Holiday Rentals in Ossipee

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Holiday Rentals in Ossipee

Minnesota Cabin w/ Deck & Private Beach

9.4 out of 10, Exceptional, (20)
"Really nice lot down to the lake. Enjoyed our stay. Would only recommend adding a railing at the interior stair and replacing some of the deck boards that are rotting. Overall really nice place to stay. "
Minnesota Cabin w/ Deck & Private Beach

Quiet, Cozy Lake Cottage North of Brainerd, Merrifield, Great Getaway!

10.0 out of 10, Exceptional, (91)
"We stayed at Pine Cone Cottage for a much needed getaway. It was perfect! Sandy was very accommodating and friendly. The cottage was very clean and had everything we needed. Sitting by the water, watching water fowl was so relaxing. Seeing the northern lights was a plus! We would definitely stay again!"
Quiet, Cozy Lake Cottage North of Brainerd, Merrifield, Great Getaway!

Lake House with amazing park like setting!!

9.8 out of 10, Exceptional, (23)
"Last minute decision to get family together over the Labor Day holiday when I found this beautiful home large enough to fit us all. Plus was they allow our furry family members to be with us. Can’t say enough how fun the home & property are. "
Lake House with amazing park like setting!!

Nature Link Resort

3.0 star property
9.8 out of 10, Exceptional, (35)
"Great Lake views!"
The price is €102
includes taxes & fees
26 Nov - 27 Nov
Nature Link Resort

Stunning 4 Bedroom Lake Home close to everything!!

10.0 out of 10, Exceptional, (42)
"The home was lovely. A little disconcerting to have any traps on the kitchen counter though. Tried to contact owner for departure instructions and they never answered so we just did what most vrbo renters have asked. Also, instructions regarding entry need updating. Talks about turning something but it is digital and you need to hit the lock symbol. Also, we brought steaks for the bbq seen in photo. It is a pellet stove. We are unfamiliar with that and there were no instructions. A beautiful...
The price is €752
includes taxes & fees
24 Nov - 25 Nov
Stunning 4 Bedroom Lake Home close to everything!!

Quaint Cabin on Sibley Lake PONTOON INCLUDED thru early October.

10.0 out of 10, Exceptional, (159)
"We came up for a wedding and fall colors and had such a great time! The cabin is super cozy and very obviously well cared for. The master suite makes it a perfect getaway for a couple and the bunk house would be an awesome spot for older kids to sleep! We loved enjoying the lake, large patio and amazing sauna while also enjoying all of the close by parks and downtown nisswa and Pequot lakes. Krista, the host, was extremely communicative, helpful and went above and beyond to make our stay...
Quaint Cabin on Sibley Lake PONTOON INCLUDED thru early October.

Beautiful Cabin On Upper Hay Lake

8.8 out of 10, Excellent, (60)
"We decided to stay here as it would be enough room for our whole group, me, my husband, his kids, my kids, and our grandkids. There were 13 of us total. We really like this rustic cabin. It is definitely outdated, but that was fine by us as then we didn't have to worry about the grandkids so much. The place was clean and we were spread out a bit in the three different sleeping areas. The bunk house area worked good for my daughter and her husband and three kids to sleep in. It would be nice if...
Beautiful Cabin On Upper Hay Lake

Lakeside Haven at Upper Hay Lake

9.2 out of 10, Wonderful, (17)
"Beautiful property right on the water. They have kayaks that we used and a sauna! They have two large cabins and plenty of beds. Very clean. Super quiet so if you want a relaxing vacation, here’s the spot. I definitely recommend. Also the hosts were really good at communicating and nice. "
The price is €411
includes taxes & fees
4 Dec - 5 Dec
Lakeside Haven at Upper Hay Lake

Classic Minnesota Cabin on Beautiful Lake O'Brien - Includes Pontoon Boat

10.0 out of 10, Exceptional, (296)
"Cozy comfortable cabin in the woods perfect for a romantic getaway!"
Classic Minnesota Cabin on Beautiful Lake O'Brien - Includes Pontoon Boat

Discounted November Dates - Quintessential Lake Cabin with Woodburning Fireplace

10.0 out of 10, Exceptional, (304)
"My friend and I created our own impromptu writing retreat. We were able to spread out and were very productive in this beautiful setting!"
Discounted November Dates - Quintessential Lake Cabin with Woodburning Fireplace

Cuyuna Lakes Stay

3.0 star property
9.2 out of 10, Wonderful, (45)
"Great and relaxing. Really enjoyed it. "
The price is €112
includes taxes & fees
4 Dec - 5 Dec
Cuyuna Lakes Stay

River Cabin on the Pine River- Adult only

9.8 out of 10, Exceptional, (90)
"I absolutely loved this place. The location is great, quiet, peaceful and Pine river is beautiful. The cabin is awesome, it has everything you need for a memorable vacation getaway. "
River Cabin on the Pine River- Adult only

1/2 Off All Nov Dates at Modern Rustic Cabin - Woodburning FP & Sunsets!!

