Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite

A rec room is illuminated by natural light streaming through large, angled windows, offering a serene view of the lake. A pool table is positioned near the windows, with cozy seating visible, enhancing the inviting setting.

Cabin in Winchester

4.95 out of 5 average rating, 21 reviews

A frame cabin on Lake Metigoshe, Canada

AndresRating, 5 stars1 week ago

This home is even more beautiful than the photos. The large windows offer a breathtaking view, especially during sunset, which quickly became one of our favorite moments each day. One of the things we appreciated most was how the layout of the house allows everyone to do their own thing while still feeling connected—whether playing pool, relaxing, or cooking together. The pool table was a hit and kept everyone entertained throughout our stay. The house is fully equipped with everything you might need, making it feel like a true home away from home. It comfortably accommodated both my family and friends, and everyone had a great time. Sierra is a fantastic host—attentive, kind, and thoughtful. I highly recommend this place and we’re already looking forward to coming back as soon as we can.

A cozy outdoor area features a fire pit with logs burning brightly. Colorful hammocks are suspended between trees, and string lights provide a gentle glow. The calm river reflects the evening sky, creating a serene backdrop for relaxation.

Cabin in Souris

4.81 out of 5 average rating, 42 reviews

Rustic Cabin on the Souris River

NaomiRating, 5 stars3 weeks ago

We felt right at home as soon as we arrived to this serene retreat! The rustic decor, wood fuelled (wood supplied) fireplace and the stunning riverfront and pasture views were highlights. The property is remote and we loved the location as it’s very close to drive into Souris. Would definitely return!

Superhost

A scenic view of Dromer Lake is presented from a wooden deck surrounded by vibrant autumn foliage. The deck, featuring a small seating area, overlooks a serene stretch of water with a small wooden dock extending into the lake.

Cabin in Deloraine

4.89 out of 5 average rating, 93 reviews

Mountain Escape

BaileyRating, 5 stars2 months ago

The cabin is beautiful! We had a nice relaxing weekend. The cabin looked just like the photos and it was very neat and tidy. There were lots of supplies for cooking and the kitchen was spacious. We stayed for a few days in the winter and it was warm and cozy. However, the road right before the cabin was extremely icy and steep. Our car could not make it up on its own. Needed a tow up the hills. If you do not have a 4 wheel drive car the drive may be difficult in the winter. Once the drive was over our stay was great.

The exterior of the cottage features a wooden upper deck with string lights, enhancing the inviting look of the home. A stone facade is visible on the lower level, surrounded by snow and trees. Large windows provide views into the living space.

Cabin in Metigoshe Lake

New place to stay

Lake Front Cottage

Welcome to this six generation family cottage which is perfect for family getaways. Prepare to fall in love with this stunning oasis. Bask in breathtaking sunsets and enjoy a magnificent view of Lake Metigoshe. Unwind in the hot tub surrounded by nature. This cottage boasts 3 bedrooms, 2 bathrooms and a large lake view deck which is a perfect escape for family and friends. It has plenty of space with sleeping room for 8. The cottage has everything you need to enjoy your stay.

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Popular amenities for Winchester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Winchester

Superhost

Cabin in Deloraine

4.89 out of 5 average rating, 93 reviews

Mountain Escape

BaileyRating, 5 stars2 months ago

The cabin is beautiful! We had a nice relaxing weekend. The cabin looked just like the photos and it was very neat and tidy. There were lots of supplies for cooking and the kitchen was spacious. We stayed for a few days in the winter and it was warm and cozy. However, the road right before the cabin was extremely icy and steep. Our car could not make it up on its own. Needed a tow up the hills. If you do not have a 4 wheel drive car the drive may be difficult in the winter. Once the drive was over our stay was great.

Cabin in Souris

4.81 out of 5 average rating, 42 reviews

Rustic Cabin on the Souris River

NaomiRating, 5 stars3 weeks ago

We felt right at home as soon as we arrived to this serene retreat! The rustic decor, wood fuelled (wood supplied) fireplace and the stunning riverfront and pasture views were highlights. The property is remote and we loved the location as it’s very close to drive into Souris. Would definitely return!

A gray and white building is viewed from the street corner, featuring a single entry door and large windows. A bench is positioned in front of the building, under the shade of a bare tree, with a clear blue sky above.

Apartment in Souris

4.58 out of 5 average rating, 52 reviews

Souris #1 1 bedroom apt. w/hidabed

DanielleRating, 5 stars3 months ago

We loved staying here. It was perfect for us. Great location and gorgeous setting. The place was clean and well kept. The amenities were exactly as listed and made our stay super easy and enjoyable.

A peaceful countryside landscape features a wide expanse of green grass, dotted with a few grazing horses. A natural wooden fence lines the foreground, while a backdrop of trees provides shade and privacy. The sky is overcast, contributing to a serene atmosphere.

Home in Hartney

4.73 out of 5 average rating, 15 reviews

Little Patch of Heaven B & B

SemiRating, 5 stars43 months ago

Great place, nice and clean ! Jolene was really helpful i would definitely go back !

Guest favorite

A serene deck offers comfortable seating overlooking a calm lake at sunset. Potted plants add natural greenery, while a round table provides a space for relaxation. The scene captures tranquil water and scenic views, creating an inviting outdoor setting.

Cabin in Metigoshe Lake

5 out of 5 average rating, 19 reviews

Beautiful family home on Lake Metigoshe, Canada

MichaelaRating, 5 stars6 months ago

Beautiful! Can’t wait to come back.

Guest favorite

Cabin in Winchester

4.95 out of 5 average rating, 21 reviews

A frame cabin on Lake Metigoshe, Canada

AndresRating, 5 stars1 week ago

This home is even more beautiful than the photos. The large windows offer a breathtaking view, especially during sunset, which quickly became one of our favorite moments each day. One of the things we appreciated most was how the layout of the house allows everyone to do their own thing while still feeling connected—whether playing pool, relaxing, or cooking together. The pool table was a hit and kept everyone entertained throughout our stay. The house is fully equipped with everything you might need, making it feel like a true home away from home. It comfortably accommodated both my family and friends, and everyone had a great time. Sierra is a fantastic host—attentive, kind, and thoughtful. I highly recommend this place and we’re already looking forward to coming back as soon as we can.