Vacation rentals in Side Lake

Cozy Stone Cottage overlooking Smith Lake

You'll love this unique and romantic escape. The Stone Cottage on Smith Lake is the perfect historic space with modern amenities. You can fish off of the dock or make use of the provided boat and Kayak. Use the Traeger grill and outdoor seating area, hike local trails, roast marshmallows over one of several fire pits, and then cozy up for a meal cooked in the gorgeous modern kitchen. We have a library of books and games on hand for you to enjoy, comfortable beds, and an incredible view!

Green Gate Guest Houses - Birches Condo

Renovated in 2025, the updated Birches condo includes well-appointed kitchen with induction cooktop, stainless appliances, living room with queen sleeper sofa, gas fireplace and lake views, private bedroom with queen bed, and full bath with tiled tub/shower and laundry center. The Giants Ridge alpine lifts and XC ski trails are just a short walk away in the winter season, while summer guests can enjoy the lake, beach, seasonal pool/hot tub, walking trails and golf/bike trails nearby

Quiet Cottage in the Woods on the Edge of Town

This lovely cottage has woods, hiking trails, and perenial gardens right outside the door. There are ski trails a mile away and the Redhead Mountain Bike park 8 miles away. The 2 Bdrm, 2 Bath home is fully furnished and has been completely renovated. The kitchen has everything needed to dine at home. The deck provides a peaceful view of the woods; and the 3 season porch and loft den offer lovely places to relax and read. In the winter the wood stove provides a toasty ambiance.

Lofted Cabin Two @ Mallard Point Cabins

Our little peninsula has been a Northwoods getaway for the past century. Formerly Mallard Point Resort, we're keeping the tradition alive by welcoming guests at two of our cozy cabins. Enjoy exploring the many nearby trails, paddling Prairie Lake, or just enjoying the lake views. This is the kind of place where you can expect to see other guests and share outdoor spaces. We're less than 10 minutes from downtown and 20 minutes from Tioga MTB trails. This listing is for Cabin 2 only.

Lake Vermillion's Pike Bay Prime Location

Perfect location for Snowmobiling/ Skiing/ Fishing. On a dead end road, this year round cabin has stunning views and 120 feet of private lakefront on incredible Lake Vermillion. Get away and create memories with family and friends with access to a private dock, patio, fire pit, large flat yard and 2 decks. Newly renovated 5 bedroom 3 bathroom 2 living rooms sauna game table Pac Man Arcade. Kitchen fully stocked. Huge parking space for trucks and trailers and boat landing onsite.

Lakefront 4 bedroom 3 bath Villa at Giants Ridge

Golf, Ski, Bike, Snowmobile, Swim, hike This 4 bedroom 3 bath Villa is a great place for a romantic getaway at the lake, an adventurous ski vacation, or a group trip to two of Minnesota's best golf courses. The well appointed open concept main floor is a great place to hang out as well as the game and entertainment room in the basement. The loft has gorgeous lake views and all three levels have updated bathrooms. There is a gas fireplace on the main level as well as downstairs.

Large cozy cabin, snow, sauna in the Chippewa

Secluded cozy hand scribed log home nestled in the woods on the shores of Minnesota’s clearest lake. Sauna, wood fireplace, outside fire ring, private dock, big yard, trails right out your door. If you’ve been wishing you had a cabin where you can hike, play, swim, fish and connect nature this is it. Book this one of a kind handcrafted log cabin on Minnesota's clearest lake. Start a family tradition. We have been here 25 years and plan to be here another 50. Lic.#3891-16215

The Hygge Suite at Giants Ridge Ski & Golf Resort

* Luxury 1 bed / 1 bath condo fully renovated in 2020 * Across the street from Giants Ridge Ski & Golf Resort * Located on Wynne Lake with lake access * Pet friendly (see house rules) * Outdoor swimming pool, hot tub and tennis court (open seasonally) * Wi-fi and 50” smart TV * Fireplace * Fully stocked kitchen * Luxury bedroom with queen bed and high quality linens * Spa-like bathroom with whirlpool tub and fluffy towels * Private deck with lake views * Games provided

Chickadee Hideaway: Cozy Cabin in the Northwoods

This woodland cabin has all the modern conveniences of home (air conditioning, fast wifi, whirlpool tub!) while offering northwoods peace and quiet. Surrounded by public forest and near the Sturgeon Lake chain, hours of outdoor activities await you. If you'd rather spend your time indoors, this comfy cabin has everything you need for a romantic getaway, a family vacation, or a weekend with friends. Pet owners: Please review our pet policy before booking (see below!)