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Cottage holiday rentals in Oakwood

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Top-rated cottage rentals in Oakwood

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Top guest favourite
Cottage in Trent Lakes
4.99 out of 5 average rating, 135 reviews

Panoramic Lake Views Inside & Out, Cozy & Relaxing

Enjoy the panoramic views of Lower Buckhorn Lake with the whole family! Relax perched atop the rocks of the Canadian shield & nestled among the tall pines. This newly updated waterfront cottage features 3 bedrooms & an open concept living space. Over 280 feet of waterfront for you to enjoy the sunrise & sunset views & fish off the dock! Get cozy on the couch, play games, or watch movies. Take a stroll around the island. Hi speed Wi-fi to work or play. 6 minutes to town, less than 2 hrs from GTA.

Guest favourite
Cottage in Brechin
4.92 out of 5 average rating, 172 reviews

COTTAGE ON LAKE SIMCOE -4 BEDROOMS /2WSHRMS

Welcome to our cozy cottage in Simcoe County, just a short drive from Toronto. It's the perfect spot for bringing together family and friends. Here, laughter fills the home, and nature's beauty is right outside your door. Dive into clear waters for some fun kayaking and boating, and wake up to beautiful sunrises from our private dock. Take a walk on scenic paths, enjoy outdoor BBQs, and paddle around in our kayaks. Book your special getaway today and start making heartwarming memories that last.

Guest favourite
Cottage in Georgina
4.95 out of 5 average rating, 119 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

Top guest favourite
Cottage in Kirkfield
4.98 out of 5 average rating, 108 reviews

Brookside on Balsam. Rest.Relax.Restore.

Clean, modern, open concept, vaulted ceilings, chef's kitchen views. 2 bedrooms with additional sleeping space on lower level. 2 separate bathrooms include soaker style tub and walk in tiled shower. Nature abounds! A charming brook, lakeside views, swimming, BBQ, outdoor dining, firepit** fire ban for April** year-round hot tub. Bicycles, kayaks and snow shoes are yours depending on the season. Short walk to Balsam Lake Provincial Park. Minutes to village shopping. Consistent Super Host!

Guest favourite
Cottage in Washago
4.99 out of 5 average rating, 145 reviews

Relax at The Rock: Muskoka Waterfront Cottage

Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

Top guest favourite
Cottage in Bracebridge
4.99 out of 5 average rating, 136 reviews

Tiny Luxury Cottage with Hot Tub

This tiny luxury 2 bedroom cottage with loft is perfect for a romantic couple or small family getaway. Nestled on 1.5 acres among majestic trees and granite outcrops, creates beautiful views from the deck with BBQ, fire pit, hot tub or massive windows throughout the cottage. Water dam and river across the road create relaxing waterfall sounds that are heard from deck or enjoy it close up from the private shoreline deck and dock. Explore the Muskoka River on the kayak, SUP or river tubes.

Top guest favourite
Cottage in Haliburton
4.96 out of 5 average rating, 193 reviews

Highlands Lakefront | Sauna | Woodstove | 3BR

Lakefront, A-frame, 4 season cottage in the Haliburton Highlands with convenient access to Haliburton. Indoors ➤ Floor to ceiling windows (20ft+) ➤ 3BR - 1 King, 2 Queens ➤ Fireplace - wood provided ➤ Fully stocked kitchen ➤ Linens provided ➤ Reliable internet Outdoors ➤ Screened-in lake view porch ➤ Sauna seats 6 ➤ Bonfire pit - firewood provided ➤ Weber BBQ ➤ Great swimming & fishing from our 40ft dock Our pricing includes HST. 2.5 hrs from GTA on Long / Miskwabi Lake

Top guest favourite
Cottage in Cobourg
4.98 out of 5 average rating, 315 reviews

Hideaway: Upscale Victorian Coach House

🏆 Featured by Explore Ontario as a Top 10 Stay in 2022 | Described by Narcity Canada as “Like Living in the Holiday” Follow us @coachhouse_cobourg ✨ Your Charming Countryside Retreat Awaits Step into a 150-year-old coach house nestled on a stunning 5-acre Victorian estate. This beautifully restored guest house combines historic charm with modern comforts, offering a private hot tub, a cozy fireplace, and a serene escape minutes from Cobourg’s vibrant downtown and pristine beaches.

Top guest favourite
Cottage in Kawartha Lakes
4.93 out of 5 average rating, 141 reviews

Ke's Rustic Retreat in Kawartha Lakes

WELCOME TO KE’S PLACE! This rustic, private, 4 season, lakefront cottage on Pigeon Lake features 3 bedrooms, 3 full/double sized beds, large bright living room with sleeper sectional, newly renovated kitchen, updated bathroom, private dock, indoor fireplace, enclosed patio room, outdoor fire pit, and large yard for games and more. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for families and friends to escape the hustle and bustle, relax and unwind.

Top guest favourite
Cottage in Brechin
4.92 out of 5 average rating, 112 reviews

Cottage on Lake Simcoe Amazing lake Views

Lakefront 3-bedroom cottage on Lake Simcoe – perfect for families! . Please note You can see the lake from living room. Features a fully equipped kitchen and two 3-piece washrooms .Enjoy stunning lake views, BBQ, fishing, and crystal-clear shallow water safe for swimming (weather permitting). Apple picking in Fall and icing fishing in winter! Water access and beach area are shared with a few friendly neighbors. Fast starlink internet! Owner Allergic issue ,so please NO PET allowed.

Superhost
Cottage in Kawartha Lakes
4.89 out of 5 average rating, 225 reviews

Cabin on the Creek (4 season)

Escape the hustle and bustle to this cozy log cottage on a quiet creek, short trip from the city only 1.5hrs away from Toronto. The property gets disinfected after each stay! Four spacious bedrooms! Backyard which includes a large deck also has a private dock to relax on or to take the canoe out on the creek. The creek opens up to Sturgeon Lake! Also, a boat launch just 7 houses down at the entry of the street! 15 minutes from Lindsay and 12 minutes from Bobcaygeon

Guest favourite
Cottage in Minden
4.99 out of 5 average rating, 114 reviews

Kabin Tapoke | Wild Kabin | Hot tub-Sauna-Sunsets

Welcome to Kabin Tapoke – a signature retreat by Wild Kabin Co. A beautiful newly built waterfront cottage located in Minden Hills, Ontario. The 4 bedroom, 2 bathroom cottage is positioned high in the trees and has incredible views of Moore Lake, situated on 1.13 acres and 255ft of shoreline. This gorgeous private forest setting, only 2 hours from the GTA is perfect for a family getaway! STR24-00016

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