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Vacation rentals in Winchester Springs

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester Springs

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

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Top guest favorite
The living room features plush seating arranged around a central coffee table. A large TV is positioned on a wooden stand. Natural light filters through the windows, complemented by neutral-colored curtains, while a ceiling fan hangs above for air circulation.
Home in Waddington
5 out of 5 average rating, 13 reviews

Relax, fish, boat, BBQ enjoy

Forget your worries in this spacious and serene space. This 3 bedroom 2 full bath house is perfect for the family getaway or a group of fishermen as well as sightseeing or an overnight stay along your travels. BBQ on the porch, enjoy the fire pit, go canoeing, fishing or kayaking in the backyard with access to the St Lawrence River from Little Sucker Creek, you will be minutes away from the Waddington docks with plenty of room to park your boat right in the driveway, it’s a fishermen’s dream.

Top guest favorite
A bright dining area is surrounded by large windows offering views of the waterfront. A round table is surrounded by six upholstered chairs, while natural light fills the space, highlighting the wooden ceiling and flooring.
Home in Manotick
4.96 out of 5 average rating, 100 reviews

The River Retreat on the Rideau

Discover the charm of The River Retreat on the Rideau River, just outside of the quaint town of Manotick, Ontario and 30 minutes from downtown Ottawa, the Capital of Canada. It is the perfect blend of organic design, modern features and breathtaking views. Enjoy the beautiful and colourful sunsets at this unique waterfront property. This vacation home has everything you need and more for an incredible getaway with a group of friends, family gatherings, a business trip or corporate retreats.

Top guest favorite
A secluded guesthouse is shown, featuring a rustic exterior with grey wood siding and a vibrant red door. A path leads to the entrance, complemented by a welcome mat and a recycling bin. Flowering plants add a touch of color to the outdoor space.
Guesthouse in Newington
4.92 out of 5 average rating, 547 reviews

Trees, open spaces, and the milky way at night

8 min. from 401 & St Lawrence River, at Ingleside, pet friendly, secluded studio guesthouse, tranquil, safe location for those seeking a road break or destination traveler's seeking the St Lawrence and its environs. Sit by a fire, listen to wind and birds or watch the sky. $50 cleaning fee per pet through extra fee request if necessary before arrival. There is no reliable internet but good cell coverage available; the smart tv can tether to your own device and streaming service provider.

Guest favorite
The living area features a dark sectional couch positioned near a wall-mounted TV, with shelves holding decorative plants. A wooden dining table with four upholstered chairs occupies the space, complemented by a small plant centerpiece. Natural light enters through a nearby window.
Bungalow in Mountain
4.84 out of 5 average rating, 62 reviews

Cozy Country Bungalow

Our cozy bungalow is easily accessible from the city. You will immerse yourself in a natural setting with woods, ponds and trails. The bedroom has a double bed, plus a Roku TV and dresser. The couch pulls out to a queen sized bed. There is another TV in the living room area. You can access your own accounts for Netflix, Prime or whatever subscriptions you have as well as regular TV channels. The bathroom also contains a washer and dryer for your convenience. Laundry soap is provided.

Superhost
An aerial view of the outdoor area reveals a heated pool surrounded by a fenced yard. Two hot tubs are visible, along with a wooden deck and a screened-in gazebo. Red Adirondack chairs are arranged around a fire pit on the lawn, providing a relaxing space.
Home in Carleton Place
4.89 out of 5 average rating, 117 reviews

Ultimate Gamers Retreat, Arcade, pool & Hot Tub

POOL SCHEDULE May 15- Oct 1 -Heated pool 80 degrees minimum -Hot tub -BBQ -screened-in gazebo, huge deck & patio -hammocks -fire pit -arcade (thousands of games) Pool table, Foosball, ping pong & table hockey -Star-wars Pinball -Original Nintendo & SNES & PS3, Atari -75 inch TV (Netflix, Disney & Prime) main room -TV in bedroom -King Suite, 2nd bedroom in loft & pull out couch sleeps 6 -Stocked kitchen -3 piece washroom -Laundry & parking -Keurig -condiments -laundry soap -toiletries

Top guest favorite
The cabin is surrounded by tall trees in a natural setting. A spacious deck is visible, providing a space for outdoor seating. The sloped green roof adds a rustic charm, while the gravel pathway leads to the entrance, emphasizing the peaceful atmosphere of the woodland property.
Cabin in Potsdam
4.97 out of 5 average rating, 263 reviews

Riverside Cabin & Nature Trails

Enjoy our 160 acres in a private natural setting. Owls, trout, heron, osprey, mergansers and the occasional loon will add to your stay. There are over 4 miles of private trails for hiking along the river and in the woods. Kayaks & fishing poles provided. Enjoy a romantic riverside fire-pit, professional massage table & new Finnish wood fired sauna. We sanitize everything 110% before your arrival and offer self check in. We celebrate diversity and welcome people from all communities.

