
Vacation rentals in Winchester
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Guest favorite

Farm stay in De Kalb Junction
4.95 out of 5 average rating, 110 reviewsAmber 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

Home in Clarence-Rockland
4.97 out of 5 average rating, 30 reviewsHome 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

Cottage in Morristown
4.85 out of 5 average rating, 102 reviewsCozy 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 reviewsCozy 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

Home in Carleton Place
4.86 out of 5 average rating, 29 reviewsHome 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 reviewsBeautiful 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

Home in Iroquois
4.84 out of 5 average rating, 129 reviewsRelax 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 reviews4 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!!!
Destinations to explore
- Island of Montreal Vacation rentals
- Prairies River Vacation rentals
- Laval Vacation rentals
- Mont-Tremblant Vacation rentals
- Pocono Mountains Vacation rentals
- Mississauga Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Hudson Valley Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Québec City Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Canadian Museum of History
- Calypso Theme Waterpark
- Ottawa Hunt and Golf Club
- Royal Ottawa Golf Club
- Camelot Golf & Country Club
- Rideau View Golf Club
- Canadian Museum of Nature
- Canadian War Museum
- Mont Cascades
- Hotel Fairmont Le Château Montebello Golf Course
- Brockville Country Club
- Rivermead Golf Club
- Champlain Golf Club
- Eagle Creek Golf Club
- Golf Le Château Montebello
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes