Ossipee Holiday Rentals

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Holiday Rentals in Ossipee

Property grounds
Quiet, Cozy Lake Cottage North of Brainerd, Merrifield, Great Getaway!
10.0 out of 10, Exceptional, (78)
"Stayed 3 nights. Enjoyed the birds, seeing the work of the beavers, took the canoe out. Read books sitting on the dock. The lake is small, private and quiet. No loud jet skis and speed boats disrupting your peace and quiet. We watched two DVDs they had on site one night. What a special treat that was. We didn't cook much but the kitchen seemed well stocked. Well stocked bathroom. The bed was very comfortable. Lots of seating options in the living room. The chairs on the deck are comfortable to...
Quiet, Cozy Lake Cottage North of Brainerd, Merrifield, Great Getaway!
Exterior
Minnesota Cabin w/ Deck on Silver Lake!
9.2 out of 10, Wonderful, (10)
"My family really enjoyed staying at the property, it was just the right size to get everyone together. It was winter when we visited, but the lake had just frozen over and it made for some beautiful sunrise photos! Would love to come back during the summer!"
Minnesota Cabin w/ Deck on Silver Lake!
Interior
Lake House with amazing park like setting!!
9.8 out of 10, Exceptional, (15)
"Thanks Shirley, our stay was fantastic. Plenty of room, really clean and no shortage of fun. The kitchen stove is amazing. It was pretty well stocked with all the stuff you need. We had family in for a day, there were 20 of us. (yes, it was nice when they left at the end of the day). We were all able to sit on the deck and had a great time. The young kids started fishing when they arrived and didn’t stop. Really fun to see. The grounds are beautiful. Take a walk and explore. So worth it. Wish...
Lake House with amazing park like setting!!
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Down duvets, blackout curtains, free WiFi, bed sheets
Cuyuna Lakes Stay
3.0 star property
9.6 out of 10, Exceptional, (21)
"This is a cute motel. The property was clean and we had excellent communication. We were able to get an early check in when we called which was wonderful. Check in and check out was easy and convenient which doesn’t always happen with motels which have been updated. The walls are paper thin, so if you are a person that needs quiet I would say this is not the place for you. The bathroom was clean but the tub was not updated(think pink). This meant a nice big tub even if it was pink from another...
The price is NZ$197
per night
21 May - 22 May
Cuyuna Lakes Stay
Interior
Stunning 4 Bedroom Lake Home close to everything!!
10.0 out of 10, Exceptional, (33)
"We had grandma and her sisters coming MN to visit us. It’s a wonderful time to spend time together."
Stunning 4 Bedroom Lake Home close to everything!!
Interior
Beautiful Cabin On Upper Hay Lake
8.8 out of 10, Excellent, (55)
"Nice little cabin with extra bed accommodations in the garage / side cabin. Good sized yard for outdoor activities with a dock right on the lake for all sorts of water activities."
Beautiful Cabin On Upper Hay Lake
Lake
River Cabin on the Pine River
9.8 out of 10, Exceptional, (64)
"Weekend away wheeling around and enjoying the outdoors. Cabin was cute, clean and had everything we needed. Eric was very welcoming and shared great local information. Would definately recommend!!! We plan to stay again next winter to check out the area snowmobiling"
The price is NZ$202
per night
22 May - 23 May
River Cabin on the Pine River
Sequoia Cabin Residences
Nature Link Resort
4.5 star property
9.6 out of 10, Exceptional, (19)
"Very peaceful! Beautiful property and amenities."
The price is NZ$218
per night
23 May - 24 May
Nature Link Resort
Smart TV, fireplace, table football, ping pong
Lakeside Haven at Upper Hay Lake
10.0 out of 10, Exceptional, (3)
"We spent two weeks here in the winter. It was a much-needed retreat away from the city. We spent the morning sipping coffee before the beautiful stone fireplace, afternoons in the sauna, and evenings grilling. The cabin was fully equipped with extra towels and blankets, and games. The kitchen e was great, and we enjoyed having extra room in the guest cabin to work or read silently. The location was beautiful, and the ice started to melt while we were there, and we could hear it. Plenty of...
The price is NZ$732
per night
21 May - 22 May
Lakeside Haven at Upper Hay Lake
Fridge, microwave, oven, stovetop
ENJOY this New Construction! Private! Rustic! Mollie Lake Cabin! No SMOKING/PETS
10.0 out of 10, Exceptional, (178)
"This was a really nice spot for our girl's weekend out of the cities! Lots of space and great views. Had a little bit of an issue with the dirt roads getting there, but it all worked out. Would definitely consider staying here again!"
The price is NZ$600
per night
27 May - 28 May
ENJOY this New Construction! Private! Rustic! Mollie Lake Cabin! No SMOKING/PETS
Fridge, microwave, oven, stovetop
Quintessential Lake Cabin on Pristine Lake O'brien - Includes New Pontoon Boat!!
10.0 out of 10, Exceptional, (290)
