Guesthouse vacation rentals in Durham Region

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Durham Region

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

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Guest favorite

Guesthouse in CA

4.92 out of 5 average rating, 24 reviews

Adorable GH in beautiful Claremont/scenic view

Take it easy at this unique & tranquil getaway, located in Claremont, ONT. Enjoy privacy, while only 45mins from Downtown Toronto. Central to Markham, Stouffville, Uxbridge, Ajax, Whitby & surrounding areas. 10 Minutes to 407, 17mins to 401. Full kitchen, washroom, upper level bedroom, patio (bbq), laundry etc. Winter ice rink in backyard. Fully contained unit. Transportation: To/From Airport To/From Toronto DT Not included in price, msg to inquire 5 Mins to Country Restaurant See house rules⁹

Guest favorite

Guesthouse in Uxbridge

5 out of 5 average rating, 38 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

Welcome to Redwood Haven, your lavish Uxbridge retreat! 2 bedrooms await, comfortably accommodating 4 guests. Be captivated by breathtaking views, immerse yourself in luxury, taking a dip in the inviting heated pool (shared by attached East and West units residents and guests). Embark on thrilling equestrian adventures for an extra touch of excitement. With ample parking, heating, and AC, ensuring the ultimate comfort throughout your stay. Unleash unforgettable memories in this enchanting haven.

Top guest favorite

Guesthouse in Whitby

4.97 out of 5 average rating, 199 reviews

One bedroom apartment/guesthouse.

Welcome to your peaceful private getaway located north of the 401 in Whitby. Guest will have the entire apartment with separate entrance to themselves. This newly constructed apartment is equipped with a fully functional kitchen, bathroom, living room and bedroom. Apartment comes with Wifi, 43” television with Amazon Prime TV services. Guest will have a designated parking space on the driveway. Please refrain from smoking inside the unit, smoke alarm are interconnected, and are highly sensitive.

Guest favorite

Guesthouse in Uxbridge

4.94 out of 5 average rating, 150 reviews

Guesthouse in nature mins to Durham trails & 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 Pickering

4.98 out of 5 average rating, 88 reviews

Luxury Ground-Level "Suite Escape"

"Suite Escape" offers a luxurious private guest suite in Pickering, Ontario. Fully equipped w/ a cozy Queen Bed, spa bathroom, workstation, 65” TV, A/C, fireplace, & kitchenette. Conveniently located to Hwy 401 & 407, GO Train, Durham Transit, malls, cinemas, casinos, waterfront & hiking trails, golf courses + wineries within a short walk or drive. Downtown Toronto & Pearson Airport is 30-40 mins away. Immerse yourself in luxury, tranquility, and easy access to the best of Pickering and beyond.

Guest favorite

Guesthouse in Cavan

4.87 out of 5 average rating, 227 reviews

Cozy Seldom Scene Cottage

Note-when submitting your booking request, please acknowledge you have read and agree to all of our house rules. Romantic get away or family fun. Wooded, setting minutes from Peterborough and Millbrook. We are approx 3 min off the 115 highway, 15 min off the 407 hwy, <2 hours from Toronto. Our Bunkie is perfect for anyone looking for a furnished getaway in the Kawarthas nestled in a natural setting that includes wifi-STARLINK Our log home is approx 150 ft directly located from the Bunkie.

Top guest favorite

Guesthouse in Oshawa

4.95 out of 5 average rating, 22 reviews

The Farmhand’s Cottage

*Welcome ! The Farmhand’s Cottage is an adult retreat, located on a country farm property. Open fields for as far as the eye can see, this quaint little farmhouse has everything you need to enjoy a relaxing getaway. Enjoy the outdoor pond and chair swing, or sit out on the private patio overlooking the farmers fields. We are just outside of Oshawa (15 minutes north , and 10 minutes off the 407). We are a 10 minute drive south of the beautiful and historic Port Perry lakefront & theatre.

Guest favorite

Guesthouse in Toronto

4.98 out of 5 average rating, 162 reviews

Adorable, modern tiny home in Leslieville

Kick back and relax in this calm, stylish space. 10 minute walk to History! 15 minute walk to the beach! Complete with kitchenette, 3 piece bathroom, and an upstairs bedloft (watch your head - 5'3"). There's a queen bed upstairs and a Spaze pullout sofabed downstairs. Rounding out the space is a TV, highspeed internet, and a minisplit ductless AC/heat pump. Linens and towels are provided. Please note steep stairs and low headroom in the loft. Operator Registration STR-2109-FMGHHC.

Guest favorite

Guesthouse in Newcastle

4.88 out of 5 average rating, 212 reviews

Bee Keeper's Cabin - a very private retreat

91 acres, trails, total privacy, spring fed lake, solar power/propane heated, gas stove top, propane fridge, out-house, firepit, wi-fi ; canoe/paddleboat (seasonally) Self check in and self cleaning For those who leave a "light foot print" Basic kitchen utensils, pots, pans, and dishes are provided, BUT guests must bring their own drinking water, pillows and bedding. We ask our guests to leave the cabin better than you found it and to take all garbage and recycling home with you."

Top guest favorite

Guesthouse in Port Perry

5 out of 5 average rating, 107 reviews

Lakeside Guest Suite, on Lake Scugog, Port Perry

WATERFRONT PROPERTY….Enjoy stunning sunsets from the basement walkout guest suite. Take in views from the living room, bedroom (queen bed), or large 34 foot long private patio! The backyard leads directly to the lake including a fire pit for your use. Please note that the natural slope of the yard (40 stairs) may not be suitable for those with mobility issues. While the suite doesn't feature a kitchen, Port Perry is only an 8 min drive and offers many culinary options.

Guest favorite

Guesthouse in Pickering

5 out of 5 average rating, 6 reviews

Beautiful Private Guest House

This beautiful one bedroom unit is great for a romantic getaway and it's 5 min driving to Frenchman's Bay Beach. The private patio is beautiful with space to relax and enjoy. Separate entrance from the main unit. Utilities and wifi included. Wifi and TV with free Netflix and Crave installed. The kitchen is spacious with full appliances, Fridge, Stove, Microwave, Dishwasher, Coffee maker, Toaster and Kettle. Dishes and cookware are available in the kitchen.

Top guest favorite

Guesthouse in Uxbridge

4.95 out of 5 average rating, 62 reviews

Private Guest House Retreat

Private guest house retreat 2 minutes from downtown Uxbridge. Uxbridge, the trail capital of Ontario, offers serene hikes and small-town charm. World class golf courses and the best biking trails in Ontario. This small town retreat will surely be a favourite. This 1 bed (Queen), 1 bath guest house offers a full kitchen, washer and dryer, outdoor patio with fireplace, along with hot tub.