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Compare 74 Cottages in Ossipee with updated reviews, rates, and availability.

Family Friendly - Flat Sandy Beach - Next to Paul Bunyan Trail
Fall 2023
Family Friendly - Flat Sandy Beach - Next to Paul Bunyan Trail
10.0 out of 10, Exceptional, (95)
"We stayed At the Hubert Hideaway because a family member was getting married at The Catalyst. We couldn’t have asked for a better location, more equipped, cabin, and awesome view!"
Family Friendly - Flat Sandy Beach - Next to Paul Bunyan Trail
Pet-friendly Cottage: 8 Mi to Paul Bunyan Land!
Exterior
Pet-friendly Cottage: 8 Mi to Paul Bunyan Land!
3.0 star property
Pet-friendly Cottage: 8 Mi to Paul Bunyan Land!
6000 Sq Feet w/Year Around Indoor Pool-King Beds
Indoor pool
6000 Sq Feet w/Year Around Indoor Pool-King Beds
9.4 out of 10, Exceptional, (56)
"The house was everything we were hoping for! Stayed there with friends for a golf trip. Rooms and beds were great, pool was awesome, very clean. Would definitely stay again."
6000 Sq Feet w/Year Around Indoor Pool-King Beds
Secluded - Cottage - Fire Pit- 5 Acres
Exterior
Secluded - Cottage - Fire Pit- 5 Acres
9.6 out of 10, Exceptional, (21)
"It's close to everything yet serene and secluded. It was a great experience. Very comfortable beds, well stocked kitchen. Book it, you won't regret it."
Secluded - Cottage - Fire Pit- 5 Acres
Cozy 3 Bedroom Cottage 2 Blocks From Lake, Firepit, Boat and Snowmobile Parking
Exterior
Cozy 3 Bedroom Cottage 2 Blocks From Lake, Firepit, Boat and Snowmobile Parking
9.6 out of 10, Exceptional, (17)
"Our stay was perfect! Plenty of necessities to get us through a wonderful week in Pequot Lakes. I highly recommend."
Cozy 3 Bedroom Cottage 2 Blocks From Lake, Firepit, Boat and Snowmobile Parking
Mahnomen Cottage: Hike, Bike, Fish, & Relax only 2 hrs north of the Twin Cities!
Exterior
Mahnomen Cottage: Hike, Bike, Fish, & Relax only 2 hrs north of the Twin Cities!
10.0 out of 10, Exceptional, (13)
"Our stay was just what we needed for our family reunion weekend in Garrison! The property had a beautiful country setting with lots of room for our dog ti explore and run. The house itself had all we needed and was very cutely decorated in authentic retro styling. Thank you for a great weekend getaway!!"
Mahnomen Cottage: Hike, Bike, Fish, & Relax only 2 hrs north of the Twin Cities!
Pet-Friendly Cottage: 8 Mi to Paul Bunyan Land!
Brainerd Vacation Rental | 3BR | 1.5BA | 1,360 Sq Ft | Stairs Required
Pet-Friendly Cottage: 8 Mi to Paul Bunyan Land!
10.0 out of 10, Exceptional, (1)
"We came in from NY for our Grandsons’ graduation from Brainerd HS and to visit with family for a few days. The location of the house was perfect; it was spotless and well stocked with everything we needed! The manager and owner were quick to respond to us during our stay and we hope to stay there again in the future."
Pet-Friendly Cottage: 8 Mi to Paul Bunyan Land!
MTB Heritage Parkside Cottage
Exterior
MTB Heritage Parkside Cottage
10.0 out of 10, Exceptional, (13)
"So thankful for the ability to use the lake and biking around Crosby. Great for our family!!"
MTB Heritage Parkside Cottage
North Pine Cottage #1
Lake side
North Pine Cottage #1
10.0 out of 10, Exceptional, (49)
"This was an absolutely beautiful and extremely clean lake home. Several family rooms and two floors to spread out in. Awesome large kitchen with plenty of nice dishes, pots and pans, and seating. King bed in master bedroom not a queen as stated in website, and this was nice! Nice front loader washer and dryer. Please note the dock shown in the website picture is for the home next door. "
North Pine Cottage #1
Family boating cottage on Whitefish Chain of Lakes
Come and enjoy the lake!
