Cottage holiday rentals in Richmond Hill

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Top-rated cottage rentals in Richmond Hill

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Superhost

Cottage in Port Perry

4.77 out of 5 average rating, 13 reviews

Pet friendly, Hot Tub and Unli Wi-Fi w/Great View!

Discover the perfect pet-friendly haven just 45 mins from Downtown Toronto with hot tub, unlimited Wi-Fi, stunning sunset & sunrise views! Lakeridge Hideaway is 1km from 2 ski resorts and steps to the private dock on Chalk Lake. Sleeps 6 adults + 4 children, featuring open-concept living, fully renovated kitchen & rooftop outdoor shower. Explore mountain bike trails & enjoy the canoe & kayaks. Cozy up with the woodstove, 55” smart TV with Netflix & Disney+ and DVD library. Escape the city today!

Cottage in New Tecumseth

4.84 out of 5 average rating, 58 reviews

THE WHITE HOUSE ON THE HILL Beautiful Country Home

Located in the quiet town of Beeton, Ontario, this gorgeous luxury country home is located on 2 acres of private property. Its warm county feel will make your stay a memorable experience. Enjoy stunning sunrise mornings sipping coffee on the private lounging/dining porch and cozy sunset evenings around the fire pit telling stories and making memories. Located less than 30 min. from GTA. You will enjoy the best of both worlds: Country living only minutes away from outdoor activities and shopping.

Guest favourite

Cottage in Goodwood

4.83 out of 5 average rating, 75 reviews

Family fun! Hot tub/snooker table/Movie Room!

We offer discounts for 3 nights and more :) Our house is built like an old English-style stone house cottage and is approximately 1 hour from downtown Toronto. The house is great for special occasions and getting away from it all with a group of friends or family. We've included some fun extras such as a projection theater room, slate snooker table, cable TV, BBQ and an outdoor hot tub for those nights you want to relax. We supply seasoned firewood for the indoor wood fireplace, so have fun :)

Guest favourite

Cottage in High Park North

5 out of 5 average rating, 11 reviews

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!

Cottage in Richmond Hill

4.4 out of 5 average rating, 15 reviews

Cottage Bungalow Retreat

"Escape to Nature: Bungalow Retreat with Outdoor Party Space" Experience the best of both worlds in our bungalow retreat, where nature meets convenience. Situated on five acres of scenic land, this cozy hideaway resembles a charming cottage. Whether you're looking for a quick getaway or a longer stay, our space accommodates all needs, including outdoor parties or private events. Rest assured, ample parking ensures a stress-free experience for you and your guests. DM for private party price.

Guest favourite

Cottage in Kettleby

4.89 out of 5 average rating, 56 reviews

Gorgeious 5 Bedroom Countryside Cottage in King ON

Gorgeous 5-Bedroom Countryside Cottage - located in a quiet family neighborhood at a beautiful 3-acre lot with a huge lawn and woodlot, Lots of Parking, a minute's drive to The Manor Event Center, Hwy 400 & 427, groceries, restaurants, Golf Club, beautiful trails, Green Belts, farmers markets, Apple and strawberry picking. 20 min. to Lake Simcoe boating and fishing, many nearby shopping malls, TTC Subway, Go Station, and Canada's Wonderland. Please Note: Strictly no drug and booze parties.

Superhost

Cottage in Brampton

4.88 out of 5 average rating, 8 reviews

100% Private & Spotless ~ 5BR Cottage ~ Hot Tub

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!

Superhost

Cottage in Uxbridge

4.78 out of 5 average rating, 80 reviews

Cozy Hobby Farm Cottage in Uxbridge

*4 SEASONS COTTAGE*Stunning cottage retreat at Uxbridge,where you can enjoy the perfect balance of tranquility and entertainment.Our 4-bedroom cottage sleeps up to 12 guests, it's the ideal location for families or groups of friends looking to unwind and make lasting memories. You can also take advantage of our BBQ space,you can grill up mouthwatering burgers and steaks while taking in the fresh country air.The barn is not part of the rental and there are no animals inside or in property.

Superhost

Cottage in Innisfil

4.71 out of 5 average rating, 111 reviews

20-Acre Resort-Hot Tub, Sauna, Pool, Firepit

Wake up to birdsong 🌲 and sip your coffee surrounded by peaceful forest views. This private 20-acre escape in Innisfil is your family’s playground for rest, reconnection, and relaxation. Swim, soak, explore—your unforgettable getaway starts here. ✅ 20-acre private woodland in Nottawasaga Conservation Zone ✅ 5 min – Belcroft Estates wedding venue ✅ 10 min – Innisfil Beach Park, grocery stores, & local shops ✅ 20 min – Tanger Outlets & Friday Harbour ✅ 1 hr – Toronto

Superhost

Cottage in Richmond Hill

4.94 out of 5 average rating, 156 reviews

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

Cottage in Keswick

4.75 out of 5 average rating, 79 reviews

Cheerful and by the Water 4 Bedroom Cottage

Newly renovate Spacious cottage near to Toronto. This Gem Of A Home On A Massive 100 By 150 Foot Lot On The Canal. Have Direct Access To Lake Simcoe. Maximize Your Stay With Year-Round Activities Including Boating & Water Sports, Fishing, Ice Fishing, Skating, Atving (your own) & So Much More! S/S Appliances: 36 Inch 6 Burner Blue Star Stove, 36 Inch Fresh Door Fridge, Built-In Dishwasher. Stacked Lg Washer & Dryer. Electrical Blinds In Living & Master.

Cottage in East Gwillimbury

4.3 out of 5 average rating, 10 reviews

Perfect 3 Acre Cottage Home 15 mins from the beach

Newly renovated cottage home only a 15 minute drive away from Georgina Beach and Lake Simcoe. Can fit up 12 cars on the driveway. You can find restaurants, grocery store and LCBO nearby. Enjoy time and find relaxation with family and friends in our spacious 3 acre yard with a playground, trampoline, patio, BBQ, and pool. Tenants occupy the basement.