Family-friendly holiday rentals in Oswego

Spacious! Walk to Downtown Shops & Restaurants!

Experience the perfect blend of modern comfort & Victorian charm in this expansive 1400sq ft upper apartment. Featuring 3 bedrooms & 2 full bathrooms, the space is ideal for families/groups. Fully-equipped kitchen & large, covered balcony with fire pit and BBQ offers the perfect spot to relax. Centrally located, you’ll be just a 5-minute walk from downtown shops & restaurants. Whether you’re here for a short getaway or a longer stay, this home provides the perfect base for exploring the area.

🌙 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.

The Gingerbread House

The Gingerbread house is known as the Nesbitt house Built and maintained by the Well known author and city Historian Rosemary Nesbit. This grand home was totally renovated to modernize but keep all the old charm! It boasts 3 full bathrooms and 4 bedrooms! The location in center of Oswego affords walking the 2 blocks to downtown and 4 blocks to the lake and marina. There are ample Bistro, and bars in close walking distance! Come enjoy the Oswego neighborhood nestled in the historic district!

Lakefront Cottage- Come Relax at The Shore House

Gorgeous, New Home w/65 ft of private/direct Lake Ontario frontage. Stylish/modern decor new home w/ attention to detail. Chef's kitchen. Gorgeous Panoramic views. Massive furnished deck to listen to the water, enjoy a morning cup of coffee, meal, or glass of wine. Experience breath taking sunsets. Rocky beach just steps away from the deck with super easy access to water activities. Huge fire pit set on limestone pad overlooking lake. Tranquility on the lake and close to all Oswego offers.

GEORGEous Sanctuary Lake Ontario

Experience breathtaking views of the lake from this serene, recently renovated home perched on a bluff. The views are only the beginning! Walk down to the water, explore the rocky private beach, swim, and kayak. The house is near a world famous bird sanctuary with hiking trails. Close to Oswego, Fulton, Pulaski, and the Salmon river/fish hatchery. Only 40 min from Syracuse! The home is near a couple of apple orchards, and minutes from Port Ontario, Selkirk and Mexico Point State Parks.

Luxurious Private Apt 4 Best King Bed WiFi ROKU TV

Relax with the whole family, snuggle w a friend, or enjoy some time alone. This peaceful private apt suite is full of amenities you will love. Free 24hr parking, Most Comfortable King Bed EVER :), Sofa Queen Pullout bed, WiFi, 48 inch ROKU TV, Keurig, Full kitchen, Pots, Pans, 6 Place settings..., Dishwasher, Armoire, Chest of Drawers, USB ports on night stands, Huge Luxurious Shower w RGB lights - you can set the mood:), Bidet Toilet w Heated Seats, Dining area w 4 chairs Plus Much More

#4 Studio Apartment

Casual & comfortable studio in a country setting. Private outside entrance with 2nd story covered deck. Shared back yard and patio. Great to relax or hang with your pet. ($30 pet fee) 5 min to beautiful Lake Ontario and boat launch. 12 min to SUNY Oswego. 5 minutes to the Oswego Speedway. Antique shops and wineries in the area. Queen size bed, microwave, college size refrigerator, full bathroom with shower. No third party rentals. Guest booking must be staying on premises.

Oswego Downtown District

Nestled in the heart of the downtown district with beautiful views of City Hall. Minutes from the acclaimed Salmon fishing in either Lake Ontario, or the Oswego River. A short drive to the Oswego Speedway or SUNY Oswego. Inside our home you are greeted by tasteful decor, a convenient gas fireplace, two full baths, two bedrooms sleeping six, and a dining area with ample seating. Our kitchen is stocked with all the necessities to prepare a meal, or a short walk to many eateries.

Stars and Sage Farm Hippie Hideaway

Living off the grid in a cozy cabin surrounded by nature sounds like a unique and peaceful experience. The addition of chickens, geese and a beekeeping experience adds to the charm of the stay. This is a small Hobbie Farm with a cute rustic cabin with a compost toilet and a mini woodstove. Nestled in its own little yard wildlife may be about. Deer , fox, even little mice and bunnies scurry about. We want our guests to understand this is a rustic listing with an off grid menu.

Home Sweet Home

Bring the whole family to this great place with lots of room for fun. No hidden fees. 3 large bedrooms and 2 full baths with washer and dryer. It does list 6 but you are able to sleep more especially with kids. This is pet friendly. what your pet leaves please pick up. Close to the speedway. Quiet neighborhood. BBQ Grill and utensils provided. Fire pit and setting area in the back with wood to purchase. Stay for a few nights or a few months.

Breathtaking Waterfront Cabin On Lake Ontario

Get ready to be WOWED!!! Welcome to the most breathtaking lakefront cabin on the coastline of Lake Ontario. This century-old cabin boasts panoramic views of the lake from the top of the bluffs with a rock beach right in front of the house. Spend cozy days inside the cabin overlooking water views from every window, outside at the many common areas, or on the water right in front of the cabin.

The Reid-Tanner House

The Reid-Tanner House exemplifies the timeless beauty of Oswego's golden age. Located in the historic Washington Square District, the double lot and buildings were owned by the Reid family, founders of Reid & Company hardware established in the late 1800s. The Reid family owned the property for fifty years before transferring to the Tanner family who also lived in the house for decades.