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Guesthouse holiday rentals in Thousand Islands

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Thousand Islands

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite
An inviting outdoor fire pit area is surrounded by four Adirondack chairs, with a stone circular seating arrangement at its center. The guesthouse's wooden exterior is visible in the background, framed by lush greenery and a lawn, offering a peaceful and open atmosphere.
Guesthouse in Mallorytown

Adorable country guesthouse on Graham Lake

Enjoy the countryside on 15 acres of woods backing on to Graham Lake. Tucked away from the road, our guesthouse is family and pet friendly. The bathroom is newly renovated. Outdoors it boasts a lovely campfire area, a patio table and a large grass yard. Enjoy our gardens in the summer and our laying hens year-round. Take a 5 min stroll down a wooded path to the lakefront where you will find another campfire pit, a dock, canoe, kayak and SUP to use and plenty of space for activities year-round.

4.91 out of 5 average rating, 163 reviews
Top Guest favourite
A serene lakeside scene is captured at dusk, showcasing a vibrant sunset with deep orange and pink hues reflected on the calm water. The rocky shoreline stretches along the lake, while silhouettes of trees and structures are visible in the background.
Guesthouse in Chaumont

Lakefront Getaway

This completely private attached guest house is newly renovated and just steps away from Lake Ontario.  Some amenities include: Private entrance and deck Large yard Easy water access to swim, fish, & kayak Fabulous views of Chaumont Bay Spectrum wifi & cable Outdoor Grill & Fre Pit Air Conditioning Full Kitchen Smart TV in each bedroom 10 miles from the St Lawrence River Wonderful restaurants and the Thousand Islands are just a short drive away. Come enjoy the beauty Upstate NY has to offer!

4.96 out of 5 average rating, 111 reviews
Top Guest favourite
A charming guesthouse is set in a vibrant garden, featuring a spacious deck overlooking the landscape. Lush greenery and flowers surround the building, enhancing the natural environment. A tree provides shade, and clear blue skies add to the serene atmosphere.
Guesthouse in Township Of Frontenac Islands

Wolfe Island Oasis

Welcome to our cozy country retreat. Our guesthouse offers everything you need to unplug from the hustle of the city. Whether its enjoying a coffee on the lounge chair while watching the sunrise; stargazing on the patio; enjoying an evening stroll at sunset; or falling asleep under our son's handcrafted cedar strip canoe: this retreat was designed to maximize a unique experience. The building is completely separate from our family hobby-farm and offers a secluded space for our guests.

4.98 out of 5 average rating, 184 reviews
Top Guest favourite
The exterior of the Carriage House showcases a well-maintained façade with light wood siding and a pitched roof. A private garden area is bordered by a wooden fence, featuring a stone fire pit surrounded by gravel and lush greenery.
Guesthouse in Prince Edward

The Carriage House on Queen

Located right downtown Picton, this spacious, modern and very clean Carriage House offers private parking for 2 cars, outdoor seating with BBQ and 2 large bedrooms that comfortably sleeps 4 people. Perfect for a couples retreat or a friends get-away! Quiet and cozy neighbourhood with beautiful historic century homes. Minutes walking to Picton main street that offers amazing restaurants, bars and fabulous shopping. Under 15 min drive to Sandbanks Provincial Park. STA License #: 2025 - 0068

4.98 out of 5 average rating, 255 reviews
Top Guest favourite
The open-concept guest house interior features a spacious sleeping area with a large bed. Natural light enters through sliding glass doors and tall windows, illuminating warm wooden beams and light-colored walls. A cozy seating area with two chairs and a table is visible, complemented by decorative plants.
Guesthouse in Bloomfield

The Bloomfield Guest House

Are you looking for an awe-inspiring, peaceful, retreat-like setting for your visit to The County? Book this well-crafted private guest-house in charming Bloomfield, perfectly located between Wellington and Picton. The expansive farm-field view will instantly ground and settle your being. Every aspect of this luxury offering has been designed and built with integrity and care. We welcome you to embody a felt-sense of coming home. Follow us @thebloomfieldguesthouse Licence # ST-2022-0076

4.99 out of 5 average rating, 170 reviews
Guest favourite
A small bunkie features a sloped green metal roof and light-colored log siding. A front deck, accessed by a few steps, is framed by trees, providing a natural setting. A large window is positioned beside the door, allowing natural light.
Guesthouse in Cloyne

Log Bunkie w/ Loft, Bon Echo Park

This bunkie, sided in Vermont Maple, was built in 2018. Tastefully decorated in barn board and v-joint pine inside, it features 7 cu. ft. fridge, large air circulator, kitchen cart, microwave, bbq, coffee maker, etc. It has a wardrobe, loveseat, end table and dining table for two. The queen bed is up the ladder in the loft. Great view onto Lake Mazinaw. New 36' dock, deck, stand up paddleboards (SUPs), kayaks, canoe, Aqua Cycle and pedal boats. Minimum 3 night booking on long weekends.

