Guesthouse vacation rentals in Caledon

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Top-rated guesthouse rentals in Caledon

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

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Guest favorite

A quaint wooden dock leads to a peaceful creek with gentle water flowing over rocks. A small bridge connects the dock to a modern structure nestled amid lush greenery. Tall trees provide a serene backdrop, enhancing the natural setting.

Guesthouse in Acton

4.96 out of 5 average rating, 287 reviews

Treehouse in the forest

Treehouse in the Forest is the perfect getaway. Like living at a cottage, minutes away from the city. This place is fully equipped with a bedroom, own kitchenette, and private bathroom. We are just 45 minutes from Toronto with a short drive to both Georgetown & Acton. 10 Minutes to 401. This guesthouse is nestled on a hill with spectacular views, surrounded by 16 acres of towering trees overlooking a creek with a private waterfall and walking trails. Perfect for photographers and influencers.

Guest favorite

An aerial view of a modern staircase leads to a lofted sleeping area with a queen bed. Natural light filters through flowing curtains, illuminating a live edge walnut table and a stool. Open shelving displays decorative items, enhancing the cozy ambiance of the compact space.

Guesthouse in Aurora

4.91 out of 5 average rating, 147 reviews

Adorable Guesthouse Apartment With Free Parking

This beautiful brand new suite offers, Separate private guesthouse with vaulted ceilings & heated floors throughout. Private bathroom with standing shower. Queen loft bed & pull out couch. Flat screen smart TV. Kitchenette which includes: Fridge, cooktop & cookware, toaster oven, kettle, coffee maker. Live edge walnut table with 2 stools. Free wifi. 1 Free parking space. Close to Go Train. Fresh bed sheets & towels are provided. Phone charger and blue tooth speaker. Instagram @blueheronloft

Guest favorite

Guesthouse in Hamilton Beach

4.84 out of 5 average rating, 200 reviews

Hamilton Beach Guesthouse with guest Kayaks

LAKEFRONT* renovated lakefront small cottage with two Kayaks situated on the Hamilton Waterfront beach trail. Enjoy fantastic views of the Toronto Skyline and secluded sandy beach. Relax on large deck, overlooking the lake. Right on the waterfront trail, roller blade, bike, kayak or enjoy the sandy beach. Very central for a Niagara winery and Toronto trip. Includes: Smart TV, 1 Parking spot, Tetherball, good Wi-Fi, Fire-pit , BBQ, Kayaks Queen size bed Coffee, condiments &cooking ingredients

Guest favorite

A doorway opens to a private deck featuring two wooden chairs with white cushions and a small table between them. The view showcases lush greenery and rolling farmland, under a clear sky.

Guesthouse in Lincoln

4.93 out of 5 average rating, 163 reviews

Little Blue Barn on the Bench

Beautifully situated in the heart of Niagara's wine country and minutes away from the Bruce trail and other hiking favourites, our guest house boasts peaceful views of rolling farmland. Built on top of a barn-style workshop, this private and peaceful studio space is the perfect Niagara getaway for a couple or an individual. Come catch a stunning sunset on your own private deck while you sip a glass of wine or enjoy a coffee. Other perks for your enjoyment: king size bed and out door firepit.

Guest favorite

The inviting living area features warm wood accents and a cozy seating arrangement. A brick fireplace stands as a focal point, complemented by large windows that flood the space with natural light. Ferns add a touch of greenery, enhancing the relaxing atmosphere.

Guesthouse in Uxbridge

4.96 out of 5 average rating, 137 reviews

Guesthouse in nature mins to Ski hills and Spa!

Relax and unwind at this peaceful and private guesthouse situated on 25 acres of forest. We are family friendly and invite you to roam the land and visit our resident ducks! If you are feeling more adventurous, enjoy a hike on our private onsite trail or on one of the many local trails within walking distance in the Trail Capital of Canada! Later we'll get the Woodstove lit for you (Dec - Feb). Catch up on your fav programs with Roku TV. Enjoy the therapeutic rainfall shower guests rave about!

Top guest favorite

Guesthouse in Mansfield

4.99 out of 5 average rating, 105 reviews

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

Top guest favorite

A private outdoor hot tub is nestled under a wooden structure with soft, glowing lights. Surrounding stones and gravel create a path, complemented by an inviting garden area with plants and rocks, enhancing the serene atmosphere.