"This place was perfect for our Mother’s Day weekend. It is appealing from the moment you pull into the driveway. The cabin is nested in its natural surroundings as if it were always there. The large windows give spectacular views from all sides. The design and décor make you feel comfortable and relaxed. There is room to play games, ample supplies for preparing meals, and very comfortable beds. The screen porch was the place to watch and listen to the birds as the sun rose each morning. The dock...
Quintessential Lake Cabin on Pristine Lake O'brien - Includes New Pontoon Boat!!
TV, fireplace, DVD player
Classic Minnesota Cabin on Beautiful Lake O'Brien - Includes Pontoon Boat
10.0 out of 10, Exceptional, (279)
"This was our second stay at The Cabin. Everything is as shown in the listing. Actually, the patio chairs are now Adirondack type. The owners are accommodating and make the rental process easy. There was a strong winter storm during our visit, but we still made use of the patio and fire pit after some shoveling. We look forward to coming back again when the lake is not frozen and we can use the pontoon and screened back porch."
Classic Minnesota Cabin on Beautiful Lake O'Brien - Includes Pontoon Boat
Property grounds
Family Getaway on Two Private Lakes
10.0 out of 10, Exceptional, (2)
"All was great!"
Family Getaway on Two Private Lakes
Pool
Remodeled Cabin, Grill, Outside Seating, New Heating & AC, Dock, Swimming & More
10.0 out of 10, Exceptional, (19)
"Nice cabin, great price to be on the lake."
Remodeled Cabin, Grill, Outside Seating, New Heating & AC, Dock, Swimming & More
Dining
Cozy Ironton Getaway w/ Fire Pit, Gas Grill!
10.0 out of 10, Exceptional, (5)
"This property was just what we were looking for in a biking vacay! It was clean, yet not too fancy. It felt like a cabin, where we could bring kids and pets without feeling like we were going to break something or ruin something."
Cozy Ironton Getaway w/ Fire Pit, Gas Grill!
Fridge, microwave, dishwasher, coffee/tea maker
Lakefront Brainerd Cabin - Great Rice Lake Fishing
9.0 out of 10, Wonderful, (75)
"Overall nice, quaint place. Quiet, peaceful location. Beds/mattresses need to be updated. Would benefit from more comfortable seating (ie larger couch) in the main area. Had a wonderful, delicious meal from local establishment (Dunmire’s), highly recommend it."
Lakefront Brainerd Cabin - Great Rice Lake Fishing
Exterior
Modern Rustic Cabin-Includes Pontoon Boat & Sunsets on Fantastic Lakeside Porch!
10.0 out of 10, Exceptional, (129)
"Beautiful cabin and location. We went as a family and had such a relaxing time. Just played games, listened to the loons and other birds, did a little fishing and pontoon-ing. The cabin owners communicated with us well, everything was clean and comfortable. Just had a great time. Highly recommend!"
Modern Rustic Cabin-Includes Pontoon Boat & Sunsets on Fantastic Lakeside Porch!
1 bedroom, free WiFi, bed sheets
Vintage 1920's Lakefront Red Log Cabin known as "Camp David"
9.6 out of 10, Exceptional, (59)
"The cabin is cozy and adorable. Close to the lake which is beautiful. The furniture, while old fashioned, was extremely comfortable. We spent a ton of time relaxing on the red couch! Had a few minor issues. The chain in the toilet kept coming loose, causing issues with flushing, and the water pressure in the sink and shower were near nothing. It was also extremely cold in the bedroom, despite us adjusting the heat, and the portable heater in the bedroom did not work. Overall, we seriously...
Vintage 1920's Lakefront Red Log Cabin known as "Camp David"
Exterior
Vintage Cabin on Beautiful Lake O'brien - Includes Pontoon Boat
10.0 out of 10, Exceptional, (135)
"We loved our stay here! Everything was so beautiful! Our favorite places to hang out were the firepit and the outdoor porch. The bedding and mattresses are so comfortable! We went hiking at a local trail, came back and made soup on the stove, played cards and had s’mores by the firepit. The fact that we could bring the dogs too was so nice! I love all the decorative touches in both cabins. Perfect getaway. Can’t wait to come back!"
Vintage Cabin on Beautiful Lake O'brien - Includes Pontoon Boat
Smart TV, ping pong, printers
HOT TUB Luxury Cabin on Mississippi River, Dock, Pool Table, Fishing, Fire Pits
10.0 out of 10, Exceptional, (10)
"We rented this house for a Bachelorette Gathering. We had 6 ladies celebrating altogether. Typically, pics look better than the real thing, but in this case, the opposite was true! It was better than the photos. Such a perfect space! Lots of rooms and beds; enough bathrooms even. Everything was clean and perfectly made up. All utensil and utility drawers were well labeled and made everything really easy to find. Alexandra was very helpful with all of our questions and concerns with the hot tub,...
HOT TUB Luxury Cabin on Mississippi River, Dock, Pool Table, Fishing, Fire Pits
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See all available properties in Ossipee
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Ossipee you may be interested in

