Holiday houses in Pillar Point

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Top-rated holiday rentals in Pillar Point

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A serene lakeside view features a wooden dock extending into calm waters, reflecting warm sunset hues. Smooth stones line the shoreline, with a kayak resting nearby. Gentle trees frame the scene, creating a peaceful backdrop for relaxation.
Cabin in Three Mile Bay
4.98 out of 5 average rating, 118 reviews

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

Top Guest favourite
A warm kitchen displays an orange accent wall complemented by a wooden dining table surrounded by white chairs. A black refrigerator and a vintage hutch add practicality, while natural light streams through bright windows adorned with floral curtains.
Home in Watertown
4.94 out of 5 average rating, 89 reviews

Whole House Hosted By Lisa

Relax with the family at this peaceful home located in the Town of Watertown. 2 bedrooms with 1 queen & 1 full size bed. Newly renovated & beautifully landscaped. Private driveway just 5 mi from Shopping District, Restaurants, & Downtown Watertown. 3 mi from Dryhill Ski Area & just 5 min. from Samaritan Hospital. Not far from airport or Lake Ontario Offered is a Full Kitchen, 3 Wifi smart TV's in bedrooms & living room, Internet, fireplace, front & rear entrance, decks on front & back doors, AC

Top Guest favourite
An outdoor pool area is showcased, surrounded by well-maintained greenery and tall conifer trees. A sun deck with wooden steps leads to the pool's edge, which is framed by potted plants featuring vibrant flowers. Comfortable seating can be seen in the background.
Apartment in Watertown
4.89 out of 5 average rating, 125 reviews

Northside Lodging

Keep it simple at this peaceful & centrally-located place. Northside Lodging is a quiet, clean, comfortable, beautiful & relaxing lodging spot with multiple amenities, conveniently located within minutes of shopping, dining & pharmacies, also located within a short drive of the areas attractions & landmarks including Ft. Drum, Lake Ontario, Fishing & Marina access points, Hospitals and I-81 corridors. Patio & outdoor accessibility and off-street parking included. Open to adult visitors, no pets.

Guest favourite
The living area features two light-colored sofas arranged around a wooden coffee table. A ceiling fan hangs above, and large windows allow natural light to illuminate the space. The ceiling is finished in warm wood, complementing the neutral walls.
Home in Watertown
4.86 out of 5 average rating, 154 reviews

Cozy Cottage next to Thompson Park

Cozy Cottage located only 15 minutes away from Fort Drum! ONE block away from Thompson Park/Zoo and only a 10min drive to Watertown mall! Fishing boats fit in Driveway. Bed is Firm! For any tourist visiting any upstate New York attractions, or simply looking for home away from home, this is your place! Two camera are installed; One in front entrance and one in the back. If you decided to book please mention if you'll have guest visiting and how many vehicle's you'll have, two vehicles max!

Top Guest favourite
A serene lakeside scene is captured at dusk, showcasing a vibrant sunset with deep orange and pink hues reflected on the calm water. The rocky shoreline stretches along the lake, while silhouettes of trees and structures are visible in the background.
Guesthouse in Chaumont
4.97 out of 5 average rating, 102 reviews

Lakefront Getaway

This completely private attached guest house is newly renovated and just steps away from Lake Ontario.  Some amenities include: Private entrance and deck Large yard Easy water access to swim, fish, & kayak Fabulous views of Chaumont Bay Spectrum wifi & cable Outdoor Grill & Fre Pit Air Conditioning Full Kitchen Smart TV in each bedroom 10 miles from the St Lawrence River Wonderful restaurants and the Thousand Islands are just a short drive away. Come enjoy the beauty Upstate NY has to offer!

Guest favourite
A spacious living area is highlighted by a deep blue sectional couch adorned with decorative pillows. Large windows allow for abundant natural light and provide a view of the water. A round dining table and a decorative plant enhance the inviting ambiance.
Cottage in Chaumont
4.94 out of 5 average rating, 152 reviews

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.

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.
Guesthouse in Chaumont
4.99 out of 5 average rating, 123 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!

Guest favourite
Home in Adams Center
4.85 out of 5 average rating, 142 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.

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
4.97 out of 5 average rating, 112 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.

Guest favourite
A spacious dining area is showcased, featuring a long wooden table with intricate carvings. A chandelier hangs from a green ceiling above. The room is illuminated by natural light from large windows, revealing exposed brick walls and a cozy seating area in the background.
Home in Kingston
4.9 out of 5 average rating, 167 reviews

Victorian Boutique Apartment-Steps from Lakeshore!

Enjoy the elegance of a by-gone era while staying in this stunning Victorian loft, located on a quiet leafy boulevard in the heart of Kingston’s most historic and architecturally eclectic neighborhood! Beautifully decorated and featuring a bright vaulted grand living room with a tin clad mezzanine supported on original exposed beam, exposed brick, period furniture, and a stunningly unique black-and-white tiled bathroom.

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, 60 reviews

Black Bay Chalet- Ice Fishing Paradise!

Relax on the couch while enjoying the breeze off the lake through the sliding doors. All while hearing the waves crash just a few feet away. Admire the stunning panoramic views of Lake Ontario from our cozy living room or outside on the back deck. The views never disappoint! This home is a great place for couples or families to create lasting memories and enjoy the calming effects of the lake.

Top Guest favourite
A red Adirondack chair is positioned on well-manicured grass, facing a serene view of Lake Ontario. Nearby, a stack of smooth stones rests on a large rock, adding a natural element to the tranquil setting. The calm water stretches out under a clear sky.
Cottage in Dexter
4.98 out of 5 average rating, 59 reviews

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.

Popular amenities for Pillar Point holiday rentals