Guesthouse in Angus

4.98 out of 5 average rating, 219 reviews

Serene Comfort. Hot Tub, Full Suite with Kitchen

Welcome to Centre Street Studio! Our 600 sq/ft bachelor suite offers a private, clean and cozy retreat. Enjoy access to a beautiful private 2 person hot tub and/or explore our local trail system on foot or by bikes available on site. Looking for R&R? Discover Scandinavia Spa or Vetta Nordic Spa, both within 40-min. Barrie, Creemore, & Wasaga Beach are all within 30-mins, while Collingwood & Blue Mountain are just 40 min. A 2-min drive to town amenities. Book now for your ultimate getaway!

Guest favorite

Guesthouse in Schomberg

4.92 out of 5 average rating, 425 reviews

Country Cabin Escape | King Bed | Pet Friendly

Tucked away on our peaceful family farm, this private retreat offers tranquility and comfort—while not secluded in the woods, it provides a true countryside experience. ✨ Full kitchen 🔥 Wood fire pit & propane BBQ 📶 WiFi + 40” Smart TV 🚿 Cozy 3-piece bathroom 🧺 Laundry access 🌲 Scenic walking trails Located near our farmhouse, Country Suite, and Event Barn, the cabin remains fully private with blinds for added comfort. We look forward to welcoming you for a restful and memorable stay!

Top guest favorite

Guesthouse in Lincoln

4.99 out of 5 average rating, 201 reviews

Cottage On Lake Ontario Niagara

OPEN TIMESLOTS MAY 11-23 (Mothers Day still available) MAY 25-31 JUNE 1-13 JUNE 17-22 JULY 1-30 AUGUST 1-31 Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. We are located along the south shore of Lake Ontario amongst the fruit belt of the Niagara. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging on-site.

Top guest favorite

A private deck is shown featuring comfortable patio furniture, including a red sofa and chairs. Potted flowers add color to the space, while surrounding trees provide a natural backdrop. The deck is constructed of wood, enhancing the rustic charm of the guesthouse.

Guesthouse in Niagara Falls

5 out of 5 average rating, 171 reviews

Bosco Hilltop Hideaway

A unique, newly renovated guesthouse nestled on 5 acres ,surrounded by trees with a private walking trail. Just 10 minutes from Niagara Falls and Niagara on the Lake!! 2 minutes to the Niagara Wine Route and many restaurants, wineries, and shopping. Right off the 405, from Toronto and 2 minutes from the Queenston Lewiston Border. Modern farmhouse charm and decor throughout this open concept one bedroom guesthouse. A perfect retreat to relax, restore and explore Niagara.

Guest favorite

A welcoming entrance is presented with a pathway leading to a white door, framed by green grass and colorful flowers. Two outdoor chairs sit invitingly on one side, surrounded by lush greenery, creating a serene and private outdoor space.

Guesthouse in Brantford

4.88 out of 5 average rating, 144 reviews

Charming Garden Guest House with Modern Comforts

Take it easy at this unique and tranquil getaway and enjoy a delightful stay in a separate studio garden suite for your Brantford trip. The guest house is equipped with AC, heating, and WIFI to make your stay comfortable. Our guest house is less than five minutes away from Hwy access, restaurants, bars, parks, and the Wayne Gretzky Sports Center. A great location for you to discover Brantford the best way. We look forward to hosting you!

Guest favorite

The exterior view features a charming brick cottage with a small set of wooden stairs leading to a deck. Lush green foliage provides shade, while a pathway lined with small stones leads alongside a waste bin. A cat is seen walking along the path.

Guesthouse in Kitchener

4.91 out of 5 average rating, 211 reviews

Charming Private Guesthouse in Downtown Kitchener

You'll be pleasantly surprised by this cozy cottage in the middle of Kitchener! Welcome to our charming guesthouse. You'll have complete private access to our guesthouse bungalow if you choose to book with us. Located just a 5 minute drive from Downtown Kitchener, 12 minutes from Waterloo, and 5 minutes off the highway, you'll be able to easily get to where you need while you're in Kitchener/Waterloo.