Exterior
Minnesota Cabin w/ Deck on Silver Lake!
9.2 out of 10, Wonderful, (10)
"My family really enjoyed staying at the property, it was just the right size to get everyone together. It was winter when we visited, but the lake had just frozen over and it made for some beautiful sunrise photos! Would love to come back during the summer!"
Minnesota Cabin w/ Deck on Silver Lake!
Indoor pool
Nisswa Inn and Suites
2.0 star property
6.8 out of 10, (846)
"Came up to Nisswa to see the Northern Lights. Nice basic hotel to sleep. Nice staff."
The price is NZ$139
per night
22 May - 23 May
Nisswa Inn and Suites
Property grounds
Grand View Lodge
3.5 star property
9.2 out of 10, Wonderful, (645)
"Beautiful property, clean and updated and wonderful service"
The price is NZ$310
per night
22 May - 23 May
Grand View Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find holiday rentals in Ossipee?

Yes, there are holiday rentals close to the most popular sights in Ossipee, or you can select a more secluded option if you're looking for a relaxing stay. Ossipee is known for its lake views.

What are some of the best holiday rentals that Ossipee has to offer?

Family Getaway on Two Private Lakes: This holiday home rental outside of Ossipee is located on a lake, and has a selection of games, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Ossipee?

Choose from 8 Expedia holiday rentals in Ossipee for a memorable holiday.

What can I see and do in Ossipee?

While exploring the area, visit family-friendly sights like Nisswa Family Fun Center, or get outside and enjoy nature at Mississippi River. In the wider area, you’ll find The Pines Golf Course and Brainerd International Raceway.

What are holiday rentals like in Ossipee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ossipee. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family gatherings.

Recent reviews of Ossipee properties
Expedia verified reviews

Days Inn & Suites by Wyndham Baxter Brainerd Area

Days Inn & Suites by Wyndham Baxter Brainerd Area

5/5 Excellent
"The agent who checked me in was stellar. "
A verified traveller stayed at Days Inn & Suites by Wyndham Baxter Brainerd Area
Posted 3 days ago
Days Inn & Suites by Wyndham Baxter Brainerd Area