Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite

A spacious gazebo features a comfortable seating area with a gray wicker sofa and red Adirondack chairs. A fire pit is centered on a stone patio, surrounded by lush green grass and views of the lake beyond. Nearby, a dock and additional outdoor items are visible.

Cottage in Carleton Place

4.97 out of 5 average rating, 31 reviews

7th Heaven Waterfront Cottage on Mississippi Lake

Welcome to 7th Heaven! Stunning Sunsets on Mississippi Lake. Lake life doesn't get any closer to the city. Waterfront cottage with a bunkie only 7 minutes to all amenities and historic Carleton Place. Watch the sunsets around the fire pit or on the dock and make memories to last a lifetime. Work from the cottage with high speed internet or commute a short distance to the city. Only 35 mins from downtown Ottawa! Located in a quiet bay on a private road with the most breathtaking sunsets.

Top guest favorite

Home in Norwood

5 out of 5 average rating, 35 reviews

The Owlet’s Nest 🦉 on Norwood Lake

Located 10 minutes or less from Clarkson University, SUNY Potsdam, Canton-Potsdam Hospital, and Windy Point Stables, this property is an excellent choice for families, groups, healthcare professionals, and wedding guests. Enjoy 2 beaches, kayaking, grilling and campfires right in the large backyard. Play pickleball, street hockey, and basketball on the large parking lot. Enjoy the convenience a dedicated workspace w a WiFi printer, an 85" smart TV w cable, fitness equipment, & a washer/dryer.

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

Featuring 2 large bedrooms with queen beds, an enormous bathroom on the top floor and a bonus room located on the ground floor with 2 futons/double beds. Large open concept main floor features a living room, dining area for 6, a powder room and a kitchen with everything you’ll need. Enjoy over 25k free movies and 5k TV series during your stay. BBQ on rear deck. Patio furniture May to October. Fantastic location, movie theatre, restaurants, NHL arena, downtown and much more in minutes!

Guest favorite

Large windows provide a scenic view of the waterfront and surrounding nature. The wooden ceiling adds warmth, while a cozy yellow chair and a small side table are positioned to enjoy the vista. A covered porch and barbecue grill are visible outside.

Bungalow in Dunrobin

4.93 out of 5 average rating, 15 reviews

Serenity Beach House

Kick back and relax in this stylish, modern, private waterfront escape. The house has been renovated from top to bottom creating an inviting functional and well-appointed space. The kitchen has been stocked with all of the essentials. A new washer and dryer, with lots of fresh linens and towels. And the new beds, simply divine. We’ve been super hosts for years and are committed to ensuring your stay is relaxing and enjoyable. Don’t hesitate to reach out if you have any questions

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

Breathtaking views of the St. Lawrence Seaway from this Lake-house among mature trees, lawns and perennial gardens. Three bedrooms, one with on-suite bathroom, in total sleeps 8 with two double beds, a queen bed, a double sleeper sofa bed and a set of bunk beds. 2 kitchens w/gas stoves, family room w/walk-out to patio & BBQ. Living and dining area with walk out deck. The shared beach is good for Swimming, canoeing, fishing in Butternut Bay. Watch cargo ships navigate the river.

Top guest favorite

A modern kitchen features sleek white cabinetry and a large black countertop. Stainless steel appliances, including a refrigerator and oven, are included. Natural light floods the space through a nearby window, complemented by a small floral arrangement on the counter.

Home in Orléans

5 out of 5 average rating, 14 reviews

The Pizzicato: Comfort and Convenience

Welcome to The Pizzicato! Experience this newly built 3-bedroom home in Orleans, perfect for business or leisure. Meticulously furnished for your comfort, it’s conveniently located near groceries, shopping, and just 15 minutes from downtown with convenient access to public transportation. Nestled in a calm residential neighborhood, the home includes parking, a ping pong table, and workout equipment in the garage. Enjoy a peaceful and convenient stay at The Pizzicato!

