
House holiday rentals in Ossipee
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Top-rated house rentals in Ossipee
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Lakefront Oasis XL Hot Tub Game Room Fish Hike FUN
Escape to this private renovated lakeside retreat, perfect for the whole family & dog! New Deck, Hot Tub, privacy fence. Thoughtfully designed for comfort and entertainment with fully stocked kitchen, new furniture /attached 1200sq ft barn/game room, XL washer/dryer. Pond with private dock & beach/swim raft, 32” Blackstone bbq, comfy beds, blackout shades, and ultra-fast WiFi. Smart TVs, games, a loft, dedicated workspace. ~1.5 hours north of Boston—your perfect getaway awaits! Gr8 Trout Fishin

Aspen Cottage - Charming Cottage with Beach Access
Nestled in the trees, at the end of a quiet road, you’ll find your next restful getaway. Central location perfect for relaxing or adventuring. Less than a 10 minute walk to multiple points of beach access or sunset viewing at Lower Beech Pond, a 155-acre lake within the Ossipee Mountain range, known for its excellent water quality and recreation. A 15 minute drive to downtown Wolfeboro and Lake Winnipesaukee. In the winter months, find miles of snowmobiling through NH's extensive trail system.

Pet-friendly cabin with hot tub and beach access!
Feel right at home in our open-concept year-round vacation gem within the Chocorua Ski and Beach community half a mile from the Moore’s pond. The cabin is nestled in the woods providing privacy. It boosts a double-sided fire-place and hot tub perfect for the cooler nights, a wraparound deck, as well as an enclosed porch. On the basement level, there is a pull-out couch, bedroom, TV, and full bathroom allowing for extra hang out and sleeping space. Follow us on insta: #sandypinestamworthnh

Spacious home near mountains and lakes
Enjoy this spacious home that includes 3 bedrooms, a great kitchen ( upgraded cookware), and a huge game room downstairs with a pool table, new ping pong table, and foose ball table. Within minutes, you can be on Silver Lake, North Conway, Storylalnd, Kangamangus or make a visit to the White Mountians . Shop at the Settlers green outlets. Enjoy the comfort of the newly installed central air! Located in a nice quiet neighborhood. Come and go skiing at King Pine or many others in the area.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

White Mt Retreat w/ Beach Pass, New Kitchen, W/D
Get away from it all in our lovely, spacious home with its new kitchen, in Eaton, only 15 min to the shops and restaurants in North Conway and five minutes to King Pine Ski Area. Our property comes with a lake access pass to Crystal Lake public beach. Our place is ideal for outdoor enthusiasts, couples, chefs, and families. Our two floor home, with over 1600 sq. ft of living space, has two living room spaces providing private spaces for children and adults. We are owner-operated.

The LOTUS welcomes you, stay a while
The Lotus is your zen home away from home. Enjoy peace and tranquility on your private back deck, the amazing salt water hot tub (exclusively use) new sauna, heated seasonal outdoor shower, deep bathtub (showering is tricky for people taller then 5'5)with bluetooth speaker.Comfortable king size bed with European bedding and a single fold out foam mattress on the 1st floor, that was just finished as another relax area, with 70" TV, record player, hammock & hanging chair.

Our Mountain Retreat – Lake Ossipee Access
Spacious 5 bedroom home with convenient lake access, just a short walk or 5-minute drive to beautiful Lake Ossipee. Enjoy easy proximity to King Pine Ski Area and a quick 25-minute drive to Conway, where you'll find outlet shopping, scenic hiking trails, and a variety of restaurants. This property features a large yard with a fire pit, and a hot tub for ultimate relaxation. The master bedroom includes a private deck—perfect for morning coffee or stargazing at night.

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, beach, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Get 10% OFF for weekly or longer stays!

Luxurious Eagle Ridge Log Home at Newfound Lake
This stunning one of a kind log home, featured in Log Home Living Magazine, built in 2020 is located at the end of a tree lined driveway on 3.5 acres overlooking beautiful Newfound Lake, NH. This 1,586 Sq Ft home can house a MAX of 6 guests in 3 bedrooms. Amenities are 100 mbs Wi-Fi, TV, gas fireplace, gas grill, hot tub, whole house generator, central A/C, screened porch and huge patio. Parking pass to the private town beach that is less than 1/4 mile away.

Waterfront, Wood stove & Private beach, Solo Stove
Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.

Wren Cabin + Wood fired Sauna
We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.
Popular amenities for house rentals in Ossipee
House rentals with a pool

Coolidge Falls Condo-Slope Views

The Lodge at Hidden Pines

Cottage on 50 Acres | Lakeside + Pool + Hot Tub

Unique Church Accommodation • Sebago Lake • Pool • Fire Pit

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Spectacular log home with private pool and hot tub

On Attitash - Ski, Hike, Swim!

River Access|Gas stove|Min to N. Conway, Attitash
Weekly house rentals

Winni Retreat Steps from the Lake!

Cozy Cabin near Tuftonboro & Lake Winnipesaukee

Relaxing hidden gem in Wolfeboro

Spacious, renovated 2-bedroom home on golf course!

Private lake access, cozy retreat, skiing, shops

Basecamp - Province Lake

Beautiful, private, lake front, flat, sandy beach.

Quaint Ossipee Home
Private house rentals

Beautiful House 2.5 Miles from Ogunquit Beach

Baby Chocorua A Frame in the mountains sleeps 8

New Modern A-Frame | Hot Tub | Sauna & Cold Plunge

The Lake House in Acton

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit

Alpine Retreat

Cozy White Mountain Home Minutes from Conway!

Moody Farm Retreat
When is the best time to visit Ossipee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $312 SGD | $320 SGD | $320 SGD | $293 SGD | $307 SGD | $335 SGD | $359 SGD | $391 SGD | $339 SGD | $342 SGD | $311 SGD | $326 SGD |
| Avg. temp | -5°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -1°C |
Quick stats about house rentals in Ossipee

Total holiday rentals
Explore 80 holiday rentals in Ossipee

Nightly prices starting at
Ossipee holiday rentals start at $76 SGD per night before taxes and fees

Verified guest reviews
Over 2,540 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
80 of Ossipee holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ossipee rentals

4.9 Average rating
Ossipee stays are highly rated by guests – averaging 4.9 out of 5!
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- Waterfront rentals Ossipee
- Cottage rentals Ossipee
- Family-friendly rentals Ossipee
- Pet-friendly rentals Ossipee
- Rentals with lake access Ossipee
- Beachfront rentals Ossipee
- Rentals with outdoor seating Ossipee
- Rentals with a kayak Ossipee
- Rentals with a patio Ossipee
- Rentals with beach access Ossipee
- Cabin rentals Ossipee
- Rentals with a fireplace Ossipee
- Rentals with a washing machine and dryer Ossipee
- Rentals with a firepit Ossipee
- House rentals Carroll County
- House rentals New Hampshire
- House rentals United States
- White Mountain National Forest
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Pats Peak Ski Area
- Loon Mountain Resort
- Scarborough Beach
- York Harbor Beach
- Mount Washington Cog Railway
- Willard Beach
- Short Sands Beach
- East End Beach
- Cape Neddick Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- King Pine Ski Area
- Gooch's Beach
- Omni Mount Washington Resort
- Gunstock Mountain Resort
- Cranmore Mountain Resort





