Chalet holiday rentals in Kingston

Chalet On The Bay at Waupoos w/ Hot Tub

Relax and unwind at Chalet On The Bay in beautiful Waupoos. Located just 10 minutes from Picton the property is ideally situated as a hub for accessing all the County has to offer. A new home w/ hot tub that features cathedral ceilings, loft style master and all modern finishes with a rustic feel. A great space for family outings, wine touring or a getaway with friends. Please note we DO NOT have access to water off of our property and don't allow parties or pets. Home is on private road.

Evergreen Log Home with Hot Tub + Pool

The Evergreen is a cozy, modern 4-season log home with 2 bedrooms & an office. This family home boasts open-concept living and a tranquil 2.5-acre private yard with a hot tub! Fire pit, above-ground pool, BBQ and screened-in gazebo open seasonally. The Evergreen is a safe, inclusive space where everyone is welcome! This is an older home, not a hotel; we love its imperfections and we hope you do too! Firewood not included, BBQ unavailable in winter months. Our pool reopens in late spring 2025.

The Chalet @ Angeline's Inn

The Chalet at is a quaint cabin nestled in the back gardens at Angeline's Inn in Bloomfield. This secluded retreat faces the lush meditation labyrinth and medicine wheel and boasts the best view of the property. This spot is a perfect escape for those wishing to feel immersed in nature with a rustic feel but with luxury amenities. Angeline's Inn proud to offer a unique design boutique experience. We're committed to excellence in service, style, and a passion for County heritage preservation.

Hay Bay waterfront retreat -Sunshine’s cottage

NEW 2025 ! New renovated 1.5 bathrooms+ water filtration system !! A cozy waterfront cottage in the quiet Hay Bay area. Perfect for a family gateway and reunion. This cottage offers beddings, high quality hotel style mattresses and stainless steel kitchen appliances. Enjoy this charming and peaceful cottage nestled on 3 acres of waterfront land. Take in the amazing lake view from every window and a renowned fishing spot steps from the cottage. The sunrise, sunset and night sky are incredible!

Lake House on Cole Lake

Bring the gang to the lake house. Sit back, relax & enjoy! It's a great place to make new memories with friends & family. Approximately 3,500 sq ft, 4 season home with a hot tub, a granny suite, 2 full kitchens, 3 sitting areas, 5 bedrooms & a large deck. We are on a quiet lake great for fishing, swimming & boating. We have 3 kayaks, a canoe, a play park for the kids and lots of green space to enjoy. Finish the day off with a campfire down at the lake. Your next family getaway awaits!!

Fall colors time! 2BR Suite-dog friendly-hot tub !

Dog friendly! Relax with the family or a couple of friends at the Alex Bay Ranch! Just outside the village of Alexandria Bay, but not too close. Share a firepit, take a country walk right outside your front door, cook a steak outside, watch the stars and satellites. Then when you're ready take a 5 minute drive to go visit the sites and attractions of the Alex Bay and Thousands Islands area! You can use our place as your base for exploration, or just stay, no reason to even leave!

Waterfront Lodge Retreat w/ Hot Tub

Situated on the Salmon River this private newly custom built lodge features wooden beam ceilings on the main floor giving it a warm & cozy feeling. A short drive to local beaches and provincial parks. Enjoy the landscape out back around the fire pit overlooking the river. Lounge in the hot tub overlooking the river and stargaze at night. Truly a getaway in nature to unwind & reconnect with friends and family. LCBO, bakery, diner, pharmacy & grocery store all within 5 minutes drive.

Exceptional lakefront chalet without compromise

Beautiful new four season chalet on a very private waterfront location on calm, quiet Garrison Lake. Two story home with dual walk-out to huge south-facing deck and gazebo overlooking sparkling lake. Open concept main level with soaring 25 ft ceiling and monster stone fireplace. Paddle boat and water toys available for no extra cost. Great for nature lovers to enjoy the 70 lakeside acres and extreme privacy with no visible neighbours! Mature, responsible guests only please.

5 mins to Sandbanks / Close to Wineries / Spacious

MAXIMUM 8 ADULTS, PLUS CHILDREN. NO EXCEPTIONS. Under The County’s STA bylaw, we are legally permitted to accommodate a maximum of 8 adults, plus children. Enjoy 3000+ sq ft of bright, open-concept cottage with high vaulted ceilings. The backyard is spacious too! 5 acres total. 4 Bedrooms (includes 3 king beds!) + 3 full baths. Whether it's a family vacation, couples getaway, girls weekend – we have tons of space.

The Wolfe Lake House - Great Wifi by Westport

Located on Wolfe Lake in the coveted South Frontenac Region (Right by the famous town of Westport), the Wolfe is a year round oasis with modern amenities to ensure that you and your friends and family enjoy your get-a-way from life! Located just 3 short hours from the GTA with fast wifi speeds that make working from home a breeze. For summer 2025 we are accepting 7 day bookings from Sunday to Sunday.

Lakewood on Opinicon Lake- Chaffey's Lock

This rustic log cabin is in a private setting on the very popular Opinicon Lake. The screened-in porch across the front of the cottage provides a comfortable vantage point to view the beauty of the lake. Enjoy fishing and water sports from this private cottage set back in the trees! Sit and watch the stars as you roast marshmallows in the fire pit by the lake, or visit the historic towns in the area.

Family cottage on Private island

Surrounded by the Charleston Lake Provincial Park, Sheep Island harbors two beautiful summer homes for families up to 20 members. Explore Twenty hectares of mature forest and diverse ecosystem around the private island. On the shore, dip your toes in the water by the beach, swim to the raft, and tan on the dock. Grab a canoe, kayak, or paddleboard and go explore.