Ossipee holiday homes

We found 587 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Ossipee that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include parking and a pool. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Ossipee

Showing deals for:18 Dec - 25 Dec

Private kitchen
Terrace/patio
Living area
Living area
Exceptional
(11 reviews)

Horseshoe Lake Cabin w/ Hot Tub, Beach, Games, Fire Pit, Kayaks + Paddleboards

Merrifield

8% off
NZ$9,230
for 7 nights, 1 cabin
NZ$1,319 per night
includes taxes & fees
Horseshoe Lake Cabin w/ Hot Tub, Beach, Games, Fire Pit, Kayaks + Paddleboards
Backyard looking from trail to lake
Living area
View from kitchen looking into Family room
Kitchen
Exceptional
(147 reviews)

Beautiful New Home On Private Lake Across From Gull Lake And Other Local Spots!

Nisswa

8% off
NZ$6,217
for 7 nights, 1 cabin
NZ$888 per night
includes taxes & fees
Beautiful New Home On Private Lake Across From Gull Lake And Other Local Spots!
Main house bedroom #1 with Queen bed
View of Daggett Lake from deck.  Access all of White Fish Chains 14 lakes!
Centrally located and open kitchen.  High end appliances and view of the lake.
View of main house from lake.  Large yard, slight incline to water from house
Exceptional
(53 reviews)

Crosslake Family Lake Retreat + Guest Cabin - Sleeps 13 - Dock - Minutes to Town

Crosslake

7% off
NZ$4,922
for 7 nights, 1 home
NZ$703 per night
includes taxes & fees
Crosslake Family Lake Retreat + Guest Cabin - Sleeps 13 - Dock - Minutes to Town
Interior
Outdoor dining
Property grounds
Bedroom has queen bed and bunk beds
Exceptional
(20 reviews)

Cabin on Rice Lake access to Mississippi River 1 bedroom/1 bath sleeps 4

Brainerd

8% off
NZ$3,021
for 7 nights, 1 cabin
NZ$432 per night
includes taxes & fees
Cabin on Rice Lake access to Mississippi River 1 bedroom/1 bath sleeps 4
Master bedroom on 2nd floor sleeps 2: queen log bed. Has private bathroom.
Living area
Living Room.
Exterior
Exceptional
(167 reviews)

Last availability for summer 2026: August 21-24!

Merrifield

7% off
NZ$5,244
for 7 nights, 1 home
NZ$749 per night
includes taxes & fees
Last availability for summer 2026: August 21-24!
Dining Area
Living area
Sand beach with gradual slope entry into crystal clear water
Kitchen
Exceptional
(42 reviews)

Beautiful waterfront lake home on Round Lake - connected to Gull Lake Chain!

Brainerd

8% off
NZ$7,574
for 7 nights, 1 home
NZ$1,082 per night
includes taxes & fees
Beautiful waterfront lake home on Round Lake - connected to Gull Lake Chain!
Property grounds
Interior
Dining
Children’s area
Exceptional
(50 reviews)

Private Beach, Beautiful Lake Home, Fishing, Recreation - Everything You Need!

Crosslake

8% off
NZ$5,780
for 7 nights, 1 cabin
NZ$826 per night
includes taxes & fees
Private Beach, Beautiful Lake Home, Fishing, Recreation - Everything You Need!
Room
Property grounds
Property grounds
Interior
Exceptional
(44 reviews)

Cozy Cabin on Dewdrop Lake

Crosslake

13% off
NZ$3,966
for 7 nights, 1 cabin
NZ$567 per night
includes taxes & fees
Cozy Cabin on Dewdrop Lake
Terrace/patio
Private kitchen
Games room
Exterior
Exceptional
(6 reviews)

Secluded Towering Pines in the Heart of Nisswa 4 bedroom

Nisswa

20% off
NZ$6,715
for 7 nights, 1 home
NZ$959 per night
includes taxes & fees
Secluded Towering Pines in the Heart of Nisswa 4 bedroom
Living area
Living area
Private kitchen
Great firepit area
Exceptional
(58 reviews)

LOCATION LOCATION LOCATION! 3 Bed/3 Bath Cabin In Breezy Point On Golf Course

Pequot Lakes

8% off
NZ$5,041
for 7 nights, 1 cabin
NZ$720 per night
includes taxes & fees
LOCATION LOCATION LOCATION! 3 Bed/3 Bath Cabin In Breezy Point On Golf Course
Dining
Interior
Property grounds
Private kitchen
Exceptional
(7 reviews)

