Holiday rentals in Henderson Harbor

1066 Hastings House

A romantic escape for no reason? Maybe a special Easter egg hunt for the season? For a small fee, I can fill plastic eggs, hide inside/outside for family fun! We welcome to the 1066 Hastings House, responsible 25 yr olds and up, 1-2 well behaved house trained dogs. Hosting, up to maximum of 5 guests. From the dining & great room, enjoy the sun rising. As the day draws to a close, snuggle up by the fireplace in the greatroom, enjoy the sunsets. Watch the lights of night wake up over the Bay.

Location · Family · Nearby

Stone Cove Cottage overlooking Lake Ontario

One of a kind vacation home with stunning Lake Ontario and sunset views throughout. Large home with a private cove for swimming and beautiful garden landscape surrounded by historic preserve park. Step out onto a battlefield of the War of 1812. Walking distance to shops, dining, and nightlife in Sackets Harbor Village including their many community events/festivals. Public boat launch and marina in town for vessels of all sizes. Short drive to Wescott Beach Park, I-81, and St. Lawrence River.

Location · Family · Biking

Modern Lakeside Family Retreat w/ Private Beach

Relax at this modern lakeside retreat nestled amidst the serene beauty of Lake Ontario. This 4-bed, 2.5-bath home offers the perfect haven for groups. The spacious kitchen, large dining table, loft sitting area, furnished deck, and finished basement offer endless spaces to gather. But don't forget about the beach! Head to your dedicated space on the private beach to swim, kayak, or just soak up the sun. Watch the incredible sunsets then end the night stargazing around the beach firepit.

Location · Family · Layout

Henderson Harbor Hideaway

Henderson Harbor Hideaway is a cozy water front two bed room Cottage located next to the Historic Henderson Harbor Yacht Club that rests on the Eastern end of Lake Ontario. Henderson Harbor boat launch is a 1/2 mile away, and boasts two, very wide boat launch areas, along with plenty of parking. Restaurants, bait shop, small grocery store, and fishing charters are walking distance from the cottage. Southwick Beach State Park, and Westcott Beach State Park are less than 10 minutes away.

Family · Location · Quiet

Lake Ontario Beachfront Retreat | House 1

Welcome to Littlefield Lake House! This is one of two houses on this property (closer to the beach) with direct beach access to beautiful Lake Ontario. The sandy beach is perfect for lounging and building sand castles. This house can be rented on its' own or with the other house (see other listings on my profile). Nightly rates are increased for less than one week bookings and vary, please message for details on pricing. We provide discounted rates for bookings greater than 1.5 weeks.

Value · Location · Hospitality

Lake Cottage Perfect for Fall Summer & Fall Fun

Your waterfront getaway in scenic Henderson Harbor awaits. Now's the perfect time to enjoy all fall has to offer in Northern New York. Book a quick romantic getaway, family getaway, or spring trip! Our cottage has front-row seats to the most beautiful sunsets, a new crib dock giving easy access to boating & fishing, and nearly 100' of pristine waterfront for enjoying Henderson Harbor's waters. Whether it's calm and quiet to escape the daily grind or fun & excitement, we have it!

Location · Family · Indoor spaces

The Hideaway Cabin

Welcome to the Hideaway Cabin, where you can unwind in the embrace of nature. Here, you can sizzle your favorites on the grill, lounge in the Adirondack chairs on the balcony, or simply relax indoors. Come evening, gather by the firepit on the porch to watch the fireflies dance or relax in the hot tub on the back porch. It's the ideal blend of natural serenity and homely comfort. In the winter, cozy up by the woodstove in the living room and catch up on your favorite TV shows.

Value · Location · TV

Lake Ontario Waterfront w/ dock & kayaks

Lakefront retreat sleeps 11 with 4 bedrooms, 2 baths, and parking for 6 (or 4 with full RV hookup). Features a fully updated kitchen, cozy indoor fireplace, and waterfront access with unrestricted lake views. Multiple outdoor spaces include a fire pit overlooking the water—perfect for gatherings and relaxation for the entire family. Sit back, kick your feet up and watch the sunset set over the Lake Ontario from the upper or lower deck!

Family · Location · Access

Lake House Retreat

Welcome to our lake house, where stunning sunsets are a daily highlight! Nestled on the shores of a serene lake, this retreat offers breathtaking views and a peaceful escape from the hustle and bustle. Whether you're lounging on the deck, fishing off the dock, kayaking, swimming, or simply enjoying the evening sky, you're in for a memorable stay. We hope you make the most of this beautiful setting and create some unforgettable moments.

Value · Location · Accuracy

Black Bay Chalet- Charming Lakeside Hideaway

Relax on the couch and let the gentle lake breeze drift through the sliding doors, accompanied by the calming sound of waves. Enjoy breathtaking panoramic views of Lake Ontario from the comfort of the living room or while sipping a drink on the back deck—views that truly never disappoint. Perfect for couples or families, this cozy lakeside home is made for slowing down, unwinding, and creating fun, lasting memories by the water.

Family · Location · Outdoor spaces

Cute 1 bedroom Cottage lakeside

This one bedroom cottage with direct access to Lake Ontario on Bolton's Beach in historic Sackets Harbor NY is a perfect destination for a quiet waterside getaway. Located within 1 mile of Main Street in Sackets Harbor NY. The one bedroom has a full sized bed. The cottage also has a pullout twin sized sleeper sofa in the sunroom.

Location · Value · Cleanliness

Road Tree House

Waterfront cottage on beautiful Lake Ontario. Relax with the whole family at this peaceful place to stay. 4 bedrooms, 1 bathroom with shower. All bedding, towels and beach towels included. Breathtaking sunsets. Private dock. Beautiful view of Lake Ontario from the cottage and the deck. 20 minutes from historical Sackets Harbour.

Family · Location · Beach