Cottage vacation rentals in Cherry Island

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Top-rated cottage rentals in Cherry Island

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Top guest favorite

A charming A-frame cabin is framed by lush trees, featuring a green metal roof and large windows that create a bright atmosphere. A wooden deck extends from the entrance, with a firepit surrounded by four Adirondack chairs positioned on a grassy area.

Cottage in Huntsville

4.98 out of 5 average rating, 371 reviews

Muskoka A-Frame + NEW HOT TUB | Arrowhead | Beach

Welcome to Muskoka A-frame, the perfect couple’s getaway or solo retreat. Relax in the **NEW HOT TUB**. Wake up to swaying treetops, make gourmet meals & relax by the fire, with 2-story forest views. This classic 70’s A-frame cabin has been re-imagined for the modern world. Hide away or make it your base for 4-seasons of adventure. 3 min to a private beach. Hike, canoe or swim at Arrowhead or Limberlost Forest. And visit Huntsville for restaurants, breweries & local amenities just minutes away.

Top guest favorite

A charming cottage is nestled among mature trees, showcasing a mix of modern and antique design elements. The exterior features a metal roof and wooden accents, with a welcoming staircase leading to the entrance. Large windows provide views of the surrounding natural landscape.

Cottage in Huntsville

5 out of 5 average rating, 267 reviews

The Rock Lodge, At Mary Lake (+ Hot Tub)

A charming little “Old meets New”cottage in the heart of Port Sydney, Muskoka. less than 5 min walk away from Mary Lake where you can enjoy the beach, have a picnic or even Launch your Water vessels into the lake for a relaxing day. Across the beach you can find a community centre with a play ground and basket ball court perfect for our younger guests. 2 km away from North granite ridge Golf Club; Our area is surrounded by preserved woodlands perfect for scenic hikes and spotting wildlife! ✨

Guest favorite

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

4.98 out of 5 average rating, 123 reviews

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

Top guest favorite

A modern cottage is set against a backdrop of tall trees, featuring a large wraparound deck illuminated by warm lights. A fire pit sits on a granite outcrop, surrounded by outdoor chairs. The peaceful evening sky casts a calm ambiance over the scene.

Cottage in Bracebridge

4.99 out of 5 average rating, 130 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.

Guest favorite

A sunlit living space features large windows with views of the lake, allowing natural light to fill the room. A cozy striped armchair and a simple wooden coffee table are positioned on a wooden floor. A round table with decorative placemats complements the inviting atmosphere.

Cottage in Parry Sound

4.92 out of 5 average rating, 143 reviews

Muskoka Waterfront w/ Hot tub (Silver Linings)

*No extra fees* Come enjoy our designer furnished, newly-built, 4-season, Silver Lining Muskoka Lakehouse. This cottage offers you and your loved ones the perfect getaway with tons to do and memories to make with Insta sunsets over a lake wrapping around the entire property, a sandy beach to dip your toes, hot tub to warm up with friends, fire pit for roasting marshmallows. Other amenities: fully stocked kitchen, treehouse, games, BBQ, 1 acre of privacy, pet bed, well maintained hot tub.

Guest favorite

An A-frame cabin is nestled among lush greenery, illuminated softly by outdoor lighting. The large windows reflect warmth and offer a glimpse of the cozy interior. Stone steps lead up to the entrance, surrounded by trees and natural foliage.

Cottage in Haliburton

4.96 out of 5 average rating, 186 reviews

Highlands Lakefront | Dock | Screened Room | Sauna

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

Top guest favorite

The tranquil Long Line Lake is depicted, showcasing a peaceful expanse of water reflecting the surrounding trees and sky. Lush greenery lines the shore, contributing to the serene atmosphere of this private retreat. Soft clouds are seen in a blue sky above.

Cottage in Baysville

4.99 out of 5 average rating, 127 reviews

Tranquil Muskoka Lake House

Welcome to your private retreat on tranquil Long Line Lake. The perfect blend of modern convenience and nostalgic Muskoka cottage character. This cottage is newly renovated throughout and features a new rustic yet modern kitchen and main floor three piece bathroom. With over 1600 square foot of living space and two full bathrooms, this cottage is ideally suited to accommodate multiple families with kids. -Unlimited high speed internet -Large, screened in Muskoka Room -Expansive dock

Top guest favorite

A wooden dock extends into the water, leading to a welcoming gazebo and multiple red Adirondack chairs arranged on the shore. The lush greenery frames the scene, while the two-story cottage is visible in the background, surrounded by natural landscaping.

Cottage in Huntsville

4.99 out of 5 average rating, 121 reviews

Escape to Falconview, Huntsville-Muskoka

Enjoy a piece of Muskoka in this beautiful waterfront cottage! This four bedroom home is only minutes away from historic downtown Huntsville, as well as many grocery stores and restaurants! Located on the Vernon Narrows, close to the mouth of Lake Vernon-Also, with boat access to Lakes Mary, Fairy and Peninsula, and a boat launch only a short ride away, it’s sure to impress! If you’re looking for a place to explore or just a spot to sit back and relax, we’ve got you covered!

Top guest favorite

A wooden dock extends over calm waters, featuring four Adirondack chairs in red and yellow. The serene lake reflects the surrounding trees and sky, with a light morning mist gently hovering above the water's surface.

Cottage in Port Carling

4.99 out of 5 average rating, 121 reviews

Gorgeous Muskoka Getaway on stunning private lake

Enjoy the perfect cozy Muskoka cottage "The Perch" on a beautiful private lake. This family and pet-friendly home is your year-round retreat. Your family will be close to everything when you stay at this centrally located place but you will feel like you are at a peaceful cottage surrounded by nature. With all of the amenities that you would need, you will find that The Perch is everything you are looking for to create memories with friends, families or a loved ones.

Top guest favorite

A serene waterfront view is presented from a deck, showcasing calm water surrounded by lush green trees. Comfortable seating arrangements are visible, creating a perfect spot for relaxation while enjoying the natural landscape.

Cottage in Torrance

4.97 out of 5 average rating, 232 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Modern 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct Minimum 6 nights with a Sunday check in.

Guest favorite

A warm living area features a stone fireplace as the focal point, with a cozy fire burning inside. Comfortable leather seating is arranged around a rustic wooden coffee table, complemented by small decorative items and soft textiles, while glass doors lead to another space.

Cottage in Tiny

4.94 out of 5 average rating, 293 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. License #STRTT-2025-008

Top guest favorite

A modern boathouse is situated on a tranquil lake, surrounded by tall trees. The building features multiple windows and a spacious deck on the roof, providing scenic views of the water. Sunlight reflects on the calm lake surface, enhancing the serene environment.

Cottage in Windermere

4.98 out of 5 average rating, 102 reviews

Lake Rosseau Boathouse Getaway for 2

Beautiful boathouse on Lake Rosseau. 650 square feet, 1 bedroom, 1 bath with kitchen and living space. Wrap around deck with stunning cliff and lake views. Bring your own boat, free public launch ramp next door. Easy dock access for swimming and to tie your boat. Enjoy boating, fishing and swimming on Muskoka’s “Big Three” lakes. Space is ideal for 2 adults. Additional adults (over 12) are $50/night each to a maximum of 4.