Holiday rentals in Pipestone

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Top-rated holiday rentals in Pipestone

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Top guest favourite

A stylish living area features a combination of blue sofas and an accent chair adorned with floral patterns. A round white coffee table is positioned centrally, with candle holders placed atop. In the background, a modern kitchen is visible, showcasing sleek cabinetry and bright lighting.

Home in Virden

4.9 out of 5 average rating, 31 reviews

Lyons Manor Newly renovated character home

Renovation of the home will be completed Feb. 7th Bookings welcome. Lyons Manor has been renovated throughout with “Vintage-Modern stylings by JT Interiors Design Group! A stylish blend of contemporary amenities while honoring the rich history of the home. Nestled in the heart of Virden, steps away from beautiful parks, scenic creeks, and walking trails Explore downtown's shops and eateries. HisWhether you're here for relaxation, work or adventure, our home is the perfect base for your stay

A well-organized kitchen features white cabinetry with wooden accents. The space is equipped with a stove, microwave, and coffee maker. A small potted plant adds a touch of greenery, while a neutral-colored mat is positioned on the floor.

Home in Maryfield

Private, Furnished Pet-Friendly

The Master bedroom has a double-sized bed, TV/stand, clothes closet and a dresser/night-stand with drawers. There is a sofa-bed in the Living Room. The Bathroom has a tub (with shower). Pets are welcome, and in the back yard is a dog run/kennel. ***Please note that there is no wifi or cable/satellite service for the TV.*** Many upgrades have been made but I don't have updated pictures of this particular unit yet. Also, the suite is actually a mirror image of the suite shown in the pictures.

Top guest favourite

The living area is adorned with a comfortable seating arrangement, accented by a stylish clock on the wall. A dining table with white chairs sits at the forefront, while a vibrant blue refrigerator complements the kitchen space in the background.

Guest suite in Oak Lake Beach

4.97 out of 5 average rating, 35 reviews

Oak Lake Beach Glamping; Golf Beach Basement Suite

New 3 bedroom basement apartment with private entrance. Private Suite with Full kitchen. Oak Island 18 hole Golf course located next door, 71 par over 6000 yards. Main beach access, park with play structures are just steps away. It is located in a quiet crescent Backyard includes BBQ, Firepit, Dining Table, Hammock & room to relax. Great for a family, or just a romantic getaway. Ice fishing draws many to the lake in the winter. Free WIFI. No smoking or vaping No pets No parties!

Top guest favourite

The cabin's exterior showcases a blend of wood and stone elements, with large windows allowing natural light to enter. The pathway is lined with stones and bordered by greenery, leading to a welcoming entrance. Parking is visible, along with the garage on the right.

Cabin in Oak Lake

5 out of 5 average rating, 14 reviews

Raven's Roost Getaway

This stylish cabin is perfect for trips to the lake or stay right beside the Oak Island Golf Course (18 Hole Championship Course less than 900 ft walk from front door)! Put supper on the smoker and enjoy a round of golf, then relax on the patio or sit around backyard bonfire. The Oak Lake beach and Provincial Park less than a 5 minute walk. Oak Lake Marina is a 3 minute drive. 1 King, 2 Queen beds, full kitchen, TV (Netflix, ROKU), patio, hi-speed wifi Could rent 2 kayaks for additional fee

Guest favourite

A private deck is visible, featuring a round table surrounded by four white chairs. Lattice work frames the deck, while a milk can adds character. Lush green grass and trees surround the area, creating a peaceful outdoor space.

Home in Elkhorn

4.89 out of 5 average rating, 28 reviews

Quaint Little House with Character! Private deck!

Cozy 3 bedroom home on corner lot with lots of parking. House has spacious bright kitchen with fridge, stove, washer/dryer and mic. Kitchen is equipped with all cooking necessities, coffee maker, coffee, tea, sugar and basic cooking necessities like oil, seasonings and spices. LR has a comfy couch, 3 chairs, flat screen TV & Shaw satellite. Main bathroom has had an extensive reno (June 2019) including a new beautiful tile shower. Private deck overlooking a secluded peaceful back yard.

Guest favourite

A spacious deck is featured, with a combination of comfortable seating and a dining area. Lush greenery surrounds the space, providing a serene view. A small gazebo is visible, and a patterned area rug adds a decorative touch. A dog is resting quietly on the deck floor.

