Cottage holiday rentals in Wellington County

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Top-rated cottage rentals in Wellington County

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

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Guest favourite
The cottage's exterior showcases a blend of natural stone and wooden accents, surrounded by lush greenery. A wide pathway leads to the double wooden doors, framed by large windows that invite natural light into the spaces within.
Cottage in Caledon
4.88 out of 5 average rating, 8 reviews

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.

An expansive view of the property reveals a two-story stone house surrounded by lush green fields. A landscaped pathway leads to the entrance, while ample outdoor space and trees provide a serene atmosphere. The surrounding countryside enhances the tranquility of the setting.
Cottage in Limehouse
4.48 out of 5 average rating, 33 reviews

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

An inviting outdoor space features a hot tub surrounded by a wooden deck and a patio set with gray chairs under a large umbrella. A glimpse of a wood-burning sauna is visible, along with a spacious green lawn and distant trees.
Cottage in Erin
4.84 out of 5 average rating, 115 reviews

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!

Top guest favourite
An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.
Cottage in Mono
4.95 out of 5 average rating, 153 reviews

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

Cottage in Fergus
4.8 out of 5 average rating, 10 reviews

Four Seasons get away! Pool, Hot Tub, Sauna & Gym!

Featured in Forbes "5 Charming Towns In Ontario" Summer or winter it has more to offer than a resort! Indulge in the longest waterfront view from a cottage, atop a hill with breathtaking view. With an array of luxurious amenities ✨ heated pool ✨ Hot tub ✨ Sauna ✨ Gym ✨ Gas and wood Fire pits ✨ multiple patios This retreat exceeds all expectations. 4 family rooms, offices, chef's kitchen, 10-person dining table, your every need is catered Professionally cleaned between guests

Top guest favourite
A unique double A-frame house is framed by lush greenery, with a spacious driveway leading to the entrance. The structure features a combination of wood and stone elements, while flower beds with emerging blooms add color to the natural surroundings.
Cottage in St. Jacobs
4.99 out of 5 average rating, 199 reviews

St. Jacobs Triangle House - Countryside Escape

Welcome to Triangle House, a unique double A-frame situated on a private 1.7 acre lot, fronting on the Conestogo river Only 6 minutes drive from St.Jacobs center, 1.5 hours drive from Toronto, 15 minutes drive from the University of Waterloo and 25 minutes to Elora. Bring the whole family. This 3 bed, 3 bath home comfortably sleeps 6. Soak in the countryside from the sprawling deck and grounds, while enjoying all the comforts of a modern home.

An aerial view captures the spacious backyard of the cottage, surrounded by lush greenery. A circular fire pit is visible in the center, accompanied by seating. The cottage sits to one side, with pathways leading into the natural landscape, providing a tranquil setting for outdoor gatherings.
Cottage in Belfountain
4.7 out of 5 average rating, 88 reviews

Belfountain Retreat | Fire Pit, Trails & Nature

Escape the city and unwind in a private Belfountain retreat surrounded by nature. This spacious 4-bedroom home sleeps up to 8 guests and is situated at Forks of the Credit, with scenic hiking trails, and popular local attractions. Whether you're enjoying coffee outdoors, relaxing by the fire pit, or exploring the charm of a Caledon getaway, this peaceful experience is the perfect place to reconnect, recharge, and create lasting memories.

Guest favourite
Cottage in Mono
4.83 out of 5 average rating, 12 reviews

Hockley Hideaway

Unwind in the heart of Hockley Valley at this welcoming 3-bedroom, 3-bathroom bungalow set on 3.4 private acres. Surrounded by mature trees and open space, the home offers comfortable living areas, multiple decks, and a peaceful country setting just minutes from local wineries, breweries, hiking trails and ski hills. Ideal for families, couples, or small groups looking for a relaxed rural getaway.

A wooden dock extends over calm waters, featuring two Adirondack chairs in red and pale yellow. The scene captures a clear blue sky and a lush green landscape on the far shore, providing a serene space for relaxation and enjoyment of the lakefront view.
Cottage in Cambridge

Stunning Lakefront Cottage in Puslinch!

Looking for your cottage getaway but still want to be close to all the action? Discover this lake-front hidden gem in Puslinch, only 45 minutes from Toronto and just outside Cambridge, ON. This cottage has it's own personal lakefront and sitting area, ideal to watch sunsets, enjoy late-night campfires or just keep an eye on Justin Bieber's lake house (yes, he's just a few doors down).

Top guest favourite
Two dark wood-style chairs are positioned in front of a gathered stone fire pit, overlooking a calm lake. Lush grass surrounds the seating area, interspersed with trees in the background. The natural landscape provides a serene setting for outdoor relaxation.
Cottage in Moorefield
4.97 out of 5 average rating, 36 reviews

Beautiful 3 bedroom Lake House.

Relax with the whole family at this peaceful place to stay. You and your guests can enjoy each others' company and still have space to be alone. The outside space is almost 2 acres of grass area which looks onto Conestogo Lake. Enjoy time outside at the fire in the evening and exploring nature during the day.

A charming green cottage is nestled among pine trees, featuring a white door and windows that reflect the snowy landscape. The structure has an inviting roofline and is situated on a peaceful countryside setting, surrounded by a simple wooden fence.
Cottage in Puslinch
4.71 out of 5 average rating, 69 reviews

Farm style cozy cottage with hot tub

Take it easy at this unique and tranquil getaway at Quince Cottage. Reconnect with nature and relax with your family away from the chaotic city life. Experience the life in calm and serene atmosphere with no disturbance.

An expansive aerial view captures a lush landscape defined by rolling fields and patches of trees. Various structures, including a farmhouse and outbuildings, are nestled within the greenery, while winding paths and roads create connections throughout the property.
Cottage in Orangeville

Farmhouse Cottage On the outskirts of Orangeville

Farmhouse. Cottage

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