Vacation rentals in Pillar Point

Hideaway on the bay

Updated cabin with 100 feet of waterfront. Great swimming, a dock, shared kayaks, and shared kids play set. Perfect family getaway. Great for fisherman, ice fishing, or a peaceful couples get away. The cabin is on a shore well and the water is not drinkable. Guests will need to bring bottled water. I do not suggest accessing the ice in-front of the camp as the depth, current, and pressure there cause instability in ice accumulation. Guests can access the ice from long point state park 1.5m away

Full House with Black River views and access

Relax with panoramic views of the Black River from the large raised deck or venture closer to the water with safe river access. The yard slopes down to a seating area and sea wall for shore fishing and ramp access for kayaks and canoes along this calm four mile section from Black River to Watertown which follows the Black River Trail. Location is super convenient on a quiet street off Route 3, five minutes from Watertown and five minutes from Fort Drum. The Black River Drive-In is down street

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.

Lone Star North Cottage

Relax and recharge at this secluded, scenic getaway! Located on over 50 acres of farmland, this new build has 2 bedrooms, 1.5 bathrooms, a full kitchen with essentials & gas stove, two large porches with seating, parking on site, a grill, and a fire pit. Walking trails throughout the property. Boating, hunting, fishing, wildlife, and nature viewing are nearby. 4 miles from ART airport, 5 miles from Sackets Harbor & Lake Ontario, 7 miles from Watertown & Black River, and 20 miles from Fort Drum.

🌙 Olde Salem A-Frame Cottage 🔮 near Lake Ontario

You are steps away from witnessing the greatest sunsets along North Sandy Pond (across from Lake Ontario) when you stay at our relaxing, unique, and cozy A-frame - inspired by all things magical and earthy. Sit by the backyard fire, sip coffee by the electric fireplace, read a book in the bedroom nook, play board games, dance in the kitchen, and enjoy four seasons of nearby activities such as fishing, kayaking, boating, jet skiing, hiking, swimming, ice fishing, snowmobiling, and snowshoeing.

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!

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.

Bear Hill One Room Cabin with Hot Tub

Unplug during your trip in the middle of the woods, tiny rustic one room cabin with hot tub sits in Little John Forest and borders the Boylston snowmobile trail system Perfect for snowmobiling and 4 wheeling. Acres of state land for hunting. Cabin is 22 miles from the Salmon River in Pulaski NY. Sleeps 4 with a sofa bed and a bunk bed that holds a queen and full mattress. Equipped with electricity, running water,WIFI. A bathroom with shower.

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.