Top guest favorite

A bright living area features large windows that invite natural light, highlighting the wooden walls and stone fireplace. Comfortable seating is arranged around a circular coffee table, with cozy throws adding warmth to the space. A glimpse of the deck can be seen through the glass doors.

Chalet in La Peche

5 out of 5 average rating, 101 reviews

Le Stonybreck: Modern Wakefield Chalet Getaway

Beautiful, newly built and fully equipped luxury chalet. Located at La Pêche (Edelweiss) just 25 minutes from downtown Ottawa close to the quaint village of Wakefield. This four season chalet is a perfect getaway for any occasion, gathering, or quiet relaxation. Great for outdoor recreational activities. Surrounded by trees and overlooking a large pond. Fire pit to keep you warm on any night. Vegetable garden to pick and eat your own fresh veggies in the summertime.

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

Cottontail Cabin, nestled on 22 acres of serene woods! This is the perfect retreat for those seeking a relaxing and rejuvenating getaway in the heart of nature. The cabin is fully equipped with all the amenities you need to make your stay comfortable and enjoyable. With 2 bedrooms and a pull out couch, the cabin can accommodate up to 6 guests. The cabin features infloor heating and a woodstove to keep you warm and cozy. We have a full-size hot tub and a wood fired sauna!

Superhost

Chalet in Wakefield

4.86 out of 5 average rating, 412 reviews

A Room with a View

Wakefield waterfront on the Gatineau river. Great views of and only a few steps from the iconic covered bridge and a short walk to restaurants, pubs and cafes. Two fireplaces, two decks, and plenty of parking. This is a brand new home that we are sure you will enjoy. Respectful, courteous guests only. The magnificent views from the home and the two large decks come with some effort and this vacation paradise is not recommended for those with mobility issues.

Guest favorite

A serene bedroom features a spacious bed adorned with decorative pillows, set against a backdrop of large windows overlooking the lake. A wooden accent wall with sliding doors adds warmth, while natural light enhances the calming atmosphere. A small table with a tray is positioned beside the bed.

Cottage in Val-des-Monts

4.89 out of 5 average rating, 19 reviews

Twin Lake Retreat - Hot Tub & Private Beach

Welcome to Twin Lakes Retreat, a serene 4-bedroom cottage offering breathtaking panoramic lake views. Thoughtfully designed for comfort, this getaway features unique outdoor spaces perfect for savoring your morning coffee or unwinding in nature. Lounge on the balcony, soak in the hot tub, or gather around the fire—all with stunning lake and mountain vistas. Sleeps 8, the home is fully equipped. Enjoy the lake with complimentary kayaks and paddleboards.

Guest favorite

Home in Grenville-sur-la-Rouge

4.89 out of 5 average rating, 179 reviews

Petit Montebello Kayaks/Spa/Plage CITQ 296375

2 to 16 people max. ideal for families SPA open year-round. Massages and body treatments on site by a professional team recognized by the FQM . House with five bedrooms, one of which is open. A screen is provided on request. Located in the suburbs of Montreal and Ottawa, our round wooden home gives direct access to the Ottawa River. Access to the vegetable garden and chicken coop. Free boats, free parking. IMPORTANT: curfew after 10 p.m. for outside.

Guest favorite

Villa in Gloucester

4.95 out of 5 average rating, 229 reviews

Brand New Luxury Home W/8Beds, Hot-tub, Pool Table

New 3BR, 1 Loft Home: Modern, Cozy Retreat Welcome to our stylish 3BR corner unit, a haven in a friendly neighbourhood. This modern home, near a shopping plaza, offers a garage/driveway for 4 cars, private office, and pool table. Enjoy parks, walks, and hiking. 4-min drive to the airport, 10 to downtown. Simple check-in. No parties, No outdoor usage of the backyard, HotTub, patio ,or BBQ after 11pm. Thanks for understanding! Book your stay now!