Holiday rentals in Pillar Point

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Top-rated holiday rentals in Pillar Point

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Top guest favourite
A white, single-story house with a metal roof is framed by large trees. A welcoming porch is visible, featuring steps leading up to the entrance. Lush green grass surrounds the home, highlighting its peaceful rural setting.
Cottage in Dexter
5 out of 5 average rating, 38 reviews

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 in nearby Sackets Harbor. 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.

Top guest favourite
The gray historic home features a charming front porch with a welcoming entrance. A paved driveway leads to a small gravel area, providing space for one vehicle. Lush green grass surrounds the property, enhancing the inviting appearance of the house.
Home in Sackets Harbor
4.96 out of 5 average rating, 23 reviews

Renovated home with lake views in ❤️ of Sackets!

Welcome to our charming 2BR, 1.5BA historic home in the heart of Sackets Harbor! Just steps from restaurants, bars, and shopping, with stunning water views, our 1,395 sq ft home sleeps up to 6 guests. Enjoy new appliances, ductless AC, washer/dryer, gas fireplace, off-street parking, and TVs in the living room and master. Perfect for a relaxing family getaway. Gated boat parking available. Book your stay today! *Update: second bedroom has a dedicated wall air conditioner for your comfort.

Superhost
A spacious living area features a comfortable couch facing a television, complemented by a wooden coffee table. Light wooden flooring enhances the inviting atmosphere. A queen bed is positioned in the background, partially visible through an open archway, with natural light streaming in from a nearby window.
Apartment in Chaumont
4.73 out of 5 average rating, 51 reviews

Cozy and elegant!

Welcome to our cozy studio just minutes away from the serene Lake Ontario and public boat launch! Nestled close to town, you'll find convenience with restaurants, a hardware store, and charming gift shops nearby. Inside, you'll discover a comfortable queen bed and a plush couch (not a pull-out) perfect for relaxation. Fully furnished and equipped with Wi-Fi, our studio offers everything you need for a comfortable stay. Plus, with ample parking space, there's room for your trailer too!

Top guest favourite
The guest room features two twin beds made with rustic log frames, accented by patterned throws. Light wood paneling covers the walls, and a ceiling fan hangs above. A small nightstand is placed beside one bed, with a lamp and decorative items displayed.
Guest house in Chaumont
4.99 out of 5 average rating, 132 reviews

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!

Top guest favourite
Home in Adams Center
4.86 out of 5 average rating, 196 reviews

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.

Guest favourite
A single-story home is presented, featuring a covered front porch with wooden railing. The exterior showcases a neutral-colored siding and a brown shingle roof. Windows with white trim and dark shutters are visible. A brick walkway leads to the entrance, bordered by lush green grass.
Home in Sackets Harbor
4.79 out of 5 average rating, 33 reviews

Cozy Lake's Edge

Keep it simple at this peaceful and centrally-located place. Fabulous Lake Ontario home in an outstanding location in Sackets Harbor within 2 miles from main street cafes, waterfront dining and shopping, boat launch and marina, library, church and historical sites.This 1 bedroom home has gorgeous views of Lake Ontario, amazing shoreline that is like a beach, gradual water depth great from swimming and kayaking. You can enjoy the night skies sitting around your fire pit.

Top guest favourite
A sandy shoreline extends along a calm lake, with sunlight glistening on the water's surface. Trees line the beach, providing shade. A small fire is visible on the beach, surrounded by gathered branches. The serene atmosphere is enhanced by the expansive view of the horizon.
Home in Dexter
5 out of 5 average rating, 14 reviews

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.

Top guest favourite
A spacious deck features wooden flooring and a sturdy railing overlooking Lake Ontario. Comfortable seating is positioned for relaxation while enjoying the expansive water views and clear blue skies, providing a serene setting for outdoor leisure.
Home in Dexter
4.95 out of 5 average rating, 65 reviews

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.

Top guest favourite
A historical stone structure with Gothic architectural features is framed by lush greenery and colorful flower beds. The building is highlighted by soft evening light under a vibrant sunset sky, creating a serene backdrop for the peaceful surroundings.
Home in Chaumont
4.99 out of 5 average rating, 86 reviews

The Chez Heron. A small gothic castle in Chaumont

The Chez Heron was built in 1872 out of local limestone and was made to resemble a small Gothic castle. It is nationally registered as a historical structure. It is set up for 1 couple looking for a peaceful getaway. Full kitchen. We will have a bottle of champagne chilling for you .We have an outside Hot Tub and Fire area for you to relax and enjoy. Located within the vilage of Chaumont and walking distance to several local businesses.

Top guest favourite
A stunning sunset casts vibrant hues of orange and pink across the sky, reflecting beautifully on the calm surface of Lake Ontario. Soft clouds create a textured backdrop, complementing the tranquil waters that stretch into the horizon.
Home in Dexter
4.98 out of 5 average rating, 122 reviews

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.

Top guest favourite
An aerial view of the home reveals a rustic cabin with a green metal roof surrounded by trees. A spacious yard features a deck, outdoor seating, and a gentle waterway visible nearby, creating a serene natural setting.
Home in Sackets Harbor
4.94 out of 5 average rating, 33 reviews

Cozy Lakeview/AC Home Stays, Next to Fishing Site

^< Welcome to our home in Sackets Harbor. Our house has a beautiful scenic waterside view on a wildlife reserve about 3 miles from Downtown Sackets Harbor! You can find waterfront dining restaurants, local stores, historical sites on the battlefield, and boat lounge docks for small to large watercraft. At Sackets, a lot is going on throughout the season, including festivals and other entertainment.

Guest favourite
An open dining area features a large wooden table surrounded by white wicker chairs. Large windows offer views of the sunset over the lake, casting warm colors across the space. A decorative sign hangs above the windows, enhancing the serene lakeside ambiance.
Home in Chaumont
4.83 out of 5 average rating, 78 reviews

Bay Edge Cottage

Unwind in the beautiful village of chaumont with stunning views of sawmill bay. This lakefront property boasts a brand new dock which you can tie a boat to and a peaceful atmosphere making it the perfect place to sit with family and friends to watch the boats come in and out of the marina, hit up amazing local eateries, and enjoy the peacefulness of sawmill bay.

Popular amenities for Pillar Point holiday rentals