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
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, 9 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.

Guest favourite
The kitchen is equipped with stainless steel appliances and wooden cabinetry. A large island with seating is present, complemented by a rustic dining table. Natural light streams through a large window, illuminating the space and highlighting the textured wood features and concrete flooring.
Guest house in Deerwood
4.92 out of 5 average rating, 37 reviews

Our Slice of Heaven

Enjoy time away from your busy life in our peaceful oasis. The thing that makes this place so special is that everything in it is recycled. All the doors, window's, cabinets, wood and tin is all reused. The kitchen table was once a waterbed. Almost all of the wood for framing of the walls, furniture and picture frames were all once a pallet. Even the wall boards are old discarded boards. Once you walk into this place, a certain peace overtakes you. I hope you love it here as much as we do.

Guest favourite
A charming cabin stands under a night sky, showcasing its wooden exterior and large front porch. Warm lights highlight the structure's design, while a stone foundation adds character. Tall windows are seen on the upper level, providing glimpses of the inviting interior.
Cabin in Garrison
4.96 out of 5 average rating, 67 reviews

Lakeview Lodge, 3 BR, 2 BA fully outfitted retreat

Retreat up North to this cozy cabin with views of Lake Mille Lacs. Enjoy the serenity of quiet sunrises with your complimentary coffee, sitting in a rocker on the wraparound porch. Spend your day exploring on land or on the water. Take advantage of the many activities located within just minutes. Dine out or enjoy dinner in with the fully equipped kitchen. Sit by the fire in the evening & listen to the loons or retreat inside, taking advantage of the cozy fireplaces and three smart TVs!

Top guest favourite
The cabin's exterior features warm pine siding complemented by a covered porch. Two adirondack chairs sit welcomingly on the porch, flanked by trees and landscaping. The front door is painted in a bright hue, and a small plaque adorns the wall beside it.
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, 285 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
Two lounge chairs are positioned on a wooden deck, overlooking a calm lake under a blue sky adorned with puffy white clouds. A vibrant area rug lies beneath the chairs, adding color to the outdoor space. In the distance, a private dock extends into the water.
Home in Brainerd
4.99 out of 5 average rating, 138 reviews

Lakefront Group Getaway: 4 Kings+Dock+Kayaks

Escape to Leisure Lodge, 2 hrs from MSP or Fargo: • 4 king beds, 4 Twin XLs, pullout queen, portable crib • 3 baths (one on each level) • Fully stocked kitchen w/ indoor & outdoor dining for 10+ • Spacious year-round home with indoor garage parking, not a seasonal cabin • Hot tub + fire pit w/ wood provided • Paddleboat, kayaks, lake toys & nearby trails • Cozy gas fireplace & crisp lake views • 130+ five ⭐️ reviews, family-owned/operated •Seasonal dock late spring into the fall

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
Cabin in Upsala
4.93 out of 5 average rating, 847 reviews

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."

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!

Popular amenities for Roosevelt holiday rentals

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