Holiday houses in Pillar Point

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Top-rated holiday rentals in Pillar Point

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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, 90 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, 127 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.

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!

Top Guest favourite
A dining area is depicted with a round wooden table set for four. Light gray chairs surround the table, complemented by decorative placemats. A woven light fixture hangs above, and a door with a window allows natural light to enter. A small closet and a wall-mounted plant holder are visible.
Home in Kingston
4.98 out of 5 average rating, 152 reviews

City Retreat With Board Games

Welcome to our newly renovated detached home! The fully stocked kitchen, smart TV, board games and patio offer convenience and entertainment. Unwind on the patio with high end patio furniture and a barbecue. Enjoy our central location in Kingston for a memorable stay. This property has a garden suite on the back of the property with a separate entrance and backyard space. We look forward to hosting you! Fully licensed for short term rentals with the City of Kingston - License #LCRL20250000092

Top Guest favourite
A light-filled living area features a sofa with decorative pillows and a plush, tufted coffee table. Natural wood flooring complements the neutral decor. A ceiling fan hangs overhead, and windows allow ample sunlight, enhancing the inviting space.
Apartment in Watertown
4.98 out of 5 average rating, 271 reviews

Stylish&Modern Apartment Near Fort Drum Watertown

Nice Apartment located only 10 minutes away from Fort Drum! This place beats any hotel stay! It’s in a centralized location, clean and stylish! For any tourist visiting any upstate New York attractions, or simply looking for home away from home, this is your place! There are 4 camera’s installed. One facing the driveway entrance, one facing each door entrance one facing the driveway. If you decided to book please mention if you'll have guest visiting and how many vehicle's you'll have.

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, 153 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
A welcoming living room features a large sectional couch facing a 70-inch TV mounted on the wall. Light streams through several windows, illuminating the space. A cozy entrance area is visible, along with decorative hooks and a potted plant enhancing the atmosphere.
Apartment in Watertown
4.94 out of 5 average rating, 349 reviews

Cozy Apartment with No cleaning fee

Simple elegant space that can comfortably accommodate five adults. Two bedrooms one with a king bed and other with a twin size day bed with trundle twin bed slide in , and large deep couch. Each room has a TV. This unit is in the second floor, with a parking area for two cars, washer, dryer and 70" tv in living room. We are located ten minutes away from Fort Drum and most local attractions. Please do not leave pets unattended Pet fee $30 per pet limit 2 non-refundable

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, 147 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 serene waterfront view is captured with the sun setting over Chaumont Bay. Silhouetted trees frame the scene, while a path of stones leads towards the water. A play structure is visible nearby, providing a family-friendly outdoor space.
Tiny home in Three Mile Bay
4.94 out of 5 average rating, 108 reviews

Tiny Hideaway - Cozy Waterfront Escape

The tiny hideaway is an adorable tiny camp (might have to duck if you are over 5feet 11 in doorway and bathroom) on Chaumont bay. Year round camp. It’s great for a small family or a get away for a couple. Great private water front to enjoy with a dock. Bring drinking water as it’s on a shore well and is not drinkable. ICE FISHERMAN: I do not suggest accessing the ice in-front of the camp. Most guest access at long pt 1.5 down the road.

Top Guest favourite
A cozy living area is featured with a dark sectional sofa and light wooden flooring. The open space leads to a kitchen in the background, equipped with wooden cabinets and seating. Natural light is let in through sliding glass doors, opening to a view of the outside.
Guesthouse in Adams
5 out of 5 average rating, 142 reviews

Adams NY. The Collie Cottage Guest house.

Private and quiet apartment. 20 minutes from Watertown . 5 miles from Southwick Beach State park. Great Fishing near by. Henderson Harbor, Pulaski, Lake Ontario. Golf Coarse near by, Skiing at Dry Hill, Snowmobiling at Barns Corners. All new appliances and furniture. Very cozy and comfortable apartment. Back patio with awning and back yard. We call it the collie cottage after our beautiful Collie dog and our love for the breed.

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, 114 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.

Popular amenities for Pillar Point holiday rentals