Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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

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Guest favorite

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 stars4 days 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!

Guest favorite

A wooden dock extends into the calm lake, featuring five red Adirondack chairs arranged for relaxation. Lush green hills frame the serene water view, under a sky scattered with soft clouds.

Cottage in Val-des-Monts

4.98 out of 5 average rating, 50 reviews

Lakeside Cottage w/ New Hot Tub and Stunning Views

PaulRating, 5 stars1 month ago

We enjoyed our stay very much. The place was even nicer in person compared to the photos. Great attention to detail. The beds were very comfortable with softer & firmer pillows. The wood stove by the big TV and cushy couch was great. The hot tub was amazing. Lake side view off the deck was very nice. Strongly recommend. We’d love to come back.

Guest favorite

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

4.92 out of 5 average rating, 36 reviews

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!

Superhost

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

4.84 out of 5 average rating, 129 reviews

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!

Top guest favorite

Cabin in Merrickville-Wolford

4.97 out of 5 average rating, 194 reviews

Cottontail Cabin with Hot Tub and wood fired Sauna

AnnaRating, 5 stars3 weeks 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 .

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What guests are saying

La Vue - Mountain Top Cottage (breathtaking views)

4.88 out of 5 average rating, 24 reviews1 month ago

We had a wonderful stay at Luis’s cottage. Beautiful and modern inside and the most amazing view of the lake and surrounding nature. We felt relaxed and at home right away. Luis was also very responsive and accommodating to our needs. Definitely an A+ host and will highly recommend anyone to stay here.

Cabin in Val-des-Monts

What guests are saying

7th Heaven Waterfront Cottage on Mississippi Lake

4.97 out of 5 average rating, 31 reviews6 months ago

Myself and 3 ladies so enjoyed this peaceful fun weekend Their Air B&B was the perfect place to unwind, take walks, very clean, beautiful lakefront and sunsets were stunning Close to Carleton Place and Almonte for shopping and terrific restaurants Would certainly recommend.. Enjoy if you do book in the future!

Cottage in Carleton Place

What guests are saying

Waterfront Cottages /Scenic Views

4.94 out of 5 average rating, 65 reviews2 months ago

What a lovely place to spend a wintry weekend! My wife and I had a great time sharing this AirBnB with another couple. Melanie is a great host: she’s very flexible and a thorough communicator. The place was spotlessly clean and fully stocked with every supply you could think of. Melanie also made sure that the driveway was plowed and the sidewalk stayed passable even during heavy snowfall. The cottage stayed warm throughout the wintry weather, and it has a beautiful view of the St. Lawrence River, which is especially gorgeous in the snow. We highly recommend staying with Melanie, and we’ll be back at this place when return to the area!

Home in Ogdensburg

What guests are saying

Waterfront Cottage with Sauna, Kayaks and Fire Pit

4.96 out of 5 average rating, 47 reviews2 months ago

Dayna and David are INCREDIBLE hosts. They took care of every detail and looked after us when we were effectively snowed in. Their home is creative, beautiful, peaceful, spacious. I could not have asked for a better place to stay. The whole neighbourhood is gorgeous and talk about lovely people! We want to come back in the summer. And the sauna! Let me tell you, in the winter, this was the sweetest treat. I cannot say enough positive things about our experience and how we were treated - like close friends. They get my highest recommendation.

Cottage in Carleton Place

What guests are saying

The Owlet’s Nest 🦉 on Norwood Lake

5 out of 5 average rating, 35 reviews2 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.

Home in Norwood

What guests are saying

Serenity Beach House

4.93 out of 5 average rating, 15 reviews6 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!

Bungalow in Dunrobin

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Vacation rentals for every style

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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

Top guest favorite

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.

Home in Clarence-Rockland

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!

Guest favorite

A spacious outdoor deck is furnished with comfortable wicker seating and a glass-top table. The lush lawn leads to the lake, which is visible in the background, framed by trees and a clear blue sky. Relaxation and scenic views are offered in this inviting space.

Home in Norwood

4.98 out of 5 average rating, 55 reviews

Norwood Lakefront Oasis - whole house

SaffordRating, 5 stars6 months ago

Our stay at the “Oasis” was absolutely perfect for us. The location was just what we needed, and the view out onto the pond was so beautiful. The space and the layout of this home easily accommodated our group, giving us all our own space when needed. The owners have a very informative and organized notebook to answer any possible questions and to provide options for activities and dining. The home was clean, well stocked, warm and welcoming in every way. Definitely a “home away from home” experience to the fullest. We plan to book this location again in the future. Thank you so much!

Guest favorite

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

4.81 out of 5 average rating, 103 reviews

Entire 9 person house with Exercise equipment

NatashaRating, 5 stars3 weeks ago

Great place, very spacious, homie feeling, and the location was perfect for the event we were attending! Easy and smooth check in and check out. Would stay again and recommend!

Guest favorite

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

5 out of 5 average rating, 6 reviews

Sunsets on the St Lawrence River

Victoria,DianeRating, 5 stars7 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!

Top guest favorite

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

4.95 out of 5 average rating, 44 reviews

Gracie’s Meadow House with beautiful views

JaidaRating, 5 stars1 week 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.

Superhost

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

5 out of 5 average rating, 10 reviews

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.

Guest favorite

Home in Ottawa

4.96 out of 5 average rating, 26 reviews

Cozy Home & Porches for Intimate Weddings/Reunions

SamanthaRating, 5 stars2 weeks ago

Lily was a great host, she was responsive to any questions, we will come again and definitely recommend to others. Great spot for family get togethers!

Guest favorite

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

4.88 out of 5 average rating, 26 reviews

Home away from home

ShawnaRating, 5 stars1 month ago

My husband stayed there while working. Home was cozy, clean and how described. Across the road is a restaurant which was nice after a long day of work, he didn’t need to cook supper every night

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Vacation rentals in Winchester

Top-rated vacation rentals in Winchester

La Vue - Mountain Top Cottage (breathtaking views)

7th Heaven Waterfront Cottage on Mississippi Lake

Ship Watcher's Retreat

Waterfront Cottages /Scenic Views

Modern Lakeside Getaway Oasis

Twin Lake Retreat - Hot Tub & Private Beach

Waterfront Cottage with Sauna, Kayaks and Fire Pit

Lakeside oasis Apt with water access and views.

The Owlet’s Nest 🦉 on Norwood Lake

Spacious Home Away From Home

Beautiful Spacious apartment, close to downtown

Serenity Beach House

Vacation rentals for every style

Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Other great vacation rentals in Winchester

Destinations to explore