Holiday rentals in Roosevelt

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Top-rated holiday rentals in Roosevelt

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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

Top guest favourite
A hot tub is situated in a wooded area, surrounded by tall trees. Bubbling water creates gentle waves, and a view of the lake can be seen in the background, showcasing the natural serenity of the location.
Home in Deerwood
4.99 out of 5 average rating, 118 reviews

Hot tub, fishing, pool table, scenery, privacy!

Great fishing here, summer and winter! 4,200+ sq ft lake home on large private lot(1.5+ acres) 270 feet of lakeshore on Portage Lake within the Crooked Lake Chain. This home is most suitable for families and couples to get away and enjoy peace and nature. NO PARTIES OR EVENTS including bachelor/bachelorette gatherings. Home has beds for 18 vacationers with 5BR/3BA, game room with pool table/ping pong overlay. Hot tub and Pontoon boat avail: volleyball, swingset,corn hole,canoe, SUP boards.

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!

Top guest favourite
The entrance displays a spacious porch supported by large wooden beams, featuring a stone façade. Double doors with decorative windows welcome guests. Two chairs are positioned on the porch, creating an inviting area for relaxation.
Cabin in Aitkin
4.96 out of 5 average rating, 304 reviews

The River Lodge

The River Lodge sits on a peaceful 5 acres on the banks of the Mississippi River featuring three levels with 7 bedrooms plus additional sleeping areas in the loft and game room, making it possible to fit up to 22 guests. The great room provides a large gathering space, perfect for reunions and retreats. With 3 additional living rooms all with smart TVs, 5 bathrooms, a game room with ping pong, several outdoor sitting areas, a beautiful fire pit patio and hot tub to enjoy, there's fun for all!

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.

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 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, 75 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!

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
A lakeside deck is featured with comfortable seating, including lounge chairs and a dining table. A grill is positioned nearby, surrounded by lush greenery. A beautiful view of the lake and docks is visible, offering a serene outdoor space for gatherings.
Home in Garrison
5.0 out of 5 average rating, 38 reviews

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!

Popular amenities for Roosevelt holiday rentals