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Holiday houses in Ossawinnamakee Lake

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Top-rated holiday rentals in Ossawinnamakee Lake

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

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Top Guest favourite
A stone fireplace is featured prominently, with a warm glow emanating from the flames. Soft textures are added by a knitted throw draped over a woven basket positioned nearby. A decorative sign rests against the wall, inviting a sense of comfort.
Cabin in Fifty Lakes
5.0 out of 5 average rating, 148 reviews

Cozy two bedroom cottage with indoor fireplace.

Come get away to our peaceful home centrally located in Crosslake MN. It is a perfect location to enjoy all that Crosslake has to offer. This home features two king size beds. The cottage includes wifi and a 55" smart tv. There is a full kitchen with stainless steel appliances. The property is surrounded by large pine trees and lots of privacy. This property is located on Ox Lake which is private. The property has 16 acres. It is a short six block walk to Manhattan Beach Lodge for dining.

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
4.94 out of 5 average rating, 101 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
An aerial view captures a home surrounded by lush greenery, showcasing a spacious and private backyard. The nearby Pelican Lake glimmers in the sunlight, with trees framing the scene and distant houses nestled along the shoreline.
Home in Breezy Point
4.98 out of 5 average rating, 152 reviews

Year-Round Hot Tub! Home in Breezy Point Resort

Unbeatable relaxation! You will be staying within walking distance of Pelican Lake, golf courses, the city park, and restaurants. Prefer staying in? Enjoy the fully fenced backyard with a hot tub, perfect for privacy and relaxation. The kitchen is well stocked for all of your cooking needs. This home checks all the boxes: convenient, clean, and comfortable. We're confident you will love your stay in the heart of Breezy Point! 2 bedrooms - 960 sq ft No cleaning fees, minimal checkout list.

Guest favourite
Cabin in Pequot Lakes
4.95 out of 5 average rating, 110 reviews

Dog Friendly Up North Private Escape

Welcome to Cabin au Nord; a Scandinavian inspired cabin near Pequot Lakes, MN perfect for your up North summer getaway. Custom designed, every detail has been thought of to promote relaxation. The cabin features one queen bedroom on the first floor, large king room with nature views on the upper level, modern kitchen, spa-like bathroom, work desk area for remote workers, living/dining area with floor to ceiling windows, and an outdoor Solo Stove. 5 mins to Pequot Lakes and 10 mins to Gull.

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
4.98 out of 5 average rating, 122 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'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, 122 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.

Top Guest favourite
A rustic cabin is set amidst a wooded area, featuring a large deck with steps leading down to the grassy yard. Panoramic windows allow for ample natural light, while the surrounding trees provide a sense of seclusion and tranquility.
Home in Pequot Lakes
4.95 out of 5 average rating, 37 reviews

North Hut, Pequot Lakes

Relax in the woods at this up north getaway. Two bedroom plus sleeping loft (queen and four twins) with smart tv nestled between Whitefish Chain of Lakes and Lake Ossawinnamakee. The Ossi public boat launch is less than a mile down the same road. Easy access to boating, fishing, golfing, or snow sports. Bring all the toys - plenty of parking and room to get your trailer in and out. Lakes, golf courses and restaurants within minutes or enjoy a meal on the deck in this serene setting.

Top Guest favourite
A spacious lakehome is showcased, featuring a combination of wood and stone exterior. The design includes multiple gable roofs and large windows, surrounded by lush greenery. A paved driveway leads to a side garage, enhancing accessibility. The serene environment complements the natural surroundings.
Cabin in Pequot Lakes
4.96 out of 5 average rating, 94 reviews

Lakehome with beach, pickleball, sauna, near golf

2026 summer availability: August 23-25 Newly updated, Winnamakee Shores offers 5 generous bedrooms, 4 bathrooms and a large kitchen perfect for family/friend gatherings. The lakehome has 100 feet of level sandy beach and provides kayaks, water trampoline, paddleboard, shuffle board, ping pong, & yard games to keep everyone entertained. The community has golf courses, restaurants, & shopping. Also a great winter escape with ice fishing, cross-country skiing, & snowmobiling!

Guest favourite
Cabin in Crosslake
4.96 out of 5 average rating, 24 reviews

Lakefront Tiny Cabin Barrel Sauna Fire Pit Kayak

Situated just 50 ft off the beautiful Crosslake waterfront, this intimate cabin is perfect for a couples weekend on the lake. Built in 2023, this cabin is filled with amazing panoramic views & cozy loft for your romantic getaway. The main level has a small couch, kitchen table, full service kitchen, and bathroom with a shower. Up the ladder to the loft is your queen bed! Outside you’ll find a large deck with furniture & a fire pit just below leading to your own private dock.

Guest favourite
Tiny home in Crosby
4.87 out of 5 average rating, 126 reviews

Hot Tub + Sauna Tiny Pine A\ Cuyuna Matata

NEW TWO PERSON HOT TUB! Relax and unwind with your closest friends or loved ones in this newly built 500 sqft A Frame. The Tiny Pine A\\ is one of the three Cuyuna Matata Cabins on 8.5. acres overlooking the peaceful Pine River. An ideal nature getaway far enough away from town yet a short 10 minute drive to Cuyuna State Rec biking trails. Enjoy the new cedar wood barrel steam sauna and complimentary items such as snowshoes for the winter and kayaks in the summer!

Top Guest favourite
Cabin in Crosslake
4.99 out of 5 average rating, 139 reviews

Lakefront Beach, Hot Tub + Sauna | Near Trails

For families and friend groups squeezing every drop out of lake season, Border Point Lodge is your private slice of Fawn Lake — beach, hot tub, and barrel sauna steps from the door. Kayaks, paddleboards, and firepit s'mores are packed for you, and guests say they hear loons every day. Just 10 minutes to Crosslake dining and the Whitefish Chain, with the Paul Bunyan Byway close by when the leaves turn. Book your late-summer week — or claim a fall-color weekend now.

Top Guest favourite
Cabin in Hackensack
4.96 out of 5 average rating, 189 reviews

Modern A Frame Cabin on Private Nature Lake

Welcome to Oda Hus. A modern A Frame cabin, nestled on a secluded 12 acres of towering Norwegian Pines. Sitting on a peninsula of Barrow Lake, conveniently located across the street Woman Lake. Floor to ceiling windows, open layout, and modern appliances and amenities. Go for a swim off the dock, take the kayaks and watch the loons, or relax in our newly added cedar barrel sauna. The perfect blend of modern luxury and nature.

Popular amenities for Ossawinnamakee Lake holiday rentals