Holiday rentals in Roosevelt

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Top-rated holiday rentals in Roosevelt

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Guest favourite
A view from the deck showcases a serene lake surrounded by greenery. The water reflects the sky, while a decorative lantern hangs from a tree branch overhead. Steps lead down from the deck, with natural stone landscaping adjacent to the pathway.
Cabin in Hillman
4.94 out of 5 average rating, 16 reviews

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).

Top guest favourite
A green outdoor area is featured, showcasing two folding chairs and a small table positioned on a patterned mat. A charcoal grill is set nearby, with a potted plant enhancing the natural setting. Lush greenery surrounds the space, creating a peaceful atmosphere.
Cottage in Brainerd
4.84 out of 5 average rating, 379 reviews

Out in the country getaway

Please mind: This is a private home, it is not shared. :) Remodeled mother-in-law's house in the country beautiful area 20 acres to walk on. Restaurant and bar within walking distance less than 1 mile, great food and nice people. Lots of wildlife whether you like to fish,hunt, hike, or just sit back and take in the nature; Right on the snowmobile trails! I will also set up for special occasions w/ decorations or whatever you'd suggest; Birthdays, Valentine's, you name it! Great WiFi connection.

Guest favourite
An A-frame cabin is framed by tall trees, featuring a black metal exterior. A circular patio is surrounded by wooden posts and includes a fire pit, outdoor seating, and a propane grill. Snow covers the ground, indicating a peaceful winter setting.
Tiny home in Brainerd
4.93 out of 5 average rating, 89 reviews

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

Guest favourite
The cabin features a log exterior with a steeply pitched roof, accented by wooden beams. An American flag hangs prominently from the front. A spacious porch with seating is visible, framed by tall trees and a clear blue sky.
Cabin in Garrison
5 out of 5 average rating, 10 reviews

Pet-Friendly Garrison Retreat

Escape to the beauty of Garrison at this 3-bedroom, 2-bath cabin, perfectly situated near the scenic Northwoods Golf Course and just minutes from Mille Lacs Lake. Surrounded by peaceful woods and endless trails, this cozy retreat offers access to a wide array of outdoor adventures. Spend your days exploring Mille Lacs Lake, hiking the trails of Cuyuna Country State Recreation Area, or testing your luck at the Grand Casino. Afterward, unwind by the fireplace in the cabin’s inviting living area.

Guest favourite
Home in Brainerd
5 out of 5 average rating, 11 reviews

Treska's Trails & Lakes

Your private outdoor paradise on 5 acres, enjoy morning coffee, watching wildlife from your deck. Days conquering trails or casting for trophy fish. Evenings around the campfire under a brilliant canopy of stars. Whether hunting or just unwinding by the fire, Treska's is your perfect home base. This is your escape to nature's playground with all the comforts of home. Ideal for families, friend groups, or hunting parties seeking adventure and relaxation in the heart of Minnesota's Northwoods.

Top guest favourite
The custom-built cabin is framed by tall pines, showcasing an angled roof and a combination of gray and wood siding. A wooden seating area is visible on the patio, inviting relaxation amidst the natural surroundings.
Cabin in Ironton
4.97 out of 5 average rating, 105 reviews

Dragonfly Cabin | Near Cuyuna Recreation Area

Enjoy this design-forward 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.

Top guest favourite
The cabin is nestled among tall, leafy trees in a serene forest setting. A gravel path leads to the entrance, framed by wooden chairs positioned on a porch. Soft sunlight filters through the canopy, illuminating the rustic wooden structure.
Cabin in Long Lake Township
4.98 out of 5 average rating, 114 reviews

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.

Superhost
The A-frame cabin showcases a wooden exterior with large glass doors, allowing a glimpse into the inviting interior. Surrounded by lush trees, a spacious front deck is visible, featuring outdoor seating and a propane grill, perfect for outdoor gatherings.
Cabin in Brook Park
4.89 out of 5 average rating, 290 reviews

Stylle Hytte ///\ Northern Cabin Retreat

Our Nordic inspired A-Frame is known as the Stylle Hytte which is Norwegian for ‘Quiet Cabin’. Here you can take in 5 secluded acres of woods with trails winding down to the private riverfront. Only an hour north of the Twin Cities, enjoy modern conveniences like WIFI (60mbps), smart TV, complete kitchen, full bathroom, a bedroom and loft both with queen beds, a cozy living room with a real wood fireplace and an outdoor electric barrel sauna. Calendars are open 9 months in advance.

Top guest favourite
Four dark wooden Adirondack chairs are arranged in a semicircle on a grassy area by the lake. The calm waters are visible in the background, with a dock and boat accessible for leisure activities. Lush greenery and flowers create a natural setting.
Cabin in Hillman
4.94 out of 5 average rating, 54 reviews

5 Star! Lake Life Experience-90min to metro

Lake life at its finest! A newly rebuilt cabin just feet from the clean waters of Lake Peavy. Fish off the dock or bring your boat! Enjoy ATV trails, eagles, cranes and loons every day. Great dock for easy entry for young and old. Tree diversity makes fall a special time here. Head up to Cuyuna for world class mountain biking. Fishing supplies and water toys in the garage. Camp fire and swing located right by the water. READ OUR REVIEWS and eliminate uncertainty!

Guest favourite
Home in Garrison
4.97 out of 5 average rating, 63 reviews

Mille Lacs Getaway | Dock • Game Room • Huge Yard

⭐ Contact us about special Pricing⭐ ⭐New DNR Regulations-3 Walleye Limit Relax at our modern 3BR, 2BA home across from beautiful Mille Lacs Lake. Enjoy amazing sunrises, 250 ft of beachfront, a new dock for fishing & boating, and a huge backyard to relax or entertain. The 28×30 heated game room/garage adds year-round fun. Perfect for fishing trips or family getaways. ⭐Military, Nurses, Teachers & First Responders receive a discount — message us before booking!

Superhost
Cabin in Aitkin
5 out of 5 average rating, 4 reviews

Lakefront on Mille Lacs | Relax, Views & Game Room

🌊 Your Mille Lacs Lakefront Retreat Awaits! ✨ Enjoy panoramic lake views from this beautifully designed lakefront cabin with new furnishings and a bright sunroom 🌅 🛋️ Living space with futons and water views 🍽️ Dine overlooking the lake 🍳 Full Kitchen 🛶 Lake gear included 🕯️ Comfortable space for cozy evenings 🚤 Private dock plus 100 ft of sandy beach shoreline for walking, fun, and fishing. Perfect for relaxation and adventure right on the lake!

Guest favourite
The serene lake reflects a cottage surrounded by lush greenery and tall trees. The calm water showcases mirrored images of the landscape, enhancing the tranquil setting. A seating area is visible near the water's edge, inviting relaxation in nature.
Cottage in Deerwood
4.92 out of 5 average rating, 212 reviews

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.

Popular amenities for Roosevelt holiday rentals

  1. Airbnb
  2. United States
  3. Minnesota
  4. Crow Wing County
  5. Roosevelt