Family boating cottage on Whitefish Chain of Lakes
10.0 out of 10, Exceptional, (13)
"This is a great property to stay at especially for a family. It was just my family who stayed here, but it could work for two families. Everything is as advertised. It has all the things you would ever need plus some. Even the shower had a nice "hotel style" soap, shampoo, and conditioner dispenser which was a really nice touch. They even have a beach down by the lake which we played at every day. Our only complaint would be that the cleaning company they use does a horrible job. The...
Family boating cottage on Whitefish Chain of Lakes
Escape to Birch Narrows Cottage on The Whitefish Chain/Includes Guest Cabin
Wow, West facing sunsets are hard to beat! Welcome to Birch Narrows Cottage!
Escape to Birch Narrows Cottage on The Whitefish Chain/Includes Guest Cabin
10.0 out of 10, Exceptional, (36)
"The property is setup well for multiple families or a large group can stay. With there being 3 bedrooms in the house and the 3 season bunk room as well. It worked out great for our three families staying there. There’s plenty to do with being on the lake and the surrounding area."
Escape to Birch Narrows Cottage on The Whitefish Chain/Includes Guest Cabin
Cape Cod Meets Up North in this Gull Lake Retreat
Patio with fire pit, Lakeside
Cape Cod Meets Up North in this Gull Lake Retreat
10.0 out of 10, Exceptional, (27)
"The property is exactly as advertised. The home is very nicely decorated and well equipped. Located in a central spot on Gull Lake with great fishing close by. We would definitely return."
Cape Cod Meets Up North in this Gull Lake Retreat
Cuyuna Gnome Home - Walk to Crosbys Serpent Lake!
Living area
Cuyuna Gnome Home - Walk to Crosbys Serpent Lake!
3.0 star property
8.0 out of 10, Very Good, (1)
Cuyuna Gnome Home - Walk to Crosbys Serpent Lake!
Quaint Ironton Getaway w/ Fire Pit, Gas Grill!
Dining
Quaint Ironton Getaway w/ Fire Pit, Gas Grill!
3.0 star property
Quaint Ironton Getaway w/ Fire Pit, Gas Grill!
Pet-friendly Pequot Lakes Vacation Rental Cabin!
Living area
Pet-friendly Pequot Lakes Vacation Rental Cabin!
3.0 star property
Pet-friendly Pequot Lakes Vacation Rental Cabin!
Pet-friendly Breezy Point Cabin: 1 Mi to Beach!
Living area
Pet-friendly Breezy Point Cabin: 1 Mi to Beach!
3.0 star property
Pet-friendly Breezy Point Cabin: 1 Mi to Beach!
Breezy Point Cabin w/ Fire Pit - Walk to Lake
Exterior
Breezy Point Cabin w/ Fire Pit - Walk to Lake
3.0 star property
10.0 out of 10, Exceptional, (1)
"A lovely, nearly new cabin with every comfort. It was very comfortable for us (four adults and a toddler). Communications and instructions ahead of our visit were excellent and timely. We had a wonderful stay. "
Breezy Point Cabin w/ Fire Pit - Walk to Lake
Cozy Crosby Cabin Near Serpent Lake + Main St
Living area
Cozy Crosby Cabin Near Serpent Lake + Main St
3.0 star property
Cozy Crosby Cabin Near Serpent Lake + Main St
Lakefront Brainerd Cabin - Great Rice Lake Fishing
Exterior
Lakefront Brainerd Cabin - Great Rice Lake Fishing
3.0 star property
8.0 out of 10, Very Good, (1)
"We had a very peaceful, serene stay. The pan fishing from the dock was great and the sunsets were amazing. The grounds outside would benefit from trimming overgrownn shrubs and irradicating poison ivy. We'd be concerned about the poison ivy if we had children or a dog with us. The management was friendly and helpful. We were concerned about access as it is not easily accessable for loading and unloading and were allowed to get closer to do so."
Lakefront Brainerd Cabin - Great Rice Lake Fishing
Bright Crosby Home - Walk to Main St & Beach!
Exterior
Bright Crosby Home - Walk to Main St & Beach!
3.0 star property
8.0 out of 10, Very Good, (1)
"Great location to trails and downtown Crosby. "
Bright Crosby Home - Walk to Main St & Beach!
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 property types in Ossipee

Minnesota Cabin w/ Deck & Private Beach
Merrifield Vacation Rental | 2BR | 2BA | 1,400 Sq Ft | Half Step Required
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!
Lakeside of cabin
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!!
Living room / Kitchen
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!!
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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