Vacation rentals in Pillar Point

New Home in the Harbor by Lake Ontario!

Escape to your private Haven in the Harbor! This newly built 3-bedroom, 2-bathroom, 1200sf home in the heart of historic Sackets Harbor is perfect for a relaxing stay, close to all amenities. Features include: - Steps to downtown restaurants and shops - Open design kitchen and living space - Third bedroom / office space - Fenced yard with outdoor patio, dining table and grill - Front porch with 2 Adirondack chairs - Central A/C - Washer & Dryer - Near historic 1812 Battlefield and Lake Ontario

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 and enjoy the sunsets. Watch the lights of night wake up over the Bay.

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.

Chaumont Bay Getaway | Luxury Waterfront/Hot Tub

Escape to this unique & tranquil getaway in 1000 islands vicinity. The spacious lake-view sunroom is perfect for relaxing. The master suite features a king bed and an ensuite bathroom. Relax in the hot tub [seasonally May-December] overlooking the lake or lounge at waterfront pergola with gas fire-pit. Chaumont Bay, one of world's largest freshwater bays, is a sought-after summer destination. We are a short drive to local tourist attractions in Alexandria Bay, Clayton, and Cape Vincent.

The Boathouse

The views are surreal! With over a 200 degree view, sitting on the couch seems like sitting over the top of the water. Located on a small protected bay, also home to two yacht clubs, you'll see boaters of all kinds. The fishing is fabulous right from the dock. Located on a quiet private road, you'll be walking distance a from restaurants, an ice cream shop, shopping, banking, the local library, and even a small winery! There is deep water dockage if you plan to bring a boat.

Peaceful Getaway

Kick back and relax in this peaceful space. Guest house has two twin beds, private bathroom, microwave, toaster, Keurig, small refrigerator. WiFi access, outdoor grill with outdoor dining and seating area all under a 16x24 pavilion. This property offers incredible views, fish jumping and canoe and kayak access. End your incredible day fishing off the dock with s’mores at the fire pit. Hunters and fishermen welcome. Plenty of parking so bring your motorized toys! See you soon!

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.

Laidback Lakeside - Beachfront & Late Checkout

Private and peaceful on 6+ acres with over 300ft of pebble & sand beachfront with large lake-side yard for lawn games. Private, dead-end road. Pillar Point offers miles of scenic roadway for biking or walking. In addition to two guest bedrooms with ample closet space there is a full office setup with dual monitors, wi-fi, and a view. The bathroom has separate shower and soaker tub. Attached is the laundry room with full size washer and dryer.

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 just outside. 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.

Hazel's Lookout - relax with stunning sunsets

A perfect retreat for individuals, couples, or small families, our house boasts views of the most beautiful sunsets on the pristine waters of Lake Ontario. Whether you're looking for a peaceful stay or access to many types of adventures our house is a perfect location for both! . With ducks diving for fish right out the back door, you’re likely to spot a variety of wildlife, often including bald eagles, deer, and cranes.

Lakefront Cottage with Hot Tub

Escape to a boutique lakefront cottage on Lake Ontario, designed for a relaxing retreat. This well designed space features a private hot tub with sunset views, direct lake access, and a cozy wood-burning fireplace. Enjoy luxurious details like an espresso/coffee bar and two king bedrooms. Perfect for couples or small groups seeking privacy, comfort, and connection in a refined, spa-like atmosphere.

Sunset Cottage on Lake Ontario at Pillar Point

A peaceful place to relax on the shore of Lake Ontario, right on the point of Pillar Point. Enjoy the gentle breeze, lapping waves, and tranquil space. Take in the sunset almost every evening. You will find everything you need for a quiet, restorative getaway. Swim, kayak, read, reflect. A perfect hermitage for clergy, couples, and those who serve and care for others.