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Holiday rentals in Roosevelt

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Top-rated holiday rentals in Roosevelt

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top 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
4.96 out of 5 average rating, 27 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).

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
4.95 out of 5 average rating, 112 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
Home in Garrison
5.0 out of 5 average rating, 6 reviews

Dock, Sunsets & Lake Views | Garrison Cabin

Stay at a lakefront Garrison cabin on Little Whitefish Lake, sleeping up to 10 with a bonus sleeping loft, separate workspace, fire pit, and parking for cars, trailers, and boats. Fish or boat on nearby Mille Lacs, hike and bike world-class trails at Cuyuna, or swim at Father Hennepin State Park. Tee off at Northwood Hills Golf Course, grab a bite in Garrison, or sip craft beer in Crosby. Families will love Paul Bunyan Land and Safari North, while Grand Casino Mille Lacs offers gaming and live

Top guest favourite
A kitchen view showcases a modern gas stove, complemented by warm wooden cabinetry. Beyond, an open-concept living area is visible, featuring a dining table surrounded by black chairs and a cozy seating arrangement with large windows that invite natural light.
Cabin in Garrison
5.0 out of 5 average rating, 33 reviews

Private 5 Star Year Round Cabin on Lake Mille Lacs

Escape to our family-friendly cabin on the W side of Mille Lacs, just 90 minutes from the Twin Cities. Nestled in a peaceful harbor off St. Albans Bay, this private retreat offers stunning lake views and easy access to fishing, watersports, hiking, snowmobiling, and more-perfect for any season. Arrangement Driveway 4 BR (K,Q,Q,Q,T,T) 3 Bath Spacious dinning area (seats 12+) Huge yard and fire pit Garage games (Darts, Ping Pong, Fooseball) Check out our reviews and plz message with questions!

Guest favourite
Home in Brainerd
4.96 out of 5 average rating, 26 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 spacious wooden deck is illuminated by string lights, creating a warm ambiance in the evening. Comfortable seating is arranged around a central table, while the entrance to the cabin is visible through large glass doors. Lush trees frame the relaxing outdoor space.
Cabin in Onamia
4.92 out of 5 average rating, 88 reviews

Honey Hole Lodge

The Honey Hole Lodge is located on Wigwam Bay on the beautiful Lake Mille Lacs. 1.5 miles from the Casino and 2 miles from the golf course. Enjoy the amazing views while swimming, boating, fishing, or sitting by the camp fire. The HH has a large dock to accommodate several boats/pontoons/jet skis. This is the perfect cabin for a large family getaway or for multiple families to relax and enjoy the beauty of the Northwoods. Water sports equipment available to rent nearby or bring your own.

Top guest favourite
A fire pit surrounded by several blue chairs is visible in the foreground, with a stone border containing the flames. In the background, a spacious cabin stands amongst the trees, featuring multiple windows that reflect the evening sky.
Cabin in Garrison
4.93 out of 5 average rating, 27 reviews

McCabin Smith Lake Retreat - private sandy beach

Bring the whole family/group to the McCabin located on Smith Lake, with lots of room for fun. Kid and dog friendly. Main level has an open concept for indoor/ outdoor living with screened garage doors, full kitchen, living room, bathroom/laundry and game room, great space for large groups. Upstairs has a spacious living room bathroom and 4 bedrooms and a beautiful open loft above (5th bedroom space) . Beds include: 3 kings, 1 queen, 5 twins and a full/twin bunk! Very spacious on 4 acres.

Guest favourite
A welcoming living area is shown with deep brown leather chairs and a wooden coffee table. Natural light enters through large windows, highlighting the wooden accents and cabinetry in the open kitchen. A staircase with wooden railing leads to the upper level.
Cabin in Garrison
4.88 out of 5 average rating, 86 reviews

Lakefront Deck w/ Unmatched View - New Deck

Come enjoy a getaway at this spacious yet cozy cabin. With a high-rise deck overlooking Lake Mille Lacs, this property provides a beautiful view to enjoy a cup of coffee at sunrise and a relaxing beverage at sunset. In the summer, enjoy direct lake access for fishing/swimming while also taking advantage of nearby attractions such as golf courses, beaches, and ATV trails. In the winter, come set up an ice house near the cabin to bring in the walleyes or snowmobile on the lake and trails.

Guest favourite
A tranquil lakeshore scene showcases sandy beach and gently sloping steps leading to the water. A wooden dock extends towards a boat, with sunlight reflecting off the calm lake surface, surrounded by lush trees and a rocky border enhancing the natural setting.
Home in Crosby
4.95 out of 5 average rating, 134 reviews

Spacious lake house w/ room for the whole family!

Perfectly located near downtown Crosby on Rabbit Lake, this 2-acre lot w/ 400 ft of sandy lakeshore is the ideal up-north getaway for groups. All bedrooms are upstairs w/ 1 king bed, 7 Queens, a crib, and a standing desk. The lower level boasts a fully updated kitchen, dining room, game room/bar, & spacious living room w/ a gas fireplace, great wifi, and streaming services! Outdoor dining, yard games, beach/water toys, swim dock, propane grill, fire pit, and a 7-person Jacuzzi hot tub!

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
4.98 out of 5 average rating, 130 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.

Guest favourite
A hot tub is positioned beside the lake, surrounded by trees showcasing autumn foliage. Water can be seen bubbling in the tub, with a serene view of the lake in the background under a cloudy sky.
Cabin in Deerwood
4.87 out of 5 average rating, 101 reviews

Partridge Lake - Hot Tub, Swim, Fish, Snomobile!

Newly renovated, modern cabin. Your family will love the clear water! The lake is shallow and sandy by our property and perfect for kids to swim in summer. Pontoon may be used for an extra charge, reach out for more info. Hot tub available October-May, overlooking the lake. Robes to enjoy the hot tub provided during winter season. Miles of XC ski, showshoe, snowmobile trails within minutes! Snowshoes provided. Reach out for our winter travel guide! New 65” TV installed!

Guest favourite
Home in Garrison
4.96 out of 5 average rating, 71 reviews

Mille Lacs Lake Getaway! Dock•Huge Yard•Game Room

⭐ Contact us about special Pricing⭐ ⭐Fishing has been Amazing! 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