10.0 out of 10, Exceptional, (144)
"We celebrated our birthdays with all the grandkids and adults and it was one of my best birthday celebrations. I truly was blown away by the decor and comfort level. I would love to be able to stay again. We didn’t want to leave, took our time taking it all in. I was so empresses by the layout of all the rooms. The furniture was top notch for a rental. I loved all the decor and outside layout was perfect. "
1/2 Off All Nov Dates at Modern Rustic Cabin - Woodburning FP & Sunsets!!

Lakefront Brainerd Cabin - Great Rice Lake Fishing

9.0 out of 10, Wonderful, (82)
"Excellent "
Lakefront Brainerd Cabin - Great Rice Lake Fishing

Family Getaway on Two Private Lakes

10.0 out of 10, Exceptional, (16)
"It worked out for us as we were able to have a small family reunion and we were able to meet our 2 great, great granddaughters ages 2 and 2 months. the ponds are not usable as far as wading for our 2 mimi schnauzers but they loved smelliing all the wild animal smells from deer and squirrels and chipmunks! plenty of room and patio was nice. Since we are older, the bathroom showers could have been a little bigger and safer but we managed. the step into the house via the kitchen is dangerous. even...
Family Getaway on Two Private Lakes

ENJOY this New Construction! Private! Rustic! Mollie Lake Cabin! No SMOKING/PETS

10.0 out of 10, Exceptional, (205)
"We had a lovely stay at your beautiful cabin!"
ENJOY this New Construction! Private! Rustic! Mollie Lake Cabin! No SMOKING/PETS

PARADISE NORTH: LOG HOME CABIN IN BRAINERD, MN

9.6 out of 10, Exceptional, (46)
"This was a very excellent luxury cabin will be coming back a lot and I love the serenity and peace everything is a ten star for me what a great CABIN SO BEAUTIFUL !!!"
PARADISE NORTH: LOG HOME CABIN IN BRAINERD, MN

Remodeled Cabin, Grill, Outside Seating, New Heating & AC, Dock, Swimming & More

10.0 out of 10, Exceptional, (23)
"My long-time friend (60+ years) and I wanted a getaway to go fish for a week. This rental was great for the two of us - two bedrooms, a great room/kitchen combo, a stackable washer/dryer, reliable wifi and a smart TV. We were able to fish six different lakes in the week and brought two coolers of fish home. Host was quick to respond to any questions and email. If you're looking for high priced luxuries, this isn't it. But if you want a comfortable, reasonably priced place to stay for the week or...
Remodeled Cabin, Grill, Outside Seating, New Heating & AC, Dock, Swimming & More

Quaint Ironton Getaway w/ Fire Pit, Gas Grill!

9.8 out of 10, Exceptional, (7)
"Good communication, not the fault of the property that the power went out twice (no generator) or that there were tornado warnings to get into a basement. We did but had company, a dead mouse. All in all, a less than perfect experience. We left 2 days early."
Quaint Ironton Getaway w/ Fire Pit, Gas Grill!

Luxury Lakefront Retreat:Hot Tub, Game Room, Views

10.0 out of 10, Exceptional, (17)
"Enjoyed staying at the cabin for a golf weekend with friends. Overall everything was great!"
Luxury Lakefront Retreat:Hot Tub, Game Room, Views
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.
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Other types of properties in Ossipee you may be interested in

Minnesota Cabin w/ Deck & Private Beach

9.4 out of 10, Exceptional, (20)
"Really nice lot down to the lake. Enjoyed our stay. Would only recommend adding a railing at the interior stair and replacing some of the deck boards that are rotting. Overall really nice place to stay. "
Minnesota Cabin w/ Deck & Private Beach

The Lodge at Brainerd Lakes

3.0 star property
8.0 out of 10, Very good, (915)
"Clean rooms, excellent staff, they were friendly and very helpful. Breakfast was great. Only downside was kids in room next to us yelling in hallway, banging on walls, in and out of room and slamming the door late at night"
The price is €99
includes taxes & fees
2 Dec - 3 Dec
The Lodge at Brainerd Lakes

Grand View Lodge

3.5 star property
9.2 out of 10, Wonderful, (713)
"Great place with many options for dining and activities. Very beautiful location."
The price is €166
includes taxes & fees
2 Dec - 3 Dec
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?

Deacon's Lodge Golf: Overlooking Pelican Lake - Breezy Point: This holiday home rental outside of Ossipee is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

How many holiday rentals will I find in Ossipee?

Choose from 11 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 Paul Bunyan Land, or get outside and enjoy nature at Mississippi River. In the wider area, you’ll find The Pines Golf Course and Cross Lake Recreation Area.

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.