Vacation rentals in Winchester

Home in Sainte-Cécile-de-Masham

4.95 out of 5 average rating, 19 reviews

The Lake Escape - Waterfront, Hot Tub Sleeps 14!

KatyaRating, 5 stars1 week ago

Our family had a wonderful stay at this cottage. It was clean, it had a well-stocked kitchen and comfortable rooms to sleep. The check-in process was easy and everything was easy to find in the home. Our kids loved the ping pong table. The hot tub was especially lovely as the weather was a bit cooler than we had hoped for! Again, a lovely visit and we would highly recommend. This is an excellently kept AirBnB and a really kind and thoughtful host. We had forgotten some belongings behind and were quickly notified and he offered to ship them back to us, making our life so much easier and solving a problem that could have been a headache! We will be back in the future!

5 out of 5 average rating, 35 reviews

Home in Norwood

The Owlet’s Nest 🦉 on Norwood Lake

BillRating, 5 stars2 months ago

You know when someone says "the pictures don't do it justice"? That perfectly describes this rental. An absolutely amazing house, with tons of space to hang out and spread out. Comfortable beds, plenty of linens, and thoughtful touches in the kitchen and bathrooms. I've stayed at almost 20 rentals in the Potsdam area and I think this may have rocketed to the top on my first visit. I can wait to see it in the summertime! VERY responsive hosts, including answering questions and plowing the MASSIVE driveway and shoveling the path to the entrance.

4.92 out of 5 average rating, 37 reviews

An outdoor patio area is displayed, featuring a large umbrella over a set of dark wicker furniture, including a sectional sofa and accent chairs. A coffee table holds potted flowers, and the space is surrounded by a wooden fence and greenery.

Townhouse in Ottawa

Charming, Spacious Townhouse, Convenient Location

BrendaRating, 5 stars1 month ago

Lovely townhouse. Great tub and comfy bed! The garage was an added bonus. The hosts were very kind and helpful if we needed anything. The neighbourhood is a little busy/noisy and the bedrooms are bright in the morning so I suggest earplugs and a sleep mask if you are a light sleeper!

4.93 out of 5 average rating, 15 reviews

A modern waterfront escape is seen in the background, featuring a spacious deck with comfortable seating. In the foreground, five wooden lounge chairs are positioned near a fire pit, surrounded by sandy ground and trees that provide shade.

Bungalow in Dunrobin

Serenity Beach House

RanRating, 5 stars7 months ago

We fell in love with this beach house over the course of a month, and we are so grateful for Trevor's patience and attention to detail. The house has everything, clean kitchen and bathroom, up to date appliances, and most importantly, a view so beautiful that watching the clouds roll in every day cured all worries. Loved Trevor's house and will be back for my next vacation!

4.84 out of 5 average rating, 129 reviews

An aerial view captures a spacious lakefront property surrounded by green lawns and mature trees. A private dock extends into Butternut Bay, while a circular inflatable float rests on the calm water. The house is visible, nestled among the lush landscape.

Home in Iroquois

Relax on Butternut Bay

TraceyRating, 5 stars6 months ago

Third stay at Butternut Bay, and it truly does feel like a home away from home. We have such special family memories because of Butternut Bay and its owner, first Jeanne, and now Meagan who is continuing her legacy--and it really does feel like that. Meagan cares that your time at Butternut is one you will remember. We thoroughly enjoyed her sharing of the St Lawrence Seaway map online, so we were able to track and learn more about the ships that were passing, day and night! Looking forward to our next stay, and more amazing family moments. Thank you Meagan!

Cabin in Merrickville-Wolford

4.97 out of 5 average rating, 194 reviews

Cottontail Cabin with Hot Tub and wood fired Sauna

AnnaRating, 5 stars1 month ago

Very private and beautiful location. Cabin full of charm,functional and well appointed. Hot tub, sauna,wood burning fireplace make you feel like you are at a private spa. Lots of wild life so please watch your dog's .

