balcony/Terrace
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Why Choose Rent By Owner for your Merchants Square Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Merchants Square Vacation Rentals
Where are the best neighborhoods to stay in Merchants Square?
Discover the charm of Merchants Square in Ossining, New York, when choosing where to stay during your visit. This neighborhood offers a blend of local character and convenient access to nearby attractions, making it an excellent base for exploring the area. Whether you prefer a cozy setting or a more lively atmosphere, the options here provide a comfortable and authentic experience. Booking your vacation rentals in this part of Ossining ensures a seamless stay, with easy access to the neighborhood’s unique ambiance and the surrounding community. Trust in reliable accommodations that prioritize your comfort and convenience as you enjoy your time in this welcoming area.
Highlands
This neighborhood offers a peaceful suburban atmosphere, making it an ideal choice for travelers seeking a quiet retreat near the vibrant downtown area. Here, you can enjoy easy access to local amenities while experiencing a relaxed residential vibe within the region.
View 109+ Rentals in HighlandsNortheast Yonkers
Located just outside the main city center, this area provides convenient connectivity and a mix of urban convenience with suburban comfort. It’s perfect for visitors wanting quick access to nearby attractions and the natural beauty of the region.
View 122+ Rentals in Northeast YonkersNorth Stamford
Situated in the neighboring state, this part of Stamford offers a blend of scenic landscapes and accessible transportation options, making it an excellent base for exploring the surrounding region's attractions and amenities.
View 187+ Rentals in North StamfordBest Times to Visit Merchants Square
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the shoulder seasons when this destination offers pleasant weather and fewer crowds, allowing you to fully enjoy what this region has to offer.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you can enjoy warm daytime temperatures ideal for outdoor activities.
Fall (September to November)
Autumn offers pleasant weather with vibrant fall foliage, making it a popular time to visit the area.
Off-Season Highlights
Winter (December to February)
In winter, the region experiences cooler temperatures, providing a cozy atmosphere perfect for off-peak stays.
Spring (March to May)
Spring brings milder weather and blooming landscapes, offering an excellent opportunity for quiet exploration.
Weekly Weather Forecast for Merchants Square
How to Book Your Merchants Square Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Merchants Square
Common Vacation Rentals Amenities
What amenities can you expect?
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 access to private outdoor seating areas where you can relax and take in the fresh air.
- Benefit from well-maintained gardens or landscaped yards that enhance the outdoor experience.
- Take advantage of nearby walking trails or nature paths perfect for exploring the scenic surroundings.
- Relish in outdoor dining options, such as patios or decks equipped with tables and grills.
- Utilize outdoor recreational equipment like bicycles or kayaks, often available for guest use.
- Pause on charming porches or verandas that provide a welcoming space to unwind.
- Make use of common outdoor amenities such as swimming pools or shared courtyards to enjoy leisure time outside.
Top Attractions Around Merchants Square
What attractions are nearby?
Within this charming destination, you can enjoy a variety of nearby activities such as exploring local shops, dining at popular eateries, and taking leisurely walks along scenic riverfront areas, making your stay in this region both relaxing and engaging.

Family Activities
- Ossining Riverwalk Park: Enjoy a family stroll along the scenic riverfront, perfect for picnics and watching boats navigate the Hudson River.
- Old Croton Aqueduct Trail: Discover this historical trail that offers a fun outdoor adventure suitable for all ages within the region's natural beauty.
- Local Farmers Market: Experience the vibrant atmosphere while sampling fresh, local produce and artisanal goods during your visit to the area.
- Community Arts Center: Engage in family-friendly events and workshops that celebrate the region’s cultural heritage and creativity.
Adult Activities
- Historic Downtown Exploration: Stroll through the charming streets to discover unique boutiques, cafes, and cultural spots that showcase the area's rich heritage.
- Ossining Waterfront Park: Enjoy a relaxing day by the river with scenic views, perfect for picnics or unwinding after exploring nearby attractions.
- Local Art Galleries: Immerse yourself in the region's vibrant art scene by visiting galleries that feature works from talented local artists.
- Riverfront Dining: Savor delicious cuisine at waterfront restaurants offering picturesque views of the Hudson River, ideal for an adult night out.
Merchants Square Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Shops: Take time to enjoy the unique eateries and boutique stores nearby, immersing yourself in the area's vibrant community atmosphere.
- Plan Outdoor Activities: Utilize the scenic parks and waterfront areas for relaxing walks or outdoor recreation to make the most of the region's natural beauty.
- Visit Cultural Spots: Make sure to include local cultural attractions and events to deepen your connection with this charming destination.
- Choose a Prime Location: Select your vacation rental in a central spot within Merchants Square to maximize your convenience and access to key attractions.
Transportation Options
- New York State Thruway (Interstate 87): This major highway provides convenient access to the area, making it easy to reach your vacation rental from various parts of New York and beyond.
- Ossining Train Station: The train station offers reliable commuter rail service directly into Manhattan, ideal for exploring the city while staying in this charming neighborhood.
- Local Bus Services: Several local bus routes connect here with surrounding communities and regional transit hubs, enhancing your mobility during your stay.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available, providing flexible transportation around the region at your convenience.
Local Customs Options
- Community Celebrations: Participating in local festivals and parades reflects the area's vibrant community spirit and rich cultural heritage.
- Historic Preservation: Respect for historic landmarks and architectural styles showcases the region’s dedication to maintaining its unique character.
- Local Cuisine Etiquette: Embracing regional dining customs, such as farm-to-table practices, enhances your authentic experience here.
- Artisan Handcrafts: Supporting local artisans and their crafts offers insight into the area’s creative traditions and influences.
Frequently Asked Questions About Merchants Square?
1. What are the top vacation rentals in Merchants Square?
There are a lot of options in Merchants Square. If you plan on staying in the Merchants Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Merchants Square:
- River front with large decks and dock over the Hudson
- Faces The Hudson + Only An Hour Outside NYC
- Newly Renovated Cozy 2 Bedroom Apartment with 3 min walk to Main Street
- Family home in one of NY top-ranked school districts with Tennis court
- Neighbor's house - Welcome!
- The Best of Both Worlds: For nature lovers but close to New York City
- The Red Hill Retreat - Woods Water History Privacy
- 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
- Cozy Cottage Get Away
- Croton Nook - Cozy Getaway
2. How many Rentbyowner vacation rentals are available in Merchants Square?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 82 in the Merchants Square 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 Merchants Square.
3. What is the cancellation policy for vacation rentals in this area?
4. Are there any additional fees I should be aware of when booking?
5. How do I confirm my reservation and what is required at check-in?
6. Is it possible to modify or extend my stay after booking?
7. What amenities are included with the vacation rentals here?
Best Vacation Homes in Merchants Square
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- Wheelchair Accessible
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- Air Conditioner
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- Security/Safety
- Fireplace/Heating
- Air Conditioner
- Parking
- TV
- Balcony/Terrace
- Security/Safety
- Fireplace/Heating
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- Pet Friendly