Cottage vacation rentals in Milton

Cozy Cottage on Main St

Studio-style cottage in the heart of Jordan Village. This charming private suite is directly across from the Lincoln Museum and Cultural Centre and steps away from waterfront hiking on the Twenty Valley Trail. The cozy cottage offers privacy and a private outdoor terrace while remaining within walking distance of all the village's beautiful amenities. Cozy up in the backyard with the fire table on or stay indoors with the fireplace roaring. The cottage is private & perfect for a weekend retreat.

Explore 4BR 3BA Cottage Surrounded By Nature

Relax with the whole family at this peaceful luxury cottage with beautiful views of nature. Perfect getaway from the city. Enjoy the outdoors with hiking, biking, and walking at many trails. Minutes from Belfountain conservation area, and Caledon Ski Club. Enjoy the scenic drive on Forks of the Credit Rd with views of the river. Have a good time in the backyard with friends and family with just under 1 acre lot. Offers 4 Bedrooms and 3 washrooms. Fully Updated Cottage. Smart TV & Internet

Grimsby Beach Cottage

Enjoy a day at a quiet hidden beach followed by a night around the bonfire in this charming, cottage-style home. With this convenient location, you’ll appreciate the city-like accessibility, located minutes from public beaches and a close drive to wineries, hiking trails and the quaint town of Grimsby with an array of restaurants, pubs, and cute shops. Minutes from the Bartlett highway exit, you’re also only a short drive from Port Dalhousie, downtown St. Catharines, Niagara Falls and Hamilton.

The Cottage in High Park - free Parking

Escape to our city oasis! Nestled in High Park/Bloor West Village, our charming cottage offers urban tranquility just 15 mins from downtown by subway. Ride a bike to the beach, wander the tree-lined streets, explore boutiques in the local village, or forest-bathe deep in the trails of High Park. Return to cozy comfort, a wood-burning fireplace, a game of charades, or step out to a covered patio, perfect for BBQ creations or a movie under the stars. Your urban-cottage escape begins here!

10 Acres Private Bruce Trail Cottage for 14 Guests

Discover a hidden gem on 10 acres along the Bruce Trail, featuring a private creek and solarium with wrap-around windows ideal for yoga or a private spa. With plenty of parking and a fully equipped kitchen, this property is the perfect retreat. Only 45 minutes from Yorkdale Shopping Mall, it’s an ideal spot for summer adventures, fall colours or a cozy Christmas getaway. Immerse yourself in nature’s beauty, just a short drive from the city, offering the perfect balance of peace and convenience.

Riverside Retreat

Escape to this cozy, newly renovated basement suite nestled by the river. With its own private entrance, this peaceful getaway offers direct access to the water—perfect for a morning paddle in the provided canoe. The spacious backyard is a hidden gem: beautifully landscaped, quiet, and ideal for relaxing under the stars or enjoying a quiet coffee at sunrise. Whether you’re seeking adventure or tranquility, this charming riverside retreat delivers both. New - We just added a hot tub to the yard!

The Stone Cottage in Vineland

Relax in this two bedroom three bathroom home that comes with a fully-equipped kitchen, dining room, laundry, and spacious living room with gas fireplace. Enjoy access to a beautifully landscaped backyard, with private deck overlooking acres of quiet farmland. The perfect modern day getaway, The Stone Cottage sports up-to-date amenities that combine with the peacefulness of country living, to create the ideal vacation retreat, within easy reach of everything the Niagara Region has to offer!

Waterfront home with Pool, Boat Ramp/Canoe/Kayak

This vacation home has beautiful views, southern exposure , flower gardens and greenery all around. Surrounding the pool in the back yard beside the lake there is a flagstone patio area with a campfire pit. A perfect spot for watching dreamy sunsets. There is a fabulous pool 17x36 ft with a big deck surrounding it. A picnic table and BBQ on the upper patio terrace by the cottage, overlooking the lake. We have lots of gathering places to lounge around and relax in the outdoor patio furniture.

Barndominium retreat in Erin, hot tub & sauna

WOOD BURNING SAUNA, HOT TUB, COLD PLUNGE ⭐️ONE OF A KIND, 1800 sq. ft BARNDOMINIUM on 18 acres of total privacy! Serene, country getaway in the picturesque countryside of Erin⭐️Full-size kitchen,harvest table,spotless bathroom, couch & chairs, floor to ceiling glass doors⭐️Cozy loft with tv, comfy queen bed & oversized couch. ⭐️Soaring trees & trails,grain bin bar on concrete pad with fire-pit, tables & chairs.Wood deck with patio set.Separate cabin with double bed. You won’t want to leave!

Chestnut Cottage

Quaint Cottage in the heart of wine country. This is a recently renovated 4 bedroom, 2 bathroom house. Basement was just finished in 2021. The house is bright and clean and furnished with a modern country farmhouse feel. WIFI, cable TV, Netflix, full kitchen and central a/c are just some of its amenities. This house would be great for couples, a group of friends or even a family looking for a relaxing getaway in the country, but still close enough to numerous activities for all to enjoy.

Lake Front Heaven - Gateway to Niagara/Vineyards

A magical cottage with its own beach house on Lake Ontario. This place is special! The beach house an extra bedroom and full bath which is available during the spring/summer months. There’s a pier, boat slip, fire pit, picnic table and plenty of outdoor seating. All of this 50 minutes from downtown Toronto, 40 minutes from YYZ International airport and 25 minutes from the world famous Niagara falls. The scenic is a great base to explore the Niagara region. Operator License 24-305205

Cottage in Toronto’s West End •Walk to BMO Field•

A hidden cottage retreat in Toronto’s vibrant west end—just 15 minutes walk to BMO Field with no traffic or crowds. Tucked away on a quiet, tree-lined laneway, this fully renovated 1800s cottage offers a rare mix of charm, privacy, and location. Enjoy the energy of the city—Queen West, Ossington, Liberty Village —then come home to your own peaceful escape. Perfect for World Cup visitors, families, and remote workers. Stay close to everything, without sacrificing calm and comfort.