Holiday rentals in Roosevelt

Game Room, Theater, Fire Pit, Pet Friendly

Escape to Pine Lake Lodge – only 1 Hour from the Twin Cities Unplug at this cozy 2BR lakefront cabin, perfect for families, couples or small groups. Our guests love the private deck with amazing sunset views, fire pit & grill, and fabulous game room with 75" Roku TV. We are pet-friendly (fee), have tons of kid-friendly extras, and include free watercraft (kayak, canoe, paddle boat during warmer months). Winter fun with provided snowshoes and sleds. Right on SnoBug Trail 108 snowmobile access.

Erskine Escape: kayak, paddle board, paddle boat+

Relax with the whole family at this peaceful 3 BD/1BA cabin on Erskine Lake! Ample fishing, swimming and other water sports steps from the deck. Sandy, shallow bottom close to shore, perfect for floating and swimming with little ones! As a bonus, you are close to multiple larger lakes (Mille Lacs, Sullivan, Platte), ATV trails, and the Casino. This house offers a full kitchen, large living area, three separate bedrooms, laundry, kids kayaks, adult kayak, paddle board, and paddle boat (included).

A Frame-Sauna-Cold Plunge-Fire Pit-Seclusion

✔ Sleeps 4 – Lofted bedroom +pull-out couch (Both Queen Beds) ✔ Cozy & stylish – In-floor heating, A/C, 50” TV ✔ Fully equipped – Kitchen, Combo Washer/Dryer, fast WiFi ✔ Outdoor retreat – Sauna, Private patio, BBQ grill, firepit, string lights ✔ Secluded yet close to Brainerd Book now for the ultimate nature escape! -2 Miles from direct access to Paul Bunyon Trail -6 Miles from Northland Arboretum -7 Miles from Brainerd International Raceway -15 Miles from Crosby -20 Miles from Breezy Point

Beachfront Modern-Chic Family-Friendly Cabin

Welcome to the NEW and Improved Mil Lagos Beach House, a lakefront getaway to Mille Lacs Lake, MN. If you're looking for a chic, quaint vibe, look no further. You will fall in love with our cabin.... ✔120ft of sandy shoreline perfect for watching sunrises, swimming, and sunbathing. ✔ Large Deck great for outdoor dining and relaxation ✔ Bonfire Pit & Adirondack Chairs ✔ Tree Swing and Swingset for the kiddos! ✔ Kayaks, Paddleboat, Private Dock (shallow) ✔ Public Boat Launch next door

Quaint modern cabin set in private woodland

Escape into the forest at the Ursa Minor cabin. Built in 2017, this comfortable and tranquil getaway includes a full kitchen, bathroom with a cedar-lined shower, electric in-floor heat, a wood stove, warm pine siding throughout, and a spacious sleeping loft. A covered porch, fire pit and fully-stocked woodshed are right outside the door. Your stay includes access to more than ten kilometers of trails traversing hundreds of acres of private woodland originating steps from your door.

Dragonfly Cabin | Near Cuyuna Recreation Area

Enjoy this custom-built cabin in the pines, just one mile from the Cuyuna Lakes Trailhead and historic downtown Crosby. Perched above 20+ acres of wetlands, the cabin offers peaceful views, wildlife sightings, and beautiful sunrises. Designed by a husband-and-wife team, it sleeps four with a queen bedroom on the main level and a cozy loft. Relax on the patio or warm up by the tiny wood stove for a quiet, nature-filled getaway—close to adventure, lakes, shops, and great places to eat.

Highland House - Stunning Retreat on Big Sandy!

Highland House awaits! Escape to our enchanting 3-bedroom, 3-bathroom retreat, where rustic charm meets modern luxury. Nestled in the heart of Big Sandy Lake, this haven boasts wood frame architecture, a captivating stone fireplace, and breathtaking views visible through large windows that bathe the space in natural light. With 9-foot ceilings, a sprawling deck, and all the modern amenities you crave, this is your sanctuary on the lake. Enjoy all that Big Sandy Lake has to offer!

Tons of Games! 4 Person Boat, Kayaks, Great Bay!

Check out the onsite rentals below! Experience an east coast flavor up north in the Cove on Mille Lacs Lake. This newly remodeled lake home is above average in its quality and furnishings! The home sits on one of the best swimming and fishing bays on the west side of the lake and features a downstairs family room, fish cleaning station, and a private dock! There are a ton of games, kayaks, and amenities with this property! The owners are adding a four person paddle boat!

Treehouse (LOTR) Stargazer Skycabin

Our LOTR themed treehouse, along with our LOTR Wizard's Cottage, have been described as a "love letter to Tolkien himself." We have been featured on PBS and WJON radio. A manager lives on the acreage, about 200 ft. from the Wizard's Cottage and very far from the treehouse, which is located on the back part of the acreage. It has a fenced-in portion that makes up the Shire Garden. Down the hill is our nod to Mordor. Feel free to visit and dare to open the "Mor Do(o)r."

A Slice of Paradise

Relax with the whole family at a Slice of Paradise, a newly renovated quaint cabin on South Long Lake in Brainerd. South Long Lake is a year round recreational lake offering boating, fishing, swimming, kayaking and paddle boarding. We are located on the east side of the lake with amazing sunsets and a sandy beach . Enjoy roasting s'mores around the campfire watching the sunset and listening to loons calling across the lake. Minimum age of primary renter is 25.

Quiet Lake Cottage and Cuyuna Mountain Bike Trails

Charming cottage located in the heart of Minnesota’s Up North vacationland! A relaxing retreat on one acre wooded lot, quiet 80 acre lake with no public access. Get out on the lake for a paddle with the canoe or kayak or fish from the dock, catch and release is best. Year round fun, abundant wildlife, and vivid starry skies. Located ten miles from Cuyuna Country State Recreation's excellent single track mountain bike trails and many other lakes.

The Cuyuna Bunkhouse - New Sauna

Welcome to The Cuyuna Bunkhouse! This 768 sq ft, fully remodeled, boutique-style bunkhouse is your perfect gateway to the Cuyuna Country Recreational Area. Whether you're here to enjoy the 70+ miles of singletrack, take in the peaceful scenery, visit antique shops and more, we've got you covered. At the property you’ll have space to grill, picnic, sit around the bonfire or relax in the brand new barrel sauna!