Holiday houses in Glenwood

Dog Friendly W/Large Yard, Countryside Oasis

Home situated on 20+ acres, experience the peace and beauty of the country while being easy to get to. Close to several lakes. ✔️Roughly 10 minutes from downtown Alexandria and main shopping stores ✔️Near Holmes City and Garfield ✔️Launch your boat on Lake Mary, Lake Lobster, or Lake Latoka nearby ✔️Enjoy the summer farmers market in Holmes City just 5 miles away ✔️Golf at Hardwood Hills less than a mile away ✔️About 10 minutes from Brophy Park with biking and hiking trails ✔️Just 5 minutes from I94

Woodchuck Bluff Stunning Lake Cabin with Beach

Have fun with the whole family at this new & modern lakeside cabin, wake up to sunshine and beautiful lake views. Private sandy beach and swimming area. Full kitchen with beverage center. Cozy wood fireplace Retro Skee Ball. washer+dryer. Blades convenience store with gas + bait + liquor is a 2 min walk down the street Holmes City Farmers Market & Breakfast feed every Saturday AM - May 17 - Oct. 7 miles from Andes Tower Hills Ski Resort 10 Miles to Alexandria, MN Outdoor Sauna coming soon

The Cowdry Cottage | Pet-Friendly | Canoe | Bikes

Experience Minnesota lake living at our charming retreat on Lake Cowdry. 2-for-1! This pet-friendly property offers two separate sleeping areas. "The Main Cottage" offers modern amenities in a cozy, nostalgic setting with a kitchen, bedroom, full bathroom and pull-out sofa. "The Hut" is a converted lakeside boathouse that includes a queen bed and half bathroom. Enjoy lake views, a private dock, canoe, bikes, propane grill, and 55-inch smart TV. Perfect for a family vacation or couple's getaway!

The Hurlen Hytte (cabin, in Norwegian)

This cozy, Norwegian inspired cottage is literally steps away from Smith lake and is located between Alexandria and Osakis, Minnesota. The interior features, rustic knotty pine, hardwood floors, stone fireplace and sunlit porch. Step outside to the layered deck, grill, fire pit, log swing and dock. Enjoy our assortment of lake toys, or just sit back, relax and watch the fish jump. Rediscover the charm of simpler times and create lasting memories by booking your stay today! Douglas Co lic#2225

The Maynard Cabin, a Civil War era log cabin

The Maynard Log Cabin was erected by a homesteader after the civil war. We have moved and restored it and made it available for rent. It is off the grid, but it has a complete functioning kitchen, wood stove and sitting room downstairs. There are two antique beds with new mattresses upstairs. There is no electricity but the cabin is furnished with kerosene lanterns. The bathroom facilities consist of wash basins and outhouse. The cabin is surrounded by 40 acres of woods and meadows.

Cabin with dock/beach access to Lake Minnewaska

Escape and unwind at this peaceful cabin retreat near beautiful Lake Minnewaska. Steps from a private beach, guests can relax by the water, enjoy sunrise and sunset views, gather around the firepit, and enjoy private dock access to enjoy lake life. The cabin is within a 5-minute walk to Barsness Park, the public beach, and the Lake Minnewaska boat landing. Close to downtown Glenwood to explore local shops, restaurants, breweries, and more. Please note: Cabin is not handicap accessible.

Exceptional family friendly lake home

Enjoy our fabulous lake home. After 30 years as our summer home we are opening it up to give others the chance to enjoy the lake life. Relax and watch the kids from one of our two decks as they swim, kayak, paddle board, fish, and play outdoors. Inside you will love the open concept with seating for 12 at the dining room table, the well stocked kitchen, and the media room. Whether you are a family or group of friends; we supply most everything you will need to create fantastic memories.

Cedar Street Cottage

Experience the Perfect Blend of vintage Charm and Comfort! Relax in this freshly updated 1920s home, with 3 levels offering vintage cottage style blended with modern amenities. Enjoy a cozy porch, full kitchen, dining room, record player and games. Located in a safe, family-friendly neighborhood, this clean and inviting retreat is steps from downtown’s boutiques, cafes, antique shops, parks, restaurants, and a brewery. Perfect for families, couples, girls’ weekends and solo travelers!

Peaceful Getaway

Scenic and peaceful with a charming rustic cabin. Take a stroll through our enchanted forest on your way to the lake. The bridge will take you there! Once on the lake relax on our floating deck! Our sunsets are lovely, and nature surrounds you. We are located on Long Lake which has no public access so it’s very quiet. Bring your kayaks for some amazing bird and turtle watching. Feel like swimming? Fairly Lake beach is 4 minutes from the cabin! End your relaxing day around the firepit!

Oak Crest Tiny Home | Cozy Winter Escape for Two

Oak Crest Tiny Home – A Peaceful Winter Escape for Two Slow down and reconnect in this cozy black tiny home near Glenwood, MN. Thoughtfully stocked for rest, comfort, and simple living. Sip local coffee, curl up under soft blankets, enjoy games or TV, or unwind by the outdoor fire ring beneath twinkle lights. 💐 Baking in Bloom (optional add-on): fresh baked goods and homemade jams with 36-hour notice. 🔥 Warm, inviting, and winter-ready—perfect for cozy fall and winter getaways.

Timber Arch | Unique Lake Gem ~ Yard ~ Kayak/Board

Step into the charming 2BR 1Bath cabin on the shores of the picturesque Pocket Lake. It promises a tranquil getaway with private lake access just a stone's throw away from Alexandria and its tasty restaurants, breweries, wineries, parks, and exciting attractions. The unique arched design and rich amenity list will leave you in awe. ✔ 2 Cozy Bedrooms ✔ Open Design Living ✔ Full Kitchen ✔ Spacious Yard + Games ✔ Dock + (Kayaks, Paddle Boards) ✔ HDTV ✔ Wi-Fi ✔ Parking License #2218

Luxury, Lake Views, Golf Cart!

Brand new construction! This luxe lakeview retreat features 4 private bedrooms plus a fun bunkroom off of the ensuite for the kids, 3 baths, high-end finishes, a party-ready garage with wet bar, games & big TVs. Perched up on a hill the huge windows, patio & yard offer beautiful views of Lake Minnewaska. Grill your fresh catch while you gather by the fire pit. Explore in the included golf cart the Starbuck beach, park, restaurants & Shirley’s Treats! Perfect for families & groups!