Cottage in Oak Lake

4.76 out of 5 average rating, 29 reviews

Hobbit Cottage -A cozy retreat

Cozy cottage—cute vintage mobile home next to a world class golf course and yet surrounded by nature!! Comfortable beds , one bath , tv , and full use of kitchen. Enjoy the view of the golf course from the large deck or grab a bicycle and head to the beach and discover the riding trails around the lake.15 minutes to fine dining and shops in the next community.A year round get away - Lovely new bathroom just added this year!!-Kitchen upgraded as wellExciting news-wi-fi available!!

Home in Oak Lake

New place to stay

4 Bed, 2 bath House in Oak Lake with large kitchen

Soft opening Sept. 2025. Flat Creek Inn is supporting Adult & Teen Challenge Brandon for women recovering from addictions. Purchasing many items from the SuperThrift Brandon to give new purpose & life to our home has been the ultimate recycling. Many community members have donated items. Using our 1900s piano as a bedframe & featuring old radios, sewing machines & photos from Oak Lake's past make us unique. Flat Creek Inn is bright & cheery & waiting for you to gather.

Top guest favourite

A modern, single-story home is illustrated with a combination of blue siding and stone accents. Large windows allow natural light, and a welcoming front porch is adorned with seating. Lush green grass surrounds the house, emphasizing its outdoor space near oak trees.

Home in Sifton

4.96 out of 5 average rating, 53 reviews

Family Lake Home

Relax with the whole family at this beautiful home surrounded by oak trees. A true nature-lovers oasis, perfect for all the seasons! In the summer you can enjoy everything lake life has to offer. With a gorgeous 18 hole golf course just down the street, and a quick walk to the beach, provincial park, playgrounds, store, mini golf and more! Winter, spring and fall, cozy up to the picturesque views and enjoy a dip in the hot tub to ease the chill.

Top guest favourite

The exterior of a hand-crafted log home is showcased, featuring large windows that offer expansive views of the lake. The structure exhibits rustic charm with its natural wood finish and intricate log beams. A well-maintained lawn surrounds the home, enhancing its tranquil setting.

Home in Cherry Point

4.94 out of 5 average rating, 64 reviews

Lakefront log home, lower level. Golf Sim rental

Cozy up with loved ones at our family built lakefront log home at Cherry Point, Oak Lake Beach. MB For larger groups of 10-14 max . Come, take in these breathtaking sunsets and unwind in your private ground level suite. This is the perfect getaway to recharge & reconnect with friends and family. Kayaks available for use. Premium Golf Simulator attached to property 2 mins from Premium Oak Island Golf Course Great fishing!

Guest favourite

A cozy bedroom features a queen-size bed adorned with dark bedding. Two bedside lamps illuminate the space, complemented by framed artwork on the walls. A decorative vase with pink flowers adds a pop of color, and a patterned area rug is placed underneath.

Private room in Hargrave

4.91 out of 5 average rating, 57 reviews

Huggybears B&B: The Peloquin Room (Classy Comfort)

A classic and nostalgic space (with a nod to Paris and travel ) within a semi-attached cottage, situated on a beautiful acreage halfway between Winnipeg and Regina. The property is a peaceful peaceful, oasis of green, surrounded by farmland. The Peloquin Room was named after the second family who owned this property. It has a queen-size bed and three- piece ensuite, Roku T.V., fridge, microwave, coffee maker....

Top guest favourite

A cozy bedroom is presented with a queen-size bed, featuring a neutral-toned bedspread and decorative pillows. Nightstands with lamps are placed on either side, and inspirational wall art adorns the patterned wallpaper. A soft blue area rug lies beneath the bed.

Private room in Hargrave

4.94 out of 5 average rating, 132 reviews

Huggybears B&B: The Reid Room (Rustic Charm)

A charming, rustic -style space within a semi-attached cottage, situated on a beautiful acreage halfway between Winnipeg and Regina. The property is a peaceful oasis of green, surrounded by farmland. The Reid Room was named after the family who first homesteaded here in the early 19oo's. It has a queen-size bed, three-piece ensuite, Roku T.V., fridge, microwave, and coffee maker.

Top guest favourite

Private room in Virden

4.97 out of 5 average rating, 100 reviews

Suzanne's B & B

Our house was built in 1906 by two very interesting and important Manitobans, Dr. George Clingan and his wife, Ida Clingan. It is fully renovated with all the modern conveniences while maintaining the historic colonial charm. It is conveniently located in the heart of Virden, within short walking distance of shops, banks, post office restaurants and pubs.