Top guest favorite
A collection of vintage items is displayed against a bright yellow wall. Notable elements include a retro Pepsi-Cola sign, a vibrant red popcorn container, and various decorative mugs. A small toy car, a Polaroid-style camera, and an assortment of playful signs add character to the arrangement.
Apartment in Prescott
4.96 out of 5 average rating, 310 reviews

2 Bedroom Vintage Suite (mid-term available)

The 2 bedroom apartment is located on the 2nd floor and can accommodate 4 guests. The suite is in the Mechanic Block and dates back to 1874. The apartment was restored while keeping the historical integrity in check. With vintage sink, clawfoot tub and 7' interior walls (not reaching ceiling as shown on photos) There is private parking and separate entrance. You get the entire apartment. The main level of this historical commercial building is operated by the building owner.

Top guest favorite
Home in Morrisburg
4.9 out of 5 average rating, 272 reviews

StoneCropAcres Winery and Vineyard Guest Home

Our home is located at our StoneCropAcres Winery and Vineyard. Please check the Winery's website stonecropacres for Winery hours of operation. Our Guest Home is a country style, spacious, bright and clean home with wonderful views of the rural surroundings including our vineyard, farm fields, and the apple farm just around the corner. Both the Guest Home and the Winery are wheelchair accessible and there is an electric medical bed available for use.

Top guest favorite
Apartment in Winchester
5 out of 5 average rating, 35 reviews

Bright Modern Apartment Backing onto Golf Course

Bright, modern lower-level apartment with stunning golf course views. Perfect for couples or remote workers, this private suite offers peace, luxury, and comfort with large windows, natural light, in-floor heating, AC, advanced air filtration, and pure remineralized water. Features include a modern open layout, dedicated desk, ample parking, and thoughtful design—your ideal retreat to relax, recharge, or work in quiet comfort near Winchester.

Guest favorite
A well-maintained garden path is surrounded by lush greenery and flowering plants. A gazebo with seating is visible in the background, providing a shaded area for relaxation. A trellis adorned with climbing vines leads towards the gazebo, enhancing the peaceful outdoor setting.
Apartment in Williamsburg
4.72 out of 5 average rating, 127 reviews

Kim's Country Retreat

Come and stay in this cozy cottage-like century home/apartment complete with pine wood flooring accented with country antique decor. Clean, bright and quiet. Perfect for travelers, long and short term temporary workers or students. 10 minutes south to Morrisburg amenities, and Hwy 401. 10 minutes north to Winchester amenities, and Hwy 43. Kemptville and 416 is only another 20 minutes. Easy commute to Ottawa, Brockville or Cornwall.

Top guest favorite
The exterior of the home features a welcoming porch framed by wooden beams. A white railing surrounds the area, with a small seating arrangement positioned beneath it. The light grey siding complements the blue sky, creating a serene first impression.
Home in Winchester
4.96 out of 5 average rating, 199 reviews

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

Welcome to The Lofty Nest! Located 30 minutes south of Ottawa (Canada's Capital City) in the intimate village of Winchester. This 2-bed Century home was gutted and lovingly restored, using reclaimed materials, sweat and love. Visiting for work, play or just the experience of living in a tiny house, the Lofty Nest will charm you with its 'Instaworthy' decor and hotel standards. Perfect for 1 or 2 guests; can accommodate up to 4.

Top guest favorite
An inviting exterior view of the property features a wooden deck adorned with soft lighting. A covered seating area includes a small table and chairs, enhancing the outdoor space. Lush greenery surrounds the home, creating a tranquil setting for relaxation.
Place to stay in Spencerville
5 out of 5 average rating, 126 reviews

Honeybee Haven - Dog Friendly, Free Parking

Escape to a cozy, dog friendly haven, perfect for embracing the magic of the summer season. Nestled in a picturesque landscape, our property offers all the comforts you need for a memorable stay. Whether you’re here for adventure, romance or relaxation, Honeybee Haven is your ultimate getaway. Located minutes off of Hwy 401 and the US border crossing, an hour from both Kingston and Ottawa and two hours from Montreal.

Popular amenities for Winchester Springs vacation rentals