Cottage holiday 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.

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.

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.

Executive Cottage in a CITY on 100 Acres

NO ADULT/TEENAGER Group booking. No events/party. Great Bed & Breakfast facility Our preferred customers are family ( parent with kids, grand kids). Only guests booked/paid are allowed ( NO visitors) 4 bedroom with 3.5 washroom, on 100 acres (gated property) Internet ( free 2 GB per night )-Extra usage $3/GB Finished basement also available (Sep entrance/washroom )- at Extra cost $150/night for min 3 night +75 cleaning Person booked must be present at check-in . ID may be required

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!

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.

Rustic 5BR Cottage | Cozy Hot Tub+ Autumn Backyard

Escape to nature in our private 5BR and 4WR riverside cottage – perfect retreat for groups with premium amenities! ✓ Entire cottage to yourself – full privacy! ✓ 5 spacious bedrooms with 6 double beds and 4 washrooms ✓ Cozy Family & Living Rooms ✓ Fully equipped kitchen & High-Speed Wi-Fi ✔ Dining area with seating for 8 guests ✓ Private Backyard with hot tub & Indoor games ✓ Scenic riverfront setting near Eldorado Park ✓ Safe neighborhood Book your stay and make unforgettable memories!

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.

Grand River Cottage near Cambridge/Brantford/Paris

Escape to our cozy Grand River cottage — a peaceful retreat for nature lovers! Nestled beside grand river, our cottage offers tranquility just minutes from everywhere: 3 minutes drive to Glen Morris, 7 minutes to Paris, 10 minutes to Brantford, and 10 minutes to Cambridge. Enjoy fishing, hiking, biking, and spotting local wildlife — or simply relax by the riverside and unwind. The perfect blend of nature and convenience awaits. Book your riverside cottage getaway today!

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco