Holiday houses in Ossawinnamakee Lake

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Ossawinnamakee Lake

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Apartment in Crosslake

4.88 out of 5 average rating, 224 reviews

The Shed: Comfortable & Convenient to Everything!

We call this place "The Shed". It is part of a commercial building that we have transformed into a comfortable & cozy getaway! The name of the game is convenience! We are right on snowmobile trail, close to bike trails, close to fishing & boating on the lake, close to golf, shopping, lots of restaurants & all of the wedding venues! There is room to park your sleds, boats or trailers! Spend the day enjoying all that Crosslake has to offer then come home to cozy up to a nice warm fireplace!

10–17 Feb

$152 NZD per night

Guest favourite

Treehouse in Crosslake

4.97 out of 5 average rating, 148 reviews

Up North Cabin in the Trees! Perfect getaway.

Great Up North cabin in a serene and peaceful setting. We call this the Treetop Cabin...Located roughly between Zorbaz and Moonlite Bay. The open floor plan on the main level features a great room/kitchen/living room with a fireplace, and primary bedroom. The loft has has 2 Queen beds. It's extremely close to everything that Crosslake has to offer. The cabin includes Wi-Fi, a Roku and two HD tvs. There is full kitchen with stainless steel appliances, wood floors, and forced air and heat and a/c.

3–10 Feb

$400 NZD per night

Guest favourite

Cabin in Fifty Lakes

5.0 out of 5 average rating, 73 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 12 acres. It is a short six block walk to Manhattan Beach Lodge for dining.

21–28 Oct

$327 NZD per night

Guest favourite

Cottage in Pequot Lakes

4.94 out of 5 average rating, 266 reviews

Private Cottage w/Queen Bed + Lakes, golfing, etc.

Beautiful, cozy cottage located on owner's property. Surrounded by lakes (however not on one), world-class golf, towering pine trees and amazing restaurants and shopping. You will have the cottage to yourself. There is a private bedroom with a queen bed, also a full bath. The living room sofa pulls out to sleep two more. We are walking distance to Pequot Lakes, and just a 10 minute drive to Breezy Point or Nisswa for an amazing shopping experience. We welcome friendly, fully vetted dogs.

12–19 Apr

$141 NZD per night

Guest favourite

Cabin in Ironton

4.93 out of 5 average rating, 110 reviews

A Cozy Place to Unwind After Shredding the Trails!

Welcome to Cuyuna Country! Cuyuna Bunkhouse is a cozy little retreat situated on 1.5-acres amid the beautiful Cuyuna Iron Range. This 768 sq ft, fully remodeled, boutique-style bunkhouse is your perfect gateway to the Northwoods. Whether you're here to enjoy the 70+ miles of singletrack, take in the peaceful scenery, visit antique shops and more, we've got you covered. Follow @cuyunabunkhouse on Insta for additional content. We look forward to hosting you in one of our favorite places in MN!

13–20 Oct

$243 NZD per night

Guest favourite

Cabin in Pequot Lakes

4.96 out of 5 average rating, 45 reviews

Large cabin w/ sandy swim beach, new dock & deck

Summer dates available! August 26- 29 **10 person sauna coming this fall** 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 & snowmobiling!

14–21 Apr

$1,015 NZD per night

Guest favourite

Cottage in Pequot Lakes

5.0 out of 5 average rating, 23 reviews

Family boating cottage on Whitefish Chain of Lakes

Welcome to the simple beauty of Minnesota lake life! Sip a sunrise coffee on your lake-view deck and watch the fog lift from the water. Paddle the pristine waters of Bertha Lake on the provided kayaks and SUPs. Or rent a boat from Bertha BoatWorks just around the corner. With a sandy stretch of beach and a dock for casting a line, you can enjoy MN’s Whitefish Chain of Lakes without leaving your backyard. After a sunny day of lake activities, close the day with s’mores around the fire pit!

19–26 Jan

$565 NZD per night

Guest favourite

Home in Breezy Point

5.0 out of 5 average rating, 34 reviews

*Hot Tub* Breezy Point Resort - Private & Tranquil

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.

18–25 Mar

$420 NZD per night

Guest favourite

Guesthouse in Pequot Lakes

4.88 out of 5 average rating, 171 reviews

Pelican Lake Guest Cabin Tiki Beach Bar 🌴 🍍 🍹

"Casa Pelicano” is a 1 BR/1 BA Private Studio Guest Suite 1 mile from Breezy Point Resort on Pelican Cozy, Comfortable, Clean BRING YOUR BOAT! Amenities: Private Patio, Sand Beach/Dock, Paddle Board, Gas Grill, Beach Bar, Palapa, Palm Tree, Loungers, Hammock, Fire Pit/Wood, Roku Smart TV, DVD, CD player, Microwave, Fridge/Freezer, Keurig Coffee, AC, WIFI, Yard Games Area: Breezy Point Resort 1 Mile, Golf, Fish, Gooseberry Island Sand Bar, Boat Rentals, Restaurants/Bars, Shopping, Shuttle

8–15 Oct

$316 NZD per night

Guest favourite

Cabin in Pine River

5.0 out of 5 average rating, 8 reviews

Whitefish Chain|Cozy Fishing Cabin Vibes|DogsOK

Welcome to Eagle's Rest, our cabin on Upper Whitefish Lake. The cabin is the perfect spot for fishing, exploring the entire Whitefish Chain of Lakes, watching Eagles, and slowing down to soak up the great MN northwoods by a roaring fire. Eagle's Rest on Whitefish features; -Local ice fishing or open water fishing guide available -Access to the entire Whitefish Chain of Lakes -a dock and boat slip -Wood burning fireplace -Electronic scoring dart board -Dogs allowed *see below -Lakeside

21–28 Jun

$398 NZD per night

Guest favourite

Cabin in Crosslake

4.99 out of 5 average rating, 209 reviews

Cozy and Peaceful Little Pine River Retreat

Great Up North cabin in a serene and peaceful setting nestled among the trees along Little Pine River. Guests have said they feel as though they’re in a treehouse. Two kayaks and a few tubes are available for guests to use, or sit in a chair in the river and cool off. Enjoy the views and sounds of the river and wildlife while sitting by the fire pit, on the cozy deck or in one of the 2 screened in porches. If you feel like being more social, Crosslake is only about a 5 mile drive.

27 Feb – 6 Mar

$337 NZD per night

Guest favourite

Cabin in Ironton

4.95 out of 5 average rating, 192 reviews

Cuyuna Lake Cabin. Bike trails, SUPs and Serenity

This is a 24 X 40 foot knotty pine cabin with a very open floor plan. It sleeps a family of 4-6 nicely. It is located on great fishing lake that connects to the mighty Mississippi. It is in the heart of the Cuyuna State Park Area and all of the bike trails! A very peaceful UPNORTH location with breathtaking sunsets. The loons will hypnotize you with their calls. I travel a lot and make this cabin available when I am away. There are some kayaks and SUP's available, too!

5–12 Sep

$266 NZD per night