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Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

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Popular amenities for Winchester vacation rentals

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
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, 104 reviews

Entire 9 person house with Exercise equipment

AminRating, 5 stars4 days ago
Worth every penny. Landlord is very nice and respectful.
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 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!
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.
Superhost
The cottage features a wooden facade with a welcoming entryway, framed by colorful flower beds. Two folding chairs are placed on the porch, providing seating in a shaded outdoor area surrounded by trees.
Cottage in Morristown
4.85 out of 5 average rating, 102 reviews

Cozy 2 bedroom cottage with plenty of privacy

MichaelRating, 5 stars2 months ago
everything was great. place was clean and ready to be stayed at. no problems or concerns. great responsive host as well!!
Guest favorite
Home in Ottawa
4.96 out of 5 average rating, 27 reviews

Cozy Home & Porches for Intimate Weddings/Reunions

ErinaRating, 5 stars5 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!
Superhost
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
4.86 out of 5 average rating, 28 reviews

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.
Superhost
A modern kitchen is equipped with dark wooden cabinets and a durable countertop. A stainless steel sink is situated under a tiled backsplash featuring a geometric pattern. Appliances include a stove, oven, and a coffee maker, providing essential amenities for meal preparation.
Apartment in Aymer
4.94 out of 5 average rating, 16 reviews

Grand appartement familial

BrendanRating, 5 stars9 months ago
Excellent stay! An amazing apartment. It was spotless and very comfortable. I would highly recommend staying here if you are in the Gatineau/Ottawa area. Beautiful kitchen! Location was great, with only 15-20 minutes from Parliament hill. A very peaceful neighbourhood.

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