4.9 out of 5 average rating, 134 reviews
Top Guest favourite
A cozy cedar bunkie is nestled among tall trees, featuring large windows and a welcoming porch. A gravel path leads to the entrance, while a campfire pit and two chairs create a peaceful outdoor seating area, ideal for enjoying the serene surroundings.
Guesthouse in Central Frontenac

Waterfront on Kennebec Lake - private Cedar Bunkie

Kick back and relax in this calm stylish space. Double sized murphy bed, bistro set and kitchenette are all you need to live simply. A 3 piece bathroom (private) is available in the main house . You will be welcomed by our friendly and loveable chocolate lab Deacon. Relax on this quiet lake with 2 kayaks from your private dock. Build up an appetite hiking 7 miles of Wilderness Trails across the street and BBQ fresh fish for dinner under the covered deck. **Winter booking available **

5.0 out of 5 average rating, 101 reviews
Top Guest favourite
Guesthouse in Prince Edward

A Sandbanks Retreat

STA2024-0154 Bonfire?Volleyball?Walk to the Beach?Sunsets on the beach. This brand new home was designed for entertaining & enjoying the charm of the county. Walk to the beach in 20 minutes, drive in 3 minutes or 10 mins to downtown Picton,Bloomfield,Wellington. Make A Sandbanks Retreat a great memory. Easy access to touring wineries, antiquing or enjoying the restaurants and shops PEC has in store for your trip. Take an outdoor shower after the beach or relax in the veranda and BBQ.

4.98 out of 5 average rating, 124 reviews
Top Guest favourite
A spacious living area features wooden flooring and natural light filtering through large windows. A decorative mirror and house plants add warmth. A wood-burning stove stands against an accent wall, while a dining area is visible in the background with a round table and chairs.
Guesthouse in Prince Edward

The sunroom on Maple

Enjoy this spacious bright apartment steps to Main St and a five minute walk to downtown Picton's cafes, restaurants and shops. The sunroom is everyone's favourite spot in the house to spend time with loved ones or relax. There is also a fireplace and back yard with fire pit, barbecue and patio furniture available for your use too. During the summer months, we'll lend you a Sandbanks access pass and kayak or paddle board to make your summer stay unforgettable. License No. ST-2020-0198

4.96 out of 5 average rating, 135 reviews
Guest favourite
A scenic view of Adolphus Reach is captured from the cabin's vantage point, showcasing calm waters and a passing boat. Surrounding trees display autumn colors, contributing to the natural beauty of the landscape under a mix of blue and cloudy skies.
Guesthouse in Prince Edward

The Edge. Stunning view. EV Friendly

This private cabin and deck has a stunning view of Adolphus Reach from the top of a 200' escarpment. The property is located immediately east of Lake on the Mountain Provincial Park. Have a look on Google Maps. Day use at Sandbanks must be reserved. Text me for details of how I can reserve for you using my seasonal park pass saving you the $21 park fee. I'm required to charge HST if you choose to book via Airbnb but not otherwise. Posted price includes HST. ST-2019-0310

4.86 out of 5 average rating, 336 reviews
Top Guest favourite
The guest room features two twin beds made with rustic log frames, accented by patterned throws. Light wood paneling covers the walls, and a ceiling fan hangs above. A small nightstand is placed beside one bed, with a lamp and decorative items displayed.
Guesthouse in Chaumont

Peaceful Getaway

Kick back and relax in this peaceful space. Guest house has two twin beds, private bathroom, microwave, toaster, Keurig, small refrigerator. WiFi access, outdoor grill with outdoor dining and seating area all under a 16x24 pavilion. This property offers incredible views, fish jumping and canoe and kayak access. End your incredible day fishing off the dock with s’mores at the fire pit. Hunters and fishermen welcome. Plenty of parking so bring your motorized toys! See you soon!

4.99 out of 5 average rating, 142 reviews
Guest favourite
Guesthouse in Kingston

Downtown Coachhouse |Queens University|LakeOntario

Step back into the 1850’s and stay in a piece of Kingston’s history. This beautiful limestone coachhouse is located on the largest private historic estate in Kingston, directly across from the Lake Ontario waterfront and nestled on historic Centre Street. This unique, upscale 2-bedroom, 2-bathroom property is blending curated eclectic design with premium comfort for families, couples, or academic and business travelers seeking a private, boutique downtown sanctuary.

4.95 out of 5 average rating, 19 reviews

Popular amenities for Thousand Islands guesthouses