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Winchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winchester's top sights

Mary's Restaurant4 locals recommend

Country Kitchen3 locals recommend

Mr. Mozzarella Pizza and Wings3 locals recommend

Seaway Valley Pharmacy3 locals recommend

Foodland - Winchester3 locals recommend

Winchester District Memorial Hospital3 locals recommend

Other great vacation rentals in Winchester

Home in Clarence-Rockland

A private deck features a luxurious wooden surface with two slatted lounge chairs positioned for relaxation. A covered BBQ grill is located nearby, and a glass patio door provides access to the interior of the home.

4.97 out of 5 average rating, 30 reviews

Home away from home

JulieRating, 5 stars1 month ago

This was our second time staying at Sheila’s, we felt right at home. Thank you for everything!

4.81 out of 5 average rating, 104 reviews

An aerial view showcases the backyard, featuring a round above-ground pool surrounded by a wooden deck. A garden shed is visible beside the pool, and greenery from various trees and plants creates a natural border around the space.

Home in Orléans

Entire 9 person house with Exercise equipment

AminRating, 5 stars2 days ago

Worth every penny. Landlord is very nice and respectful.

5 out of 5 average rating, 6 reviews

A wooden dock leads to a cottage set back from the water, surrounded by lush greenery. The clear blue sky complements the scene, and a screened-in porch on the cottage offers views of the river. Rocks and water frame the dock, enhancing the natural setting.

Cottage in Ogdensburg

Sunsets on the St Lawrence River

Victoria,DianeRating, 5 stars8 months ago

Janet is very attentive to details and her camp has everything you could need! The beautiful screened in porch was amazing to keep us out of the rain but could still enjoy the view! The camp was spotless and we had an amazing stay, thank you Janet! Would recommend this property to anyone who wants to enjoy a getaway from home!

4.95 out of 5 average rating, 44 reviews

A screened porch features a dining table with four red cushioned chairs. Behind, expansive windows offer a view of a green landscape, with trees visible in the distance. A wooden deck adds to the inviting outdoor seating area.

Cottage in Lisbon

Gracie’s Meadow House with beautiful views

JaidaRating, 5 stars2 weeks ago

Small home located in a quiet Amish community. It was cozy and secluded. Greenhouse on property. Lovely view of the sky at night! About a 15 minute drive from Canton. I would recommend doing any necessary traveling during the day as the area is dark at night and there are plenty deer and other animals. Host was very responsive and polite. Would recommend.

5 out of 5 average rating, 10 reviews

An aerial view of a two-story cottage is framed by lush greenery, highlighting its wooden exterior and large windows. A staircase leads to a deck accessible from the main level, surrounded by trees, enhancing the sense of seclusion.

Cottage in Val-des-Monts

Spectacular six-bedroomed lake cottage

MariaRating, 5 stars36 months ago

My family and I had a great time at this beautiful cottage. It far exceeded our expectations and would highly recommend it.

4.96 out of 5 average rating, 27 reviews

Home in Ottawa

Cozy Home & Porches for Intimate Weddings/Reunions

ErinaRating, 5 stars3 days ago

Hi Bin and Li, Just wanted to send a huge thank you for hosting our family reunion and civil wedding. The house was perfect—cozy, welcoming, and just a few minutes from our family home in Ottawa, which made everything so convenient. Every guest loved the vibes of the house, especially the event hall. It was beautifully set up and created the perfect atmosphere for our ceremony and reception. The BBQ dinner was a hit, and everyone had a blast enjoying the meal together. A special shoutout to the lovely lady who took care of the cleaning. She was not only efficient but also incredibly kind and attentive, ensuring everything was spotless and comfortable. Your place has definitely earned a spot on our Ottawa Airbnb favorites list. We’re so grateful for the wonderful experience and highly recommend it to anyone looking for a beautiful and accommodating place to host special events. Thanks again for everything. Huge thanks from Erina, Family and Friends!

4.86 out of 5 average rating, 28 reviews

A bright entrance area features a modern round mirror and a decorative welcome mat. Natural light enters through a glass-paneled front door. Stairs with wooden treads lead to the upper level, complementing the neutral color scheme of the walls and flooring.

Home in Carleton Place

Home away from home

MarcRating, 5 stars2 weeks ago

We had a group of 5 of us staying in this home plus a dog and we were very comfortable. The house is very clean and well furnished. Hosts responded promptly. Lots of space to relax plus a fenced in yard for the dog. I would definitely stay here again.