Cozy 2 Bedroom Lakefront Cabin on Crosslake w/ Sauna

Crosslake

7% off
NZ$2,983
for 7 nights, 1 cabin
NZ$426 per night
includes taxes & fees
Cozy 2 Bedroom Lakefront Cabin on Crosslake w/ Sauna
Seats at the end of the dock are great for catching up on reading or relaxing!
Roomy kitchen island with plenty of storage.
Hallway to main living area, coming from the garage.
Side yard by the lake and firepit.
Exceptional
(59 reviews)

Lake Daze - a spacious, family-friendly home right on beautiful North Long Lake!

Brainerd

7% off
NZ$4,753
for 7 nights, 1 home
NZ$679 per night
includes taxes & fees
Lake Daze - a spacious, family-friendly home right on beautiful North Long Lake!
Terrace/patio
Living area
Exterior
Room
Exceptional
(162 reviews)

Welcome to Bearfeet Retreat on Adney Lake - Crosby Minnesota

Crosby

8% off
NZ$3,614
for 7 nights, 1 home
NZ$516 per night
includes taxes & fees
Welcome to Bearfeet Retreat on Adney Lake - Crosby Minnesota
Living area
Outdoor dining
Living area
Exterior
Exceptional
(5 reviews)

Modern 2BR Home – Near Cuyuna Trails & Downtown

Crosby

8% off
NZ$2,814
for 7 nights, 1 home
NZ$402 per night
includes taxes & fees
Modern 2BR Home – Near Cuyuna Trails & Downtown
Property grounds
Dining
Private kitchen
Exterior
Exceptional
(8 reviews)

Cozy Crosby Cabin located on Rabbit Lake with great views.

Crosby

16% off
NZ$4,953
for 7 nights, 1 cabin
NZ$708 per night
includes taxes & fees
Cozy Crosby Cabin located on Rabbit Lake with great views.
Dining
Early morning from the deck!
Master bedroom with large king bed overlooking the lake
Large Kitchen
Exceptional
(13 reviews)

Making Memories on North Long Lake

Brainerd

8% off
NZ$5,313
for 7 nights, 1 home
NZ$759 per night
includes taxes & fees
Making Memories on North Long Lake
Private kitchen
Exterior detail
Room
large kitchen upstairs with lake views
Exceptional
(5 reviews)

Lake View, Speakeasy, Sauna, Arcade, Ping Pong, Kayaks, Disc Golf, Poker, B-Ball

Crosby

6% off
NZ$3,978
for 7 nights, 1 home
NZ$568 per night
includes taxes & fees
Lake View, Speakeasy, Sauna, Arcade, Ping Pong, Kayaks, Disc Golf, Poker, B-Ball
Room
Interior
Dining
Outdoor dining
Exceptional
(11 reviews)

Peaceful & Updated Baxter Beach Cabin - Private Sandy Beach w/ Amenities

Brainerd

12% off
NZ$2,490
for 7 nights, 1 cabin
NZ$356 per night
includes taxes & fees
Peaceful & Updated Baxter Beach Cabin - Private Sandy Beach w/ Amenities
Kitchen
Kitchen Island, 6 stools available
Interior
Bedroom #1 - Main Floor - Queen
Exceptional
(46 reviews)

5 BEDS 2BA Crosby Home Just 4 blocks from Main Street & Bike Trails!

Crosby

12% off
NZ$2,861
for 7 nights, 1 home
NZ$409 per night
includes taxes & fees
5 BEDS 2BA Crosby Home Just 4 blocks from Main Street & Bike Trails!
Living area
Fully Stocked Kitchen
Living Room
Exterior detail
Exceptional
(13 reviews)

4BR 2BA The Pine Place Cabin in Crosby - Roam, Ride, Relax

Crosby

12% off
NZ$2,448
for 7 nights, 1 home
NZ$350 per night
includes taxes & fees
4BR 2BA The Pine Place Cabin in Crosby - Roam, Ride, Relax
Exterior
Property grounds
Dining
Interior
Exceptional
(5 reviews)

NEW - Cozy Breezy Point cabin on beautiful Pelican Lake

Pequot Lakes

8% off
NZ$5,426
for 7 nights, 1 cabin
NZ$775 per night
includes taxes & fees
NEW - Cozy Breezy Point cabin on beautiful Pelican Lake
Interior
Interior
Room
Living area
Exceptional
(76 reviews)

