Guest house holiday rentals in Durham Region

Guesthouse w/Woodstove in Nature Near 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 ducks and chickens! If you are feeling adventurous, enjoy a hike or bike ride on one of the many local trails within walking distance in the Trail Capital of Canada! Later cozy up to the indoor Woodstove or outdoor Firepit. Catch up on your fav programs w/Roku TV or play Super Nintendo. Enjoy the newly renovated therapeutic rainfall shower.

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.

Ajax Creative Quiet Escape. Mabuhay!

Experience autumn’s beauty from our private guest suite, tucked in a quiet neighbourhood near the Ajax waterfront. Inside, you’ll be surrounded by original artwork that transforms the suite into a cozy gallery- a warm & inspiring space to return to after crisp fall days. Step outside to admire the vibrant fall foliage and explore the 7 km Ajax Waterfront Trail. Local parks nearby burst into shades of gold, crimson and amber — perfect for scenic walks, photos, or picnic under the changing trees

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.

Peterborough Zen Retreat

4 minutes drive to Peterborough hospital, Art Gallery, Cineplex Odeon, downtown restaurant district and to Lansdowne Street with LCBO, supermarkets, restaurant chains, and Starbucks! Prepare a gourmet feast in the fully supplied kitchen. Sip wine under the crystal chandelier or curl up and watch movies on Netflix. Enjoy a queen-sized Murphy bed. A retreat for couples, solo adventurers, and business travellers. 2 people max One queen bed No smoking on property One parking spot on driveway

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.

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.

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.

Bee Keeper's Cabin - a very private retreat

91 acres, trails, total privacy, spring fed lake, solar power/propane heated, gas stove top, 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 and ice for cooler. We ask our guests to leave the cabin better than you found it and to take all garbage and recycling home with you.

Spacious fully private studio basement & parking

This large bachelor unit in basement is newly renovated. Fully private and separate entrance. This place is great for a romantic getaway and it's 5 min driving to Frenchman's Bay Beach. Wifi and TV with free Netflix and Crave installed. The kitchen is spacious with full appliances, Fridge, Stove, Microwave, Coffee maker, Toaster and Kettle. Dishes and cookware are available in the kitchen. Laundry is private.

Cozy Cottage in Kawartha Lakes

This cozy cottage will have you enjoying a tranquil experience with plenty of gorgeous views. Sitting on the edge of Lake Scugog. A plethora of opportunities await the adventurous, with trails minutes away. Historical Port Perry and Lindsay for all your dining and shopping experiences. Additionally, there is an amazing casino and an 18 hole golf course conveniently located.

Wildflower by The Bay

After a day spent by Frenchman's Bay, put your feet up in our serene backyard hideaway! A quick walk to Lake Ontario, a handful of great restaurants, bars, shops, and the expansive and scenic Waterfront Trail, this location is unbeatable. The Pickering Go Station less than a 20-min walk (or a short drive) away, bringing you to the heart of downtown Toronto in 40 minutes.