Cabin
10.0(28 Reviews)
2 Bedrooms
7 Guests
Hot Tub
Parking
Ocean View
Balcony/Terrace
US $399/Night
7 Nights - US $2,792
Ossipee Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Ossipee
10.0
House
9.0(1 Review)
3 Bedrooms
8 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $305/Night
7 Nights - US $2,135
US $443/Night
7 Nights - US $3,101
Cottage
10.0(9 Reviews)
1 Bedroom
4 Guests
Air Conditioner
Internet
Child Friendly
Laundry
US $180/Night
7 Nights - US $1,263
House
3 Bedrooms
7 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $310/Night
7 Nights - US $2,168
Cabin
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $154/Night
7 Nights - US $1,078
Cabin
4.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $405/Night
7 Nights - US $2,834
House
10.0(45 Reviews)
5 Bedrooms
16 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $1,156/Night
7 Nights - US $8,095
Cabin
10.0(14 Reviews)
4 Bedrooms
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $601/Night
7 Nights - US $4,204
Luxury Holiday Rentals in Ossipee
Over 40+ Luxury Holiday Rentals in or Near Ossipee
House
9.6(33 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,150/Night
7 Nights - US $8,052
House
10.0(11 Reviews)
3 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,060/Night
7 Nights - US $7,417
Cabin
9.6(76 Reviews)
6 Bedrooms
22 Guests
- Oceanfront
- Hot Tub
- Parking
Spa
US $828/Night
7 Nights - US $5,795
Cabin
8.2(12 Reviews)
3 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $800/Night
7 Nights - US $5,603
Cabin
10.0(11 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $752/Night
7 Nights - US $5,265
Cabin
9.2(7 Reviews)
5 Bedrooms
16 Guests
- Parking
- Ocean View
- View
- Kitchen
US $732/Night
7 Nights - US $5,126
Cabin
9.8(79 Reviews)
3 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $595/Night
7 Nights - US $4,164
Cabin
10.0(7 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $578/Night
7 Nights - US $4,049
Cabin
9.6(5 Reviews)
3 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $574/Night
7 Nights - US $4,021
Pet-Friendly Holiday Rentals in Ossipee
Over 7+ Pet-Friendly Holiday Rentals in or Near Ossipee
Cabin
10.0(1 Review)
3 Bedrooms
7 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $361/Night
7 Nights - US $2,526
House
9.8(12 Reviews)
3 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $334/Night
7 Nights - US $2,341
Cabin
9.2(37 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $259/Night
7 Nights - US $1,814
Cabin
10.0(21 Reviews)
4 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $420/Night
7 Nights - US $2,941
House
9.6(7 Reviews)
4 Bedrooms
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $470/Night
7 Nights - US $3,288
US $495/Night
7 Nights - US $3,462
Cabin
9.8(9 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $710/Night
7 Nights - US $4,968
Large Holiday Rentals and Private Villas in Ossipee
Over 8+ Large Holiday Rentals and Private Villas in or Near Ossipee
Cabin
10.0(1 Review)
3 Bedrooms
10 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $460/Night
7 Nights - US $3,221
Cabin
10.0(74 Reviews)
3 Bedrooms
12 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $298/Night
7 Nights - US $2,083
House
10.0(6 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Spa
- Ocean View
US $821/Night
7 Nights - US $5,750
Cabin
10.0(5 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $491/Night
7 Nights - US $3,435
House
10.0(1 Review)
3 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $427/Night
7 Nights - US $2,992
US $348/Night
7 Nights - US $2,435
Cabin
3 Bedrooms
16 Guests
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
US $831/Night
7 Nights - US $5,817
House
4.9(13 Reviews)
4 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $412/Night
7 Nights - US $2,884
Ossipee Private Villas and Holiday Homes Under $200
Over 2+ Ossipee Private Villas and Holiday Homes Under $200
New
Cabin
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Child Friendly
TV
US $158/Night
7 Nights - US $1,106
US $150/Night
7 Nights - US $1,050
Instantly Bookable Holiday Homes in Ossipee
Over 9+ Instantly Bookable Holiday Homes in or Near Ossipee
House
10.0(13 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $411/Night
7 Nights - US $2,875
House
10.0(8 Reviews)
3 Bedrooms
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $359/Night
7 Nights - US $2,516
Cabin
9.4(30 Reviews)
3 Bedrooms
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $334/Night
7 Nights - US $2,340
Cabin
2 Bedrooms
4 Guests
- Parking
Skiing- Ocean View
- Balcony/Terrace
US $427/Night
7 Nights - US $2,991
Cabin
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $227/Night
7 Nights - US $1,591
Cabin
10.0(4 Reviews)
3 Bedrooms
7 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $780/Night
7 Nights - US $5,457
House
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $269/Night
7 Nights - US $1,882
House
8.0(1 Review)
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $341/Night
7 Nights - US $2,390
Cabin
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $464/Night
7 Nights - US $3,248
Book a Last Minute Place to Stay in Ossipee
About Casai's Private Villas and Holiday Rentals in Ossipee
Discover more than 49 vacation rentals available in Ossipee. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Ossipee.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Ossipee, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Ossipee. On average, places to stay near Ossipee offer 1113.37 ft², with nightly prices averaging US $480.
With Casai, finding and comparing holiday rentals in Ossipee is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
There are 49 Ossipee, MN Holiday Rentals
- Prices for a holiday home in Ossipee start at US $154
- Top rated vacation home in Ossipee is Summer 2026 Fully booked-Now Booking 2027, a few fall weekends remaining!
- Most popular short term in Ossipee is *HIGH DEMAND* Sugar Sand Beach & Cozy Cabin That Sleeps 10 on Pelican Lake!
- Cheapest place to stay in Ossipee is Charming & Spacious 1-bedroom cabin in the heart of the Brainerd Lakes Region
- Most expensive holiday rental in Ossipee is Summer 2026 Fully booked-Now Booking 2027, a few fall weekends remaining!
Frequently Asked Questions About Ossipee?
What are the top holiday rentals in Ossipee?
With numerous options available in Ossipee, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Ossipee:
- Summer 2026 Fully booked-Now Booking 2027, a few fall weekends remaining!
- Cozy cabin w hot tub & fireplace, near Nisswa/crosslake
- P&P Lakeside Lodge
- Silver Lake Swimming and More
- Beautiful lake home on the sandy south shores of Pelican Lake.
- Horseshoe Lake Cabin w/Hot Tub, Beach, Games, Fire Pit, Kayaks + Paddleboards
- Cottage with Hot Tub on Upper Mission Lake
- Cozy Lake Retreat at Red Pine Hill
- Newly Remodeled Lakefront Cabin w/Hot Tub & Private Dock
- Water and Woods
Which holiday homes in Ossipee are best for families?
If you're searching for a family-friendly holiday home in Ossipee, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Ossipee:
How many Casai.nz holiday rentals are available in Ossipee?
As of 2026, Casai boasts over 49 properties listed in the Ossipee area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Ossipee.