Cozy Mountain Biking Retreat, Lake View, Walking distance to Town

Crosby

8% off
NZ$1,748
for 7 nights, 1 cottage
NZ$250 per night
includes taxes & fees
Cozy Mountain Biking Retreat, Lake View, Walking distance to Town
Exterior
Living area
Exterior
Interior
Exceptional
(76 reviews)

Cottage Charm

Nisswa

8% off
NZ$4,642
for 7 nights, 1 home
NZ$663 per night
includes taxes & fees
Cottage Charm
Property grounds
Interior
Dining
Exterior detail
Exceptional
(7 reviews)

Lovely Tiny-House Cabin on Crosslake + Sauna + Bonfire + Scenic Views

Crosslake

8% off
NZ$2,564
for 7 nights, 1 cabin
NZ$366 per night
includes taxes & fees
Lovely Tiny-House Cabin on Crosslake + Sauna + Bonfire + Scenic Views
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Delight in the lakeside landscape of Ossipee

The lake and beaches create a pretty picture of Ossipee. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Ossipee

Are you searching for attractions to visit in the area? Venture out of your cosy holiday rental and experience everything that makes Ossipee a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Deacon's Lodge Golf Course (6.3 mi / 10.2 km)
  • Whitebirch Golf Course (6.5 mi / 10.4 km)
  • Nisswa City Park (7.6 mi / 12.2 km)
  • The Pines Golf Course (9 mi / 14.4 km)
  • Brainerd International Raceway (10.7 mi / 17.1 km)
  • Mount Ski Gull (13.1 mi / 21.1 km)

Exploring the natural features in Ossipee

Whether you're an adventurous traveller or just want to take in the scenery, Ossipee is a great place to get outside. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Lake Edward (2 mi / 3.1 km)
  • Upper Mission Lake (3.2 mi / 5.2 km)
  • Pelican Lake (3.9 mi / 6.2 km)
  • Cuyuna Country State Recreation Area (6.8 mi / 10.9 km)
  • Ossawinnamakee Lake (7.4 mi / 11.9 km)
  • Nisswa City Park (7.6 mi / 12.2 km)

Travelling to and around Ossipee

Fly into Brainerd, MN (BRD-Brainerd Lakes Regional), the closest airport, located 9.6 mi (15.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Ossipee when booking a holiday rental?
When considering a holiday rental in Ossipee, Minnesota, the charming area around the Ossipee Lake is particularly appealing. This picturesque neighbourhood offers a serene lakeside experience, great for those looking to unwind and enjoy nature. The area boasts a variety of properties, ranging from cosy cabins to spacious homes, making it suitable for families or groups looking for a relaxing getaway.One of the top attractions nearby is the stunning Ossipee Lake itself, which provides ample opportunities for swimming, fishing, and boating during the warmer months. Additionally, the surrounding landscape is ideal for hiking and exploring the beautiful outdoors, with trails that offer breathtaking views of the area's natural beauty.For those seeking a touch of local culture, the nearby Ossipee Historical Society is worth a visit, showcasing the rich history of the region.
What are the top attractions in Ossipee?
In Ossipee, Minnesota, visitors can enjoy a variety of attractions that highlight the area's natural beauty and recreational opportunities. The Ossipee Lake is a central draw, offering a range of water activities such as boating, fishing, and swimming, with scenic views of the surrounding landscape. The lake's beaches provide a superb spot for relaxation and family gatherings.For those interested in outdoor activities, the nearby White Mountain National Forest offers hiking trails that cater to various skill levels, showcasing stunning vistas and diverse wildlife. The forest is also ideal for winter sports, such as snowmobiling and cross-country skiing, making it a year-round destination for nature enthusiasts.Additionally, the town hosts local events and markets that reflect the charm of small-town Minnesota, providing a taste of the community's culture and hospitality.
Are all fees included in the Ossipee holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Ossipee holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Ossipee with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Ossipee holiday homes?
You can find great discounts on holiday homes in Ossipee on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Ossipee holiday home booking on Bookabach?
To find Ossipee holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Ossipee?
A long-stay holiday home in Ossipee is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Ossipee holiday home?
Book your Ossipee holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Ossipee?
Prices for holiday homes in Ossipee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Ossipee to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.