Vacation rentals in Winchester

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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

Guest favorite
A view from the porch captures a vintage gazebo set amongst lush greenery and open fields. The serene landscape features a winding path and gentle rolling hills under a partly cloudy sky.
Farm stay in De Kalb Junction
4.95 out of 5 average rating, 110 reviews

Amber Valley Farmhouse at Indian Creek

JiteshRating, 5 stars8 months ago
A wonderful farmhouse which everyone in our group thoroughly enjoyed. The house has a lovely character. Inspite of it being very old, it's reasonably well maintained. We did hit a couple of issues but the host Robert/Paula were very responsive and took care of things. The whole area is total country side and allows one to completely disconnect from our urban lives. Overall, it was good and unique experience living here.
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!
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 stars1 week 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, 29 reviews

Home away from home

GlenRating, 5 stars2 weeks ago
Steven's place was exactly what we needed. Easter weekend we visited our son. We weren't 100% sure how many of our family were going to make the trek. The house turned out to. e perfect with 2 more of my sons showing up, so the extra space was magnificent. With my 92 year old mother in one of the rooms it was nice to have a bathroom handy. The downstairs living room with TV allowed the younger lads to stay up later and not disturb the others needing sleep. Thanks for a perfect Easter weekend.
Guest favorite
Chalet in Carleton Place
4.93 out of 5 average rating, 68 reviews

Beautiful Chalet on the Lake

SiddharthRating, 5 stars2 weeks ago
Amazing property and hosts. Erin & Sadique were extremely responsive and answered all our questions. They even provided a high chair for my daughter on request. The property is expansive and you will truly feel like you have a private lake. The living room is so spacious and the wood makes it feel cozy despite the big size. The rooms are top notch much much better than your average Air BnB sinking mattresses. The bathroom in the main bedroom on the ground floor is just amazing. Our group made full use of the hot tub, easily accommodated 5 at a time and was the highlight of our trip. Highly recommend this place!
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!
Superhost
Home in Hammond
4.97 out of 5 average rating, 33 reviews

4 Bedroom 2 Bath Home on Beautiful Black Lake

SergeyRating, 5 stars3 months ago
I don't even know where to start! This is incredible! The house is really clean! Cozy! Light! Warm! Friends work in construction business and they checked the house with a special black light!Everything is perfectly clean! This is the house i would like to rent in the future! Thank You Nicholas and team! Great job!!!

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